*This post was updated in November 2024.

I’ve written a LOT about Maui on this blog (read through the archives here) and while I usually try to be objective and stick to the facts, the whole point of a blog is to share opinions ; )

While I usually sprinkle them throughout everything I write , I thought it would be fun to gather them ALL together in one place.

So if you want my personal opinions (based on MANY trips to Maui plus my time spent living there) and the travel advice that I give to my friends over coffee, this is it…

My Maui “Hot Takes”

This post may contain some affiliate links, which means I’ll make a little money on anything you choose to purchase. But of course, I only recommend my absolute favorites to you. Thank you for supporting the brands that make HulaLand possible.

1. Stay in South Maui.

Maui is a big island, but the two main places visitors stay are the south side (Wailea & Kihei) and the west side (Lahaina, Kaanapali & Kapalua).

People have strong opinions about this one, and I guess I’m no different. I think South Maui is the best place to stay for a long list of reasons.

I’ve hashed it out extensively here >> Wailea vs Kaanapali

But the short list is: 1) Wailea is one of my favorite places to stay in all of Hawaii. Seriously…when I’m planning a “vacation,” this is where I come. 2) If you’re on a budget, Kihei has a condo for you. And great beaches. 3) Geographically speaking, it’s a MUCH more convenient homebase if you’re planning to explore the whole island.

Now don’t get me wrong, I really do like West Maui (you should DEFINITELY plan to explore that side of the island), and every few trips I take I like to stay in Kapalua or Kaanapali for a change of pace, but when I have friends going to Maui for a once in a lifetime trip, I always steer them towards staying in South Maui.

2. Not all luxury resorts are created equally

I’ve practically made a career out of helping people pick the right hotel in Hawaii ; ) So believe me when I say…not all “luxury” resorts are on the same level. And honestly, you really can’t go based on price. EVERYTHING on Maui is expensive these days.

And that’s kind of my point…if you’re going to pay $$$ for a stay at a luxury beach resort, you want to make sure you pick the right one.

Depending on if you’re traveling with kids, it’s an adults only trip, or if you’re trying to cash in hotel reward points, some options are definitely better than others.

I’ve stayed at all the big luxury resorts in Wailea, and ranked them here >> Wailea Resorts Ranked

3. The Grand Wailea is a kids hotel

On that note…the Grand Wailea is widely recommended as one of the best resorts on Maui (it’s the original “flagship” resort in Wailea and guests have STRONG generational loyalty – it’s the kind of hotel a certain demographic of kids have memories of visiting annually growing up), but unlike what the price suggests, it’s far from the most luxurious resort on Maui.

If you have kids (let’s say ages 3-15), it is THE place to be. And if you don’t have kids…it’s the place to avoid ; )

Whenever I see the Grand Wailea recommended as a top honeymoon resort I’m always pretty baffled.

Now don’t get me wrong, it’s very “Grand,” but I think people often confuse the size and scale of the resort for it being nice. Honestly, it’s almost a little too big, and while the waterpark is an undeniable draw for kids, the rest of the resort is subpar compared to what’s in the area.

The property has undergone a major renovation in the last couple of years, but the things they’ve done “right” aren’t things you need to be staying there to enjoy (the spa, restaurants, etc.) and generally I’ve found the rooms, service, and adults only pool to be not so great for the money.

4. You NEED to rent a car.

Once you’ve been to Maui, this is pretty well agreed upon, but a lot of people in the planning phase still think maybe they can get by with just using Uber/Lyft.

Well, you can’t. Hawaii is not an all-inclusive destination where you’ll arrive by shuttle and never leave your resort (I mean you could do that…but it’s pretty expensive just to get to Hawaii so most people want to actually see Hawaii. If you want a cheaper resort only vacation, just go to Mexico).

The islands are pretty large so unless you’re just going a few miles, taking Ubers and Lyfts isn’t really feasible (you could be talking $100 one way to go to another part of the island and then not be able to get a ride back).

So even if you’re staying in a “resort bubble,” you’ll most definitely want a rental car for your stay.

I always book through Discount Hawaii Car Rentals. They’re seriously the only company I ever use. They’ll give you the very best prices, you don’t have to reserve with a credit card or pay until you show up, you can cancel and re-book anytime if you find a better rate, and they usually have a special that adds additional drivers for no fee. It’s a no brainer. Click here to check rates for your trip.

**I’ve started using Turo quite a bit when I travel other places because I love being able to pick out my specific car and not having to wait in a line to pick it up (I don’t find it to be any cheaper once you add the insurance though), but none of the airports in Hawaii let you pick up and drop off at the airport.

So if you do go the Turo route, plan on having to take an Uber/Lyft to and from the airport to your car. I think that’s a bit of a hassle especially on the Big Island and Kauai where things are a little slower and sleepier (especially early in the morning when most flights leave). And it adds a little layer of stress to me the morning of departure.

***Want to save major $$$ on your trip to Hawaii? I get asked ALL the time how I’m able to travel so often to Hawaii and stay at really nice resorts. Well, my favorite travel hack is cashing in points to score free airfare and free nights at some of Hawaii’s most high end resorts. Read my full guide on the exact system I use to max out credit card rewards here. Seriously, it’s going to save you soooo much money.

5. Support the local businesses in Lahaina, but don’t snoop around.

I feel like this should go without saying, but the destruction of the Lahaina wildfires is not a place to looky lou. It’s been an absolutely devastating event not just for those who lost their homes and loved ones, but for everyone on the island and it’s super insensitive to try to go “sight see” the damage.

There are more and more businesses that are starting to reopen on the outskirts of Front Street though like the Old Lahaina Luau, Cannery Mall, Aloha Mix Plate, Star Noodle, Honu, Mala Ocean Tavern, etc and they really need your support.

Something that I’ve seen posted about on social media (and on signs in these establishments)…these businesses and workers need and want your support, but don’t initiate conversations asking them about their experiences in the wildfires. It’s painful for many to talk about and while well meaning, I’m sure it gets exhausting being asked about by every person you encounter each day.

6. Don’t book a GUIDED TOUR to Haleakala for sunrise

I’m normally all in favor of a good guided tour, but this is one that I don’t really recommend. When it all works out, I’m sure it is FABULOUS. But here’s something that some people don’t think about…sunrise is a natural phenomenon. Yes, you’re guaranteed that the sun will rise each morning. But you’re not guaranteed to be able to see it from the summit of Haleakala.

I’ve been to the summit for sunrise three times: One time it was incredible. Textbook experience. Everything I hoped for. One time it was COMPLETELY rained/clouded out (we couldn’t see 20 feet in front of us). And one time it was shaping up to be perfect and at the last minute clouds came in and blocked the sunrise completely (although we were able to see colors on the other side of the island).

All three of those times, there were people at the summit on guided tours. Only one of those groups got the experience that they hoped for. All three paid for it.

If companies know in advance that the sunrise will be a total wash, they’ll cancel tours and refund your money. But a lot of the time the weather blows in once you’re already up there. If you’ve been loaded up in a van and driven to the top of Haleakala and gotten the full tour and breakfast snacks, you can’t really expect them to refund you because the weather didn’t cooperate.

All this to say…$150/person is a lot to pay for a chance to see sunrise.

I think it’s very doable to do sunrise (or sunset) at Haleakala on your own (and soooooo much cheaper), but you should definitely read this post first.

7. Maui Ocean Center & Maui Tropical Plantation aren’t necessarily MUST DOs

I don’t have anything against either of these places, but you should do the research to make sure it’s worth the time and money for YOUR group.

I think Maui Ocean Center is a great diversion if you have little kids, but the price is pretty steep ($50/adult and $40/child) for a solid little aquarium (but likely on par with the aquarium you’ll find near where you live).

Wildlife is so plentiful on Maui that if you go out snorkeling you’re likely to see turtles and an abundance of tropical fish. I’d put that money towards a snorkeling excursion or take a trip up to the north shore to see the turtles resting on the beach at Ho’okipa or Kua (Tavares) Bay.

And Maui Tropical Plantation is a nice place for lunch (Cafe O’Lei at the Mill House has a great setting), but I would skip the “plantation tour”, ziplining, etc.

Now here’s what I will say…BOTH of these places have GREAT gift shops that stock a lot of made on Maui products. So if you’re in the area, it could be worth stopping just for a little shopping.

8. Mama’s Fish House really is worth the money.

I’m not sure this is really a “hot take” (it’s pretty widely regarded as the most show stopping dining experience on Maui), but there are still people who question the price.

When I go, we usually spend about $120-150/person. (That’s with about one drink per person so your cost could EASILY balloon if you’re hitting it hard). Yes, that’s a lot of money, but it’s actually pretty reasonable when you compare it with a luau or honestly most other “nice-ish” restaurants on Maui.

9. Do your research on restaurants & drink spots

I know, I know, I know…not everyone wants to do “research” for their vacation, but the cost of dining is pretty high in Hawaii so if you just like to walk around and stumble onto a restaurant or lounge, you could end up spending $$$ on a pretty mediocre meal.

I’m always a little flummoxed by people who will say that they can’t possibly afford Mama’s Fish House but will end up at a ho hum restaurant in the tourist sphere where they’ll inadvertently spend 70-80% of the price of a dinner at Mama’s.

If you’re frequenting food trucks, and local plate lunch spots, GREAT. But if you’re in Wailea, Kaanapali, and Lahaina, it’s easy to spend quite a bit of money on a restaurant that’s not necessarily even a special occasion spot.

And the same goes for drinks! On my last trip, I ended up at the hotel/pool bar at sunset and had one of the worst/most expensive mai tais I’ve ever had in Hawaii. Come to find out, there was an INCREDIBLE tiki cocktail bar a five minute walk away with half price drinks ; )

10. If you don’t get upcountry, you haven’t seen the real Maui

I feel really passionately about this one ; ) When I lived on Maui, I lived upcountry in Kula and it forever has my heart.

Most visitors see a brief glimpse of Maui’s upcountry as they’re racing down the mountain after sunrise at Haleakala to get back to the beach but I think it deserves a bit more of your vacation time ; )

Stretching to include the cowboy country of Makawao, the farmland of Kula, the eucalyptus forests of Ulupalakua, and the slopes of Haleakala, in a lot of places, if you couldn’t look out and see the ocean, you’d swear you were in the high meadows of Colorado or the Texas hill country.

With its sweeping ocean vistas, rugged green hills, purple jacaranda trees, mom and pop shops and restaurants, and many farm tours, it’s definitely a place that you’re going to want to spend some time visiting.

I’ve written a full post about the upcountry here >> Things to Do Upcountry Maui

But my short list is:

Maui Wine

Breakfast at Grandma’s in Keokea

Ali’i Lavender Farm

Maui Pineapple Tour

Shopping in Makawao

11. Most resort luaus are skippable

Luaus are big $$$ these days and with a mediocre (at best) meal, it’s hard to justify the price tag let alone feel like they’re “worth it.”

I have two exceptions:

First, the Old Lahaina Luau. I think this is hands down the best luau in Hawaii and if you’re in any way contemplating a luau, this is the one it needs to be. I’ve got a full write up here >> Old Lahaina Luau

Second, if you want to see the show and cut out all the other “fluff”, then I LOVE the Wednesday night Hula Show at South Maui Gardens. For about $100/person (sometimes they have discounts online), bring your own chairs or blankets to set up on the lawn and enjoy a solid hula show.

They have dozens of food trucks on property, but my favorite is Kitoko. They have a special menu for the hula show nights and it’s AMAZING. The crispy pork belly with sweet potato gnocchi is a don’t miss.

You’ll get the show, a nice atmosphere, and waaaaaaay better food at a fraction of the price of a resort luau.

Find more details here.

12. The Road to Hana is incredible, but exhausting

Maybe this is my most controversial take??

Here’s my honest truth…the sites you’ll see along the Road to Hana are top tier (black sand beaches, a red sand beach, rainbow eucalyptus trees, endless waterfalls, gorges, and the most incredible views of the jungle along the coast).

Seriously, it’s hard to describe how magnificent this drive is. AND I won’t lie…I’m always exhausted after. Like miserably so.

The Road to Hana has some of the most special and magnificent places that exist in Hawaii (in the world!), but it is NOT something that I do on every trip. Honestly, it’s something I usually only do when I’m taking somebody that’s never been before.

I can’t tell you to skip it (that would be a SHAME!), but I think it’s good to go into the day with the right expectations. It is a mega ADVENTURE day not a pleasant little drive down the coast in between coffee on the beach and a romantic sunset dinner.

I recommend doing it early on in your trip, and making the day after a low key beach/resort day with no plans to recover.

That being said…if you don’t like being in the car, if you get at all carsick, if winding roads with little to no shoulder make you nervous, if you have small kids, and if your trip is focused on being a relaxing getaway, then doing the big Road to Hana day trip MAY not be for you. And that’s ok.

13. Listen to locals about “sensitive spots” on the Road to Hana

In recent years, a surge in the numbers of visitors mixed with infrastructure that’s not equipped to handle it has made driving the Road to Hana a sensitive situation with locals.

Basically, there’s one road from the remote town of Hana that connects to the main part of Maui and while it’s a spectacular drive that’s become a pilgrimage of sorts for visitors, it’s also the road that locals use for going to work, school, running errands, etc.

So a steady stream of vehicles driving too slow, stopping in the middle of the road to take pictures, parking illegally, etc is a growing nuisance to locals. While they’ve already started to crack down on illegal parking, other interesting developments to help manage tourism in this area are starting to take shape.

In March 2024, the Hawaii Tourism Authority and Maui Visitors and Convention Bureau announced a partnership with three community based programs to help manage tourism in Hana as part of the East Maui Tourism Management Pilot Program.

Exactly what this will entail in the future remains to be seen (it seems like they’re still largely in the data collection phase right now), but for now, the East Maui Ready (EMR) group has issued an advisory that visitors avoid Waiʻoka (Venus Pools) and Kaihalulu (Red Sand Beach) near Hana.

These are two popular stops on the Road to Hana that have been controversial among locals for a while now. Partially because they’re beloved local spots (with almost no parking and no maintained access) that have become overrun with tourists and partially because they both see high emergency response rates (dangers from flash flooding and steep and crumbling trail conditions).

I’ll admit that in the past, hiking to the Red Sand Beach has been one of my favorite things to do along the Road to Hana. It’s spectacular. Here’s the deal…I’m a pretty average hiker. I don’t do extreme hikes, but I’m also not a baby. Every time I’ve hiked this, it’s turned out okay. But I’ve also always spent most of the time thinking about how it could easily go wrong.

The trail is high off the ground (with plenty of sharp rocks at the bottom), covered in slippery pine needles, and a large part of it along a narrow rocky ledge that’s prone to rock slides when it rains. The ocean is also particularly rough once you get to the beach so needless to say it’s a spot where emergency responders are often called.

In the past, I’ve taken the approach of “I’m going to tell you exactly what this is like so you’re prepared” and you can decide for yourself if you want to do it or not, but I think it’s time to move on.

Besides it being fairly dangerous (the trail isn’t remotely “maintained” and the owners of the land don’t try to block people from accessing it but deny all accountability if you do trespass), for ME the deciding factor is that the people who live here are asking you not to.

And it’s not because they’re trying to hide something from you that they want for themselves. There are serious dangers associated with these places (especially because they’re not maintained or monitored in any way) and when visitors need to be rescued, it diverts resources away from the small, isolated community.

14. Snorkeling boat tours don’t take you places that are WILDLY better than the off the beach spots

My favorite Maui snorkel tour is pretty $$$ (worth it, but $$$) but the good news is you do NOT have to go out on an organized tour to do some great snorkeling.

While Molokini is really something to see, I’ve snorkeled all around Maui (on tours off a boat and from the beach), and honestly…popular spots around the island like Black Rock at Ka’anapali, Napali, Kapalua, Olowalu, Honolua Bay, and Ulua Beach are as good or better as places you can only get to via boat in terms off the reef and the fish you’ll see.

That said, if you have the money, going out on a snorkeling trip is always a fun way to spend the day and there’s a lot to be said for having a crew of people handling everything (from food to safety).

If you’re staying at a resort, most of them include complimentary snorkeling equipment to snorkel at the beach in front of the hotel (most hotels in Wailea and Kaanapali have decent snorkeling off the beach).

If you’re really into snorkeling, do a weekly rental from a place like Boss Frog and you can snorkel to your heart’s content.

And just a bit of personal advice…I’m an excellent swimmer but in recent years I’ve started always wearing a flotation belt when I’m out in water over my head. It’s something to think about.

15. “Resort life” is something to be experienced

Yes, yes, yes everybody wants an “authentic” experience nowadays and to “live like a local” and you 100% need to get out and explore the island and see what makes Hawaii so great, BUT resort life is pretty great.

Maui has some of the best beach resorts in the WORLD.

If you’ve got the cash to splash out on a luxury resort for your whole trip, great! But even if you don’t, here are two ways to get a taste of “resort life” for less:

1- Split your stay and stay at an affordable condo for the first part of your trip (while you’re out doing all of your exploring and adventuring) and then splurge on a fancy beach resort for the last couple of nights and just vacation.

2- Have you heard of Resortpass? Some hotels and resorts that aren’t at capacity sell daypasses to their pools and amenities for a fee that is WAY less than the price of a room.

One time when I was staying at a budget hotel, I ended up with a free unplanned day so we booked a cabana at the Fairmont Kea Lani through Resortpass and it was SUCH a great way to spend the day.

Availability changes seasonally and different resorts have different prices and offerings, but you can check out Maui resorts here.

It’s a great way to spend a full day living “resort life” on Maui without paying “resort prices.”

16. I’d rather do a nice dinner on land than a sunset dinner cruise

I’ve never gotten the allure of a sunset dinner cruise. You can have a MUCH better meal at a restaurant on land (with sunset views!) for less money usually!

And while I LOVE a day out on a catamaran, I’d much rather go during the day and squeeze in a little snorkeling or trip to Lanai.

So that’s my advice, if you’ve got the money to spend on a boat excursion, go during the day for snorkeling and have dinner somewhere nice…on land.

17. During whale season, do a snorkeling trip instead of a whale watching trip

Same principal. If you want to see whales, I would book a snorkeling trip instead of a whale watching trip. You’ll get to snorkel AND see whales.

How I Booked 3 FREE Trip to Hawaii (Including Airfare & Hotels) in the Last Year

I’ve been on THREE trips to Hawaii in the last year with free flights AND free hotels ALL booked using points and miles.

That’s:

One trip to Maui staying at the super swanky Wailea Beach Resort and doing my favorites like sunrise at Haleakala, the Road to Hana, and soooo much beach time.

One trip to the Big Island staying at the Mauna Kea Beach Hotel to visit Hawaii Volcanoes National Park, tour a Kona coffee farm, and see the manta rays after dark.

And one trip to Maui staying at the Ritz Carlton Kapalua to explore the west side beaches, drive the Kahekili Highway, and do a day trip to Lanai.

WITH FLIGHTS FOR TWO PEOPLE.

Some people call it “travel hacking,” but basically…it’s using credit card points & mile systems to cover travel experiences, usually in a more luxurious way than you would normally if you were paying cash.

I’m certainly no expert in this industry, and I’m sure there are people who do this WAY better than me (and on a bigger scale), but I do travel to Hawaii a lot and I’ve saved a LOT of money using points and miles. So I’m going to tell you how I do it ; )

First of all, a BIG Disclaimer: You should NEVER go into credit card debt to do this. And you should never use this to justify spending more money on things than you normally would because you’ll “get points.”

Also, let’s be clear. Stringing together free stays and amazing deals isn’t as simple as applying for one credit card and getting a free trip. It usually involves a little more strategy and synchronization (and sometimes just time to accrue points).

But here’s how to start:

Pick an Airline

I like Southwest and they’re the only airline I fly to Hawaii anymore. They’ve also got BY FAR the easiest credit card point system to use plus bags are free I think they have the most flexible rebooking/cancellation policy.

I have this Southwest Premier Rapid Rewards Visa card through Chase. The current sign up offer is 50,000 points. Depending on where you live and fly from, that’s at least one completely FREE ticket to Hawaii and it could be two depending on the time of year (or more if you catch a crazy sale).

The card also gives you:

2 Early Bird Check-Ins per year (super nice when you’re going to Hawaii and the perfect seat is really important)

6000 anniversary points

3x points on Southwest purchases (more points for your next flight)

If you’re new to the “travel hacking” game, I think this is a REALLY good place to start. You’ll get some free flights right away and honestly, I feel like Southwest points rack up sooooo fast when you’re using the card for your everyday purchases.

Again, use >> this link << to get 50K bonus points when you sign up.

But my FAVORITE Southwest points feature is the Companion Pass. If you rack up enough points in a calendar year (through credit card spending and flights flown), you get a Companion Pass. For the entire year, every time you fly, you get to take somebody with you FOR FREE (whether you pay cash or book with points).

The Companion Pass is good for the rest of the year when you qualify plus the entire next year (for example: if you qualify in October, you get the Companion Pass for the rest of that year plus the entire next year)

So once you qualify for a Companion Pass, your points actually end up going twice as far.

It’s too good to pass up. Details >> here <<

Later in this post I’ll get into logistics about picking the best airline that makes sense for YOU to fly (based on where you’re flying from) and I’ll layout options with Southwest, American, United, Delta, Hawaiian, and Alaska.

So keep reading!

Pick a Hotel

Hotels and resorts are my FAVORITE thing to use credit card points on because there’s such a spectrum of what you could save. Flights cost what they cost, but using points on a luxury hotel could save you up to $1500 PER NIGHT.

My go to is Marriott. They have by far the most options available of any of the major hotel chains plus they’ve got a ton of luxury and boutique options (which are my favorite).

This Marriott Bonvoy Boundless card through Chase is probably my most used credit card.

As soon as you sign up for this card (and meet the minimum spend requirement) you get 3 FREE nights to use anywhere you want! The free nights attached to this card are good for hotels worth up to 50K points per night (plus you can add 15K points to each of those certificates) meaning you can book three nights at a hotel that’s valued at up to 65K points per night. There are quite a few hotels in Hawaii that will fall into that category (even more if you go during shoulder season – spring or fall).

Again, use >>this link<< to get 3 FREE nights when you sign up for this card.

But I have a “go big or go home” philosophy when it comes to travel, so I like to DOUBLE DIP on Marriott Bonvoy rewards with the Marriott Bonvoy Business Amex.

If you’re self-employed, a freelancer or contractor, a gig economy worker, if you own rental properties, etc…you qualify for a business card. (And you don’t need to be registered as an LLC or corporation. You can apply as a sole proprietorship with just your social security number.)

This card comes with three free 50K nights (the same as my Marriott Bonvoy Boundless through Chase) so right out of the gate, that’s SIX FREE NIGHTS.

Plus having both really gives you a jump on hitting an “elite status level” where you get perks like free breakfast, room upgrades, late check out, etc.

AND with each of these cards…every year on the anniversary of the date you opened your card, you get a free 35K/night free night certificate. I just used a couple of these to stay at the new AC Hotel Wailea!

Later in this post I’ll get into the logistics of which Marriott properties on which islands will give you the best options for using free nights plus which properties are most “aspirational” (AKA which ones I would save up a bunch of points to spend on).

Two Free Nights at the Grand Wailea on Maui

Yes, yes, yes, I’m pretty loyal to Marriott. BUT here’s a “quick hit” that’s good to know about…

Maui’s flagship luxury resort, The Grand Wailea, is a Waldorf Astoria hotel which is owned by Hilton. If you scout around a bit, you can usually find it available for as low as 110K points per night. Right now, the sign up bonus on this Hilton Honors (Amex) is 155K.

And one of the Hilton loyalty program’s stand out features (to me) is that members can transfer points to one another without a limit (Marriott caps the number of points you can transfer to someone at 100K per year).

If your travel partner (husband, wife, daughter, friend, etc) also signs up for the card and gets the bonus, one of you can transfer your points to the other and you’ll have enough points total to book 2-3 nights!

That’s probably not going to be your whole trip, but you can either pay cash for the remaining nights (a major way to lessen the bill), or use your free nights at the end of your trip (maybe you’re staying in an affordable condo) as a big splurge.

Again, use >>this link<< to get your 155K point sign up bonus when you sign up for this card.

More about Flying to Hawaii ON POINTS

Okay, now that you know about my favorite airlines for points, here’s what you need to know LOGISTICALLY about flying to Hawaii:

Flying Southwest Airlines to Hawaii

Here’s what Southwest flights to Hawaii look like.

You can fly direct to Hawaii on Southwest from:

Las Vegas (LAS) to Maui (OGG), Oahu (HNL), Kauai (LIH), Big Island (KOA)

Oakland (OAK) to Maui (OGG), Oahu (HNL), Kauai (LIH), Big Island (KOA)

Phoenix (PHX) to Maui (OGG) and Oahu (HNL)

Sacramento (SMF) to Oahu (HNL)

San Jose (SJC) to Oahu (HNL)

Los Angeles (LAX) to Oahu (HNL)

Long Beach (LGB) to Oahu (HNL)

San Diego (SAN) to Oahu (HNL)

If you live in one of those cities, you are GOLDEN. You’ll be able to find flights fairly cheap (and low miles) and it’s an easy 4-6 hour flight.

If you do not live in one of those cities (hi, it’s me), you’ll need to do a little research into which (if any) you can fly directly from your city to.

For example, flying from Tulsa, OK, I can get direct flights on Southwest daily to Las Vegas and Phoenix, making those options for me to get to Hawaii (Southwest won’t sell you a through ticket with more than one connection).

Now, the flight times have to line up so you’ll be able to do it all in one day, but I can usually make something work even if it’s just on certain days of the week.

Maybe you noticed that from Las Vegas you can fly to all four of the main Hawaiian Islands, and that’s not by accident.

First of all, Las Vegas is a wildly popular destination with Hawaiians so there’s always demand for those flights.

Second, most mid-sized cities in the US have direct flights to Las Vegas making it the perfect “hub” for Southwest to use for people who don’t live in one of the cities with a direct flight and need to make a connection.

Live in Minneapolis, Dallas, Denver, Memphis, Albuquerque, Charlotte, Chicago, Columbus, Pittsburgh, etc? You can probably get a direct flight to Vegas which opens up Hawaii to you.

So flying to Hawaii from Las Vegas, Oakland, Phoenix, Sacramento, San Jose, Los Angeles, Long Beach, or San Diego will generally be fewer points (and a cheaper cash price) than if you have to make a connection, but you’ve got options. And that’s not even taking into account a sale.

PLUS…when Southwest entered the Hawaii market, they also added a TON of interisland flights so even if you can only get to Oahu from the mainland, you can easily island hop once you get there.

Flying United Airlines to Hawaii

If you’re flying out of any of these cities, United is a great option for Hawaii:

Chicago (ORD) has flights to Oahu (HNL), Kona-Big Island (KOA), and Maui (OGG)

Denver (DEN) has flights to Oahu (HNL), Kauai (LIH), Kona-Big Island (KOA), and Maui (OGG)

Houston (IAH) has flights to Oahu (HNL)

Los Angeles (LAX) has flights to Oahu (HNL), Hilo-Big Island (ITO), Kona-Big Island (KOA), Kauai (LIH), and Maui (OGG)

New York Newark (EWR) has flights to Oahu (HNL) and Maui (OGG)

Orange County (SNA) has flights to Oahu (HNL)

San Francisco (SFO) has flights to Oahu (HNL), Kauai (LIH), Kona-Big Island (KOA), and Maui (OGG)

Washington Dulles (IAD) has flights to Oahu (HNL)

I’m currently working on the United Explorer MileagePlus (Chase) sign up bonus for an upcoming trip to Tokyo, but one of the things I’m most excited about is that if you book a cash ticket with United, you can use your miles to upgrade your economy seat to business class.

I don’t think that’s a big deal if you’re flying to Hawaii from the west coast, but if you’re flying from the east coast (even Houston or Chicago) it’s sooooo much nicer to fly in business or first class.

If you use >>this link<< to sign up for the card, you’ll get a 50K point bonus which could be enough to book a free economy ticket to Hawaii OR upgrade your economy ticket to first class.

The other reason I love this card is because United is one of Chase’s travel partners and my Chase Sapphire Reserve card is my go to travel card in general. So I can transfer my Chase Ultimate Rewards points to United to book directly if there’s a flight that works best for me.

And United is also in a bigger airline alliance so you have a lot of options to use your points on other airlines if you travel internationally.

Grab that United 50K bonus here.

Flying American Airlines to Hawaii

If you’re flying out of any of these cities, American Airlines could be a good option for Hawaii:

Dallas (DFW) has flights to Maui (OGG) and Oahu (HNL). These two routes are AA’s “Flagship” Hawaii routes meaning they fly a widebody aircraft more commonly seen on international flights. You’ll get a full meal plus the option for premium economy seating and lie flat seats in business class. These flights are usually more $$$ even in economy.

The rest of these routes are just standard domestic flights:

Los Angeles (LAX) has flights to Oahu (HNL), Kauai (LIH), Kona-Big Island (KOA), and Maui (OGG).

Phoenix (PHX) has flights to Oahu (HNL), Kauai (LIH), Kona-Big Island (KOA), and Maui (OGG).

*AA used to fly some routes to Hawaii from Chicago and Charlotte, but those aren’t currently offered.

Flying Delta Airlines to Hawaii

If you’re flying out of any of these cities, Delta could be a good option for Hawaii:

Atlanta (ATL) has flights to Oahu (HNL) and Maui (OGG).

Detroit (DTW) has flights to Oahu (HNL).

Los Angeles (LAX) has flights to Oahu (HNL), Kauai (LIH), Kona-Big Island (KOA), and Maui (OGG).

Minneapolis (MSP) has flights to Oahu (HNL).

New York (EWR) has flights to Oahu (HNL).

Salt Lake City (SLC) has flights to Oahu (HNL).

Seattle (SEA) has flights to Oahu (HNL).

Delta also offers interisland flights so you can connect to another island through Honolulu.

Flying Hawaiian Airlines to Hawaii

If you’re flying out of any of these cities, Hawaiian Airlines could be a GREAT option for Hawaii (get those aloha vibes going before you even get there ; )

Austin (AUS)

Boston (BOS)

Las Vegas (LAS)

Long Beach (LGB)

Los Angeles (LAX)

New York (JFK)

Oakland (OAK)

Ontario, California (ONT)

Phoenix (PHX)

Portland (PDX)

Sacramento (SMF)

Salt Lake City (SLC)

San Diego (SAN)

San Francisco (SFO)

San Jose (SJC)

Seattle (SEA)

Hawaiian Airlines also offers an extensive network of interisland flights.

Flying Alaska Airlines to Hawaii

This west coast based budget carrier isn’t something that’s ever on my radar (since I fly from the middle of the country), but if you’re flying out of one of these cities, they’re usually very competitively priced.

Anchorage, Alaska (ANC)

Portland (PDX)

Los Angeles (LAX)

San Diego (SAN)

Seattle (SEA)

San Francisco (SFO)

San Jose (SJC)

Always Book Directly with the Airline

Whichever airline you choose, be sure to follow the cardinal rule of air travel. ALWAYS BOOK DIRECT. Under no circumstances should you ever book airfare through a third party company like Expedia, Travelocity, and I hate to say it but even Costco. Air travel is WILD. Wildly undependable.

Flights get delayed, they get canceled, plans get derailed. And when you’ve booked through a third party, you can’t deal with the airline directly. You can literally be in the airport at the gate and depending on what the problem is (flight canceled, flight delayed and you’re going to miss your connection, etc) the gate agent may not be able to help you.

You haven’t known frustration until you’re literally standing in front of a human that handles flight changes for the airline and they can’t help you because you have to call Expedia and be on hold with them for 6 hours instead. When you book with a third party, THEY hold the reservation, not you.

Here’s the other thing…these booking sites hardly ever have prices any cheaper than the actual airline anyways. Do your research using Expedia or whoever you like to shop and then go directly to the airline to book.

More about Using Marriott Points in Hawaii

Besides the traditional Marriott marquis hotels, Marriott’s brands in Hawaii also include Sheraton, Westin, Ritz Carlton, Courtyard, Residence Inn, Marriott Vacation Club, and the Luxury Collection & Autograph Collection (collections of boutique hotels like the Royal Hawaiian, Moana Surfrider, Mauna Kea Beach Hotel, and the Laylow – these are some of my favorites ; )

So there are a LOT of great hotel choices in Hawaii under the Marriott umbrella – whether you’re looking for a once in a lifetime destination resort, a boutique hotel with fun vibes, or a good bang for your buck hotel.

Hawaii Hotels to Use 50K Free Night Certificates

In Hawaii (depending on dates), that could work at hotels like:

Oahu: The Laylow, Royal Hawaiian, Moana Surfrider, Courtyard Waikiki Beach, Sheraton Princess Kaiulani, Waikiki Beach Marriott, Renaissance Honolulu Hotel, AC Hotel Honolulu, Residence Inn Kapolei, and Courtyard North Shore.

Maui: Sheraton Maui Resort, Westin Maui Resort, AC Hotel Wailea, Courtyard Kahului (in August 2024 the Wailea Beach Resort has redemptions for 55K/night!!)

Kauai: Sheraton Kauai Coconut Beach Resort, Sheraton Kauai Resort

Big Island: Courtyard King Kamehameha’s Kona Beach Hotel, Waikoloa Beach Marriott

But I’ve saved my favorite thing about using Bonvoy points to book Marriott hotels for LAST:

When you book four nights using points, you get a FIFTH NIGHT FREE. So after I use my free night certificates (that have max point values like 50K or 35K per night), I only use my Marriott points for “big” stays where I have enough points to book four nights and get the fifth free. It’s by far the best way to max out the value on your points.

Side note: You cannot combine free night certificates with points to take advantage of the fifth night free promo.

Last year, I cashed in 325K points to stay for 5 nights at the Mauna Kea Beach Hotel on the Big Island. And I’m getting ready to stay at the Ritz Carlton Kapalua for 5 nights for 330K points.

And obviously, if you’re not staying at premium luxury properties, you can get stays for a LOT less. Or stay a lot longer ; )

I mentioned a list of hotels above that are good places to get the best “bang for your buck” on points and use free night certificates above, but if you’re like me, and you have a “bucket list” of great hotels, here’s also a list of the top aspirational Marriott properties in Hawaii (places that are worth hoarding your points for a big splurge):

Wailea Beach Resort (Maui)

Ritz Carlton Kapalua (Maui)

Koloa Landing Resort (Kauai)

Mauna Kea Beach Hotel (Big Island)

Royal Hawaiian (Oahu)

Moana Surfrider (Oahu)

Turtle Bay Resort (Oahu) ***This hotel JUST joined the Ritz Carlton brand earlier this year!!

Hawaii FAQs

When is the best time to go to Hawaii?

I’ve got good news for you…there’s no BAD time to go to Hawaii ; )

But depending on what you’re after (low crowds, best weather, low prices, WHALES), then some times are definitely better than others.

As far as weather goes, Hawaii is pretty temperate year round (the air and water temp only varies a few degrees), but their seasons technically match ours on the US mainland. Our summer is their summer and our winter is their winter. The biggest thing weather wise is that it rains more during the winter months.

But if you’re staying in the resort areas (Waikiki and Ko Olina on Oahu, Wailea/Kihei and Lahaina/Kaanapali on Maui, Kona and Kohala on the Big Island, and Poipu on Kauai) you’re going to be pretty good on the sunshine year round.

If you’re planning your trip with the main goal of seeing humpback whales…make it February, and make it Maui.

As far as crowds go…when kids are out of school is peak season. The summer months and winter holidays will be the most crowded (and expensive).

The best times to go to Hawaii in terms of low crowds and therefore low(er) prices are during shoulder season in the spring and fall.

I’ve been to Hawaii pretty much all times of the year and I’m constantly monitoring prices on flights and hotels and I consistently find mid April through May and mid August through mid October to be the cheapest time of year to go to Hawaii.

But my personal FAVORITE time to go to Hawaii is…February!

February is not necessarily the cheapest or the least crowded (it’s also not the most!), but there is NOTHING more luxurious than escaping the long, cold, dark winter where I live for a trip to Hawaii. I will pay a little bit more as a “winter tax” and while visiting Hawaii anytime is a treat, visiting Hawaii during the winter is my ultimate treat.

Read more about the best times to visit Hawaii here >> Best Time to Visit Hawaii

Which Island is best?

If you want gorgeous beaches, aloha vibes, water and cultural activities, good food, great hotels, and an all around amazing vacation…I can plan you the PERFECT Hawaiian vacation to ANY of the main four islands (Oahu, Maui, Kauai, Big Island). Seriously, anyone that tells you that a specific island is the best “hands down” is just biased. They’re all spectacular.

If you’re not already swayed to one island over another, some things that I would consider…

Are there direct flights to a certain island from where you live? Sometimes the easiest logistics will sway my vacation planning.

Are there specific activities that you’re interested in or sites you want to see that are unique to a certain island? Always wanted to see Waikiki and Pearl Harbor? Head to Oahu. Hawaii Volcanoes National Park and swimming with manta rays? The Big Island. The Road to Hana and Haleakala National Park? Maui. Those jagged green Jurassic Park mountains? Kauai. While all of the islands have some version of what you’ll expect from a Hawaiian vacation, there are a handful of unique experiences on each island.

Start with these posts about things you can ONLY do on each island: Maui, Big Island Kauai, Oahu.

If we’re making the vaguest of generalizations, people usually say that Oahu is city and has the most things to do. Kauai is country and is the most undeveloped. Maui is the best overall island. And the Big Island is the most undiscovered.

I can (and do) argue all of those points in this post if you want to read more about picking the best island for YOU.

How many days on Maui? Or Kauai? Or Oahu?

Well, you’ve only got however many days you’ve got, but if you’re wanting the best overall vacation, I wouldn’t suggest less than one week (probably 6 full days, but you could do a lot in 5 full days too) on any one island.

If you’re short on time (doing a quick long weekend getaway from the west coast), you can still have a great trip just as long as your expectations are more about resting and relaxing.

But in general, if you’re wanting to explore the island and still feel like you’ve had a relaxing vacation, you’ll want at least 6 full days. I also don’t recommend splitting up a one week vacation between two different islands. Just stick to one and really experience it.

The exception to this is if you’re going to spend a week on one island and add on a few days on a different island because there’s something really specific that you want to see.

Which airport to fly into?

These days, the four main islands are all easily accessible from the mainland US (or a quick layover in Honolulu). Here’s a list of each island’s major city and airport code:

Oahu: Honolulu (HNL)

Maui: Kahului (OGG)

Kauai: Lihue (LIH)

Big Island: Kona (KOA) or Hilo (ITO)

What’s the best airline to fly?

The short answer…it’s the airline that offers the best flight options from YOUR home airport.

For me, that’s usually Southwest (I’ve written a full post about why they’re my airline of choice here).

For you, that could be American, United, Delta, Hawaiian, or Alaska Airlines.

This post has all my best info about flying to Hawaii.

Do I need a rental car?

In a word, yes.

Hawaii is not an all-inclusive destination where you’ll arrive by shuttle and never leave your resort (I mean you could do that…but it’s pretty expensive just to get to Hawaii so most people want to actually see Hawaii. If you want a cheaper resort only vacation, just go to Mexico).

So you’ll most definitely want a rental car for your stay even if you’re staying in a resort area. I always book through Discount Hawaii Car Rentals. They’re seriously the only company I ever use. They’ll give you the very best prices, you don’t have to reserve with a credit card or pay until you show up, you can cancel and re-book anytime if you find a better rate, and they usually have a special that adds additional drivers for no fee. It’s a no brainer. Click here to check rates for your trip.

Where should I stay?

My favorite question!!

I am a hotel PERSON and I’ve stayed at a LOT of hotels in Hawaii.

On Maui, the first thing you’ll have to decide is which part of the island to stay on. Most visitors either stay on the South Side (Wailea and Kihei) or the West Side (Kaanapali and Kapalua). Both have beautiful beaches, plenty of restaurants, and all of the vacation amenities you could want. I’ve got a full comparison/breakdown of the two areas here >> Wailea vs Kaanapali

Personally…I prefer to stay in Wailea. It’s a bit nicer, has everything you could ever want right there (plus soooo many restaurants nearby in Kihei), AND it’s more conveniently located for exploring the rest of the island.

As far as specific hotels, the Four Seasons Maui is the go to if you’re looking for luxury. But I’m becoming partial to the Andaz for the price. I also think it’s on the best resort beach on Maui.

But I’m also a Marriott Bonvoy member which often pushes the Wailea Beach Resort to the top of my list.

Soooo much info on my specific Maui hotel recommendations here >> Where to Stay on Maui

And if you’re visiting Maui on a budget, or you prefer more space, I’ve got a pretty comprehensive breakdown of where to book condos on Maui here >> Maui Condos

On Kauai, the north shore is hands down the most beautiful part of the island, but I usually opt to stay in sunny Poipu on the south side and do day trips up to the north shore. Read the pros and cons of staying in Princeville vs Poipu plus my specific hotel recommendations here >> Where to Stay on Kauai

On the Big Island, I like to stay on the Kona side of the island because it’s where the best beaches and resorts are but the island is so huge that some people like to do a split stay and stay 3-4 days on the Hilo side and 3-4 days on the Kona side >> Kona vs Hilo

Also, the Big Island has some of the best beach resorts in Hawaii. I’ve ranked them all here >> Big Island Beach Resorts Ranked The Mauna Kea Beach Hotel has a prime location on what I think is the best beach in Hawaii. But the Four Seasons Hualalai, Kona Village, and Mauna Lani Resort all get top points for luxury.

On Oahu, you’ll find the best deals in Waikiki and it’s a great basecamp for exploring the island. The Royal Hawaiian is iconic, but you can find such good value for the money at smaller boutique hotels like the Laylow, Kaimana Beach Hotel, Surfjack, Wayfinder, etc. >> My Favorite Boutique Hotels in Waikiki

But if you want a real vacation and to see the best parts of the island, you’re going to want to stay outside of Waikiki >> Where to Stay on Oahu BESIDES Waikiki I personally love staying in Ko Olina at Disney’s Aulani Resort or the Four Seasons and can’t wait to stay at Turtle Bay on the North Shore now that it’s joined the Marriott Bonvoy family as a Ritz Carlton.

Tips for saving money on hotels?

YES….SO MANY! I love staying in a fabulous hotel, but I’m always looking for ways to save some $$$.

Some of my best tips:

Do a split stay. Spend the first part of your trip at a more budget friendly hotel or condo and do the bulk of your “exploring” and sightseeing. And then switch to a nicer place the last few days and just “vacation.” You’ll get the best of both worlds.

Visit during shoulder season. There’s not much of an off season in Hawaii anymore, but I usually find the best rates on hotels in late April through May and late August through September.

Also, just picking the “right” days can save you a bundle. Prices vary throughout the month and even week (especially if standard rooms are sold out for certain dates and they’re showing you the price of a suite). If you can view the 30 day calendar and pick your dates more strategically, you can save $$$.

More details here >> How to Save Money on Hotels

But my FAVORITE way to save money on hotels is TRAVEL HACKING. I’ve done THREE trips to Hawaii in the last 18 months staying at luxury resorts for FREE using credit card points.

Here’s how I do it >> Travel Hacking Guide