Hawaii

How to Create the Perfect Maui Itinerary

You probably think that after you book your flights, your accommodations, and your rental car, you’ve got it made in the shade, right? Not so fast. Surprisingly, many people find laying out a daily itinerary for their trip the trickiest part!

While Maui has some of the best beaches you’ll find anywhere, it’s too far to go and too expensive to just lay around and work on your tan the whole time. Most visitors want to get out and really explore the island. But how do you know how much you can you do in a day? What are the “don’t miss” spots and what’s overrated? Do you need to do organized tours or can you see everything on your own? And how can you see it all and still have time to lay on the beach (because you need to come home with a tan, right?)???

Don’t panic! ; ) I’m going to break down everything you need to know so you’ll be able to see all the best things to do in Maui!

Island Breakdown

First up, you need to know a little bit about how Maui is laid out. Maui is the second largest Hawaiian Island and it’s a lot bigger than most people think. It has a lot of unique geographical areas as well. It’s divided into five areas:

West Side: The west side is the largest (and oldest) resort area and includes the historic whaling town of Lahaina, the resort complex of Ka’anapali, and the planned golf resort community of Kapalua. This side has plenty of gorgeous beaches and so many shops and restaurants but can feel a little isolated from the rest of the island.

South Side: The south side is the driest and sunniest part of the island, and it’s home to Kihei (an area with a boat load of affordable condos), and Wailea (Maui’s most upscale resort area). This side has plenty of swimmable beaches and shops and restaurants, yet feels a bit quieter than the west side.

Central Maui: Most tourists don’t see much of central Maui besides the airport and Costco (both in Kahului) since until recently the valley has mostly been used for sugar cane production.

North Shore/Upcountry: Maui’s north shore and upcountry towns (Paia, Makawao, Haiku, and Kula) feel very “local” but are a still a big draw for tourists wanting to see the “real Maui.” These former plantation and ranch towns are full of restaurants, boutiques, and art galleries.

East Maui: Mostly jungles and waterfalls, east Maui is typically experienced via the Road to Hana. While some choose to stay overnight in Hana (or for a few days), it’s very “off the grid” and most visitors see east Maui on a day trip.

What to Pack for Hawaii

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Packing is usually the thing I hate most about a trip-I mean, how do you ever know exactly what you need? But hindsight is always 20/20 so once you’ve been to a destination you know EXACTLY what you need (or don’t need)! So I’m here to tell you (based on experience) what to wear in Hawaii.

The Weather: “It’s the beach so it’s warm all the time right?” Well, pretty much. If you’re staying down near the beaches and resort areas (pretty much anywhere on Kauai and Oahu), the weather will be pretty nice. Temperatures usually hover in the mid-80s year round. It can get breezy at night so you might want layers, and because you’re on an island and the weather can change in a minute, it’s usually nice to have some sort of lightweight rain jacket (especially in the winter months). If you’ll be visiting (or staying) in the upcountry areas of Maui and the Big Island, you’ll want to pack layers so you can bundle up, especially in the mornings and evenings.

Island Style: As far as the vibe of the island, everything in Hawaii is casual and laid back. Shorts and slippahs (flip flops) are respectable pretty much anywhere. If you’re wearing a swimsuit, most places will want you to have a cover up on. Even the fanciest restaurants will only have a “resort wear” dress code, which basically means “try not to look like you just came from the beach.” Khaki shorts and aloha shirts for men and sundresses for ladies are about as fancy as you’ll ever need to get in Hawaii.

Shopping: The good news is that Hawaii is pretty developed so if you leave anything at home you’ll be able to easily pick it up at Walmart/Target or CVS. While prices are higher in Hawaii, you likely won’t notice much of a difference on vacation basics (sunscreen, bug spray, beach gear, etc.). Each main island (Oahu, Maui, Kauai, and the Big Island) has a Costco and Walmart, and each island except Kauai has a Target. Long’s is a drug store chain owned by CVS (similar to Walgreens).

What to Pack

Beach Basics: You’ll want to pack all of the beach basics for your Hawaii trip. Think…shorts, tees and blouses, sundresses, bikinis, cover up, flip flops, hat, sunglasses, beach bag, rash guard/sun shirt. In my experience, you’ll want more casual “knock around” clothes and fewer dress up clothes. I like to pack several breezy sundresses that can be worn as beach coverups or out to dinner. Also, keep everything pretty casual. Unless you like getting all dolled up, simple sundresses and sandals are the fanciest you’ll ever need to be and at most places shorts and shirts are fine.

Hiking/Adventure Necessities: If you’re planning on doing some hiking or other adventure activities, make sure you pack the right gear. Bring your hiking/athletic shoes, reef/water shoes, lightweight rain jacket, and a backpack. If I’m doing a catamaran snorkeling trip where they load from the beach, sometimes I’ll pack my waterproof backpack. And if you don’t have a waterproof case for your phone, you may want to bring a plastic bag to keep it in.

Warm Clothes/Layers: If you’re planning to go up to Haleakala (Maui) or Mauna Kea (Big Island), you’ll need to dress warm, especially if you’re going for star gazing or for sunrise since it’ll still be dark when you go up. And I don’t mean cold for Hawaii. It’s not uncommon for it to be in the 20s and 30s at that elevation (Fahrenheit). So plan to bring along pants, layers, a heavy jacket/coat, a hat/scarf/gloves, and I’d even grab

What to Pack for a Day at the Beach

This post may contain some affiliate links. This means I may make a little money on anything you choose to purchase, but as always I only share my absolute favorite things with you. Thank you for supporting the brands that make Hulaland possible.

If you’re anything like me, you’re always trying to improve your packing game. And by improve I mean avoiding situations where you’re throwing random things in your suitcase at midnight before your 6AM flight and then thinking of everything you forgot during the drive to the airport. Oh wait…that’s only me? Well then. If you’re wondering what to pack for the beach, I’ve rounded up what I consider to be essentials for a beach vacation to Hawaii. Now obviously, since you’ll be flying to Hawaii, you won’t be packing some of these things, but if you’re road tripping to the beach on the mainland, these are good ideas, and you also may want to rent some of these (chairs, umbrellas, coolers, snorkel gear, etc), if it won’t be provided by where you’re staying in Hawaii.

So here’s what you should always pack for a trip to the beach:

When Is the Best Time to Go to Hawaii?

This is a question I get asked a lot. Deciding what time of year to visit Hawaii is likely the first decision you’ll make about your trip. A trip to Hawaii isn’t cheap and it’s a long haul over there so most people want to make sure they’re picking the best time to go. While I think anytime is a perfect time, some months are better than others depending on what’s important to you. When choosing dates to travel, most people are driven by weather, price, or wanting to experience something seasonal (like seeing the humpback whales).

What is the weather like?

As far as weather goes, Hawaii is pretty temperate year round, but their seasons technically match ours on the mainland. Our summer is their summer and our winter is their winter. “Winter” is a relative term in Hawaii, but what it mostly means are big waves and more rain. Winter is the wet season in Hawaii so while most resort areas on the Hawaiian islands occupy the leeward (dry and sunny) side of the island, if you’re venturing to the north shore or any jungle areas, you’ll likely experience more rain in the winter months. It’ll also be much lusher and greener and you’ll see more waterfalls.

The winter months also bring big swells and surf competitions (on Oahu) and many stellar snorkeling spots (Honolua Bay on Maui, Waimea Bay on Oahu, and Tunnels on Kauai) aren’t snorkelable (is that a word??) in the winter. But you will get to see some of the best surfers in the world taking on some of the world’s most famous breaks.

How to Find Cheap Flights to Hawaii

For most travelers, airfare is the single biggest expense of a trip to Hawaii…after all, it’s a looooong ways over there. And if you’ve never booked international airfare before (I know it’s the US but because of the distance, flights to Hawaii work much more like international than domestic), it can be kind of overwhelming. First up, I’ll let you in on a few of the biggest things you need to be aware of before you start looking at airfare to Hawaii. Next, I’ll let you in on my 6-step system for booking the best airfare deal and finally, suggest a few scenarios where I think it’s worth it to pay a little more for a better flight.

Before I dive into some of my favorite money saving strategies, you should know that the single biggest factor that will save on airfare is picking the cheapest time of year to travel to Hawaii (read all about that here). Once you have a good idea of your general travel dates as well as the island(s) you’re headed to, you’re ready to start searching for bargains!

So first up, exactly how long is the flight to Hawaii?

Well it depends where you’re traveling from. From the west coast, flights are only 5-6 hours (6 hours going, 5 hours coming home). From the midwest, flights can be 7-9 hours (hey, the US is a big country and there’s a big difference between Denver and Atlanta). And from the east coast, flights can be 10+ hours (yikes!). Now I have not flown direct from the east coast, but I have flown direct from Dallas, TX (8 hour flight) so I have some personal experience here. I will say, these are DIRECT flight times (my preferred method of travel), but the majority of flights to Hawaii connect on the west coast so you’ll be able to break it up.

Things to Know About Booking Airfare to Hawaii

Before you start bargain hunting, here are a few general strategies that I’ve found save money on airfare no matter where you’re traveling:

Be flexible: Obviously, the more flexible you are on dates (within your general time frame) the more likely you’ll be able to find a deal. If you can pick a 2-3 week time frame and then search for dates within that block, you’ll find the best deals.

Check out nearby airports: If you live in an area with several airport options, make sure to investigate all of your options. It may also be worth it to drive a bit to fly out of a different airport, especially if they have a good connection to a west coast hub.

Know your connections: The lowest priced flights usually have the most connections. If you have more time than money, being willing to make another connection (especially through Los Angeles or Honolulu) will often save you money. Also, flights with long layovers (especially coming home) are usually the cheapest.

Fly on weekdays: As a general rule of thumb, weekday flights are always less expensive than weekend flights. Everybody wants to leave on a Friday morning and come home the next Saturday or Sunday so naturally that will always be the most expensive option. Being able to travel on a random Tuesday or Wednesday can really save you some big bucks.

Consider breaking the trip up. Narrow your airfare search to a west coast hub (Los Angeles, San Diego, San Jose, San Francisco, etc.) because those are where you’ll find AMAZING deals. $200 round trip tickets to Maui anyone? Once you snag an awesome deal, then stalk flights from your hometown to that city. You can often save quite a bit using this method but it does require more planning.

Check to see how full your flight is. Once you find a flight itinerary that you like but you’re not sure if the price is at rock bottom or not, go to the airline’s website and look up the seating chart. That will tell you how full it is. If it’s mostly filled up, don’t expect the price to go down much. If it has plenty of availability, you might take the gamble of waiting to see if the price drops.

Check out Alaska Airlines. Although the name may confuse you, Alaska Airlines has a surprising amount of flights to Hawaii and they’re considered a budget airline so they’re usually some of the best options. They fly out of almost a dozen locations on the west coast, so always look into them as an option.

Southwest Airlines is now a player. Southwest has announced plans to begin flights to Hawaii (as well as interisland flights), so if you’re loyal to the airline, this is a great opportunity to cash in those points and check some free bags! Definitely keep an eye out for great rates with Southwest!

When in doubt, fly Hawaiian. Unless you’ve been to Hawaii before, you likely won’t have much experience with Hawaiian Airlines, but I really like them. They only fly out of a handful of hubs on the US mainland (although they have flights from Las Vegas and JFK in addition to the regular west coast hubs), but they have good partners so you can usually book with them from quite a few cities. In my experience, their places are always nice and they really nail the ambiance. They also partner with Jet Blue so if you have miles with them, you can use them to book Hawaiian.

Which Hawaiian Island Should You Visit?

If you’ve never been to Hawaii before, planning a trip there can be completely overwhelming. And the first big decision you’ll have to make is which Hawaiian Island to visit.

In this post I’m going to give you the lay of the land (or the islands : ) so you’ll be able to make that decision and choose the best Hawaiian Island to visit.

Before I start, I feel like I should clarify: there is no “best” Hawaiian Island to visit. All of the islands are very unique and appeal to travelers for different reasons. In my opinion, all of the Hawaiian Islands are pretty fabulous. But depending on how you like to vacation, and what you expect to see in Hawaii, there may very well be a “best” island for YOU.

There are six main inhabited Hawaiian Islands, but I like to think of it as four main islands plus two small bonus islands:

Oahu: This is the most visited of the Hawaiian Islands. This is where the capital, Honolulu, is located as well as world famous Waikiki Beach. Pearl Harbor is also on Oahu as well as the north shore surf scene with big breaks like the Bonzai Pipeline and Waimea Bay.

Maui: Maui is known as the “honeymooner’s isle” and draws many celebrities looking for peaceful seclusion. Maui is famous for its beautiful beaches, winding Road to Hana, and gorgeous sunrises from the summit of Haleakala. It’s also the best island for whale spotting.

Kauai: Kauai is the oldest of the Hawaiian Islands and also the smallest. It’s most famous sites are the Napali Coast and Waimea Canyon. Kauai is very “country” and feels less developed and spoiled than some of the other islands.

Big Island: The Big Island (also just called “Hawaii”) is…you guessed it…the biggest of the islands. It’s also the newest. Many people mistakenly think that Oahu is the Big Island but we’re talking about two separate islands. This is where you’ll find Hawaii Volcano National Park, the only active volcano in Hawaii.

Lanai: Lanai is a small island off the coast of Maui and is easily accessible as a day trip. You’ll find two Four Seasons on the island but little else. It’s known for its rugged beauty.

Molokai: Molokai is also right off the coast of Maui. Molokai is probably the most “Hawaiian” of all the islands. It’s also the least visited. Its major attraction is Kalaupapa National Historical Park, which was originally established as a leprosy settlement in 1866.

RELATED: Where to Stay on Oahu

Where to Stay on Maui

Where to Stay on Kauai

Where to Stay on the Big Island

The four main islands are all easily accessible from the US mainland. While the majority of direct flights are to Oahu and Maui, there are plenty of direct flights to Kauai and the Big Island. There are also hundreds of interisland flights between the four main islands daily (plus Lanai and Molokai). Most flights only take 30-40 minutes. You can reach Lanai via ferry from Maui. Here are the cities you’ll fly into on each island:

Oahu: Honolulu (HNL)
Maui: Kahului (OGG)
Kauai: Lihue (LIH)
Big Island: Kona (KOA) or Hilo (ITO)

Now that you have the lay of the land and a brief description of each island, I’ll break down the four main islands more in depth to help you decide which one is best for you. If you’re traveling on a budget, a major factor in lowering the price of your trip will be which island you choose to visit. Some Hawaiian islands are much more accessible (many more flights daily from the mainland), which makes them cheaper to fly into.

Generally speaking, Oahu and Maui are usually the cheapest islands to fly to because they have so many more direct flights than Kauai and the Big Island. But depending on the type of accommodation options you’re looking for, some islands may be better suited to it than others. But here’s a breakdown of each island:

How Much Does a Trip to Hawaii Cost?

How to Save $1000 on a Trip to Hawaii

Where to Stay in Kauai

If you’re planning a vacation to Kauai then you’re one lucky dog! It’s one of my favorite Hawaiian islands and probably the prettiest one at that. If you’re very far into the planning process, you’ve probably realized that picking the right place to stay is likely the trickiest (and most important) things you’ll have to do. Where you stay on Kauai can make or break your vacation and there are soooo many options that it can be overwhelming. Not to worry! I’m going to break it down for you, give you an overview of the island.

Side note: After you read up on the lay of the is(land) and know which part you want to stay on, check out these posts for specific recommendations:

7 Kauai budget hotels

12 Kauai beach resorts

20 cool Kauai Airbnb rentals

5 Best Family Friendly Resorts on Kauai

5 best Kauai honeymoon resorts

Top 10 luxury resorts in Hawaii

12 Favorite boutique hotels in Hawaii

Here’s everything you need to know about where to stay in Kauai:

Lay of the Land

Kauai is divided into four major sections (North Shore, East Shore, South Shore, and West Shore). Each section has its pros and cons and own individual personality. Depending on what you’re looking for and what’s most important to you (budget, convenience, stellar views, beautiful beaches, luxury resorts, etc.) one area of the island may be more desirable. Here’s a breakdown of Kauai’s four main areas:

North Shore: In my opinion, the north shore of Kauai is the most gorgeous place on the planet. It has beautiful beaches and the lush green mountainous landscapes that most people’s Hawaiian dreams are made of. As you might guess, it’s so lush because it rains more here than other parts of the island (especially in the winter). The north shore is home to the charming little surf town of Hanalei and some pretty spectacular luxury accommodations. While it’s stunningly gorgeous, it’s also a bit remote if you’re planning on exploring sites on the south and west sides of the island.

East Shore: The east shore is often referred to as the “coconut coast” and is the most developed part of the island. This is where you’ll find the most reasonably priced accommodations and it central location makes it a convenient location from which to explore the north and south shores. There are of course lovely beaches on the coconut coast (hello, this is Hawaii!) but you won’t find any awe inspiring backdrops as you will on the north shore and the amenities are usually not as convenient as those on the south shore. You’ll find more “local” beaches on the east side.

South Shore: Kauai’s south side is the driest and sunniest part of the island, which makes it very popular with tourists. There are plenty of big resorts so you’ll find plenty of shopping and dining options. You’ll also find a nice selection of beaches but expect them to be more crowded than beaches on other parts of the island. The south side is a convenient place from which to explore the west side (Waimea Canyon and Polihole beach) but not so convenient for seeing north shore sites.

West Shore: The west shore is definitely the least visited part of Kauai (except for visitors to Waimea Canyon) and not very many people stay here. It’s very barren, dry, and isolated, and not convenient to seeing the rest of the island. Really the only people who are going to be staying over here are hikers and backpackers.

RELATED: 15 Things to Do on Kauai

How to See the Napali Coast

Where to Eat on Kauai

Where to Stay on Oahu: Waikiki or Not?

Oahu is Hawaii’s most visited island (largely because it’s home to the state’s capital, Honolulu, and its major tourist hub, Waikiki). Waikiki (a beachfront neighborhood in Honolulu) is home to about 95% of the island’s hotel rooms, so by default, it’s where most tourists end up. Waikiki is basically a big city on the beach. Think endless high rises, flashy shopping centers, all the major chain restaurants, and a million people. All of the major hotel chains are represented as well as plenty of budget options and even trendy new boutique hotels.

And then there’s the rest of the island. So the big question is…to stay in Waikiki or not?

Psst…once you finish reading this post and have a better idea of where you might like to stay, read these posts for specific suggestions:

25 amazing Oahu Airbnb Rentals

10 Oahu budget hotels

12 Oahu beach resorts

5 Best Family Friendly Resorts on Oahu

5 best Oahu honeymoon resorts

Top 10 Luxury Resorts in Hawaii

12 Favorite Boutique Hotels in Hawaii

Why You Might Like Waikiki

So…if it’s so crowded, why do people stay there? Simple. It’s Hawaii’s oldest resort area (the Moana Surfrider was built in 1901), and people have been flocking there ever since. It’s also a really beautiful beach with stunning views of Diamond Head in the background. Most people who have never been to Hawaii end up in Waikiki, usually because flights to Honolulu are cheaper than the other islands, and because they’ve heard of it. They think, “it’s popular for a reason…it must be where you’re supposed to go.”

Here are a few more reasons why people like staying in Waikiki:

You can find cheap hotels. Just like any major city, the more hotel rooms there are, the more competitive prices are.
You don’t need a car. Shuttles are a dime a dozen from the Honolulu airport to Waikiki and most visitors just stay in Waikiki/Honolulu and don’t venture out to the rest of the island.
Waikiki is pretty densely populated with attractions (museums, historic and cultural sites, the zoo and aquarium, etc.) so most of it’s easily walkable.
There’s a good (and reasonably priced) trolley system around Honolulu/Waikiki and Oahu has a decent public bus system for getting around to some of the major tourist attractions.
There’s a LOT of shopping. From luxury designer brands at the Ala Moana to major chain stores at the Royal Hawaiian Center, to cheap souvenir outlets everywhere, Waikiki is a shopper’s paradise.
There are a ton of restaurants. You’ll find major chains (Cheesecake Factory, Hard Rock Café, etc.) and pricey resort restaurants as well as local joints (as you venture away from Waikiki into Honolulu).

Why You Might NOT Like Waikiki

Now, a few reasons you may not like Waikiki:

It’s very crowded. On the beach, you’ll be shoulder to shoulder with fellow sun worshipers.
There’s soooo much traffic! Even if you have a car and you’re willing to get out and explore, expect a headache getting around.
There’s so much to see on the island besides Waikiki (the truly beautiful parts!) and getting around by bus isn’t too convenient.
If you do rent a car, many Waikiki resorts charge as much as $40/day to park it.
You may come home feeling like you’ve had more of a city vacation instead of an island vacation.