A Tropical Travel Blog
by Cate Lincoln

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 can plan the perfect Maui itinerary!

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.

RELATED: Not very familiar with Maui? Read up on the lay of the is(land) and where to stay plus my favorite beach resorts, budget hotels, condos, honeymoon resorts, family friendly resorts, luxury resorts, and boutique hotels plus my area specific guides (including where to stay, eat, and things to do) for Wailea, Ka’anapali, the north shore, and upcountry plus my review of staying at the Four Seasons Maui.

Don’t Miss List

West Side

Ka’anapali Beach: This bustling beach (its three mile stretch is home to Maui’s mega resorts) is probably Maui’s most popular beach. There’s excellent snorkeling near Black Rock.

Kapalua Beach: A beautiful, calm bay, this is the perfect place to wile away an afternoon, swimming, snorkeling, and paddle boarding.

Snorkeling Honolua Bay: Summer months are perfect for snorkeling in this bay where you’ll almost always see plenty of fish and turtles. It’s a rocky beach though, so not a place where you want to hang out.

Old Lahaina Luau: If you want to do a luau on Maui, make it this one!

Whale Watching Trip: If you’re visiting during whale season (October through April), then a whale-watching trip with the Pacific Whale Foundation is a must.

Explore Lahaina: This historic whaling town is full of shops, restaurants, and art galleries just begging to be explored.

South Side

Big Beach: Maui’s prettiest beach is also one of its most dangerous. Waves here break big and on the shore so watch out when entering and exiting the water!

Wailea Beach: A calm and tranquil beach if ever there was one. Not only is it a gorgeous beach, but it’s fronted by two of the poshest resorts on Maui, the Four Seasons and the Grand Wailea.

Snorkeling at Molokini and Turtle Town: Snorkeling at Molokini Crater is a bucket list experience for many people, but I think Turtle Town steals the show. Do a snorkeling excursion that stops at both.

Central Maui

Iao Valley: Iao Valley is one of the lushest and prettiest spots in Maui. These jagged green peaks will remind you of scenes from Jurassic Park.

RELATED: Best Maui Snorkeling Spots

15 Things to Do on Maui

25 Things to Know Before You Go to Maui

Maui Beach Guide

Complete Guide to Road to Hana

North Shore/Upcountry

Sunrise at Haleakala: This is the number one don’t miss experience on Maui! Seeing the sun rise through the clouds at the summit of Haleakala is a moving experience for many people.

Ali’i Lavender Farm: Come for the farm, but stay for the views. You can see practically the whole island from up here.

Maui Wine: Get a dose of old fashioned Hawaiian hospitality at Maui’s only winery. They have an exceptional tasting room and offer several complimentary tours daily.

Ho’okipa Beach: A big surfing beach, don’t miss the sea turtles that nest at the east end of this beach. In the early evenings, I’ve seen as many as 25!

Explore Paia & Makawao: These charming towns (a surf town and cowboy town respectively) are not to be missed. You’ll find local boutiques, art galleries, and good food.

Dinner at Mama’s Fish House: If sunrise at Haleakala is the #1 don’t miss experience on Maui, dinner at Mama’s Fish House is my #2. It’s that good. Go before sunset (and make reservations!).

East Maui

Black & Red Sand Beaches: These are two of the most epic stops on the Road to Hana and you definitely shouldn’t miss either.

Waterfalls: You’ll see countless waterfalls on the Road to Hana. Some are drive-bys (seen from the road) and some require a hike. My favorites are the upper Waikani Falls, Wailua Falls, and Waimoku Falls.

Pipiwai Trail: This favorite hike on Maui takes you through an incredible bamboo forest before depositing you at the bottom of a 400-foot waterfall. It’s only about 3 miles round trip but it always feels longer.

Tips for Creating the Perfect Maui Itinerary

Tip #1: Know your vacation style. How you like to vacation will have a huge impact on how you plan your trip and how much you’ll be able to see and do. So what exactly is a “vacation style?” Well, simply put, it’s how you like to spend your vacation!

Are you the type that’s up with the sun and out about adventuring all day only to return to your room to shower and sleep? Are you the type who enjoys spending the majority of your time hanging out at your beach resort? Or do you like a bit of both?

Everyone has a different idea of vacation so the first thing you’ll have to do is decide which suites you best. Are you always on the go, do you spend most of your time beach bumming, or do you do a combo of both? Part of your decision will be based on your personality and likely part will be based on where you’re staying.

For me personally, when I’m staying in a condo or budget hotel, I’m more likely to be out and about everyday, but when I’m staying at a nice beach resort, I’m more inclined to spend time lounging by the pool or on the beach. If you’re the type who’s always on the go, you’ll be able to see a lot of the island. If you want beach time too, I recommend renting beach gear (chairs, umbrella, snorkels, cooler, etc.) for the length of your stay and throwing them in the car so you’ll have them wherever you end up. If you’re staying at a nice beach resort, I would suggest planning a different activity each morning and spending each afternoon at the resort. You may need to set aside an entire day for certain adventures like seeing the north shore. Once you’ve nailed down your vacation style, you’re ready to start making your “must do” list.

Tip #2: Don’t Overplan. If I could only give you one piece of advice about planning your trip to Hawaii, this would be it. I know…it costs a lot of money to get to Hawaii (and it’s so far away). For a lot of people, it’s a once in a lifetime trip and of course you want to see absolutely EVERYTHING. But trying to cram it all into one trip will likely leave you feeling like you spent your whole trip in the car (or in airports) and now need a rest from your vacation upon returning home. But I mean, you still want to see the good stuff right? So how do you know how much to plan and when to take it easy?

Here’s how I always lay out my trips:

As I’m researching my destination (yes, I do a LOT of research), I keep a running list of things I want to do, places I want to visit, restaurants I want to eat at, shops I want to go to, etc. From my main list, I break it down into three categories:

A “don’t miss” list: This could be anything from seeing sunset at Haleakala to driving the Road to Hana. These are the things that you ABSOLUTELY have to see/do or you’ll return home heartbroken. Okay, that’s a little dramatic, but you get my point.

A “nice to see” list: These are things that you really want to see and experience, but they might be a little more minor. For example, seeing the sea turtles at Ho’okipa beach or snorkeling at Black Rock. These are just examples, obviously, what might be a “nice to see” for somebody may be a “don’t miss” for you.

A “if there’s time” list: I think you can guess what this list is for. Things that you’d like to see or do if there’s time, but won’t be upset about if you miss.

As you lay out each day, plan ONE thing from your “don’t miss” list each day. Combine it with one or two things from your “nice to see” list, and a smattering of things from your “if there’s time” list. Prioritize your “don’t miss” item every day (whether it’s doing it first thing or making sure you have a reservation for it) and fill in the rest of the day with things from the other categories.

Tip #3: Organize activities by part of the island. Once you have your lists of activities and things to do, the best way to sort them into days is by their location on the island. Many people underestimate how big each of the islands are and due to a lack of roads (and traffic) it can take quite a while to get around. So don’t waste time crisscrossing all over the island, and try to plan each day’s activities on one part of the island.

My favorite way to start sorting activities and sites into days is by using a Google Map. Plot all of your locations on a Google Map and then you’ll be able to see which ones are near each other and start planning your days that way. Of course, this can also be done on a paper map, but on a Google Map, you can create layers for different days or different types of activities and sites and organize things that way.

While generally speaking, focusing your day on only one part of the island is the most efficient strategy, there are some times when this doesn’t make sense. The major scenario where this doesn’t work is when you’re staying at a nice beach resort that you want to spend a lot of time at. In this case, I would plan a mornings worth of activities on one part of the island, return to your resort for an afternoon of playing on the beach or at the pool, and then don’t be afraid to venture back out somewhere for dinner.

Side Note: If you’re looking for a rental car for your trip, I LOVE 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.

Tip #4: Book activities in advance. So many people ask me if they should book ahead or wait until they arrive to arrange their activities and while I know some people like to be spontaneous, you really need to do your research ahead of time (before you arrive in Hawaii) and book directly through the tour operator. If you wait until you arrive on the island, many activities will be booked up and they’re less likely to offer discounts when the tour is almost full and people who waited until the last minute are competing over a few remaining spots.

Many companies offer a discount if you book online directly through them. This is because most tours rely heavily on resort concierge desks to promote their tours to the guests. The concierge get a commission for referring guests to the tour company (sometimes up to 40%) so tour companies have to keep their prices high so they walk away with a decent profit on the tour after paying out commissions. So if you go directly to the tour company, they’re often willing to cut you a deal because they don’t have to pay a commission to a concierge for your spot. For example, if a company pays a 40% commission for concierge recommendations, they’ll still come out ahead if they offer you a 20% discount for booking directly. But this way, you also come out ahead.

Also, if you go this route, you can do your research on companies ahead of time (I recommend TripAdvisor) and read honest reviews about the tours and pick which one you feel is best for you. If you go with a concierge recommendation, not only are you usually paying more, but 99% of the time, you’re just being recommended the tour provider who pays out the biggest concierge commissions, not necessarily the best one. If the tour provider’s website doesn’t advertise a direct booking special, I would still call and ask for their best price. You never know until you ask!

To be on the safe side, I recommend booking tours and activities (this includes luaus) about 2-3 months out. On my last trip to Maui, I really wanted to do the Old Lahaina, but I waited too long and it’s sold out! Bummer. One more thing about booking activities: I recommend booking fairly early on in your trip in case bad weather means they need to reschedule to a later day in your trip.  If you wait until your last day to do your helicopter tour, snorkel trip, etc. and it’s cancelled because of weather, you’ll be out of luck!

Besides planning your tours and activities in advance, I also like to have a plan for dining. While it’s fun to be spontaneous and see where the day takes you, often in Hawaii, it can end up taking you to an overpriced tourist trap. Do plenty of research ahead of time (I love using TripAdvisor), and keep a running list of restaurants in different areas that are highly recommended. For some of my favorite restaurant recommendations, read these. And come join my Facebook group, From Hawaii with Aloha, to get recommendations from others.

Tip #5: Be flexible. I think this last tip is the secret to making a good vacation great!  It’s so simple, yet key to really having the best experience in Hawaii. I think that a good plan is essential, but you have to know when it’s time to go to plan B. Or do something else entirely.

The major thing you’ll have to be flexible about in Hawaii is the weather. While the temperature is always pretty balmy (unless you’re in the upcountry area of Maui), a good rainstorm can change your plans pretty quick! A word of warning: it’s not unusual for a 10-14 day forecast to predict rain everyday in Hawaii so don’t panic and think your trip is going to be a total wash! It’ll likely just be quick storms that roll in and roll out. But for days where the local forecast truly is predicting rain, you might have to mix things up! One good thing about the Hawaiian Islands is that they’re pretty large so except in the case of a major storm system, the weather will likely be different on different sides of the island. Check the weather forecast the night before (or morning of) and you may decide to rearrange your days based on the weather. Obviously this may not work if you have activities or tours booked, but otherwise, don’t be afraid to swap out days in your itinerary to go chasing the sunshine!

Thanks for sticking around and reading this whole post! It’s always my goal to provide a TON of value to YOU. To that end, lately I’ve been packing my Instagram (@hula.land) FULL of content and adventures that you might want to check out. A lot of my post captions are like mini blog posts with travel info, I’ve got IGTV review videos for luaus and excursions, and helpful story highlights like grocery store prices and hotel reviews. Not to mention that my feed is pretty much the ultimate tropical eye candy! You can follow me here and share my account with your friends! Your support really helps me to keep this blog running!

Also, if you have ANY questions about planning your trip to Hawaii, you can join my free Facebook group here. I’m in there answering questions every day and there are 5000+ other friends who have a ton of Hawaii information to share!

Feeling a little overwhelmed with trying to plan the perfect Hawaii itinerary? I’ve got just the thing for you!

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These aren’t week long itineraries, but daily itineraries so you can pick and choose what works best for your trip. If you’re the go-go-go type, then pick 6 different daily itineraries and string them together into one adventure packed trip. If you’re staying at a nice beach resort and wanting to take advantage of the amenities, then pick 2-3 daily itineraries and spend the rest of the week chilling at the resort/beach. If you’re going on an island hopping extravaganza trip, use the daily itineraries to figure out how many days to spend on each island and what to do!

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