5 Days in Maui: The Ultimate Itinerary

I took my first surfing lesson in Maui, saw the biggest living turtles ever, and even got my first tattoo there. There’s no short of activities to do in Maui. And the fact that San Francisco is just a 6-hour plane ride away from Hawaii means I took every chance I had to visit the tropical island. From the three times that I’ve been, I’ve accumulated a list of things I love doing in and curated this 5 Days in Maui Itinerary for you. The itinerary will cover everything from activities to food, sightseeing, as well as ways you can enjoy the island without taking one step out of your hotel.

Day 1 – Take a Stroll on Front Street

A flight from San Francisco to Hawaii takes roughly six hours. Knowing that SF is one of the closest cities to Hawaii, I’m going to guess your flight will take at least that amount of time to arrive. And flights rarely land at the break of dawn, so I’m also going to guess that you’ll arrive in the afternoon or evening. Did I get it right? Anyways, six hours is a long time. This means day 1 on the island should be all about settling in and taking it easy.

Get to Know Your Stay

green palm tree near body of water
Photo by Jess Vide on Pexels.com

Once you arrive in Maui, get situated in your hotel/Airbnb/camp site (read more about camping in Maui). Use this first day to learn all about the amenities offered where you’re staying.

If you’re at a hotel, figure out where the pools are, the dining options, and the hours for each amenity. Also get a good grasp on the different tours offered through your hotel. Many hotels work with tour companies to offer pickups from your lobby so take advantage of those. If you haven’t done so prior to arriving in Maui, sign up for activities during your first or second day there so you get the best picks on times and tour styles. You’ll thank yourself later for doing all this research early.

Take a Stroll on Front Street

I recommend staying in Lahaina either during the first or entire part of the trip. There’s a ton of hotels in the western part of the island, an entire street of shopping, and beaches close by. It’s definitely one of the more popular places to stay and easy to get acquainted to since everything is so convenient.

In the evening, wear a long dress (the more flowy the better 🙂 ) and take a stroll on Front Street. Admire the water on one side and the various shops offering everything from shaved ice to seashell souvenirs on the other. If it’s still light out, take a quick rest under the banyan tree and pay respects to the 150 year-old tree that has stood the test of time.

Enjoy Dinner with a Sunset

Then enjoy fresh Mahi-Mahi at Lahaina Fish Co. Be sure to grab a seat by the water for a nice view! If you come right before sunset, you’ll also have the opportunity to take some pictures and share with friends and family that you’ve safely arrived. But mostly so they see the pics and experience FOMO.

Dip Your Toes in the Hotel Pool

Finish off day 1 with a swim, or by dipping your toes in the hotel pool. Just be sure to check the hours so you don’t arrive only after the pool has closed. It’s happened to me before.

Day 2 – Learn How to Surf

woman in pink bikini surfing on water
Photo by Jess Vide on Pexels.com

Learn How To Surf

Both times I’ve visited Maui, I took surfing lessons, and it’s one of the most rewarding experiences you can have on the island. Just imagine fearing for your life as the wave comes rushing towards you, but then seeing the most beautiful view you have ever laid eyes on as you stand up on the board. I took a group lesson with Maui Surfer Girls and really enjoyed it. We even got lost on the way to the lessonand the instructor was kind enough to wait 20 minutes for us! Talk about the aloha spirit.

Wanderer Tip: Some sunscreens can be very harmful to corals, so be careful to avoid any sunscreens with oxybenzone or octinoxate in them. You can also buy one of these reef safe sunscreens. Do your part to help preserve Hawaii’s marine life!

Lunch at The Fish Market

Lahaina has plenty of food options, but if I had to recommend one place to go, I’d suggest The Fish Market. From fish tacos to poke and lobster bisque, there is plenty of variety for seafood lovers here. They usually list their freshest fish of the day so if you love all seafood and just want what’s freshest, look for “fresh catch of the day” on their menu or ask. Their food is delicious and very reasonably priced. You can’t go wrong here. Also, can you really say you’ve been to Hawaii if you didn’t try their freshest seafood during your 5 days in Maui?

Chill at the Beach

Grab your favorite summer read, a few beers or a piña colada and head on over to a beach to do what you came here for: R&R. Olowalu and Kaanapali are two of my favorite beaches to visit. Kaanapali is one of the most popular beaches on the island and is also a resort favorite – there are 20 resorts along its 3-mile stretch!

Grab a Beer Flight at Maui Brewing Company

I normally get my fair share of beer while dining at restaurants, so I don’t venture out to breweries much. But Maui Brewing Company had such a cool space that I had to give their beer a try. They carry all kinds of beers, and many of them pineapple or mango flavored (YUM!) It’s both a fun place to hang out and a good place to learn about your beer preferences.

Day 3 – Road to Hana

grandma's coffee house maui
Grandma’s Coffee House

Get ready – because Road to Hana is one of the most memorable yet strenuous experiences you’ll ever have. Road to Hana is a beautiful drive along the eastern part of the island. The drive is treacherous, with narrow roads, steep cliffs, and some “two-way streets” that are only wide enough for one sedan. But it’ll all be worth it once you see the waterfalls, eat banana bread from a local stand, get coffee at Grandma’s Coffee House, and see the sun set over the landscape. This is the one part of the 5 Days in Maui itinerary you don’t want to miss.

Wanderer Tip: You can either drive yourself or hire a car. The route does contain some narrow and unpaved road, so hiring a driver that’s done the route before can give you some peace of mind while going through the more dangerous parts. On the flip side, driving yourself means you can stop whenever you want and for however long. If you decide to hire a car, check to see if your hotel offers a Road to Hana tour.

Day 4 – Snorkel at Molokini Crater

Snorkel at Molokini Crater

If you’ve dreamed of experiencing a Finding Nemo moment in the underwater world, Maui will definitely be able to fulfill that wish. Molokini Crater is about an hour’s boat ride from the main Maui island, and is perfect for snorkeling. If possible, book for a day when conditions are good so you can see clearly under the water.

Lunch with a View at The Mill House

The Mill House Maui
The Mill House

To me, a meal becomes 100 times better when you have a view to go with it. And The Mill House really delivers on good food, a good view, and delicious cocktails. Dining here on day 4 will give you some room to sit and just admire your surroundings as you near the last stretch of your 5 Days in Maui itinerary.

Dessert at Leoda’s

Leoda's Pie Maui
Leoda’s Pie

I only discovered Leoda’s the second time I went to Maui. So I made sure I went twice the third time I visited the island. I don’t know what they put into their pies, but they’ll make you want to come back for more!! I like the macadamia pie the most, but if you’re not a nuts person, there’s fruity, chocolatey, and many other flavors of pie to choose from. Their pies are also just a little bigger than the size of your palm so you won’t feel guilty trying more than one flavor.

Day 5 – Watch the Sunrise at Haleakalā National Park

Watch the Sunrise at Haleakalā National Park

Haleakala National Park offers sunrise and sunset hikes. No matter which one you decide to do, make a reservation in advance (you can book up to 7 days in advance). If you sign up for the sunrise hike, be prepared to wake up at 4 AM to give yourself ample time to drive up the mountain and make it in time for sunrise. Bring a blanket and maybe some hot cocoa. It can get chilly up there.

Other Things to Consider

Glamp at Camp Olowalu

Camp Olowalu Maui

If you want an experience that’s closer to nature, try glamping at Camp Olowalu. The camp site offers regular camping, car camping, and Tentalows (big tents raised on a platform that have a private shower and sink attached). Since the first two were too close to nature for me, we went with the Tentalows.

The initial reason we booked Camp Olowalu for two days was to save money for the air-conditioned resort living that was to follow, but I honestly missed Camp Olowalu after we left. It was one of the most relaxing experiences ever! Spending 5 days in Maui is quite a long time, so this is something you can seriously consider.

Remember the Aloha Spirit

No matter where you end up in Maui, you will find one thing you love about the island. And by the end of day five, I’m sure you’ll have gotten used to the aloha spirit – the spirit of being fully present, going with the flow, and just being nice to everyone around you! If you channel that spirt you’ll have a good time no matter what you’re doing on the island. And if all else fails, you can always just visit another beach 🙂

Lush greenery, tropical fruits, beautiful beaches, and welcoming locals are just some of the things you can expect when you visit Hawaii. I hope the 5 days in Maui itinerary I’ve planned for you will help you experience the island to its fullest, or at least give you some inspiration on what to expect once you set foot there.

*Restaurants may be closed due to COVID-19. Check the latest on their individual website.

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Maui 5 day itinerary

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