Domestic Travel, Itineraries & Trip Planning

The Perfect 5 Day Maui Itinerary

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Like so many islands, Maui is full of natural wonders. From the pristine, sigh-inspiring beaches it’s famous for to the volcanic crater that looks like another planet, spending time on Maui is like moving from one world to another. Here’s a perfect 5 day Maui itinerary for anyone looking to escape to island bliss.

Perfect 5 Day Maui Itinerary_ how to spend 5 blissful days in paradise

Where to Stay on Maui

I’m a huge fan of vacation rentals, especially when traveling with friends as we did when going to Maui. Of course, like any island, Maui also has many hotels and resorts to choose from.

We found Kihei to be the perfect home base for exploring the island, and that’s the location this itinerary starts off from.

Day 1: Relax and enjoy the aloha spirit

Hop on an early flight to Maui and feast on some local dishes as soon as you land.

Da Kitchen, located a 5-minute drive from the airport, serves up its famously humongous and delicious dishes each weekday from 11 a.m. to 9 p.m. Arriving on a weekend? Their Express location in Kihei is open daily.

Their signature plates of local Hawaiian food are incredibly affordable and can feed two people per dish. The sizes certainly didn’t derail us from each ordering our own plates, though.

Da Kitchen Maui
We maybe got through half…

Then take the rest of your first day of vacation easy as you relax by the beach.

Maui has more than 30 miles of gorgeous beaches, so no need to worry about finding the perfect one. If the one you hit up first isn’t your favorite, simply pick up your stuff and stroll down the coastline to find another.

Maui beaches

Wind down at Monkeypod Kitchen with their spectacular mai tais that are made with honey lilikoi foam.

If you like it, go for another round, because it truly is the best drink on their menu. The food selection is good though overpriced in my opinion.

mai tais at Monkeypod Maui

Day 2: Go snorkeling with sea turtles!

Having gone snorkeling in Hanauma Bay on Oahu (basically for free because we had our own equipment), I was initially a little unsure if I wanted to pay $120 to go snorkeling in Maui.

But I’m super glad that we did!

molokini crater
Look at that blue!

While our snorkeling stops at Molokini Crater and Turtle Town couldn’t compare with the colorful waters of the Thai islands (in which we snorkeled last Thanksgiving), we had a fantastic time sunning on the boat, pointing out cool fishies, and swimming with the turtles.

Plus, our tour operator served mai tais in the water! Snorkeling with drinks? I’m down!

Maui snorkeling

I’d highly recommend Pride of Maui if you’re considering snorkeling while on the island.

The entire process is well-run, the food was good, and did I mention the slides and open bar that starts after the second snorkeling stop? The company also provides everyone with reef-safe sunscreen, which is super important to help make sure the gorgeous seas of Hawaii continue to thrive without the damaging effects of regular sunscreen. The tour departs at 8 a.m. and disembarks around 1 p.m.

Once you’ve had a chance to clean up and rest up, get ready for an evening out and hit up the town of Laihaina, the island’s largest. (And if you happen to pass Leoda’s Kitchen and Pie Shop on your way to Laihaina, make sure to stop in and indulge on a mini pie or two.)

Lahaina Maui
Lahaina Old Town

In Laihaina, explore the old town with its historic lighthouses, ancient banyan tree (the largest in the U.S.), and other historical landmarks.

If you happen to be in town on a second Friday, there’ll also be a block party for both locals and tourists. (And no worries if you’re not in town on a second Friday — there’s a party on Maui every Friday, it just rotates to a different town each week!)

Check out the many bars and restaurants along Front Street and elsewhere in town and eat and drink to your heart’s content.

Day 3: Explore Haleakalā National Park

Remember the volcanic crater that I mentioned up top? That’s Haleakalā!

But Haleakalā National Park is also so much more than just the crater itself.

From the entrance of the park to the summit, you cross through so many elevations. On the drive up you traverse through multiple ecosystems from dry alpine deserts to rainforests — and we didn’t even go to the coastal area of the park. The diverse plant life of Haleakalā was one of my favorite parts of the drive.

Once up at the summit, it’s up to you how far or long you want to spend hiking in the famous crater. It’s approximately 7 miles by 2 miles, so there are a lot of possibilities.

Do keep in mind that the Haleakalā summit is 10,023 feet up in the air, so even if it’s nice and toasty elsewhere on the island, it’s likely to be windy and much colder up top. (It was also periodically raining when we were there.)

The mix of browns, reds, and yellows truly made hiking in the crater feel like we were trekking on the surface of another planet.

haleakala crater

Apparently, it is possible to stay overnight inside the crater if you reserve it through the National Park Service, but that was not in our plans for this trip.

You can also reserve tickets to view sunrise at Haleakalā, which is supposed to be spectacular. We actually booked our tickets and then backed out on waking up so early to drive up there. Plus, as you can see from this photo, we were woefully underprepared for the colder temperatures even during the day!

haleakala national park
See this lovely cardigan wrapped around my neck like a scarf?

Since Haleakalā is a national park, there’s a $25 per car entrance fee. Bring your own food and hydration and make sure your gas tank is full. None of that is available in the park.

(Pro tip: Need some cheap food on the go? Foodland is a chain of grocery stores with great Hawaiian to-go options like poke bowls and spam musubi. Or check out one of Maui’s many food trucks.)

On your way back to wherever you’re staying, stop by cute Maui towns such as Makawao and Pukalani and spend some time walking around.

Then head to the island’s most famous gastronomic institution, Mama’s Fish House, for dinner. Reservations are highly recommended (probably necessary), and get there early to spend some time on its beach and at the bar.

Mama's Fish House Maui
The beach at Mama’s Fish House

And yes, I totally went there for this black pearl dessert.

Day 4: Explore the waters and coastline

After spending a day inland, it’s time to get back to the water.

Hit up a local watersports shop and rent some equipment. We went with paddleboards, but you can also get kayaks, surfboards, boogie boards, and more.

I loved being able to paddleboard down the coast to different beaches, including one where we tried our hands at paddle surfing!

paddleboarding Maui

Since there are 30+ miles of coastline to explore, it’s your choice how and where you want to go for your days in the sun. We spent some time on the beach after paddleboarding before getting some large fish tacos at Coconut’s Fish Cafe and chilling under the shade at the pool at Aston at the Maui Banyan.

The rest of our day revolved around food, booze, and beaches.

I loved our time at Maui Brewing Company’s tasting room. The open and spacious design made it feel like I was still on the beach even though I was in a Costco-like warehouse away from the shores. Finding a beachside bar for the sunset is also highly recommended, though I can’t honestly recommend where we went.

Day 5: Drive the Road to Hana

On your last day on Maui, get some relief from the sun and hit up the island’s most famous drive: the Road to Hana. It’s not for those easily car sick or those who hate driving on curvy roads, but the views are so worth it. Click on that link above to find a guide on the drive.

And don’t forget to bring snacks and fill up before you hit the road! We loved the absolutely scrumptious Hawaiian dishes at Kihei Caffe as well as the Hawaiian twists on classics like French toast.

Who wants to go to Maui next weekend?!?

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Perfect 5 Day Maui Itinerary_ how to spend 5 blissful days in paradise

12 thoughts on “The Perfect 5 Day Maui Itinerary

  1. I love this! I saw your post on FB regarding your Airbnb HQ Speech vs Italy and then happened upon your Maui itinerary, which is perfect since I’m currently figuring out my 6 night December Maui vacation! I lava all the tips haha. Hope you’re doing well.

    1. Yay, I’m so glad you found this helpful! Also so excited for your Maui trip. It’s such a relaxing place.
      Haha yea, it’s unfortunate and ironic about the speaking opp. Hopefully another opp comes up soon.
      Hope you’re doing well, too!

  2. Love the post! It reminds me of these beautiful places we visited in Maui – the National parks, beaches and the resort itself. Amazing pictures

  3. Great itinerary- we were just on Maui for 5 days too! Swimming with the sea turtles was by far the coolest thing I’ve ever done!!! We found a cove about 20-30 minutes north of Lahaina that had TONS of turtles! We ended up not making down to Turtle Town because we loved this little cove so much.

  4. A great itinerary for Maui! I visited a few years ago but I’m not a huge water person so I did more of the land activities, hahaha! Didn’t get to visit Haleakalā National Park though, will have to go back for it!

    1. Ooh I’m such a water person, we forewent most of the hikes and such. What other great land activities did you experience?

  5. I love the Hawaiian Islands and Maui is one of my favourite islands. Thanks for a great post – I spent most of time reminiscing.

  6. This looks like a great itinerary! I love the variety of activities you included and all the food tips! Saving this for the day I finally get to Hawaii!

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