5 Day Maui Itinerary

5 day Maui Itinerary

This 5 day Maui itinerary provides an overview of the best things to do and explore while in Maui. It also includes how to get there, when to visit, where to stay, and how to get around.

I went to Maui with my now fiancé, Jason, back in October 2019. We went to Oahu for the first part of our trip and then came to Maui. We were so excited to explore the remote coastlines, small towns, and tropical scenery! Read below to see details about our trip and my tips for visiting the island.

How to get there: Maui has one main airport, Kahului (OGG). It is pretty centrally located on the island. Most major airlines fly to Maui. Depending on the airline and your base location, you may be able to get a direct flight or have a layover in Honolulu. Kahului Airport is located 30 minutes from Wailea, where I stayed, and is about 20-40 minutes to most towns on the island.

When to visit: I visited in October and it was absolutely beautiful. Maui has gorgeous weather year round, with the rainy season in the winter. However, I went to another Hawaiian Island in February one year, and it was just as amazing. The tourist season is in the summer so I personally would recommend aiming for spring or fall for your visit to avoid the crowds.

Where to stay: When I went, my fiancé and I stayed in Wailea at the Marriott Beach Resort. There are many mainstream resorts in this area. If you’re looking for more off the beaten path places, I’d recommend checking out Airbnb or even look into renting a camper van for your trip!

Getting around: I would highly recommend getting a rental car from the airport if you’d like to explore the island and make an adventure of your trip.

Day 1: Haleakala Crater and get settled (3 hour drive)

We flew into Kahului Airport in the morning and picked up our rental car. We aimed for a Jeep Wrangler for doing Road to Hana, but ended up with a Mustang convertible instead and decided to make the most of it! After that, we headed straight to Haleakala Crater. This is the highest elevation in Maui at just over 10,000 ft above sea level. It is a beautiful drive that takes about 1 hr and 20 minutes from the airport. We decided to go here straight from the airport since we knew we would be doing a lot of driving the next day too (for the Road to Hana). At the top, we explored around and did a short portion of one of the trails. We saw many people backpacking into these trails and thought that could be a great idea for another time!

After exploring, we drove back down to sea level and checked into the Wailea Beach Resort by Marriott. This is where we stayed for our entire trip. There are many resorts in Wailea. If you’re on more of a budget or looking for a less resort style vacation, I would check out Airbnb. Also, there are some great camping spots throughout the island that some of my friends have stayed at.

Day 2: Road to Hana (5-6 hours depending on your route)

Day 2 of the 5 Day Maui Itinerary is a full day of exploring and driving along the curvy narrow road. I recommend bringing snacks and lots of water along for the ride. Wear a bathing suit in case you’d like to stop for a swim and hiking shoes/chacos if you plan to do some hiking! I recommend driving in a clockwise order and once getting to Hana, continuing through the backside of the island. It is less kept and has unpaved roads for a good part of the drive, but is so beautiful and remote. We did it in our mustang convertible and had no issues – just had to take it slow through some areas. As you plan your trip, you’ll find that there are many places to stop and explore along the Road to Hana. I recommend having a few “must see” stops and extra stop options.

Here are my favorite Road to Hana stops:

Paia Bowls for breakfast in Paia
Ho’okipa Lookout to watch the surfers
Twin Falls for a quick walk to waterfalls with a swimming hole
Bamboo Forest hike up Na’ili’ili-haele Stream to waterfalls
Halfway to Hana for the most incredible banana bread
Wailua Falls (can see from the road)
Really all the waterfalls…they are just so beautiful!
Many spur-of-the-moment stops along the way

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Day 3: Snorkel and enjoy the resort!

Our driving days on the island were complete so now we were ready to relax and enjoy the water! We went out on a morning snorkel tour out of Wailuku (30 min drive from Wailea). This tour was on a catamaran that took us to a reef at Molokini Shoal Marine Life Conservation District. After snorkeling at the reef, we went over to Turtle Town to snorkel with the sea turtles. It was so amazing to see all the marine life!

After the tour, we headed back to the resort and enjoyed the pool.

Day 4: Surf & explore the town

We rented long boards from a surf shack about 15 minutes north of our resort in Kihei to go surfing. Renting the boards was super easy and then we just walked across the street to a great beginner wave spot. This was the highlight of our trip! The waves were nice, small, and uncrowded, and we even saw sea turtles!

Throughout our stay, we found a few great places in Kihei to eat at:

Paia Fish Market South Side for lunch for fish tacos
Wow Wow for amazing acai bowls and lemonade
Cuatro for dinner. I still think of how delicious the spicy tuna nachos were!

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Day 5: Head out / head to next island

We had a nice slow morning and then packed up and headed to the airport We returned our rental car and caught our flight out of Kahului Airport back to Oahu for the last 2 days of our trip.

I hope this 5 day Maui itinerary helps plan your trip! Feel free to reach out on my Contact page if you have any questions!

5 Day Maui Itinerary