5 Days on Maui Itinerary

Heading to Maui? We’re sharing a detailed 5 days on Maui itinerary and guide with everything you need to know before you visit including where to stay, the best food and drinks, the best things to do in Maui, and more! Ready to plan your own Maui adventure? Keep on reading!

Hawaii is our favorite place in the whole world! We are madly in love with the culture, scenery, different ecosystems, small towns, the food, the people, the beaches, and the hiking.

We have been to Hawaii 6 times together, including 2 trips to the gorgeous island of Maui, once for our honeymoon and once just for fun (you can read about our latest trip here).

In both of those visits we have explored many of the island’s beaches, natural sites, restaurants, and towns. We tend to be more adventurous and busy travelers, so our trips to Maui have been jam packed with beaches, activities, and tons of food. But even in two trips to Maui, we have yet to explore it all!

We’re excited to share our 5 days on Maui itinerary with our favorite must-visit spots, cheap eats, and more—organized into an easy to follow guide based on different areas of the island. We hope the guide helps you plan a magical Hawaiian vacation!

More Maui Guides:

Heading to Oahu, the Big Island, or Kauai? Check out our other Hawaii guides:

A few disclaimers before we dive on in:

  • This guide does include a decent amount of driving, but the drives are amazing! We tried to structure this Maui itinerary so that you will stay in one area the majority of the day.
  • We prefer fast casual spots over fancier sit down restaurants, so our guide includes more affordable, quick places to eat. But if you’re looking for more restaurant ideas, we’re including tons of suggestions in our “if you have extra time” section!
  • We are not lay out at the beach all day type people. We like to spend our days doing a mix of beaches, hiking, eating, and exploring towns, so our guide definitely caters more to our travel style, but it still will give you tons of ideas of things to do on Maui even if you prefer to travel differently!

Before embarking on your adventure, please review the Leave No Trace principles to ensure you leave every place better than you found it, so that others can enjoy these beautiful places for many years to come!

These seven principles include planning ahead and preparing, hiking and camping on durable surfaces, disposing of waste properly (pack out what you pack in!), understanding campfire rules and always fully extinguishing your fires, respecting wildlife, and being considerate of other visitors. 

Note: this blog contains affiliate links. Full disclosure– if you click on these links and make a purchase, we get a small commission at no extra cost to you. We will only ever recommend products we truly love, actually use during our adventures, and think you can benefit from too!

About the Island of Maui

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Maui is the second largest Hawaiian island and is the second most visited island, after Oahu. However, unlike Oahu, the island doesn’t feel nearly as busy.

It’s a popular island for families and for honeymooners and offers tons of activities for everyone enjoy, like beautiful beaches, cute small towns, driving the Road to Hana, snorkeling, whale watching, waterfalls, and even hiking on a volcano. In one day you could go from 10,023′ above sea level with possible snow to a sandy beach…pretty crazy!

The island is broken up into five main areas: West Maui, Central Maui, South Maui, Upcountry, and East Maui. During our two trips to Maui, we’ve explored all of these areas and love how different they are.

Similar to the other islands, each region has a different ecosystem, so while some areas may be lush and green, some are a bit drier, making you feel like you’re visiting multiple places in one trip!

General Maui Tips

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  • We found that the best weather website for the Maui (and Hawaii in general) is Hawaii Weather Today. Typical weather websites said we would have rain every day of our trip and during our trip we only experienced rain once on the Road to Hana (which is very normal). So don’t panic if it says it’ll rain!

    This website is great because you can view the weather by region, which is crucial since the islands have many different ecosystems and weather patterns!
  • Speaking of rain, bring a rain jacket or umbrella! Ideally you won’t need it, but it’ll be a lifesaver if you have one!
  • Learn some Hawaiian words before you go! Not only does this help you understand some of the words you’ll see often, but it helps you get immersed into the culture more. And it’s nice to know how to pronounce them too!

When to visit Maui

We have visited Maui in both October and February and both trips were incredible! Well, minus that surprise and not super common tropical storm during our October honeymoon, but thankfully it didn’t ruin much of the trip. 🙂


Similar to the other islands, there are different ecosystems on Maui, which means that the weather varies a lot across the island. The western and southern sides of the island are warmer, sunnier, and drier than the rest of the island, while the eastern side of the island, where the Road to Hana is, is very wet and lush. So just because it’s raining in one area doesn’t mean that the whole day is ruined!

Crowds + Prices

The busy season for Maui is the winter and summer, when people are trying to escape cold weather or are on summer vacation. The prices will be higher and there will be more people, so make sure to plan ahead (and be prepared for a little less seclusion).

The off season on Maui is April-May and September-November. During these months you’ll experience less crowds and lower prices and these are also some of the best months for weather, so it’s a triple win!

Whale Watching Season

Something else to consider when deciding when to visit Maui are the whales. In November-May, thousands of North Pacific Humpback whales come to Maui, so if you want to see the whales (they are amazing!) we’d suggest visiting during this time.

However, no matter when you visit, there is truly not a bad time to visit Maui. You may experience the occasional rain storm or not have a beach to yourself, but you’ll still have a magical Hawaiian getaway!

Getting to Maui

Maui is home to one airport, the Kahului Airport (OGG), which is located on the northern part of the island. It’s approximately 40 minutes to Lahaina and Kaanapali and 20 minutes to Kihei.

Most major airlines fly to Maui, some with non-stop flights from the mainland and many with layovers in Honolulu.

​Where to stay on Maui

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There are a few main areas to consider when choosing your lodging in Maui. Here are the top ones we suggest based on location and availability of resorts and Airbnbs! Any of these areas will work great for this Maui itinerary too 🙂


​Located on the SW shore of Maui, Kihei is home to many restaurants and beautiful beaches. It’s centrally located to many spots on the island and has tons of Airbnb options across multiple price points.


  • Option #1: A super nice 1 bedroom, 1 bathroom condo
  • Option #2: A 2 bedroom, 2 bathroom condo with a nice view
  • Option #3: A 1 bedroom, 1 bathroom condo
  • Option #4: A 2 bedroom, 2 bathroom house

There aren’t many resorts in this area, but down the road in Wailea you can find a handful of more luxurious resorts, like Wailea Beach Resort- Marriott, Andaz Maui, Grand Wailea Maui, and Four Seasons Resort Maui. Warning: these are all a bit pricey!


This is the large and busy tourist area of Maui full of beachfront resorts. These resorts can be pricey, but if you want a lot of amenities, such as restaurants on site, large pools, maid service, etc, this is a great spot to stay.


  • Option #1: A studio with golf and ocean views
  • Option #2: A 1 bedroom, 1 bathroom ocean view condo
  • Option #3: A studio in Lahaina, but a good option if you want to be close to the shops


Kapalua/Napili Bay

Kapalua and Napili Bay are right next to each other in West Maui and offer a mixture of resort and condo options for your stay. This area is home to some of our favorite beaches and great golf. It’s a little farther away from some island attractions, but it’s more peaceful, secluded, and quieter than Kaanapali and Kihei.


  • Option #1: This is where we stayed last time–it was great! It’s a studio, but felt spacious to us
  • Option #2: A beautiful studio condo



Paia is on the north side of the island and is probably our favorite area! It has a small town vibe, lots of beaches, cute shops, and more! We definitely want to stay over here next time for at least part of the trip.

It’s also the beginning of the Road to Hana, so it would be a good place to stay before or after. There are no large resorts over here, just some Airbnbs!


  • Option #1: A 1 bedroom, 1 bathroom condo with a lanai
  • Option #2: A 1 bedroom, 1 bathroom condo close to the beach
  • Option #3: A nicely designed 1 bedroom, 1 bathroom condo

Rent a van!

Want to explore Maui without having to choose one destination to call home each night? Rent a van for all or part of your trip! As full time van-lifers, we can’t think of a better place to van life than Maui!

We recommend checking out Outdoorsy to find the perfect van rental for you! This van also looks super nice too!

Getting Around Maui

One of our favorite things to do on Maui is leaving the resort areas and exploring the more remote coastline, small towns, and mountains.

While there is the option to Uber or take a taxi on Maui, we highly recommend renting a car for the flexibility it will give you, especially if you want to drive the Road to Hana!

We found a great deal for a convertible for just a few bucks more than a car and it was sooo worth it!

5 Days on Maui Itinerary

Spending 5 days on Maui? Our Maui itinerary is almost exactly identical to both of our Maui trips and includes all of the best food, beaches, hikes, and things to do on Maui!

While this itinerary is if you have 5 days on Maui, you could definitely modify the itinerary depending on your interests and length of your trip. We spread out the days by different areas so that no matter where you’re staying, you will have some days with less driving. But you can reorganize the days however you’d like and still have an amazing trip! 

Day 1: Haleakala, Kihei, and Makena

  1. Kick off your morning by watching the sunrise at Haleakala. Some important things to know:
    • You’re required to make reservations up to 2 months in advance
    • You need about 2-3 hours to drive to the top depending on your starting location
    • We suggest going your first morning while you’re still on your normal time zone
    • Make sure to pack warm clothes–it’s freezing up there!​
    • If the weather looks bad, we’d recommend skipping it. Both times we have gone to the top it has been fogged out. Sunset is another good option and doesn’t require a reservation, so in the future, we plan to pick a very nice day and head up there for sunset!
  2. After getting up early for Haleakala, you’re gonna need some coffee! We love Akamai Coffee in Kihei!
  3. Grab breakfast at Kihei Caffe. Their cinnamon rolls are amazing! Note: This spot is cash only
  4. Spend a few hours at Secret Cove, also known as Makena Cove/Pa’ako Cove. This was one of our favorite beaches on the island!
  5. Pack a picnic lunch to enjoy at the beach.
  6. Next up: head to Big Beach, right next to Secret Cove. This beach, as the name implies, is really big! Make sure to hike up the cliff on the side to see the beach from higher up (the photo above!)
  7. We love to beach hop and recommend watching the sunset at Keawakapu Beach. But if you’re not wanting to hop around, Big Beach is a great spot too!
  8. ​Have dinner at Coconut’s Fish Cafe. Their tacos are amazing!

Day 2: West Maui Mountains and Kapalua

Maui hikes
  1. Have a quick and early breakfast at Island Vintage Coffee. We recommend getting their Island Latte and an acai bowl!
    1. Note: If you’re staying in Kaanapali or Napili/Kapalua, Island Vintage Coffee will be on your way to the trail. If you’re staying in Kihei, we recommend checking out Brekkie Bowls ​instead!
  2. ​Hike the Waihee Valley Ridge Trail4-5 miles, 1,519 ft elevation gain, and beautiful views! Try to get there early (around 8 AM) before the clouds roll in.
  3. Drive along Highway 340 to KapaluaWARNING: it’s a very sketchy road and has one lane along cliffs at times. But the scenery is beautiful and the experience is one you’ll never forget.
  4. Grab banana bread at Julia’s Banana Bread
  5. Stop at the Nakalele Blowhole on Highway 340. We tried to do this once in flip flops and it can be muddy and slick, so wear good shoes!
  6. Have a late lunch at The Fish Market Maui.
  7. Spend the rest of the day at Kapalua Bay Beach. We love this beach–the water is calm and good for snorkeling and the views are beautiful!
  8. For dinner, here are a couple options:
    1. Duke’s Beach HouseGet the Hula Pie!
    2. Miso Phat Sushi
    3. Down the Hatch

Day 3: Kaanapali and Lahaina

  1. Have breakfast at Leoda’s Kitchen and Pie ShopTheir french toast is amazing and don’t forget to get some pie! #BreakfastofChampions
  2. Walk around the shops in Lahaina. Front Street is a really cute street right across from the water with a lot of touristy shops, but it’s still really fun to explore.
  3. Have lunch at Lahainaluna Cafe!
  4. Get shave ice at Ululani’s–our favorite on the island! Make sure to get the Mac Nut ice cream on the bottom and snow cap on top!
  5. Spend the rest of the afternoon at Black Rock Beach in Kaanapali.
  6. Freshen up a bit and head to the Old Lahaina Luauthis is a super fun activity if it’s your first trip to Maui!

Day 4: The Road to Hana

Get an early start! This is a full day of driving–between 12-15 hours including all of the stops. It sounds daunting, but it’s SO worth it!

To see all of our Road to Hana tips, what to pack with you, and details about our favorite stops on the Road to Hana, such as location, cost, and any hiking information, check out our Road to Hana guide! But we’re listing a handful of the best stops below too!

Our favorite stops:

  1. Jaws Country Store for coffee, breakfast, and snacks
  2. Twin Falls (make sure to grab a fresh coconut and coconut candy!)
  3. Keanae Peninsula
  4. Upper Waikani Falls
  5. Coconut Glen’s for AMAZING vegan ice cream
  6. Lunch at Aloha ‘aina BBQ
  7. Wai’anapanapa State Park (black sand beach)
  8. Kaihalulu Beach (red sand beach)
  9. Wailua Falls
  10. Pipiwai Trail to Waimoku Falls–4 miles, 800 ft elevation gain

PS: Make sure to download the GyPSy Guide Hana app to guide you through the road. Even when you don’t have service it knows where you are and provides commentary and history about the area, as well as alerts you when to stop.

Day 5: Napili Bay and Paia

Maui itinerary
  1. Enjoy breakfast with a view at The Gazebo. We suggest getting there a little bit before they open. The line gets long!
  2. Spend the morning relaxing at Napili Bay Beach, which is right next to The Gazebo!
  3. Drive to Paia (north shore) and grab a coffee at Paia Bay Coffee, which is a cool cafe in an outdoor courtyard!
  4. Walk around our favorite town of Paia. We hadn’t spent much time here before this trip and instantly regretted it! We love the laid back, surfer vibe of this town and it feels less touristy to us than Lahaina.
  5. As you’re walking around, grab an acai bowl at Paia Bowls.
  6. Watch the surfers at Ho’okipa Beach and lay out on the beach for the rest of the afternoon.
  7. Have a final Hawaiian dinner at Paia Fish Market, which is one of our favorite spots for fish tacos! Flatbread Company is a great, affordable option too.

If you have extra time…

Have more than 5 days on Maui or just looking for more things to do? Here are some other activities and restaurants to check out!



Dreaming of Maui?

Pin this 5 Days on Maui Itinerary to help plan your trip!

about us

Hi y’all! We’re Adam, Kathryn, and Kona, an adventurous married couple (+ pup!) living on the road in our self-converted sprinter van! You can often find us driving all around the US and Canada, scoping out the best coffee shops, eating tacos and ice cream (we’re a 5+ taco and 2+ scoop household), and enjoying nature.


affilliate disclosure

This website contains affiliate links from websites such as MileValue.com, Amazon.com, Booking.com, and Rentalcars.com. If you use the links provided and make a purchase, we get a small commission at no extra cost to you. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. We only recommend products we truly love, actually use during our adventures, and think you can benefit from too!


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  1. Eric Wilson

    Well this adventure is unforgettable .

    • Kathryn Frazer

      We love Maui, there’s sooo much to do! Are you going there soon?


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