5 Days on Maui

5 Days on Maui Itinerary | Things to do on Maui #Maui #Hawaii #MauiGuide #MauiItinerary

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 5 times together, including 2 trips to the gorgeous island of Maui (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.  Here’s 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!

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

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!

​Where to stay


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:


​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.


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.

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.


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!

PS: If it is your first time staying at an Airbnb, click this link to get $40 off your first stay!

Rent a van!

Our Instafriends Klara and Brandon rent out THE COOLEST 1975 Volkswagen Camper Van. If you want to experience Maui in style, you can rent it here!

Getting Around

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 and especially if you want to drive the Road to Hana!

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

  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 Paia Fish Market or 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! 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.

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 Nahiku Roadside
  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

Day 5: Napili Bay and Paia

  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
  3. Drive to Paia (north shore) and have coffee + lunch at Paia Bay Coffee. 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. Grab an acai bowls at Paia Bowls.
  6. Watch the surfers at Ho’okipa Beach
  7. Have a final Hawaiian dinner at Mama’s Fish HouseWe have yet to eat here, but if you want to splurge a little, this is one of the top restaurants on the island. A cheaper option:Flatbread Company

If you have extra time…




Dreaming of Maui?

Pin our 5 Days on Maui itinerary to help plan your trip!
5 Days on Maui Itinerary | Things to do on Maui #Maui #Hawaii #MauiGuide #MauiItinerary



Plan your next trip with our travel guides


  1. Eric Wilson on March 21, 2019 at 4:20 am

    Well this adventure is unforgettable .

    • Kathryn Frazer on March 21, 2019 at 4:32 am

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

Leave a Comment