The Perfect Maui Itinerary: How to Spend 5 Days in Maui

Planning a getaway to the tropical paradise known as Maui?  Having lived on Maui for over 10 years, I put together the perfect Maui itinerary for 5 days.  This article will include the best things to do, where to eat, where to stay, the best time to visit and all the necessary travel tips to ensure a swift and seamless vacation.

Maui is known as the ‘valley isle’ and is the second largest Hawaiian island.  Known for its stunning coastline, world class resorts and next level surf, Maui is where adventure meets luxury. 

Maui is a bucket list destination, you could easily spend 2 weeks here and not experience all that Maui has to offer. Don’t you fret, 5 days in Maui is enough time have a few adventures, indulge on tasty farm to table cuisine and allot some much needed beach time.

Maui Itinerary 5 Days – A first timers guide

5 days in Maui sample itinerary
Disclaimer: This article contains affiliate links. I may make a small commission if you make a booking using my links at no extra cost to you which helps pay for the running of this blog.

Day 1:  Explore West Maui
Airport Beach West Maui travel guide
West Maui is one of Maui’s most popular areas and the place that I call home.  You can’t have a Maui itinerary without driving the West Maui loop, which starts at Maalaea and ends as far north as you’d like to go.

Spend the morning driving North along the West Maui coastline.  Stop at various sights along the way that isn’t a beach.  Don’t worry you’ll get your beach time in this afternoon.  These are the best stops driving West Maui.

Lahaina town
View of Front Street Lahaina
Lahaina is a historic town perched on the waters edge.  Filled with ocean view restaurants, boutique shops, art galleries and surf schools you could easily spend the whole morning here.

This is the best place to grab breakfast before you start the adventure up North.  These are some of the best restaurants in town.

  • Down the Hatch: Awesome breakfast, southern inspired Hawaiian cuisine with a fun atmosphere.
  • Fleetwoods on Front Street: Lahaina’s only rooftop bar, views, cocktails, menu and live music.
  • Star Noodle: The tastiest Asian fusion cuisine.
  • Papakea: Delicious breakfast at the harbor.
  • Mala: On the water ocean side dining, brunch and the ahi bruschetta.
  • Lahaina Grill: Fine wine and dining experience with exquisite cuisine.

Dragon Teeth

Dragon’s Teeth is a formation that resembles teeth of a dragon.  The unique structures were formed when lava from the West Maui Volcano poured into the ocean.

Combining strong winds and powerful waves, the lava was pushed back thus forming what resembles great black teeth. You can simply walk down the path and wonder around Makaluapuna Point aka Dragon’s Teeth.

Honolua Bay
Honolua Bay maui 5 days itinerary
Honolua Bay is a rocky beach located North of Slaughterhouse beach.  The primary draw is snorkeling and surfing.

In winter, storms bring excellent surf to Honolua, one of the best surf breaks on Maui.  When the surf is up, surfers flock here in droves. There is an overlook on the east cliff where you can pull up to watch the action.

Nakelele Point and the blowhole

Nakalele Point is an area of rugged coastline with main attraction being the blow hole. This blowhole is roughly the size of a manhole cover and is powerful enough to easily blast 50+ feet high in the air.

Safety Tip:  Observe the waves for some time before walking down to the blow hole.  Look for signs of water sweeping across the area and stay back from areas that are experiencing wave action.  Larger unexpected waves can sweep across the lava thus pulling visitors into the ocean.

Julia’s banana bread

If you’ve made it this far North, through a few sketchy parts of the road without guard rails, then reward yourself by stopping at Julia’s banana bread.  This small stand on the side of the road is Julia’s and she bakes and sells the BEST banana bread on Maui.

Although you didn’t drive that far in mileage, with all the twisty curves and one lane roads you’ll be ready to relax by the pool or the beach.  These are the best beaches on the West side.
Napili Bay Hawaii

  • Kaanapali Beach: The closest beach to all the major resorts.  Over 3 miles of soft, golden sand.  On the far north end you can enjoy snorkeling, cliff jumping and swimming.
  • Napili Bay: Postcard perfect crescent shaped bay.
  • DT Fleming’s: Ample parking, walkable from the Ritz and life guards on duty.
  • Slaughterhouse: Located next to Honolua bay.  This beach always feels like an adventure.

Day 2:  The Road to Hana
Road to Hana Maui
The road to Hana is one of Maui’s top attractions.  52 miles of one lane bridges and twisty curves, this activity is all about the journey, not the destination.  Or at least not in this post as you only have 5 days on Maui.

This is an all day excursion and if you are staying on West Maui, it will take even longer as you are an hour farther away.  That shouldn’t deter you, as these are the best stops along the road to Hana.


Paia town

Paia is where you’ll want to fill up with gas and grab breakfast before you embark on the journey.  These are the best restaurants in Paia.

  • Paia Bay: Awesome breakfast - fresh baked croissants, acai bowls and Maui roasted coffee.
  • Cafe Des Amis: Pleasant outdoor seating area, curries and crepes.
  • Flatbread: Great for large parties and wood fire pizza.
  • Nylos: Fine dining experience on the North shore.
  • Cafe Mambo: Vegetarian and vegan friendly menu.

Twin Falls

Twins Falls is a short family friendly walk/ hike to get to 2 flowing water falls where you can swim beneath them!  If you’re traveling with kids or want a trail with waterfalls that doesn’t require much effort, then you’ll love Twin Falls.

Painted Forest

A cluster of rainbow eucalyptus trees.

Ke’anae Peninsula

This is a beautiful place to stop and watch the waves crash onto the volcanic coast line.

Upper Waikani Falls

Three waterfalls ranging is sizes of small, medium, and large.  Appropriately named after the 3 little bears children’s story.

Waianapanapa State Park
Waianapanapa State Park Maui
A beautiful state park home to an elegant black sand beach.

Travel Tip: Reservations are now required to enter the park if you are a visitor.  Book a few weeks prior to visiting and same day reservations are not permitted. 

Hana Town

You’ve made it to Hana.  There are a handful of food trucks and a few restaurants to eat before you turn around and make the journey back to your hotel.

Of course there are lots of other great adventures to have in Hana including hiking the Pipiwai Trail, Waioka Pond and Hamoa Beach but can’t fit them in this 5 day Maui itinerary.  If you have more time to allot, I’d recommend staying a few nights to be able to experience Hana’s magic.

Day 3: Sunrise over Haleakala & Explore Upcountry
Haleakalas Sunrise Maui five day itinerary
Sunrise at Haleakala Summit

There’s nothing quite like watching the sunrise above the clouds at the summit of Haleakala which sits at 10,000 feet.  This activity requires an early wake up call.  You’d have to leave by 3:30 AM at least from West Maui in order to make it to the top of the summit in time for sunrise.  Reservations are required in advance.

Travel Tip:  Dress warm!  Year round temperatures range from 50°-65°F.

Upcountry Maui

You can either head back to your hotel to relax by the pool after your early morning or you can check out Upcountry Maui for a few hours.  These are some cool spots to stop at when exploring this part of Maui.

  • The Ocean Distillery: A beautiful 80-acre organic farm on the slopes of Haleakala in Kula.  Brand new restaurant on site which is worth the stop alone.
  • Surfing Goat Cheese Dairy Farm: Baby goats and a gift shop where you can buy all the different flavors of goat cheese.
  • Maui Winery: Sample a wine made from pineapples for an authentic Hawaiian experience.
  • Hali’maile General Store: Across the street from Pau Vodka Distillery, this restaurant has been around since 1988 and a great place to grab lunch.

Day 4: South Maui

Molokini Snorkel Tour

I couldn’t write a 5 day Maui itinerary without some fun in the ocean.  Start your morning with a fun snorkel tour to Molokini.  Molokini is a horseshoe shaped volcanic crater and also a fish sanctuary.


With an array of marine life and clear visibility, this is by far one of the best things to do in Kihei.  This excursion is usually paired with Makena’s Turtle Town, which is an area known for its large population of sea turtles and tropical fish.

South Maui Beaches

South Maui in my opinion contains the best beaches in Maui.  After a snorkel tour spend some time lounging on a world class beach.  These are the best beaches on South Maui.

  • Big Beach: Over a half a mile long, white sandy beach.
  • Wailea Beach: Nestled at the foot of the Grand Wailea and the Four Seasons, this beach is perfect for swimming.
  • Secrets Beach: A wide, shallow, sandy shore perfect for swimming and spending the day.
  • Kam III: Boogie boarding, snorkeling and facilities.

Attend a Luau

A bucket list item for some when visiting Hawaii is to attend a luau.  A luau takes you through Hawaii’s history and legends by showcasing the beautiful Hula dance, music and chants.  Plus you’ll get to sample authentic and local cuisine.

If you don’t go to a luau these are the best places to eat in South Maui.

  • Miso Phat: Fresh, local sushi caught in house.
  • Nalu’s South Shore Grill: Locally sourced ingredients, fresh fish and generous portions.
  • Pint & Cork: Premiere gastropub featuring craft beer, handcrafted cocktails,’hard to find’ whiskeys and fine wines with a Hawaiian inspired pub food menu.
  • Monkeypod Kitchen: The poke tacos alone are worth eating here.
  • Maui Brewing Company: Live music and local brews.

Maui brewco 4 days

Day 5: Anything you want!

Chances are is something you wanted to do in Maui but I may not of covered in this sample itinerary.  There are so many things to do, I mean there’s a reason that everyone wants to travel to this island.

Whale Watch

If you are traveling here during the winter months, you can’t miss out on going on a whale watch.  Every year the Pacific Humpback whale makes the journey from the cold waters of Alaska to their breeding ground in the shallow Hawaiian waters.

Whale watches are relatively inexpensive around $40 a person.  There’s not many places in the world that you can witness these majestic beauties up close in their natural habitant.


There are a ton of beginner surf spots perfect for learning all around the island.  Book a lesson to get familiar with the fundamentals/techniques of the sport, how the line ups work and a better understanding of the waves and ocean.


If you love hiking as much as I do, there’s tons of Maui hiking trails that offer great views, a cardiovascular burn and of course waterfalls.  These are the top hikes on Maui.

  • Pipiwai Trail – A dreamy bamboo forest and ends at a 400 foot waterfall.
  • Waihee Ridge Trail – A moderate hike along a ridge offering epic coastal views.
  • Kings Trail – Filled with wild goats and wild flowers as it traverses an old lava flow along the coastline. 
  • Sliding Sands – Haleakala Crater hike that takes you down to the crater floor. 

Sunset Cruise

Watch the sunset in style as you wine and dine on the water.  This is how life is meant to be lived.

The list could go on.  Maui has a way of stealing ones heart in more ways than one. 

Maui Travel Tips

  • The best time to visit Maui is December through March for whale season.
  • Renting a car is necessary to travel around and get to experience all that Maui has to offer. To find the lowest price, compare rates between different car rental companies on www.discovercars.com.
  • Maui’s average temperature is 80° but it can get cold on the summit of Haleakala. 
  • Maui’s average budget is around $200 per person.

Where to Stay on Maui for a First Timer

Most visitors stay in West or South Maui.  Both areas have luxurious resorts, beautiful beaches and plenty of food options close by.

For the purpose of this 5 days in Maui sample itinerary I wrote it as if you stayed in West Maui.  If you decide to stay in South Maui just swap days 1 & 4 as the first day on Maui you’ll probably be hanging in the area of your hotel.

There are plenty of hotels and vacation rentals to choose so finding a place to stay in your price range will leave you lots of options but I’ll suggest a few hotels that are worth the splurge.

West Maui: The Westin Resort & Villas

Located on Ka’anapali Beach.  This is a great resort, perfect for families, couples and solo adventurists.  Walking distance to water activities, boat tours, tasty restaurants and shopping.

Click here to read reviews and see latest prices.

South Maui | The Andaz

Located in Wailea on the beautiful Mokapu beach.  The perfect resort if you are celebrating your honeymoon.  Staying at the Andaz puts you in better location (less drive time) to reach Haleakala summit and to drive the road to Hana. 

Click here to read reviews and see latest prices.

There you have it, the best way to spend 5 days in Maui.  Maui is full of adventure, luxury and relaxation.  Truly paradise on Earth.   I hope you enjoy this 5 day Maui itinerary as much as I love living in Maui.

Author Bio:
I'm Jess Traveling Blog Bio
Jess is a bikini wearing, coffee loving, temple chasing explorer.  When she’s not galavanting around the world you can find her on Maui, working on her blog I’m Jess Traveling and building the life of her dreams.
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5 days in Maui hawaii itinerary


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