5 Days in Maui: Uncovering Hawai'i’s Romantic Paradise

Advisor - Annie Decker
Curated By

Annie Decker

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  • Active Travel

  • Adventure Travel

  • Beaches

  • Hawai'i

  • Maui

  • Local Culture

  • Local Food

  • Coastal

Beach view with blue colored water and skies.
Curator’s statement

As someone who usually shies away from beach destinations, Maui is a dream destination that transcends the typical beach getaway. Maui is a paradise perfect for travelers, especially couples and honeymooners, looking to enjoy a balance of relaxation and adventure. From the awe-inspiring Haleakalā National Park to the vibrant town of Lahaina, this island offers a myriad of experiences. Immerse yourself in the rich Hawaiian culture, indulge in world-class dining and explore the island's diverse landscapes.

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Insider knowledge

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Where to stay

Andaz Maui At Wailea Resort - a Concept by Hyatt

Guests come to Andaz Maui for its luxe accomodations, but stay for its vibrant cuisine and cascading infinity pools overlooking the ocean.

Fora Perks
  • $100 hotel / resort credit.

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

Grand Wailea A Waldorf Astoria Resort

A beachfront belle on forty tropical acres, known for its authentic cultural workshops, huge pool and pampering spa, and gorgeous over-lagoon restaurant.

Fora Perks
  • $100 hotel / resort credit.

  • Breakfast daily.

  • Upgrade whenever possible.

Fairmont Kea Lani - Maui

An expansive Maui resort with an array of amenities, pools and beachfront access.

Fora Perks
  • $100 food / beverage credit.

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

Advisor - Annie Decker

Unlock perks by contacting Annie to book your trip.

Day 1: Natural sightseeing

A coastal view with palm trees near the seashore

Your time in Maui will start in the central part of the island as you land at Kahului Airport. Pick up your rental car and make your way to Iao Valley to swim or make the 0.6-mile walk to the scenic viewpoint of Kuka‘emoku (a.k.a. the Iao Needle). From here, make your way West to Kapalua. Visit Dragon’s Pointe, a rock formation group that gains its name from its sharp and pointed edges, resembling dragon’s teeth. Just down the road from this is the Kapalua Coastal Trail which guides you along Oneloa Beach for breathtaking views. In the evening, explore the town of Lahaina, making sure to not miss Banyan Court Park, home of the largest banyan tree in the US. Go shopping on Front Street and grab dinner at Down The Hatch in the Wharf Cinema Center Shops.

Day 2-3: South Maui

A man in blue shorts diving in water

Plan to spend two days in the south part of the island to give yourself time to enjoy the beaches and great snorkeling spots. Consider making this your home base while in Maui as it is easy to drive to all of the other parts of the island from here. South Maui is home to the majority of the island’s resorts and several excellent golf courses. Spend some time enjoying the top beaches in the area: Wailea, Makena and Maluaka. Enjoy the Te Au Moana Luau at The Wailea Beach Resort to learn about the history and culture of some of the Polynesian islands.

Go snorkeling at Molokini Crater, a partially submerged, crescent-shaped volcanic crater, and Turtle Town, which is made up of lava formations from eruptions long ago that have since become home to coral reefs, fish and Hawaiian green sea turtles just off the coast of Maluaka Beach. Spend time exploring the lava fields on land at La Perouse Bay and enjoy the views of Haleakalā. Enjoy laid-back dining at Akamai Coffee, The Maui Market and Maui Brewing Company. For a nicer dinner, consider Humble Market Kitchen or Monkeypod.

Day 4: Road to Hana

Sunlight piercing through the palm trees near the shore.

Wake up bright and early to set out on the road to Hana. With over 50 one-way bridges and extremely narrow roads, be prepared for an adventurous drive. I’d recommend driving straight to the Kipahulu Visitor Center in Haleakalā National Park to avoid the crowds. From the Kipahulu Visitor Center, hike the Pipiwai Trail (4 mi), stopping to admire the Falls at Makahiku, the giant banyan tree, the wild bamboo forest and at the end: Waimoku Falls, a 400 ft tall waterfall. After this, enjoy the shorter Kuloa Point Trail (0.5 mi) to see the Oheo Gulch and its accompanying black sand beach. On the drive back to Paia explore the famous pit stops along the mile markers. I’d suggest not missing Hana Town (mile marker 34), exploring at Wai‘anapanapa State Parkgrabbing (mile 32 - reservations required), grabbing some snacks from the Halfway to Hana stand (mile marker 17) and snagging some photos of the Rainbow Eucalyptus Trees (mile marker 7). Once in Paia Town, visit the art galleries, boutique shops, and Ululani’s Hawaiian Shave Ice. Grab dinner at Paia Fish Market or make a reservation at Mama’s Fish House.

Day 5: Upcountry

Turtles on the seashore

Spend your last day on the island exploring Upcountry. Enjoy watching the sunrise at the summit of Haleakalā. In the afternoon, visit Ali’i Kula Lavender Farm to experience the wild lavender fields, gardens and homemade treats. Or consider visiting Ocean Vodka Organic Farm to enjoy a tasting tour. The tour is relatively short but informative on how they distill their spirits and the types of sugar cane and other crops they have on the plantation.

Since opening in 2004, they have expanded their spirit offerings from their flagship product Ocean Vodka to include Kula Rum (toasted coconut, silver and dark) and Fy Gin, all of which are included in the tasting. As most flights from Hawaii to the mainland US leave in the late evening or night, consider grabbing dinner at Cafe O'lei at the Mill House on the grounds of the Maui Tropical Plantation before heading to the airport.

Need to Know

Looking for more travel inspiration? Check out my guide, Experiencing the Magic of Scotland in 7 Days.

Advisor - Annie Decker

Travel Advisor

Annie Decker

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This guide is part of our ongoing series on travel to Maui.