Curator’s statement
Maui is a truly special destination because it offers the perfect blend of natural beauty, relaxation, and adventure all in one island escape. From golden beaches and crystal-clear snorkeling bays to lush rainforest and breathtaking Road to Hana, every day feels unforgettable. Maui has it all: luxury, romance, and outdoor exploration. It really is the ideal vacation spot that feels like paradise.
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Day 1: Relaxation begins
Wailea Beach Path
Start your first morning in Maui with a phenomenal breakfast, complete with fresh coffee and warm malasadas—Portuguese-style doughnuts that are fluffy, lightly fried, and coated in sugar.
After breakfast, enjoy a peaceful stroll along the Wailea Beach Path, where ocean breezes and lush resort landscaping create the perfect tropical welcome.
Spend the afternoon exploring the charming town nearby before returning to the Grand Wailea to unwind.
End your day poolside with a refreshing drink in hand, watching the sky light up with one of Maui’s unforgettable sunsets.
Day 2: Discover Lahaina & sunsets in Ka'anapali
Sunrise driving to Lahaina
Today, head over to the historic town of Lahaina, once a bustling whaling village and now filled with charming shops, art galleries, and island history.
Stop for lunch at the beloved Down the Hatch, a local favorite known for fresh seafood and fun Hawaiian flavors.
Afterward, continue on to Kāʻanapali to explore Whalers Village, where you can browse beachfront boutiques and enjoy the lively resort atmosphere.
End the day with sunset dinner at Duke’s Beach House, the perfect spot to savor island-inspired dishes while watching the sun melt into the Pacific.
Day 3: Molokini snorkeling adventure & a Grand Wailea lu'au
Molokini Crater snorkel trip
Begin your day with an unforgettable snorkeling excursion to Molokini Crater, one of Maui’s most famous underwater sanctuaries, where crystal-clear waters reveal vibrant coral reefs and tropical fish. Keep an eye out for Hawaiian green sea turtles as you swim alongside these gentle creatures in their natural habitat.
After your ocean adventure, spend the afternoon exploring the laid-back town of Kīhei, perfect for beachside shopping, local cafés, and a relaxed island vibe.
End your day back at the Grand Wailea, unwinding in paradise before enjoying a traditional Hawaiian lūʻau filled with music, dance, and island flavors.
Day 4: Road to Hanā
Hana-Maui Resort at sunset
Today is all about experiencing Maui’s legendary Road to Hāna, one of the most scenic drives in the world, filled with lush rainforests, waterfalls, and dramatic coastal views.
Take your time as you stop along the way at highlights like Twin Falls, the colorful Garden of Eden Arboretum, Waiʻānapanapa State Park with its famous black sand beach, and local roadside stands for fresh banana bread.
This evening, arrive in peaceful Hāna and settle in for an unforgettable overnight stay at the beautiful Hāna-Maui Resort, surrounded by the island’s most untouched landscapes.
A note from Mandy
Enjoy the journey slowly, soaking in every viewpoint and hidden tropical treasure that makes this drive so special.
Need to know
Maui is truly magical, offering the perfect balance of adventure and relaxation depending on the kind of getaway you want. The Grand Wailea is a stunning, luxurious resort that beautifully suits both romantic escapes and family vacations, while also serving as an ideal home base for exploring the island. On site, dining at Nobu is an unforgettable treat, and nearby favorites like Monkeypod Kitchen by Merriman and Matteo’s Osteria make Wailea a paradise for food lovers—just be sure to make reservations well in advance.
Road to Hāna
No trip to Maui is complete without savoring warm banana bread along the Road to Hāna as you journey toward one of the island’s most dreamlike destinations. The town of Hāna feels like a hidden paradise, and waking up to incredible coffee from Da Mean Bean food truck next to the Hāna-Maui Resort is a must. Along the drive, stop at Waiʻānapanapa State Park to see the famous black sand beach (reservations are required), and take time to hike through the area and soak in the breathtaking coastal views. Another fun stop is the Hāna Lava Tubes, a unique adventure through Maui’s volcanic landscape.
While in Hāna, enjoy casual meals from local food trucks, dinner at the charming Hāna Ranch Restaurant, and relaxing afternoons by the pool at the Hāna-Maui Resort.
Haleakalā & beyond
If you have an extra day, head to the Kipahulu Visitor Center in Haleakalā National Park to hike the Pīpīwai Trail and the Kūloa Point Trail. After your hike, stop at Koki Beach for an authentic lunch at Uncle Russell’s Legendary Koki Huli Huli Chicken, where you can sit back and enjoy the waves, surfers, and cool ocean breeze. End your evening with pizza and live music at Hāna Farms, then return to the resort for a peaceful sunset by the pool.
From snorkeling and whale watching in the winter months to golf, hiking, and unforgettable island scenery, Maui truly has something for everyone. Hawai‘i is the perfect island escape, and Maui is a destination you’ll never stop dreaming about.
Travel Advisor
Mandy Wisenbaker
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