Ultimate 5-Day Maui Adventure Itinerary Itinerary

Kick off the day with a visit to the majestic Haleakala Crater. Witness the breathtaking sunrise from this sacred summit and feel the spiritual energy of the island. Breakfast can be enjoyed with a view at the Haleakala National Park Visitor Center.

After descending from the crater, refuel with a picnic lunch amidst the lush surroundings of the Hali'imaile Pineapple Farm. Post-lunch, embark on a guided Kahului Guided Rainforest and Waterfall Walk to discover hidden waterfalls and the diverse flora of Maui's rainforests.

Conclude your day with a sumptuous dinner at Merriman's Kapalua, offering panoramic ocean views and a menu featuring the best of local ingredients. As you dine, reflect on the day's adventures and prepare for the days ahead.

Start with a breakfast at Cafe O'Lei Kihei, known for its innovative fusion cuisine. Post-breakfast, set out on an From Kihei Adventurous Humpback Whale Watch to witness the mesmerizing dance of humpback whales in their natural habitat.

For lunch, head to Coconut's Fish Cafe for their famous fish tacos and refreshing tropical drinks. Spend your afternoon exploring the scenic Wailea Beach and the upscale shops of The Shops at Wailea.

As the day winds down, enjoy a delightful dinner at Star Noodle, offering Asian-inspired dishes in a casual setting. Cap off the evening with a South Maui Sunset Prime Rib or Mahi Mahi Dinner Cruise, cruising along the coast with live music and the warm breeze as your companions.

Begin with breakfast at Mala Ocean Tavern, where you can enjoy ocean views and a menu filled with local flavors. Post-breakfast, take a scenic drive to the historic town of Lahaina and explore its charming streets and art galleries.

For lunch, visit Monkeypod Kitchen by Merriman and indulge in their handcrafted pizzas and unique cocktails. Afterward, visit the Baldwin Home Museum to learn about the missionary history of Maui and the island's plantation era.

Dine at Fleetwood's on Front St., owned by rock legend Mick Fleetwood, and enjoy a meal to the sound of live music. After dinner, take a leisurely walk along the Lahaina Historic Trail and soak in the ambiance of this former whaling village.

Enjoy a relaxed breakfast at The Mill House, set in the midst of a plantation with panoramic views. After breakfast, take a guided tour of the Maui Tropical Plantation to learn about the island's agricultural history and the diverse crops grown on Maui.

For lunch, savor the flavors of the island at Honu Seafood and Pizza, known for its sustainable seafood and artisanal pizzas. Spend your final afternoon visiting the Makena and La Perouse Bay areas, exploring the rugged lava fields and hidden coves.

Conclude your Maui journey with an elegant dinner at Lahaina Grill, one of the island's top fine dining establishments. Raise a glass to the memories made and the beauty of Maui, and perhaps plan your return to this paradise.