Ultimate 5-Day Kaanapali Dining and Adventure Experience Itinerary

Start your day with a hearty breakfast at Monkeypod Kitchen by Merriman - Kaanapali, Maui, offering a farm-to-table dining experience. After breakfast, drive to the lush Iao Valley State Park in nearby Wailuku. Take a guided nature walk and learn about the valley's history and unique flora.

For lunch, enjoy the casual ambiance and delicious poke bowls at Maui Poke. Post-lunch, continue your exploration with a visit to the Maui Ocean Center, where you can witness a diverse range of marine life, including sharks, rays, and turtles. Spend the afternoon immersing yourself in the oceanic wonders of Hawaii.

Dine at Roy's, an upscale restaurant known for its fusion of Hawaiian and international flavors. After dinner, head back to Kaanapali and unwind with a tropical cocktail at Pau Huaka'i, the perfect setting to reflect on your day of discovery.

Enjoy a relaxed breakfast at Maui Brewing Co. Kā'anapali, where you can pair your meal with one of their locally brewed beers. After breakfast, take a short drive to the Lahaina Historic District, where you can stroll through the charming streets and explore the town's rich history and vibrant art scene.

For lunch, visit Longhi's Kaanapali, a classic Italian restaurant with oceanfront dining. Post-lunch, indulge in some retail therapy at the Whalers Village, an upscale shopping destination with a variety of boutiques and galleries.

Witness a mesmerizing Maui sunset aboard a dinner cruise, departing from Lahaina. Choose a cruise that offers live music and a delicious meal, allowing you to relax and take in the panoramic views of the coastline. After the cruise, return to Kaanapali and cap off the evening with a nightcap at Lokelani Pool Bar.

Start with breakfast at Leilani's on the Beach, where you can enjoy the morning breeze and a delightful meal. After breakfast, immerse yourself in the Old Lahaina Luau, one of the most authentic luaus in Hawaii. Spend the morning learning about Hawaiian culture, music, and dance.

The luau will provide a traditional Hawaiian feast for lunch, featuring kalua pig, poi, and other local delicacies. After the luau, take a guided tour of the Sugar Cane Train, a historic narrow-gauge railway that offers a glimpse into Maui's plantation past. Enjoy the scenic ride through the West Maui mountains and learn about the island's sugar industry.

For dinner, head to The Beach Club Restaurant & Bar and enjoy a sophisticated meal with ocean views. After dinner, take a leisurely walk along the beach or relax with a drink at Inu Pool Bar, reminiscing about the day's cultural experiences.

Have a final breakfast at Dollie's Pub & Café, a local favorite known for its comfort food and friendly atmosphere. After breakfast, take a scenic drive along the Kahekili Highway, also known as Maui's "rollercoaster road," for a memorable farewell to the island.

Stop for lunch at Hale Mo'olelo, a hidden gem that offers a taste of traditional Hawaiian cuisine. After lunch, spend your last afternoon in Maui at Kapalua Beach, where you can relax on the golden sand and take in the beauty of the Kapalua coastline.

Conclude your Maui adventure with a grand dinner at Westin Maui Beach Bar, where you can enjoy a lavish meal with a view of the ocean. Raise a glass to the memories made and the experiences shared during your time in Kaanapali.