Ultimate 7-Day Wailea Adventure with Dining Delights Itinerary

Indulge in a leisurely breakfast at Kō Restaurant, offering a blend of Hawaiian, Chinese, Filipino, Portuguese, Korean, and Japanese flavors. Take a walk along the stunning Wailea Beach to kick off your day.

For lunch, experience the South Maui Gilligans' Island Luau with Dinner and Drinks for a taste of traditional Hawaiian cuisine and entertainment. Spend the rest of the afternoon relaxing at the Wailea Beach or Polo Beach.

Dine at Ferraro's Bar e Ristorante, set against a romantic oceanfront backdrop. Enjoy authentic Italian dishes. After dinner, take a stroll under the stars along the Wailea Beach Path, admiring the luxury resorts and the sound of the waves.

Start with breakfast at Ka'ana Kitchen, where you can enjoy a farm-to-table experience. Then, head to the harbor for the South Maui Lanai Snorkel & Dolphin Watch from Maalaea. Explore the waters around the neighboring island of Lanai.

Refuel with a delightful lunch at Monkeypod Kitchen, known for its casual, contemporary dining. Post-lunch, embark on the Kahului Guided Rainforest and Waterfall Walk to discover Maui's lush interior.

For dinner, choose Matteo's Osteria for an upscale yet relaxed atmosphere, serving handcrafted pastas and a variety of Italian dishes. Conclude your day with a serene evening walk at the Wailea Blue Golf Course, enjoying the tropical breeze.

Wake up early for a magical experience at the Maui Haleakala National Park Sunrise Tour. Afterward, enjoy a breakfast with a view at Humuhumunukunukuāpua'a, named after Hawaii's state fish, offering Polynesian-inspired dishes.

Take a leisurely drive to Makena Beach State Park (Big Beach) and Little Beach for some sun and sand. For lunch, head to Tommy Bahama Restaurant & Bar for a taste of island-inspired cuisine.

As the day winds down, enjoy a sumptuous dinner at Morimoto Maui for a second visit, this time to try different specialties. Conclude your evening with a relaxed drink at the Bistro Molokini.

Start with an exhilarating Maui Road to Hana Helicopter & Waterfall Tour with Landing, taking in the breathtaking aerial views of Maui's lush landscape. For breakfast, enjoy the convenience of an onboard meal during the helicopter tour.

After the helicopter tour, grab a casual lunch at Monkeypod Kitchen again, as it's a local favorite. Spend the rest of the afternoon at the Wailea Beach, relaxing and perhaps trying some water sports.

Dine at Matteo's Osteria for a refined Italian dinner. Afterward, if you still have energy, consider the South Maui PM Snorkel to Coral Gardens or Molokini Crater for a different snorkeling experience under the setting sun.

Enjoy breakfast at Ferraro's Bar e Ristorante with its stunning ocean views. Then, head out for the From Kihei Adventurous Humpback Whale Watch to catch more glimpses of these magnificent creatures.

For lunch, visit Mala Ocean Tavern for a second time, as it's that good. Post-lunch, take a relaxed drive to Wailea Blue Golf Course for some Golf if you're a fan of the sport, or simply enjoy the beautiful surroundings.

Conclude your day with a sumptuous dinner at Ka'ana Kitchen for a second visit, as it's one of the top dining spots in Wailea. After dinner, take a stroll under the stars at the Wailea Beach Path.

For your final morning, enjoy a peaceful breakfast at Kō Restaurant for a third visit, as it's one of the best in Wailea. Then, take a moment of serenity at the Wailea Beach or Polo Beach.

Have lunch at Gannon's for a second visit, and then head out for the South Maui Whale Watch Kayaking and Snorkel Tour in Kihei for a more active afternoon on the water.

As the sun sets on your trip, enjoy a farewell dinner at Tommy Bahama Restaurant & Bar, offering a relaxed, tropical ambiance. Reflect on your week in Wailea as you enjoy your meal.