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Ultimate 7-Day Wailea Maui Adventure

Ultimate 7-Day Wailea Maui Adventure Itinerary

Last updated: 2024 Jun 14

Whales, Waterfalls, and Sunset Dining

Morning
Begin your Maui adventure with a hearty breakfast at Gannon's, known for its panoramic views. After breakfast, head out for an exhilarating Ma'alaea Harbor Whale Watching Catamaran Cruise. Keep an eye out for majestic humpback whales as you cruise the waters.
Afternoon
For lunch, enjoy the fresh catch of the day at Mala Ocean Tavern. Spend your afternoon exploring the lush rainforests and cascading waterfalls on the Kahului Guided Rainforest and Waterfall Walk.
Evening
As the sun sets, indulge in a fine dining experience at Ferraro's Bar e Ristorante. Conclude your day with a leisurely stroll on the beach or a romantic drink at the restaurant's bar.
Bedtime
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Visit Ma'alaea Harbor Whale Watching Catamaran Cruise in Wailea, Maui
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Ma'alaea Harbor Whale Watching Catamaran Cruise

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Visit Kahului Guided Rainforest and Waterfall Walk in Wailea, Maui
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Kahului Guided Rainforest and Waterfall Walk

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Snorkels, Sunsets, and Luau Delights

Morning
Kick off the morning with a sumptuous breakfast at Ka'ana Kitchen, offering a modern twist on traditional Hawaiian cuisine. Post breakfast, gear up for an underwater adventure with the South Maui Molokini and Turtle Town Snorkeling Tour.
Afternoon
After working up an appetite, head to Morimoto Maui for a lunch that combines Japanese flavors with the freshest island ingredients. Spend the rest of your afternoon at leisure, perhaps lounging by the pool or exploring the local boutiques.
Evening
In the evening, immerse yourself in the rich culture of Hawaii with the South Maui Gilligans' Island Luau with Dinner and Drinks. Enjoy traditional performances and a lavish feast under the stars.
Bedtime
Find amazing hotels in Wailea, Maui.
Visit South Maui Molokini & Turtle Town Snorkeling Tour with Meal in Wailea, Maui
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South Maui Molokini and Turtle Town Snorkeling Tour

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Visit South Maui Gilligans' Island Luau with Dinner and Drinks in Wailea, Maui
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South Maui Gilligans' Island Luau with Dinner and Drinks

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Island Hops and Tropical Tastes

Morning
Start your day with a delightful breakfast at Monkeypod Kitchen, known for its casual ambiance and innovative culinary creations. Following breakfast, embark on the South Maui Whale Watching Cruise Aboard Calypso to witness the playful whales in their natural habitat.
Afternoon
For lunch, savor the flavors of the island at Kō Restaurant, where traditional Hawaiian dishes are served with a contemporary flair. Post-lunch, take a short drive to the neighboring city of Kihei to explore its charming beaches and vibrant shops.
Evening
As the sun sets, enjoy a leisurely dinner at Tommy Bahama Restaurant & Bar, offering a relaxed island atmosphere. Conclude your evening with a stroll along the Wailea Beach Path, taking in the breathtaking ocean views.
Bedtime
Find amazing hotels in Wailea, Maui.
Visit South Maui Whale Watching Cruise Aboard Calypso in Wailea, Maui
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South Maui Whale Watching Cruise Aboard Calypso

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Whale Watch Kayaks and Pineapple Pleasures

Morning
Fuel up for the day with a delicious breakfast at Humuhumunukunukuāpua'a, named after Hawaii's state fish. After breakfast, participate in the South Maui Whale Watch Kayaking and Snorkel Tour in Kihei, a unique way to observe the whales and other marine life.
Afternoon
Enjoy a leisurely lunch at Matteo's Osteria, offering a taste of Italy with a Hawaiian twist. Later, take a guided tour of the Hali'imaile Pineapple Farm to learn about the island's pineapple industry and indulge in some pineapple delights.
Evening
For dinner, head back to Wailea and dine at Ka'ana Kitchen for an unforgettable culinary experience. After dinner, consider a relaxing spa treatment to rejuvenate for the remaining days of your trip.
Bedtime
Find amazing hotels in Wailea, Maui.
Visit South Maui Whale Watch Kayaking and Snorkel Tour in Kihei in Wailea, Maui
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South Maui Whale Watch Kayaking and Snorkel Tour in Kihei

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Visit Hali'imaile Pineapple Farm Tour in Wailea, Maui
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Hali'imaile Pineapple Farm

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Road to Hana Wonders and Helicopter Thrills

Morning
Prepare for an early start with a grab-and-go breakfast from Maui Road to Hana Adventure with Breakfast & Lunch. Embark on the iconic Maui Road to Hana Helicopter & Waterfall Tour with Landing to witness the breathtaking landscapes of the island from a unique perspective.
Afternoon
After the helicopter tour, enjoy a picnic lunch at a scenic spot recommended by your pilot. Spend the rest of the afternoon exploring the historic town of Hana and its surrounding natural wonders, including the stunning Wailua Falls.
Evening
Return to Wailea and treat yourself to a well-deserved dinner at Morimoto Maui, where the fusion of Japanese and American cuisine will tantalize your taste buds. Reflect on the day's adventures as you enjoy the elegant waterfront setting.
Bedtime
Find amazing hotels in Wailea, Maui.
Visit Maui Road to Hana Adventure with Breakfast & Lunch in Wailea, Maui
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Maui Road to Hana Adventure with Breakfast & Lunch

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Visit Maui Road to Hana Helicopter & Waterfall Tour with Landing in Wailea, Maui
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Maui Road to Hana Helicopter & Waterfall Tour with Landing

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Sunrise Majesty and Underwater Serenity

Morning
Experience the awe-inspiring Maui Haleakala National Park Sunrise Tour, where you'll witness the magical sunrise from the summit of Haleakalā. Enjoy a continental breakfast as you take in the panoramic views.
Afternoon
For lunch, head to Ferraro's Bar e Ristorante and enjoy a meal with an oceanfront view. Afterward, spend a relaxing afternoon at one of Wailea's pristine beaches or opt for a spa treatment at a luxury resort.
Evening
As the day winds down, dine at Ferraro's Bar e Ristorante for an elegant Italian meal. Consider joining the South Maui Sunset Prime Rib or Mahi Mahi Dinner Cruise for a memorable evening on the water.
Bedtime
Find amazing hotels in Wailea, Maui.
Visit Maui Haleakala National Park Sunrise Tour in Wailea, Maui
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Maui Haleakala National Park Sunrise Tour

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Visit South Maui Sunset Prime Rib or Mahi Mahi Dinner Cruise in Wailea, Maui
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South Maui Sunset Prime Rib or Mahi Mahi Dinner Cruise

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Final Day Relaxation and Reflection

Morning
Enjoy a leisurely breakfast at Mala Ocean Tavern, reminiscing about the adventures of the past week. Take a morning stroll along the Wailea Beach Path or simply relax by the pool, soaking in the tropical ambiance.
Afternoon
For lunch, visit Monkeypod Kitchen once more to savor their famous wood-roasted pizzas and craft cocktails. Spend your final afternoon exploring the upscale shops and galleries of Wailea, picking up souvenirs to remember your trip by.
Evening
Conclude your Maui journey with a spectacular dinner at Kō Restaurant, where the fusion of Asian and island flavors will provide a fitting finale to your culinary escapade. Raise a glass to the memories made and the adventures yet to come.
Bedtime
Find amazing hotels in Wailea, Maui.

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