Date Night · This Weekend

(4 activities)
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    Captain's Sunset Dinner Sail (Ma‘alaea)

    Come aboard Maui's newest sailing catamaran for an unforgettable dining experience... with a view! You'll begin your evening in the best way possible -- with cocktails and sailing along the pali sea cliffs. After mooring in a protected cove, you'll be served delectable appetizers that may include smoked salmon wedge with crispy pita and fresh dill, tataki-style beef tenderloin on crostini, freshly baked breadsticks dusted with sea salt and lilikoi butter, or other delicious plates. From there on out, Trilogy Excursions crew will be quick to accommodate your every need and will serve your remaining three courses including an entree of your choice! Whether you decide to order the pan seared steak, the mahi-mahi, or a vegetarian pasta, your tastebuds are in for a treat! Dessert and drinks will be enjoyed as the sun sets on another splendid Maui day. You've never experienced luxury like this before.
    Captain's Sunset Dinner Sail (Ma‘alaea)

    11 Ma‘alaea Boat Harbor Road, Wailuku

    • Experience fine dining with an unbeatable view aboard Maui's newest sailing catamaran
    • Begin your evening with cocktails and sailing along the pali sea cliffs
    • Indulge in a gourmet entree of your choice, freshly prepared by Chef Bailey using the finest ingredients
    • Discover true luxury as you enjoy dessert and drinks as the sun sets on another splendid Maui day
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    Maui Dinner Cruise

    Ready to explore the sights of Maui like you never have before? Hop aboard the Quicksilver Dinner Cruise and see the sunset, stars, and beautiful ocean as you move through the waves. Enjoy an amazing steak, fish, chicken, or vegetarian meal while you sip on cocktails and take in the night around you. Bring your dancing shoes because there's sure to be amazing live music and a dance floor waiting. Make the most of your night in Maui with this cruise that is sure to satisfy all of your senses -- plus, you'll be back on land by 7:30 to enjoy the rest of your night in paradise.
    Maui Dinner Cruise

    101 Maalaea Boat Harbor Rd, Wailuku

    • Relax and take in the 360 degree views for sunset
    • Gaze at the islands of Lanai, Kahoolawe, and Molokai in the distance, and during whale season, there is an enormous chance you'll see and hear humpback whales!
    • Enjoy your delicious meal, the unbeatable ocean views, and your fabulous company without interruption
    • Listen to live Hawaiian music as you sip on the two drinks included in your cruise!
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    Teralani Sunset Dinner Cruise

    This sunset cruise will take you sailing past lush, rainbow-crowned mountains on one side of Maui to the islands of Molokai and Lanai. As you sail past these beautiful islands on crystal clear waters, you can enjoy your favorite beverage while dining on a delicious buffet dinner, capping off your day in spectacular fashion. Can you think of a better ending to a day in paradise?
    Teralani Sunset Dinner Cruise

    2780 Kekaa Dr, Lahaina

    • Relax and unwind with a sunset dinner cruise around Maui
    • Enjoy the spectacular views of scenic mountains and the islands of Molokai and Lanai
    • Dine on a delicious dinner buffet along with your favorite beverage as you soak in the stunning sights
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    Sunset Dinner Cruise

    As the sun sets on the horizon, your Maui sunset dinner cruise aboard the Maui Princess takes you sailing along the coast of West Maui to see the islands of Molokai and Lanai light up as the sun set. While you enjoy the spectacular views, you'll be served table-side by the Maui Princess's friendly staff. Enjoy a delicious meal, drinks, dessert and live entertainment in the air-conditioned main cabin or on the upper open-air deck. After dinner, there's live music and dancing in the main cabin, or you can stay at your table to enjoy the remainder of your evening cruise along the coastline.
    Sunset Dinner Cruise

    Pioneer Inn, Lahaina

    • Enjoy a beautiful sunset cruise off the coast of West Maui
    • Explore the islands of Molokai and Lanai and watch them light up as the sun sets
    • Relax and enjoy a dinner complete with drinks, dessert, and live entertainment
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