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Cruises & Sailing · Tonight

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— Cruises & Sailing
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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.
    $145
    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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    Discover Molokini

    So you've made it to the breathtaking island of Maui... now what? Snorkeling at the Molokini crater of course! Come aboard a spacious catamaran to experience the beautiful Hawaiian waters! You'll be taken to two prime snorkeling locations. The crystal clear waters of Molokini and the remarkable shallows of the Maui coastline are home to plenty of friendly Hawaiian sea turtles awaiting your arrival! You'll benefit from a brief snorkeling lesson before jumping into the turquoise waters and then it's time to explore the island's world-famous marine life. Not to mention you'll also ditch the crowds with these two lesser-known, yet ideal, snorkel sites. Be sure to work up an appetite as you'll feast on homemade cinnamon rolls and BBQ teriyaki chicken -- prepared by the captain himself! And, if you're over 21, you'll get to enjoy two complimentary, premium alcoholic beverages on the return sail. Who could possibly say no to an adventure that is equally scenic, delicious, and boozey?!
    $179
    Discover Molokini

    11 Ma‘alaea Boat Harbor Road, Wailuku

    • Experience the beauty of the Hawaiian waters on a spacious catamaran and visit two prime snorkeling locations
    • Snorkel in the crystal clear waters of Molokini, home to many sea turtles
    • Enjoy homemade cinnamon rolls and BBQ teriyaki chicken for lunch, prepared by your captain
    • Relax on the return sale as you sip on a premium, complimentary alcoholic beverage
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    Discover Kaanapali

    (11)
    So you've made it to the breathtaking island of Maui... now what? Snorkeling at Kaanapali Beach, of course! On this tour, you'll be taken to a prime snorkeling site off Kaanapali beach by boat! You'll be served a delicious continental breakfast on board comprised of cinnamon rolls, fresh fruit, brewed Kona coffee, tea, hot cocoa, and pineapple juice. Then, you'll arrive at the snorkeling destination! You can expect a breathtaking experience as you swim amongst Hawaii's teeming marine life. You're sure to have worked up an appetite mingling with the tropical fishies, and Trilogy Excursions wouldn't let you leave hungry! The BBQ lunch menu includes Captain Coon's hot BBQ teriyaki chicken, fresh tossed green salad with Mom's secret dressing, luau fried rice, and assorted rolls. A true first class luncheon experience! On the return sail, you'll enjoy 2 complimentary alcoholic beverages to enhance the fun! Yes, this is the paradise you've always dreamed of.
    $149
    Discover Kaanapali

    2525 Ka‘anapali Pkwy, Lahaina

    • Experience the beauty of the Hawaiian waters on a boat and visit a prime snorkel site
    • Snorkel in the protected bays of West Maui after receiving a brief snorkeling lesson
    • Enjoy homemade cinnamon rolls for breakfast and BBQ teriyaki chicken for lunch!
    • Relax on the return sale as you sip on a premium, complimentary alcoholic beverage
    BOOK NOW ← Back
    11 positive reviews
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    Deluxe Kaanapali Sunset Sail

    (11)
    Up the ante on date night with a romantic sunset sail aboard an ocean sailing catamaran! This cruise provides the most romantic way to experience the beauty of a Maui sunset. On board, you'll enjoy a delicious assortment of hot and cold, gourmet appetizers while marveling at the stunning vistas. You'll be able to see the Moloka'i and Lana'i islands, spinner dolphins, and flying fish all from the comfort of your boat. And, of course, you'll also get to enjoy a variety of alcoholic beverages. In fact, you'll get three complimentary drinks to kick off the fun! Here's to an unforgettable sail with an irreplaceable special someone!
    $105
    Deluxe Kaanapali Sunset Sail

    2525 Ka‘anapali Pkwy, Lahaina

    • Experience the beauty of a Maui sunset in the most romantic way possible -- aboard an ocean sailing catamaran
    • Marvel at breathtaking views of spinner dolphins, flying fish, and the Moloka'i and Lana'i islands
    • Enjoy an assortment of hot and cold appetizers and three complimentary alcoholic beverages
    • Indulge in an evening of luxury, delicious food, ultimate relaxation, and beautiful vistas
    BOOK NOW ← Back
    11 positive reviews
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  • Book Now

    Captain's Sunset Dinner Sail (Lahaina)

    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.
    $145
    Captain's Sunset Dinner Sail (Lahaina)

    675 Wharf Street , Lahaina

    • Experience fine dining with an unbeatable view aboard Maui's newest sailing catamaran
    • Begin your evening with cocktails and sailing along West Maui’s coastline. After mooring in a protected cove
    • 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
    BOOK NOW ← Back
    Quickview
  • Book Now

    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.
    $117
    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
    BOOK NOW ← Back
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