Cruises & Sailing

(15 activities)
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    Dinner Cruise Aboard Calypso

    Are you looking for the best sunset views Maui has to offer? Consider the Calypso dinner cruise. This stable, comfortable, triple-deck catamaran leaves from centrally-located Ma’alaea Harbor. The relaxing two-and-a-half-hour excursion gives you time to enjoy a delicious meal, explore the incredible craft, listen to great live music, and watch the sun go down from your place on top of the waves! Seating on the Calypso dinner cruise comfortably accommodates any size group, including couples, families, and even large corporate events.After you’ve settled in, follow your nose to the delicious appetizers, and pick up a fizzy soda or tropical juice. Your Calypso dinner cruise includes two free drinks, and once the catamaran has motored out of the harbor, you can order alcohol. A local live musician plays new and old favorites throughout the Calypso dinner cruise. When it’s time for the delicious main meal, our onboard chef Keoni carves the juicy prime rib. Mahi mahi, teriyaki chicken, steamed vegetables, roasted potatoes, and chocolate cake is also ready for you to eat. There is plenty of time to gaze at the islands of Kaho’olawe and Lanai in the distance. Closer to the boat, you’ll see the Kahalawai Mountains of west Maui as they stretch toward the sky. When humpback whales are visiting the Islands from Alaska, chances are excellent that you will see some of the magnificent marine mammals on your Calypso dinner cruise! You and your group will love this fun time on the sea, so follow the sun, love your loved ones, and have a great meal on the Calypso dinner cruise. Aloha!
    Dinner Cruise Aboard Calypso

    101 Maalaea Rd South Ferry Loading Dock, Wailuku

    • Take a sunset cruise around Maui and see some of the best views the island has to offer aboard the brand new Calypso boat
    • Enjoy a delicious dinner as you relax aboard a luxurious triple-deck catamaran
    • Chat and unwind with your family and friends with complimentary drinks and live music
    • If the timing is right, you’ll even see humpback whales during their visit from Alaska!
    • Plus! There is a glass bottom viewing room aboard the Calypso
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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?!
    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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    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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    Deluxe Kaanapali Sunset Sail

    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!
    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
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    Quicksilver Lahaina 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.
    Quicksilver Lahaina Dinner Cruise

    150 Lahainaluna Rd, Lahaina

    • 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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    Discover Olowalu Snorkel Sail

    So you've made it to the breathtaking island of Maui... now what? Snorkeling at Maui's Mother Reef, of course! On this tour, you'll have the opportunity to experience one of the largest turtle cleaning stations in Hawaii! You'll depart from Lahaina Harbor in the morning by boat. On board, you'll enjoy a delicious breakfast of fresh fruit, brewed Kona coffee, tea, hot cocoa, and pineapple juice. Then, it's ALMOST time to jump in the turquoise blue waters of Olowalu! First, you'll receive a brief snorkeling lesson to ensure that you have a safe and amazing time. You can expect a breathtaking adventure 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 lunch menu includes BBQ teriyaki chicken, fresh tossed green salad, hot buttered corn on the cob, and assorted rolls. 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.
    Discover Olowalu Snorkel Sail

    155 Dickenson Street , Lahaina

    • Sail to Maui's Mother Reef and experience one of the largest turtle cleaning stations in Hawaii
    • Receive a brief snorkeling lesson to ensure that you have a safe, enjoyable time
    • Enjoy a complimentary breakfast and lunch while traveling to and from Lahaina Harbor
    • Relax on the return sale as you sip on a premium, complimentary alcoholic beverage
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    Discover Kaanapali

    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.
    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
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    Atlantis Submarine Adventure and Luau

    Your once-in-a-lifetime Atlantis Submarine Adventure takes you into a spectacular aquatic world in a Maui submarine, and an evening luau is a must for any visit to Maui. The Atlantis Submarine Maui adventure begins with a 15-minute cruise to the dive site. Here, you will board an Atlantis Submarine, the world's first and most technologically advanced passenger submarine. On your 45-minute ride underwater adventure in submarine Maui, you'll see colorful coral reefs and exotic marine creatures. From December through May, you may enjoy whale watching during the ship-to-shore journey to the Maui submarine, as humpback whales make their annual migration through the warm Pacific waters. Then, in the evening, complete your Maui experience with a luau. It's an evening packed with traditional Polynesian entertainment, including a lei greeting, Polynesian music and dance, an imu (underground oven) ceremony, an all-you-can-eat buffet, open bar for island beverages, and -of course- a gorgeous Hawaiian sunset. Phew. Your traditional Hawaiian feast will held at Royal Lahaina Luau, a dazzling oceanfront property on Kaanapali Beach. Here is a sample menu:
    • Main Entrees: Kalua Pig, Kalua Turkey, Fresh Island Fish, Island Chicken
    • Accompaniments: Hawaiian Sweet Potatoes, Fried Rice, Corn, Seven Assorted Salads, Fresh Pineapple, Poi, Lomi Lomi Salmon, Taro and Guava Bread
    • Desserts: Coconut Cream Cake, Chocolate Cake, Haupia (Hawaiian Pudding)
    • Kids Buffet: Hot Dogs, Chicken Nuggets, Macaroni and Cheese, Corn on the Cob and Potato Chips
    Atlantis Submarine Adventure and Luau

    Pioneer Inn, Lahaina

    • Explore the amazing aquatic world in a Maui submarine
    • Enjoy the beautiful coral reefs and amazing sea creatures
    • Relax with a traditional Hawaiian luau featuring buffet, open bar, live music, and dancing
    • View the beautiful sunset from dazzling oceanfront property
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    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.
    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
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    Aloha Friday Sunset Sail

    Up the ante on date night with a romantic sunset sail along the Maui coastline... with live music! On this cruise, you'll kick back local-style to celebrate Aloha Friday! On board, you'll enjoy a delicious select of appetizers and a selection of tasty cocktails -- the first three are free! -- while marveling at beautiful vistas unique to Hawaii. Your jaw will drop at panoramic views of the majestic West Maui Mountains, the islands of Lana'i and Moloka'i, and much more. Here's to an unforgettable sail with an irreplaceable special someone!
    Aloha Friday Sunset Sail

    11 Ma‘alaea Boat Harbor Road, Wailuku

    • Kick back local-style with this Aloha Friday on a 2-hour sunset sail along the Maui coastline... with live music!
    • Enjoy Maui's legendary makani (the wind) as you marvel at panoramic views of the majestic West Maui Mountains, the Lana'i and Moloka'i islands, and more
    • Indulge in a selection of tasty appetizers and an assortment of cocktails -- the first three are free!
    • Experience luxury like never before
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