Cruises & Sailing · This Weekend

(13 activities)
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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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    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

    2525 Kaanapali Pkwy, Lahaina

    • 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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    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

    2525 Kaanapali Pkwy, Lahaina

    • 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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    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 Cruise and Royal Lahaina Luau

    The Royal Lahaina Luau regularly sells out weeks in advance, so book ahead to avoid disappointment! Arrive early for your luau and you can take part in traditional Hawaiian crafts that you'll find both interesting and fun. You'll know the feast is about to start when you witness the Imu Ceremony, the ancient tradition in which the roast pig is removed from the underground oven. You'll enjoy an amazing all-you-can-eat buffet dinner including modern American dishes and many Hawaiian delicacies. Then it's time to be entranced by the hula, and the various songs, dances, and stories of the islands, topped off with the thrilling Samoan fire-knife dance! Then, a romantic evening awaits you onboard the stable and spacious Kaulana for a Maui cocktail cruise through the tropical waters to watch a spectacular Hawaiian sunset. Sit back and relax with a cocktail and appetizers, or find a corner with your loved one to watch the sun slip behind the horizon, oohlala!
    Sunset Cruise and Royal Lahaina Luau

    Pioneer Inn, Lahaina

    • Witness the ancient tradition of the Imu ceremony, where the roast pig is removed from the underground oven
    • Savor modern American dishes and traditional Hawaiian delicacies in an all-you-can-eat buffet dinner
    • Watch an exciting performance filled with Hula, dances, stories, and a thrilling Samoan fire-knife dance
    • Enjoy a romantic evening aboard a cocktail cruise through the tropical waters as you enjoy the spectacular sunset
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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 Kaanapali 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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    Sunset Dinner Cruise and Royal Lahaina Luau

    At the luau, you'll enjoy authentic luau cuisine, free-flowing cocktails and the finest hula dancers on the island of Maui. Held in the landscaped grounds of the Royal Lahaina Resort, the luau features entertainment from a dynamic Polynesian revue while you eat and drink the night away. Then, when you take your Maui cocktail cruise on another evening, you'll see the magical island of Maui from a new and thrilling perspective, including the best views of the West Maui Mountains. While you take in the spectacular sunset views, you'll enjoy a freshly-prepared meal, three complimentary drinks, dessert and live entertainment. After dinner, you can have fun on the dance floor with live music, or you can stay at your table to enjoy the remainder of the cruise. Please note that there is a $10 fuel surcharge, per person, included in the price of this booking. Note when booking:This is a two night event, both activities cannot be scheduled on the same day. Please choose the date of your cruise on the calendar and enter the date of your luau following the word "luau" in the "Special Requests" field at the time of booking. Courtesy hotel transportation is provided from specific hotels, please list your hotel in the "Special Requests" field when checking out so that our partner can try to arrange pick up if possible. For dinner, you have a choice between four entrees: Prime rib (carved on board), roasted chicken, macadamia nut crusted mahi-mahi fillet with buerre blanc sauce, and vegetarian cous cous pocket. Please include your choice of entree in the "Special Requests" section at the time of checkout.
    Sunset Dinner Cruise and Royal Lahaina Luau

    Lahaina Harbor, Lahaina

    • Feast on an authentic luau cuisine, complete with cocktails and hula dancers
    • Explore Maui on a cruise to see the West Maui Mountains and perfect sunset views
    • Enjoy live entertainment and dance the night away
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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

    2525 Kaanapali Pkwy, 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 Kaanapali 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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    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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