Cruises & Sailing · This Weekend

(6 activities)
Reset Filters
  • Book Now

    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, New York

    • 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
    BOOK NOW ← Back
  • Book Now

    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!
    BOOK NOW ← Back
  • Book Now

    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
    BOOK NOW ← Back
  • Book Now

    Molokini Sail and Snorkel Adventure

    Embark on a 55-foot glass bottom catamaran and take a scenic cruise to Molokini from Maalaea Harbor. On board, enjoy a complimentary continental breakfast of fresh bagels with cream cheese, jams, tropical fruits, Kona coffee and juices. Admire the spectacular views of the stunning white sandy beaches that stretch for miles and the sparkling turquoise ocean water from your boat. Learn about the fascinating history, culture and marine life of Maui from your naturalist expert guide. Arrive at Molokini Crater, and dive into the waters where you'll find abundant sea life and colorful coral reefs. No prior snorkeling experience is necessary -- your local guide will teach you how to snorkel to explore the tropical underwater world. The fun continues on board where you can enjoy the view of the waters from the glass bottom viewing room. You'll have amazing views of the sea creatures all around you. Get a close view of the colorful tropical marine life underneath without getting wet! Choose to relax on the spacious sun deck or slide down the water slide. After snorkeling, enjoy a delicious barbecue lunch, complete with an open bar! Enjoy a choice of chicken breast or pulled pork sandwich, garden burgers, hot dogs, chips and cookies for dessert! Imbibe on beer, wine and soda.
    Molokini Sail and Snorkel Adventure

    Maalaea Harbor, Maalaea

    • Board an exquisite glass bottom catamaran and embark on a scenic cruise from Maalaea harbor to Molokini
    • Enjoy a complimentary continental breakfast with Kona coffee and juices
    • Admire the stunning view of the white, sandy beaches and sparkling turquoise ocean
    • Visit the Molokini Crater where you'll learn how to snorkel to explore the tropical underwater world
    BOOK NOW ← Back
  • 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.
    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
  • Book Now

    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
    BOOK NOW ← Back

Kind words from our customers