Best results for Sailing

    Showing 97-120 of 222 results

    Maui Sunset Sail on a Floating Tiki Bar Catamaran

    Sip island cocktails and savor appetizers as you sail at sunset aboard a Hawaiian-built catamaran

    4.8 1K reviews
    $138/ person

    Premium Sunset Dinner Cruise from Ka'anapali

    Savor a buffet dinner and open bar aboard a luxury catamaran at sunset

    4.9 2.1K reviews
    $166/ person

    Holo Holo Sunset Cocktail Sail in Maui

    Sip cocktails as the sun sets on a 2-hour West Maui sail with open bar and appetizers

    4.9 1.9K reviews
    $143/ person

    West Maui Adventure Snorkel Sail

    Sail Kaanapali and snorkel top West Maui reefs with breakfast, lunch, and open bar

    4.9 1.9K reviews
    $177/ person

    Lady Delana 8-Hour Catamaran Charter

    Sail a spacious catamaran to Crab Island with a personalized itinerary for up to 13 guests

    4.9 136 reviews
    $1,248

    Pensacola Beach Sunset Sail on the Jolly Mon

    Unwind on a 2-hour sail with cushioned seating, drinks, and chances to spot dolphins

    5.0 1.8K reviews
    $108& up

    Evening Sunset Sail on the Footloose Catamaran

    Relax on a 40-foot sunset catamaran with tropical music, dolphin sightings, and a complimentary drink

    4.9 2.7K reviews
    $47/ person

    Snorkel, Swim & Dolphin Sail on the Daydreams Sailboat

    Sail to Shell Island for snorkeling, then cruise the Gulf for dolphin sightings with a captain and first mate.

    4.9 2.7K reviews
    $132/ person

    Sunset & Dolphin Sightseeing on the Daydreams Sailboat

    Unwind on a scenic sunset sail with dolphin spotting and complimentary drinks

    4.9 2.7K reviews
    $114/ person

    The Locals Island Charter

    Sail to a secluded beach near Fort McRee for swimming, paddleboarding, and lunch on a private 6-hour charter

    5.0 16 reviews
    $1,344

    3-Hour Charter Aboard a 46' Bali Catamaran

    Sail a spacious 46' Bali catamaran for three hours with room for up to 12 guests

    $2,067

    San Diego Bay Afternoon Sail Aboard A Classic Yacht

    Sip craft beer and wine as you sail San Diego Bay on an intimate six-passenger classic yacht

    5.0 94 reviews
    $143/ person

    San Diego Bay Sunset Sail on a Classic Yacht

    Savor a San Diego Bay sunset with drinks on an intimate six-passenger sail aboard a classic yacht

    5.0 94 reviews
    $143/ person

    Key West Wind & Wine Sunset Sail

    Sip fine wines on a relaxed schooner sail at sunset with craft beers and gourmet bites

    4.9 5.6K reviews
    $148/ person

    Commotion on the Ocean: Live Music Sunset Sail

    Enjoy a Key West sunset with live music, appetizers, and complimentary beer, wine, champagne, and margaritas

    4.9 10.7K reviews
    $101/ guest

    Island Sunset and Skyway Light Show

    Savor sunset on Outback Key, spot dolphins, and cap the night with the Skyway Bridge light show

    5.0 2.3K reviews
    $85/ person

    St. Augustine Live Music Sunset Sail

    Enjoy sunset views with live music, drinks, and snacks aboard a spacious catamaran

    4.8 180 reviews
    $90/ person

    Leila Napali Sunset Sail

    Sail the Napali Coast at sunset with dinner, drinks, and views worth savoring

    4.9 5.9K reviews
    $258/ person

    Kalapaki Sunset Catamaran Cruise

    Sail a 50-foot catamaran at sunset with drinks, music, and island history

    $121/ person

    New York Harbor Group Sail

    Enjoy a 2.5-hour sail with skyline views of the Statue of Liberty and Brooklyn Bridge

    5.0 253 reviews
    $94/ person

    Two-Hour Afternoon Sail

    Ride afternoon breezes across the inlet with a brief ocean sail when conditions allow

    5.0 278 reviews
    $106/ person

    Bella Brunch Cruise

    Start your morning with coffee, mimosas, and coastal views aboard Bella

    4.9 66 reviews
    $159/ person

    Daytime Charleston Harbor Sail

    Enjoy a relaxed 2-hour catamaran sail with daylight harbor views, shade, restrooms, and a card-only bar

    $54/ person

    Charleston Harbor Sunset Sail on 55-Foot Catamaran

    Sail Charleston Harbor at golden hour with music, skyline views, and a full bar

    $54/ person
    145610