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    Best results for Sailing

    Showing 169-192 of 302 results
    Key West Wind & Wine Sunset Sail
    Sailing

    Key West Wind & Wine Sunset Sail

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

    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
    Sailing

    Commotion on the Ocean: Live Music Sunset Sail

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

    Enjoy a Key West sunset with live music, appetizers, and complimentary beer, wine, champagne, and margaritas
    4.9 • 10.7K reviews
    $101/ guest
    3.5-Hour Jolly Mon Sail and Snorkel Adventure
    Sailing

    3.5-Hour Jolly Mon Sail and Snorkel Adventure

    Sail Pensacola waters and snorkel shallow sites with gear, instruction, and a licensed captain

    Sail Pensacola waters and snorkel shallow sites with gear, instruction, and a licensed captain
    5.0 • 1.8K reviews
    $501
    St. Augustine Live Music Sunset Sail
    Sailing

    St. Augustine Live Music Sunset Sail

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

    Enjoy sunset views with live music, drinks, and snacks aboard a spacious catamaran
    4.8 • 180 reviews
    $77/ person
    Waikiki Friday Night Fireworks Sail with Drinks and Bento
    Sailing

    Waikiki Friday Night Fireworks Sail with Drinks and Bento

    Sail at sunset for front-row views of Waikiki’s Friday fireworks, with drinks and a bento included

    Sail at sunset for front-row views of Waikiki’s Friday fireworks, with drinks and a bento included
    4.6 • 1.4K reviews
    $183/ person
    Kalapaki Sunset Catamaran Cruise
    Sailing

    Kalapaki Sunset Catamaran Cruise

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

    Sail a 50-foot catamaran at sunset with drinks, music, and island history
    $121/ person
    Two-Hour Sail on the Saco River and Saco Bay
    Sailing

    Two-Hour Sail on the Saco River and Saco Bay

    Unwind on an intimate sail with coastal views and space for just six guests

    Unwind on an intimate sail with coastal views and space for just six guests
    5.0 • 376 reviews
    $127/ person
    Extended Sunset Sail
    Sailing

    Extended Sunset Sail

    Enjoy a 4-hour sunset sail with spacious seating and coastal views

    Enjoy a 4-hour sunset sail with spacious seating and coastal views
    5.0 • 376 reviews
    $299/ person
    Boston Harbor Sunset Sail on Schooner Adirondack
    Sailing

    Boston Harbor Sunset Sail on Schooner Adirondack

    Savor a 2-hour sunset cruise past Boston Harbor landmarks aboard an elegant 80-foot schooner

    Savor a 2-hour sunset cruise past Boston Harbor landmarks aboard an elegant 80-foot schooner
    4.7 • 1.5K reviews
    $95/ person
    Boston Harbor Pastries and Prosecco Brunch Sail
    Sailing

    Boston Harbor Pastries and Prosecco Brunch Sail

    Sail Boston Harbor with pastries, coffee, and skyline views

    Sail Boston Harbor with pastries, coffee, and skyline views
    4.4 • 27.5K reviews
    $85/ person
    Private Catamaran Sailing Tour from Manteo
    Private Boat ChartersUp to 6

    Private Catamaran Sailing Tour from Manteo

    Enjoy scenic Roanoke and Albemarle Sounds on a comfortable 40' catamaran

    Enjoy scenic Roanoke and Albemarle Sounds on a comfortable 40' catamaran
    5.0 • 738 reviews
    $543
    Philadelphia Waterfront Sunset Sail
    Sailing

    Philadelphia Waterfront Sunset Sail

    Enjoy golden-hour views of the Delaware River, bridges, and piers on a relaxed 1.5-hour sail

    Enjoy golden-hour views of the Delaware River, bridges, and piers on a relaxed 1.5-hour sail
    $113& up
    Daytime Charleston Harbor Sail
    Sailing

    Daytime Charleston Harbor Sail

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

    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
    Sailing

    Charleston Harbor Sunset Sail on 55-Foot Catamaran

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

    Sail Charleston Harbor at golden hour with music, skyline views, and a full bar
    $54/ person
    Charleston Shared Party Sail on a 55-Foot Catamaran
    Sailing

    Charleston Shared Party Sail on a 55-Foot Catamaran

    Celebrate on a 2-hour daytime sail with onboard bar and upbeat vibes, ages 21+

    Celebrate on a 2-hour daytime sail with onboard bar and upbeat vibes, ages 21+
    $54/ person
    Yorktown Sightseeing Day Sail on Schooner Alliance II
    Sailing

    Yorktown Sightseeing Day Sail on Schooner Alliance II

    Sail a tall ship on the York River with historic sights and chances to spot wildlife

    Sail a tall ship on the York River with historic sights and chances to spot wildlife
    4.7 • 1.9K reviews
    $61/ person
    Seattle Evening Colors Sunset Sail
    Sailing

    Seattle Evening Colors Sunset Sail

    Sail Puget Sound at sunset with skyline views aboard Seattle’s largest public sailing vessel

    Sail Puget Sound at sunset with skyline views aboard Seattle’s largest public sailing vessel
    4.8 • 346 reviews
    $69/ person
    Seattle Tall Ship Weekend Brunch Sail with Buffet
    Sailing

    Seattle Tall Ship Weekend Brunch Sail with Buffet

    Sail Seattle’s harbor with a catered brunch, coffee, tea, and juice aboard a classic tall ship

    Sail Seattle’s harbor with a catered brunch, coffee, tea, and juice aboard a classic tall ship
    4.8 • 346 reviews
    $92/ person
    Waikoloa Signature Sunset Sail
    Sailing

    Waikoloa Signature Sunset Sail

    Unwind on a 1.5-hour coastal sunset sail with a full bar and light bites

    Unwind on a 1.5-hour coastal sunset sail with a full bar and light bites
    4.8 • 498 reviews
    $160/ person
    Long Island Sunset Cruise
    Sailing

    Long Island Sunset Cruise

    Enjoy coastal views, calypso tunes, and bar service on a relaxing 2-hour evening cruise

    Enjoy coastal views, calypso tunes, and bar service on a relaxing 2-hour evening cruise
    4.9 • 93 reviews
    $43/ person
    Champagne Sunset Sail from Margaritaville
    Sailing

    Champagne Sunset Sail from Margaritaville

    Enjoy a Caribbean sunset cruise with open bar and hors d'oeuvres

    Enjoy a Caribbean sunset cruise with open bar and hors d'oeuvres
    4.8 • 4.6K reviews
    $117/ person
    Kona Signature Sunset Sail
    Sailing

    Kona Signature Sunset Sail

    Sail the Kona Coast at sunset with light bites and drinks included

    Sail the Kona Coast at sunset with light bites and drinks included
    4.8 • 498 reviews
    $115/ person
    Charleston Sunset Sail Aboard the Schooner Pride
    Sailing

    Charleston Sunset Sail Aboard the Schooner Pride

    Cruise Charleston Harbor at sunset on a classic tall ship, with a crew ready to point out landmarks as you relax.

    Cruise Charleston Harbor at sunset on a classic tall ship, with a crew ready to point out landmarks as you relax.
    4.7 • 4.9K reviews
    $113/ passenger
    Daytime Dolphin Sail On The Schooner Pride
    Sailing

    Daytime Dolphin Sail On The Schooner Pride

    Cruise Charleston Harbor on an 84-foot tall ship and help hoist the sails as you watch for dolphins

    Cruise Charleston Harbor on an 84-foot tall ship and help hoist the sails as you watch for dolphins
    4.7 • 4.9K reviews
    $57/ person
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