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    Best results for Sailing

    Showing 1-24 of 403 results
    Sunset Sailing Charter in St Augustine
    Sailing

    Sunset Sailing Charter in St Augustine

    Private 2-hour sunset sail past St. Augustine bayfront landmarks

    Private 2-hour sunset sail past St. Augustine bayfront landmarks
    5.0 • 736 reviews
    $669& up
    Sunset Sailing Cruise in Outer Banks
    Sailing

    Sunset Sailing Cruise in Outer Banks

    Sail a private 3-hour sunset cruise on a 40-foot catamaran

    Sail a private 3-hour sunset cruise on a 40-foot catamaran
    5.0 • 40 reviews
    $655
    4-Hour Private Sailing Charter in Provincetown
    Sailing

    4-Hour Private Sailing Charter in Provincetown

    Sail Provincetown Harbor and Cape Cod Bay on a private 4-hour charter

    Sail Provincetown Harbor and Cape Cod Bay on a private 4-hour charter
    $1,370
    Key West 1.5-Hour Classic Day Sailing Cruise
    Sailing

    Key West 1.5-Hour Classic Day Sailing Cruise

    Sail Key West on Schooner America 2.0 with complimentary soft drinks

    Sail Key West on Schooner America 2.0 with complimentary soft drinks
    4.9 • 2.1K reviews
    $64/ person
    2-Hour Afternoon Sailing Cruise in Provincetown
    Sailing

    2-Hour Afternoon Sailing Cruise in Provincetown

    Sail Provincetown in the afternoon on a 2-hour cruise

    Sail Provincetown in the afternoon on a 2-hour cruise
    5.0 • 35 reviews
    $64/ person
    Private 3-Hour Sailing Lesson in San Diego
    Sailing

    Private 3-Hour Sailing Lesson in San Diego

    Learn to sail in a private 3-hour lesson with a US Coast Guard certified captain

    Learn to sail in a private 3-hour lesson with a US Coast Guard certified captain
    5.0 • 811 reviews
    $689
    Sunset Sailing Cruise on Lake Erie
    Sailing

    Sunset Sailing Cruise on Lake Erie

    Sail into a Lake Erie sunset on the Black Pearl

    Sail into a Lake Erie sunset on the Black Pearl
    5.0 • 34 reviews
    $631
    Hilton Head Sailing on Historic America's Cup Yacht
    Sailing

    Hilton Head Sailing on Historic America's Cup Yacht

    Join the crew or relax on a 1.5-hour Hilton Head coastal sail aboard a historic America’s Cup yacht

    Join the crew or relax on a 1.5-hour Hilton Head coastal sail aboard a historic America’s Cup yacht
    4.8 • 7.7K reviews
    $53/ person
    2-Hour Honolulu Sunset Sailing Cruise
    Sailing

    2-Hour Honolulu Sunset Sailing Cruise

    Sail Honolulu at sunset with Diamond Head views and a full bar onboard

    Sail Honolulu at sunset with Diamond Head views and a full bar onboard
    4.8 • 2.2K reviews
    $144/ person
    Sunset Sailing Cruise From Ko Olina Marina
    Sailing

    Sunset Sailing Cruise From Ko Olina Marina

    Sail Ko Olina at sunset with drinks and light appetizers

    Sail Ko Olina at sunset with drinks and light appetizers
    $138/ person
    2-Hour Oahu South Shore Sailing Cruise
    Sailing

    2-Hour Oahu South Shore Sailing Cruise

    Sail Oahu’s south shore for Diamond Head and Honolulu skyline views

    Sail Oahu’s south shore for Diamond Head and Honolulu skyline views
    4.8 • 2.2K reviews
    $144/ person
    Sunset Sailing Charter in St Augustine
    Sailing

    Sunset Sailing Charter in St Augustine

    Private 2-hour sunset sail for up to 6 in St. Augustine

    Private 2-hour sunset sail for up to 6 in St. Augustine
    5.0 • 736 reviews
    $894
    Sunset Sailing Cruise in St Augustine
    Sailing

    Sunset Sailing Cruise in St Augustine

    Sail into sunset views of St Augustine landmarks on a small-group charter

    Sail into sunset views of St Augustine landmarks on a small-group charter
    5.0 • 736 reviews
    $201/ person
    2-Hour St. Augustine Dolphin & Nature Sailing Tour
    Sailing

    2-Hour St. Augustine Dolphin & Nature Sailing Tour

    Sail St. Augustine waters and learn about dolphins with your guide

    Sail St. Augustine waters and learn about dolphins with your guide
    5.0 • 736 reviews
    $201/ person
    Private Sailing Charter in Honolulu
    Sailing

    Private Sailing Charter in Honolulu

    Book a private sail and choose your own snorkeling or sunset plan

    Book a private sail and choose your own snorkeling or sunset plan
    5.0 • 100 reviews
    $1,809& up
    Sunset Sailing Cruise in Maui
    Sailing

    Sunset Sailing Cruise in Maui

    2-hour Maui sunset sail with live music, menu, and open bar

    2-hour Maui sunset sail with live music, menu, and open bar
    4.9 • 2.8K reviews
    $216/ person
    2-Hour Catamaran Sailing Cruise in Fort Walton Beach
    Sailing

    2-Hour Catamaran Sailing Cruise in Fort Walton Beach

    Sail Choctawhatchee Bay on a 2-hour catamaran adventure

    Sail Choctawhatchee Bay on a 2-hour catamaran adventure
    5.0 • 58 reviews
    $371
    Sunrise Sailing Charter in Destin
    Sailing

    Sunrise Sailing Charter in Destin

    Sail Choctawhatchee Bay at dawn for Mid Bay Bridge views

    Sail Choctawhatchee Bay at dawn for Mid Bay Bridge views
    5.0 • 58 reviews
    $345
    Jolly Mon 2-Hour Sailing Adventure
    Sailing

    Jolly Mon 2-Hour Sailing Adventure

    Sail Pensacola Beach with up to 6 guests and enjoy complimentary beverages

    Sail Pensacola Beach with up to 6 guests and enjoy complimentary beverages
    5.0 • 1.9K reviews
    $120& up
    3-Hour Pensacola Beach Sailing Cruise With Swim Stop
    Sailing

    3-Hour Pensacola Beach Sailing Cruise With Swim Stop

    Sail Pensacola Bay with an optional swim stop on a 27-foot sailboat

    Sail Pensacola Bay with an optional swim stop on a 27-foot sailboat
    5.0 • 1.9K reviews
    $176/ person
    4-Hour Jolly Mon Sailing Adventure
    Sailing

    4-Hour Jolly Mon Sailing Adventure

    Sail Pensacola Bay with a licensed captain, with time to swim or snorkel and spot wildlife.

    Sail Pensacola Bay with a licensed captain, with time to swim or snorkel and spot wildlife.
    5.0 • 1.9K reviews
    $523
    Daytime Catamaran Sailing Cruise
    Sailing

    Daytime Catamaran Sailing Cruise

    Relax on a 35-minute Monterey Bay sail with included drink and snacks

    Relax on a 35-minute Monterey Bay sail with included drink and snacks
    4.9 • 228 reviews
    $63/ person
    4-Hour Sunset Sailing Cruise in Kennebunkport
    Sailing

    4-Hour Sunset Sailing Cruise in Kennebunkport

    Sail for 4 hours at sunset with room to spread out

    Sail for 4 hours at sunset with room to spread out
    5.0 • 376 reviews
    $299/ person
    Take a Private 2-Hour Sailing Lesson in Maine
    Sailing

    Take a Private 2-Hour Sailing Lesson in Maine

    Private sailing lesson for up to 6 with a customized focus

    Private sailing lesson for up to 6 with a customized focus
    5.0 • 376 reviews
    $801& up
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