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    1. Local experiences/
    2. All experiences/
    3. sailing

    Best results for Sailing

    Showing 145-168 of 510 results
    Cruise San Diego Bay on a Private Sailing Charter
    Yacht Charters

    Cruise San Diego Bay on a Private Sailing Charter

    Sail San Diego Bay on a private charter for up to six guests

    Sail San Diego Bay on a private charter for up to six guests
    4.4 • 244 reviews
    $1,200& up
    Sail a Private Sunset Cruise in Monterey
    Sailing

    Sail a Private Sunset Cruise in Monterey

    Private keelboat sailing for up to 6 from Old Fisherman’s Wharf

    Private keelboat sailing for up to 6 from Old Fisherman’s Wharf
    4.9 • 229 reviews
    $996
    Kona Tradewind Day Sail
    Sailing

    Kona Tradewind Day Sail

    Glide along the Kona Coast on a 1.5-hour sailing catamaran with drinks and coastal views

    Glide along the Kona Coast on a 1.5-hour sailing catamaran with drinks and coastal views
    4.9 • 534 reviews
    $92/ person
    Sail a Private Daytime Cruise in Destin
    Sailing

    Sail a Private Daytime Cruise in Destin

    Private daytime sailing cruise with optional hands-on instruction

    Private daytime sailing cruise with optional hands-on instruction
    4.9 • 5.6K reviews
    $456& up
    Sail a Private Charter on Oahu's North Shore
    Sailing

    Sail a Private Charter on Oahu's North Shore

    Private sailing charter on Oahu’s North Shore for up to 6 people

    Private sailing charter on Oahu’s North Shore for up to 6 people
    5.0 • 58 reviews
    $1,147& up
    Learn To Sail Lesson In San Diego
    Sailing

    Learn To Sail Lesson In San Diego

    Get hands-on sailing instruction at the Marriott Marquis Marina

    Get hands-on sailing instruction at the Marriott Marquis Marina
    4.4 • 244 reviews
    $195/ person
    Learn to Sail Lesson in Coronado
    Sailing

    Learn to Sail Lesson in Coronado

    Learn basic sailing skills in a 2-hour session at Loews Coronado

    Learn basic sailing skills in a 2-hour session at Loews Coronado
    4.4 • 244 reviews
    $150/ person
    Learn to Sail in Mission Bay San Diego
    Sailing

    Learn to Sail in Mission Bay San Diego

    Learn basic sailing skills on Mission Bay with an ASA certified instructor

    Learn basic sailing skills on Mission Bay with an ASA certified instructor
    4.4 • 244 reviews
    $195/ person
    3-Hour Basic Keelboat Prep Class in St. Augustine
    Sailing

    3-Hour Basic Keelboat Prep Class in St. Augustine

    Learn sailing basics with classroom and dockside instruction

    Learn sailing basics with classroom and dockside instruction
    5.0 • 740 reviews
    $275/ person
    Sail a 2-Hour Private Cruise in Traverse City
    Sailing

    Sail a 2-Hour Private Cruise in Traverse City

    Private 2-hour sail on Grand Traverse Bay with hands-on sailing options

    Private 2-hour sail on Grand Traverse Bay with hands-on sailing options
    4.9 • 527 reviews
    $370
    Sail a 2-Hour Private Sunset Cruise in Traverse City
    Sailing

    Sail a 2-Hour Private Sunset Cruise in Traverse City

    Private sunset sail on Grand Traverse Bay with hands-on sailing options

    Private sunset sail on Grand Traverse Bay with hands-on sailing options
    4.9 • 527 reviews
    $402
    Sail a Private Waikiki Catamaran Charter
    Sailing

    Sail a Private Waikiki Catamaran Charter

    Charter your own Waikiki catamaran for sailing, snorkeling, and swimming

    Charter your own Waikiki catamaran for sailing, snorkeling, and swimming
    5.0 • 92 reviews
    $1,218& up
    Sail a Merit 25 in Mission Bay
    Sailing

    Sail a Merit 25 in Mission Bay

    Rent a Merit 25 for active sailing in Mission Bay

    Rent a Merit 25 for active sailing in Mission Bay
    4.4 • 244 reviews
    $125/ boat
    Sail the Florida Keys on a 12-Hour Charter
    Sailing

    Sail the Florida Keys on a 12-Hour Charter

    Spend a full day sailing from Key West with up to 6 guests

    Spend a full day sailing from Key West with up to 6 guests
    4.9 • 69 reviews
    $3,677& up
    Sail on a Private Charter in Maalaea Bay
    Yacht Charters

    Sail on a Private Charter in Maalaea Bay

    Book a private S/V Nova sailing charter for up to 6 guests

    Book a private S/V Nova sailing charter for up to 6 guests
    $1,637& up
    Private 8-Hour Yacht Charter in Key West
    Yacht Charters

    Private 8-Hour Yacht Charter in Key West

    Charter a private sailing catamaran or power yacht for 8 hours of snorkeling and island stops

    Charter a private sailing catamaran or power yacht for 8 hours of snorkeling and island stops
    4.9 • 54 reviews
    $6,867
    Sail a Private 1-Hour Moonlight Charter in St. Augustine
    Yacht Charters

    Sail a Private 1-Hour Moonlight Charter in St. Augustine

    Private 1-hour sailing date with bubbly, strawberries, and photos

    Private 1-hour sailing date with bubbly, strawberries, and photos
    5.0 • 740 reviews
    $1,119& up
    Evening Private Yacht Charter in New York
    Yacht Charters

    Evening Private Yacht Charter in New York

    Charter the sailing yacht Ventura for a 2-hour private evening cruise for up to 30 guests

    Charter the sailing yacht Ventura for a 2-hour private evening cruise for up to 30 guests
    5.0 • 66 reviews
    $4,134
    Afternoon Snorkel Cruise in Key West
    Snorkeling

    Afternoon Snorkel Cruise in Key West

    Snorkel the Florida Keys Reef on a sailing cruise with gear, instruction, and drinks included

    Snorkel the Florida Keys Reef on a sailing cruise with gear, instruction, and drinks included
    4.7 • 8K reviews
    $46/ person
    Hold a 2-Hour Dockside Yacht Wedding in St. Augustine
    Event Planning

    Hold a 2-Hour Dockside Yacht Wedding in St. Augustine

    Get married dockside on a luxury sailing yacht with up to 20 guests

    Get married dockside on a luxury sailing yacht with up to 20 guests
    5.0 • 740 reviews
    $10,058
    Tie the Knot Dockside in St. Augustine
    Event Planning

    Tie the Knot Dockside in St. Augustine

    Hold a dockside wedding ceremony with a sailing yacht backdrop for up to 30 guests

    Hold a dockside wedding ceremony with a sailing yacht backdrop for up to 30 guests
    5.0 • 740 reviews
    $13,095
    Turtle Canyon Snorkeling Cruise From Waikiki
    Snorkeling

    Turtle Canyon Snorkeling Cruise From Waikiki

    Snorkel Turtle Canyon with paddling and sailing on a 3-hour family-friendly cruise

    Snorkel Turtle Canyon with paddling and sailing on a 3-hour family-friendly cruise
    $128/ person
    Customize a 4-Hour Private Yacht Charter
    Yacht Charters

    Customize a 4-Hour Private Yacht Charter

    Charter a private yacht for 4 hours with snorkeling or sailing options

    Charter a private yacht for 4 hours with snorkeling or sailing options
    4.9 • 54 reviews
    $4,029
    19' Sailboat Rental in Nantucket for 2 Hours
    Boat RentalsUp to 3

    19' Sailboat Rental in Nantucket for 2 Hours

    Enjoy a two-hour self-guided sail aboard a stable Rhodes 19 from Jetties Sailing Center

    Enjoy a two-hour self-guided sail aboard a stable Rhodes 19 from Jetties Sailing Center
    5.0 • 2 reviews
    $186
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