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    Best results for Sailing

    Showing 97-120 of 403 results
    51' Luxury Sailing Catamaran Charter in Kailua-Kona
    Private Yacht ChartersUp to 6

    51' Luxury Sailing Catamaran Charter in Kailua-Kona

    Customize a private Kona yacht day with snorkeling and seasonal wildlife

    Customize a private Kona yacht day with snorkeling and seasonal wildlife
    4.8 • 498 reviews
    $2,217
    Sunset Dolphin Watch Sailing Cruise in Panama City Beach
    Dolphin Watching

    Sunset Dolphin Watch Sailing Cruise in Panama City Beach

    Sail Grand Lagoon at sunset and watch for dolphins on a 2-hour catamaran cruise

    Sail Grand Lagoon at sunset and watch for dolphins on a 2-hour catamaran cruise
    4.8 • 4.6K reviews
    $58/ person
    2.5-Hour Private Sailing Charter in San Diego Bay
    Yacht Charters

    2.5-Hour Private Sailing Charter in San Diego Bay

    Private sail on San Diego Bay with snacks and drinks for up to six

    Private sail on San Diego Bay with snacks and drinks for up to six
    5.0 • 94 reviews
    $795
    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
    $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 • 228 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
    4.8 • 498 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
    5.0 • 219 reviews
    $456& up
    Sail to Sand Island on a 7-Hour Pensacola Beach Cruise
    Sailing

    Sail to Sand Island on a 7-Hour Pensacola Beach Cruise

    Spend 7 hours sailing, swimming, and grilling on a private trip for up to 6

    Spend 7 hours sailing, swimming, and grilling on a private trip for up to 6
    5.0 • 1.9K reviews
    $773
    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 • 56 reviews
    $918& 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
    $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
    $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
    $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 • 736 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
    4.8 • 1.7K 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
    4.8 • 1.7K reviews
    $402
    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
    5.0 • 153 reviews
    $1,637& up
    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 • 736 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 • 736 reviews
    $13,095
    Sail a Moonlight Cruise in Charleston Harbor
    Sailing

    Sail a Moonlight Cruise in Charleston Harbor

    Moonlight sail past Charleston sights on a 50 ft luxury yacht

    Moonlight sail past Charleston sights on a 50 ft luxury yacht
    4.9 • 247 reviews
    $642& up
    Key West Day Sail with Snorkel & Kayak Lunch
    Sailing

    Key West Day Sail with Snorkel & Kayak Lunch

    Sail Key West's clear waters, kayak mangrove islands, snorkel vibrant reefs, and refuel with a buffet lunch—all in one day.

    Sail Key West's clear waters, kayak mangrove islands, snorkel vibrant reefs, and refuel with a buffet lunch—all in one day.
    4.9 • 5.7K reviews
    $185/ person
    Hilton Head Sunset Sail on Stars & Stripes
    Sailing

    Hilton Head Sunset Sail on Stars & Stripes

    Watch Hilton Head's vibrant sunset while relaxing or helping crew aboard the historic Stars & Stripes

    Watch Hilton Head's vibrant sunset while relaxing or helping crew aboard the historic Stars & Stripes
    4.8 • 7.7K reviews
    $75/ person
    Sail Saco Bay on a 4-Hour Cruise
    Sailing

    Sail Saco Bay on a 4-Hour Cruise

    Sail longer and see more of Saco Bay on a half-day trip

    Sail longer and see more of Saco Bay on a half-day trip
    5.0 • 376 reviews
    $256/ person
    Sail on a 2-Hour Private Charter in Savannah
    Sailing

    Sail on a 2-Hour Private Charter in Savannah

    Sail from Wilmington Island on a private 2-hour charter for up to 6 guests

    Sail from Wilmington Island on a private 2-hour charter for up to 6 guests
    4.9 • 103 reviews
    $423
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