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

    Best results for Sailing

    Showing 145-168 of 404 results
    Sail, Snorkel & Kayak Key West Sunset Cruise
    Key West, FL

    Sail, Snorkel & Kayak Key West Sunset Cruise

    Sail a historic schooner, snorkel and kayak, then cruise into the Key West sunset

    Sail a historic schooner, snorkel and kayak, then cruise into the Key West sunset
    4.9 • 5.7K reviews
    $148/ person
    Private Key West Sunset Sailing Charter
    Key West, FL

    Private Key West Sunset Sailing Charter

    Private 2-hour sunset sail for up to 30, with wine, beer, and hors d'oeuvres included

    Private 2-hour sunset sail for up to 30, with wine, beer, and hors d'oeuvres included
    4.9 • 5.7K reviews
    $3,426
    Sandbar, Snorkel & Sunset Sail in Key West
    Key West, FL

    Sandbar, Snorkel & Sunset Sail in Key West

    Sail to a Key West sandbar with snorkeling, snacks, and sunset views

    Sail to a Key West sandbar with snorkeling, snacks, and sunset views
    4.9 • 5.7K reviews
    $148/ person
    Proposal & Anniversary Sailing Cruise in Fort Walton Beach
    Fort Walton Beach, FL

    Proposal & Anniversary Sailing Cruise in Fort Walton Beach

    Sail with a licensed captain for a proposal or anniversary cruise

    Sail with a licensed captain for a proposal or anniversary cruise
    4.5 • 27 reviews
    $482
    Morning Schooner Cruise in Bar Harbor
    Bar Harbor, ME

    Morning Schooner Cruise in Bar Harbor

    Sail Frenchman Bay for sea views of Acadia National Park

    Sail Frenchman Bay for sea views of Acadia National Park
    4.4 • 461 reviews
    $48/ person
    Sunset Sailing Cruise With Live Music in Bar Harbor
    Bar Harbor, ME

    Sunset Sailing Cruise With Live Music in Bar Harbor

    Sail at sunset with live folk music on the Margaret Todd

    Sail at sunset with live folk music on the Margaret Todd
    4.4 • 461 reviews
    $61/ person
    Sunset & Fireworks Sailing Cruise in Destin
    Destin, FL

    Sunset & Fireworks Sailing Cruise in Destin

    Sail into Destin Harbor for a private sunset and fireworks view

    Sail into Destin Harbor for a private sunset and fireworks view
    4.9 • 5.6K reviews
    $741& up
    Basic Coastal Cruising Sailing Class in Sandusky
    Sandusky, OH

    Basic Coastal Cruising Sailing Class in Sandusky

    Learn basic coastal cruising skills in a 2-day sailing class

    Learn basic coastal cruising skills in a 2-day sailing class
    5.0 • 41 reviews
    $631/ person
    ASA 111 Sailing Skills Review Class in Sandusky
    Sandusky, OH

    ASA 111 Sailing Skills Review Class in Sandusky

    Review and refresh your ASA 111 sailing skills in a 3-hour class

    Review and refresh your ASA 111 sailing skills in a 3-hour class
    5.0 • 41 reviews
    $207/ person
    Private Sailing Charter on Calibogue Sound, Hilton Head
    Hilton Head Island, SC

    Private Sailing Charter on Calibogue Sound, Hilton Head

    Private captained sail on Calibogue Sound with room for your snacks and drinks

    Private captained sail on Calibogue Sound with room for your snacks and drinks
    4.7 • 344 reviews
    $345
    Afternoon Cocktail Sail Along Waikiki Coastline
    Honolulu, HI

    Afternoon Cocktail Sail Along Waikiki Coastline

    Cruise Waikiki toward Diamond Head with drinks and snacks included

    Cruise Waikiki toward Diamond Head with drinks and snacks included
    $86/ person
    Sail Ko Olina on a 1.5-Hour Sunset Catamaran Cruise
    Honolulu, HI

    Sail Ko Olina on a 1.5-Hour Sunset Catamaran Cruise

    Sail Ko Olina at sunset with live Hawaiian music and an open bar

    Sail Ko Olina at sunset with live Hawaiian music and an open bar
    $160/ person
    Ko Olina Sunset Sail & Luau Experience
    Honolulu, HI

    Ko Olina Sunset Sail & Luau Experience

    Sail Ko Olina at sunset, then head ashore for a Kaula Luau

    Sail Ko Olina at sunset, then head ashore for a Kaula Luau
    $342/ person
    Sail Provincetown on the Schooner Hindu
    Provincetown, MA

    Sail Provincetown on the Schooner Hindu

    Sail Cape Cod Bay on the historic Schooner Hindu

    Sail Cape Cod Bay on the historic Schooner Hindu
    $64/ person
    2-Hour Sunset Sail in Provincetown
    Provincetown, MA

    2-Hour Sunset Sail in Provincetown

    Sail Provincetown at sunset on the historic Schooner Hindu

    Sail Provincetown at sunset on the historic Schooner Hindu
    $94/ person
    Private Afternoon Sail in Waikiki
    Honolulu, HI

    Private Afternoon Sail in Waikiki

    Private Waikiki afternoon catamaran sail with Diamond Head views and beach boarding

    Private Waikiki afternoon catamaran sail with Diamond Head views and beach boarding
    4.9 • 807 reviews
    $2,250
    Private Sunset Catamaran Sail In Cocoa Beach
    Cocoa Beach, FL

    Private Sunset Catamaran Sail In Cocoa Beach

    Sail a private catamaran at sunset with room to lounge

    Sail a private catamaran at sunset with room to lounge
    4.4 • 125 reviews
    $339
    Sail San Francisco Bay & Alcatraz Night Tour
    San Francisco, CA

    Sail San Francisco Bay & Alcatraz Night Tour

    Combine an afternoon bay sail with an Alcatraz Island night visit

    Combine an afternoon bay sail with an Alcatraz Island night visit
    4.7 • 627 reviews
    $139/ person
    Cruise Pensacola Beach for Blue Angels Practice
    Pensacola Beach, FL

    Cruise Pensacola Beach for Blue Angels Practice

    Sail to see the Blue Angels practice from the water (up to 6 guests)

    Sail to see the Blue Angels practice from the water (up to 6 guests)
    5.0 • 1.9K reviews
    $575
    Sail to Sand Island on a 7-Hour Pensacola Beach Cruise
    Pensacola Beach, FL

    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
    Waikiki 1-Hour Friday Night Fireworks Cruise
    Honolulu, HI

    Waikiki 1-Hour Friday Night Fireworks Cruise

    Sail out for close-up views of Honolulu’s Friday night fireworks

    Sail out for close-up views of Honolulu’s Friday night fireworks
    4.8 • 2.3K reviews
    $95/ person
    Private 1.5-Hour Sailing Cruise on the Delaware River
    Philadelphia, PA

    Private 1.5-Hour Sailing Cruise on the Delaware River

    Private Delaware River day sail for up to six guests

    Private Delaware River day sail for up to six guests
    $424/ boat
    Sail the Delaware River on a 3-Hour History Tour
    Philadelphia, PA

    Sail the Delaware River on a 3-Hour History Tour

    Sail the Delaware River and hear Philadelphia waterfront history from your guide

    Sail the Delaware River and hear Philadelphia waterfront history from your guide
    $254/ person
    Golden Hour Cocktail Sail in New York City
    New York, NY

    Golden Hour Cocktail Sail in New York City

    Sail past the Statue of Liberty with a welcome cocktail at golden hour

    Sail past the Statue of Liberty with a welcome cocktail at golden hour
    4.5 • 703 reviews
    $104
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