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

    Best results for Sailing

    Showing 553-576 of 770 results
    Private Sailing Charter in Manteo
    Manteo, NC

    Private Sailing Charter in Manteo

    Reserve the Rover for a relaxed sailing cruise on the sound

    Reserve the Rover for a relaxed sailing cruise on the sound
    4.9 • 135 reviews
    $796
    2-Hour Afternoon Sail on Seneca Lake
    Watkins Glen, NY

    2-Hour Afternoon Sail on Seneca Lake

    Sail Seneca Lake aboard True Love with all ages welcome

    Sail Seneca Lake aboard True Love with all ages welcome
    4.8 • 19 reviews
    $80/ person
    Morning Sail on Seneca Lake
    Watkins Glen, NY

    Morning Sail on Seneca Lake

    A public morning schooner sail with complimentary water and juice

    A public morning schooner sail with complimentary water and juice
    4.8 • 19 reviews
    $80/ person
    Erie Sunset Cruise
    Erie, PA

    Erie Sunset Cruise

    Sail Lake Erie in the evening and watch the sunset from the water

    Sail Lake Erie in the evening and watch the sunset from the water
    4.7 • 158 reviews
    $21/ person
    Sunset Sailing Charter on the Rappahannock River
    Irvington, VA

    Sunset Sailing Charter on the Rappahannock River

    Private golden-hour sailing aboard a classic 36-foot sailboat

    Private golden-hour sailing aboard a classic 36-foot sailboat
    5.0 • 106 reviews
    $450& up
    Private Afternoon Sailing Charter From Discovery Pier
    Traverse City, MI

    Private Afternoon Sailing Charter From Discovery Pier

    Help Hoist the Sails on Grand Traverse Bay

    Help Hoist the Sails on Grand Traverse Bay
    5.0 • 48 reviews
    $493& up
    Evening Sailing Charter on Grand Traverse Bay
    Traverse City, MI

    Evening Sailing Charter on Grand Traverse Bay

    Private classic sail with room to relax above or below deck

    Private classic sail with room to relax above or below deck
    5.0 • 48 reviews
    $543& up
    Sunset Sail Charter in Salem
    Salem, MA

    Sunset Sail Charter in Salem

    A private sunset outing aboard a historic schooner

    A private sunset outing aboard a historic schooner
    5.0 • 180 reviews
    $1,454
    2-Hour Private Sailing Charter in Buffalo
    Buffalo, NY

    2-Hour Private Sailing Charter in Buffalo

    Private sailing for celebrations and group gatherings

    Private sailing for celebrations and group gatherings
    4.8 • 171 reviews
    $345
    Rincón Sunset Cruise
    Rincon, Puerto Rico

    Rincón Sunset Cruise

    Sail Rincón's coast at sunset with drinks, snacks and ocean views

    Sail Rincón's coast at sunset with drinks, snacks and ocean views
    4.9 • 458 reviews
    $90/ person
    Camden Sunset Sailing Cruise
    Camden, ME

    Camden Sunset Sailing Cruise

    Sail at sunset aboard a 49-passenger windjammer

    Sail at sunset aboard a 49-passenger windjammer
    4.9 • 2.6K reviews
    $74/ person
    Private Vineyard Sound Sailing Charter
    Tisbury, MA

    Private Vineyard Sound Sailing Charter

    Feel the power of sailing on Martha's Vineyard waters

    Feel the power of sailing on Martha's Vineyard waters
    $1,268
    3-Hour Vineyard Sound Sailing Charter
    Tisbury, MA

    3-Hour Vineyard Sound Sailing Charter

    Sail Vineyard Sound with lighthouse views and secluded swim options

    Sail Vineyard Sound with lighthouse views and secluded swim options
    $2,113
    Sunset Saxophone Sail in Grace Bay
    Grace Bay, Turks and Caicos Islands

    Sunset Saxophone Sail in Grace Bay

    Sail aboard Lady Grace with live saxophone music and an open bar

    Sail aboard Lady Grace with live saxophone music and an open bar
    4.9 • 43 reviews
    $224/ person
    Camden 2-Hour Windjammer Day Sail
    Camden, ME

    Camden 2-Hour Windjammer Day Sail

    Sail Maine's rugged coast aboard a tall ship with wide decks and seating

    Sail Maine's rugged coast aboard a tall ship with wide decks and seating
    4.9 • 2.6K reviews
    $68/ person
    Lake Erie Cruise for Up to 6
    Cleveland, OH

    Lake Erie Cruise for Up to 6

    Sail Lake Erie your way, from shoreline explorations to sunset cruises

    Sail Lake Erie your way, from shoreline explorations to sunset cruises
    5.0 • 47 reviews
    $767& up
    Skagway 2.5-Hour Sailing Adventure
    Skagway, AK

    Skagway 2.5-Hour Sailing Adventure

    Take the helm or relax as you sail Lynn Canal’s fjord scenery

    Take the helm or relax as you sail Lynn Canal’s fjord scenery
    5.0 • 26 reviews
    $203/ person
    4-Hour Sailing Charter on Bahia Banderas
    Puerto Vallarta, Jalisco

    4-Hour Sailing Charter on Bahia Banderas

    Sail Bahia Banderas with a private captain and coastal views

    Sail Bahia Banderas with a private captain and coastal views
    5.0 • 6 reviews
    $2,195
    Murrells Inlet Sunset Sailing Charter
    Murrells Inlet, SC

    Murrells Inlet Sunset Sailing Charter

    Sail Murrells Inlet aboard Miss Adventure with your private group

    Sail Murrells Inlet aboard Miss Adventure with your private group
    5.0 • 4 reviews
    $292
    Private Sunset Sail in Key West
    Key West, FL

    Private Sunset Sail in Key West

    Settle into a classic schooner for an intimate Key West sunset

    Settle into a classic schooner for an intimate Key West sunset
    4.9 • 3K reviews
    $134
    Men's Sailing Cruise in Key West
    Key West, FL

    Men's Sailing Cruise in Key West

    A clothing-optional all-male sailing trip with snorkeling, sandbar, or kayaking

    A clothing-optional all-male sailing trip with snorkeling, sandbar, or kayaking
    4.9 • 398 reviews
    $146/ person
    Naturist Sailing Catamaran Charter in Key West
    Key West, FL

    Naturist Sailing Catamaran Charter in Key West

    Sail privately in a clothing-optional setting shaped around your comfort

    Sail privately in a clothing-optional setting shaped around your comfort
    5.0 • 4 reviews
    $1,590
    Naturist Catamaran Charter in Key West
    Key West, FL

    Naturist Catamaran Charter in Key West

    Spend a private day on a clothing-optional sailing catamaran

    Spend a private day on a clothing-optional sailing catamaran
    5.0 • 4 reviews
    $1,855
    Private Sailing Charter in New Bedford
    Sailing

    Private Sailing Charter in New Bedford

    Sail New Bedford Harbor and Buzzards Bay on a private charter

    Sail New Bedford Harbor and Buzzards Bay on a private charter
    4.8 • 24 reviews
    $525& up
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