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

    Best results for Sailing

    Showing 745-768 of 770 results
    Palm Beach Shores 4-Hour Ocean Cruise
    Palm Beach Shores, FL

    Palm Beach Shores 4-Hour Ocean Cruise

    Sail a 42-foot catamaran with refreshments and open-water views

    Sail a 42-foot catamaran with refreshments and open-water views
    5.0 • 2 reviews
    $848& up
    Sunset Sailing Cruise Along Anguilla's Coast
    The Valley, Anguilla, Anguilla

    Sunset Sailing Cruise Along Anguilla's Coast

    Sail the Anguilla coast at sunset with champagne cocktails and hors d’oeuvres

    Sail the Anguilla coast at sunset with champagne cocktails and hors d’oeuvres
    5.0 • 321 reviews
    $306/ person
    Schooner Sailing in Sturgeon Bay
    Sister Bay, WI

    Schooner Sailing in Sturgeon Bay

    Captain-led schooner sailing with room to bring food and drinks

    Captain-led schooner sailing with room to bring food and drinks
    4.9 • 429 reviews
    $60/ person
    3-Hour Sailing Lesson at Hudson River Park
    New York, NY

    3-Hour Sailing Lesson at Hudson River Park

    Learn sailing fundamentals with hands-on instruction on the Hudson River

    Learn sailing fundamentals with hands-on instruction on the Hudson River
    4.6 • 118 reviews
    $133/ person
    Atlantic Highlands 2-Hour Tall Ship Cruise
    Port Norris, NJ

    Atlantic Highlands 2-Hour Tall Ship Cruise

    Sail Sandy Hook Bay aboard a restored 1928 oyster schooner

    Sail Sandy Hook Bay aboard a restored 1928 oyster schooner
    $58/ person
    Sunset Sailing Charter in St. Thomas
    St Thomas, USVI

    Sunset Sailing Charter in St. Thomas

    Sunset views, premium drinks, and hors d'oeuvres aboard a private yacht

    Sunset views, premium drinks, and hors d'oeuvres aboard a private yacht
    5.0 • 77 reviews
    $949
    Cocoa Beach Island Adventure Sailing Charter
    Cocoa Beach, FL

    Cocoa Beach Island Adventure Sailing Charter

    Private catamaran sailing with island stops, paddling, and wildlife viewing

    Private catamaran sailing with island stops, paddling, and wildlife viewing
    5.0 • 3.9K reviews
    $678
    3.5-Hour Sailing Charter in St. Thomas
    St. Thomas, USVI

    3.5-Hour Sailing Charter in St. Thomas

    Private sailing with snorkeling, open bar, and a Christmas Cove option

    Private sailing with snorkeling, open bar, and a Christmas Cove option
    $795
    St. Thomas Sunset Sailing Charter
    St. Thomas, USVI

    St. Thomas Sunset Sailing Charter

    Sail into sunset colors with sparkling wine and coastal bites

    Sail into sunset colors with sparkling wine and coastal bites
    $795
    Key West Sunday Brunch Sail
    Key West, FL

    Key West Sunday Brunch Sail

    Sunday sailing with brunch bites and bottomless mimosas

    Sunday sailing with brunch bites and bottomless mimosas
    5.0 • 365 reviews
    $124/ person
    Sunset Sail in Chelsea
    New York, NY

    Sunset Sail in Chelsea

    Take in NYC sunset views from a quiet sailboat

    Take in NYC sunset views from a quiet sailboat
    4.6 • 118 reviews
    $106/ person
    Gloucester Private Sailing Charter
    Gloucester, MA

    Gloucester Private Sailing Charter

    Private schooner sailing with captain and crew included

    Private schooner sailing with captain and crew included
    5.0 • 107 reviews
    $477& up
    Gloucester Celtic Music Sunset Sail
    Gloucester, MA

    Gloucester Celtic Music Sunset Sail

    Sail into the sunset with live Celtic tunes and sea shanties

    Sail into the sunset with live Celtic tunes and sea shanties
    5.0 • 107 reviews
    $69/ person
    Gloucester Schooner Festival Private Sailing Charter
    Gloucester, MA

    Gloucester Schooner Festival Private Sailing Charter

    Sail in company with visiting schooners during Gloucester Schooner Festival Weekend

    Sail in company with visiting schooners during Gloucester Schooner Festival Weekend
    5.0 • 107 reviews
    $477
    Irvington Moonlight Sailing Cruise
    Irvington, VA

    Irvington Moonlight Sailing Cruise

    Sail the Rappahannock beneath the full moon

    Sail the Rappahannock beneath the full moon
    5.0 • 106 reviews
    $525& up
    South Lake Tahoe Sunset Catamaran Cruise
    South Lake Tahoe, CA

    South Lake Tahoe Sunset Catamaran Cruise

    Sail aboard a 50-foot catamaran on a wind-shaped afternoon cruise

    Sail aboard a 50-foot catamaran on a wind-shaped afternoon cruise
    5.0 • 490 reviews
    $130/ person
    Sunset Catamaran Cruise in South Lake Tahoe
    South Lake Tahoe, CA

    Sunset Catamaran Cruise in South Lake Tahoe

    Sail into golden hour aboard a 50-foot catamaran

    Sail into golden hour aboard a 50-foot catamaran
    5.0 • 490 reviews
    $138/ person
    Full Moon Sailing Cruise in Camden
    Camden, ME

    Full Moon Sailing Cruise in Camden

    Watch sunset and moonrise from Penobscot Bay with live acoustic music

    Watch sunset and moonrise from Penobscot Bay with live acoustic music
    $85/ person
    Private Sunset Sail in Salem
    Salem, MA

    Private Sunset Sail in Salem

    Charter a classic yacht for a relaxed Salem sunset sail

    Charter a classic yacht for a relaxed Salem sunset sail
    5.0 • 180 reviews
    $1,229
    Private Sailing Charter in Salem
    Salem, MA

    Private Sailing Charter in Salem

    A private classic-yacht sail along the North Shore

    A private classic-yacht sail along the North Shore
    5.0 • 180 reviews
    $1,229
    Salem 2-Hour Morning Mimosa Sail
    Salem, MA

    Salem 2-Hour Morning Mimosa Sail

    Raise the sails and sip mimosas aboard a classic yacht on Salem Sound

    Raise the sails and sip mimosas aboard a classic yacht on Salem Sound
    5.0 • 180 reviews
    $62/ person
    Salem Sunday Bloody Mary Sail
    Salem, MA

    Salem Sunday Bloody Mary Sail

    Sail Salem Sound with Sunday Bloody Mary specials and hands-on sailing options

    Sail Salem Sound with Sunday Bloody Mary specials and hands-on sailing options
    5.0 • 180 reviews
    $62
    St. Thomas Match Racing Sailing Lesson
    St Thomas, VI

    St. Thomas Match Racing Sailing Lesson

    Learn racing skills and sail one-design boats at a private yacht club

    Learn racing skills and sail one-design boats at a private yacht club
    4.9 • 1.3K reviews
    $172/ person
    Seattle Intro Sailing Class
    Seattle, WA

    Seattle Intro Sailing Class

    Learn sailing basics aboard a larger cruiser with expert guidance

    Learn sailing basics aboard a larger cruiser with expert guidance
    4.6 • 1.6K reviews
    $208/ person
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