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

    Best results for Sailing

    Showing 73-96 of 496 results
    Daytime Catamaran Sailing Cruise
    Monterey, CA

    Daytime Catamaran Sailing Cruise

    Relax on a 35-minute Monterey Bay sail with included drink and snacks

    Relax on a 35-minute Monterey Bay sail with included drink and snacks
    4.9 • 239 reviews
    $63/ person
    San Diego Bay Afternoon Sail Aboard A Classic Yacht
    San Diego, CA

    San Diego Bay Afternoon Sail Aboard A Classic Yacht

    Sip craft beer and wine as you sail San Diego Bay on an intimate six-passenger classic yacht

    Sip craft beer and wine as you sail San Diego Bay on an intimate six-passenger classic yacht
    4.9 • 101 reviews
    $125/ person
    San Diego Bay Sunset Sail on a Classic Yacht
    San Diego, CA

    San Diego Bay Sunset Sail on a Classic Yacht

    Savor a San Diego Bay sunset with drinks on an intimate six-passenger sail aboard a classic yacht

    Savor a San Diego Bay sunset with drinks on an intimate six-passenger sail aboard a classic yacht
    4.9 • 101 reviews
    $125/ person
    Sail, Snorkel & Kayak Charter in Key West
    Key West, FL

    Sail, Snorkel & Kayak Charter in Key West

    Private Key West schooner charter with snorkeling, kayaking, drinks, and snacks

    Private Key West schooner charter with snorkeling, kayaking, drinks, and snacks
    4.9 • 5.8K reviews
    $2,409
    Sail a Live Music Sunset Cruise in Key West
    Key West, FL

    Sail a Live Music Sunset Cruise in Key West

    Sunset catamaran sail with live music, appetizers, and included drinks

    Sunset catamaran sail with live music, appetizers, and included drinks
    4.9 • 12.2K reviews
    $101/ person
    Enjoy a Live Music Sunset Sail in Saint Augustine
    Saint Augustine, FL

    Enjoy a Live Music Sunset Sail in Saint Augustine

    Sail Saint Augustine at sunset with live music and complimentary drinks

    Sail Saint Augustine at sunset with live music and complimentary drinks
    4.8 • 272 reviews
    $73/ person
    Waikiki Friday Night Fireworks Sail with Drinks and Bento
    Honolulu, HI

    Waikiki Friday Night Fireworks Sail with Drinks and Bento

    Sail at sunset for front-row views of Waikiki’s Friday fireworks, with drinks and a bento included

    Sail at sunset for front-row views of Waikiki’s Friday fireworks, with drinks and a bento included
    $197/ person
    Friday Night Fireworks Cruise on Kealoha
    Honolulu, HI

    Friday Night Fireworks Cruise on Kealoha

    Watch Waikiki's fireworks from a 55ft catamaran with inside seating and ocean views

    Watch Waikiki's fireworks from a 55ft catamaran with inside seating and ocean views
    $90
    Sunset Catamaran Cruise in Lihue
    Lihue, HI

    Sunset Catamaran Cruise in Lihue

    Cruise Kalapaki at sunset with music, narration, and a full-service bar

    Cruise Kalapaki at sunset with music, narration, and a full-service bar
    4.9 • 1.4K reviews
    $121/ person
    Cruise the Saco River & Saco Bay on a 2-Hour Sail
    Saco, ME

    Cruise the Saco River & Saco Bay on a 2-Hour Sail

    Sail Maine’s coast in a small group of 6 or fewer

    Sail Maine’s coast in a small group of 6 or fewer
    5.0 • 402 reviews
    $127/ person
    Sail on a Private 2-Hour Charter in Maine
    Saco, ME

    Sail on a Private 2-Hour Charter in Maine

    Reserve a private sail for up to 6 on the Saco River and Saco Bay

    Reserve a private sail for up to 6 on the Saco River and Saco Bay
    5.0 • 402 reviews
    $694& up
    Take a Private 2-Hour Sailing Lesson in Maine
    Saco, ME

    Take a Private 2-Hour Sailing Lesson in Maine

    Private sailing lesson for up to 6 with a customized focus

    Private sailing lesson for up to 6 with a customized focus
    5.0 • 402 reviews
    $801& up
    Sail to Wood Island Lighthouse Private Tour in Maine
    Saco, ME

    Sail to Wood Island Lighthouse Private Tour in Maine

    Sail to Wood Island and tour inside the lighthouse and keeper’s house

    Sail to Wood Island and tour inside the lighthouse and keeper’s house
    5.0 • 402 reviews
    $1,707& up
    2-Hour Boston Harbor Sunset Sail Near Castle Island
    Boston, MA

    2-Hour Boston Harbor Sunset Sail Near Castle Island

    Sail Boston Harbor at sunset on an 80-foot schooner

    Sail Boston Harbor at sunset on an 80-foot schooner
    4.8 • 595 reviews
    $107/ person
    Windjammer Sailing Cruise in Traverse City
    Traverse City, MI

    Windjammer Sailing Cruise in Traverse City

    Sail Grand Traverse Bay at 2:30pm for lively winds and peninsula views

    Sail Grand Traverse Bay at 2:30pm for lively winds and peninsula views
    4.8 • 369 reviews
    $65/ person
    Private 2-Hour Sailing Cruise in West Bay
    Traverse City, MI

    Private 2-Hour Sailing Cruise in West Bay

    Sail West Bay on a private cruise for up to 6 people

    Sail West Bay on a private cruise for up to 6 people
    5.0 • 86 reviews
    $317
    Cruise Grand Traverse Bay on a 6-Hour Private Sail
    Traverse City, MI

    Cruise Grand Traverse Bay on a 6-Hour Private Sail

    Private 6-hour sail for up to 6, with time to raise sails and take the wheel

    Private 6-hour sail for up to 6, with time to raise sails and take the wheel
    4.9 • 582 reviews
    $812
    Sunset Sailing Cruise in Traverse City
    Traverse City, MI

    Sunset Sailing Cruise in Traverse City

    Sail Grand Traverse Bay at sunset with a picnic and drinks included

    Sail Grand Traverse Bay at sunset with a picnic and drinks included
    4.9 • 337 reviews
    $256/ person
    Private New York Harbor Sailing Cruise
    Brooklyn, NY

    Private New York Harbor Sailing Cruise

    Private sail around New York Harbor for up to 6 guests

    Private sail around New York Harbor for up to 6 guests
    5.0 • 257 reviews
    $610
    New York Harbor 2.5-Hour Group Sailing Cruise
    Brooklyn, NY

    New York Harbor 2.5-Hour Group Sailing Cruise

    Sail New York Harbor in a small group, with skyline and Statue of Liberty views

    Sail New York Harbor in a small group, with skyline and Statue of Liberty views
    5.0 • 257 reviews
    $94/ person
    NYC Harbor Day Sail on Clipper City Tall Ship
    New York, NY

    NYC Harbor Day Sail on Clipper City Tall Ship

    Sail past the Statue of Liberty and skyline aboard NYC's only passenger tall ship

    Sail past the Statue of Liberty and skyline aboard NYC's only passenger tall ship
    4.5 • 715 reviews
    $82/ person
    Evening Wine and Jazz Concert Sail on Clipper City
    New York, NY

    Evening Wine and Jazz Concert Sail on Clipper City

    Sail past the NYC skyline with live jazz and two glasses of wine on a summer evening

    Sail past the NYC skyline with live jazz and two glasses of wine on a summer evening
    4.5 • 715 reviews
    $169
    Sail a Private Sunset Cruise in Monterey
    Monterey, CA

    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 • 239 reviews
    $996
    Sail a Private Catamaran Cruise in Manteo
    Manteo, NC

    Sail a Private Catamaran Cruise in Manteo

    Private 2.5–3 hour catamaran sail from Manteo for up to 6

    Private 2.5–3 hour catamaran sail from Manteo for up to 6
    4.9 • 597 reviews
    $543
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