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

    Best results for Sailing

    Showing 73-96 of 317 results
    Pensacola Beach Sunset Sail on the Jolly Mon
    Pensacola Beach, FL

    Pensacola Beach Sunset Sail on the Jolly Mon

    Unwind on a 2-hour sail with cushioned seating, drinks, and chances to spot dolphins

    Unwind on a 2-hour sail with cushioned seating, drinks, and chances to spot dolphins
    5.0 • 1.9K reviews
    $120& up
    Swim, Snorkel & Dolphin Sail in Panama City Beach
    Panama City, FL

    Swim, Snorkel & Dolphin Sail in Panama City Beach

    Sail to Shell Island Beach for snorkeling, swimming, and dolphin sightseeing

    Sail to Shell Island Beach for snorkeling, swimming, and dolphin sightseeing
    4.9 • 2.8K reviews
    $132/ person
    2-Hour Sunset Dolphin Sail in Panama City Beach
    Panama City, FL

    2-Hour Sunset Dolphin Sail in Panama City Beach

    Sail at sunset and look for dolphins aboard Daydreams

    Sail at sunset and look for dolphins aboard Daydreams
    4.9 • 2.8K reviews
    $114/ person
    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 • 228 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
    5.0 • 94 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
    5.0 • 94 reviews
    $125/ person
    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
    4.5 • 3.9K reviews
    $101/ person
    3.5-Hour Jolly Mon Sail and Snorkel Adventure
    Pensacola Beach, FL

    3.5-Hour Jolly Mon Sail and Snorkel Adventure

    Sail Pensacola waters and snorkel shallow sites with gear, instruction, and a licensed captain

    Sail Pensacola waters and snorkel shallow sites with gear, instruction, and a licensed captain
    5.0 • 1.9K reviews
    $501
    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 • 221 reviews
    $81/ 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
    4.8 • 4.9K reviews
    $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
    $121/ person
    Chrissy Lobster Sloop Cruises
    Bar Harbor, ME

    Chrissy Lobster Sloop Cruises

    Small, intimate cruises available for private charter

    Small, intimate cruises available for private charter
    4.2 • 2.5K reviews
    $530
    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 • 376 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 • 376 reviews
    $694& up
    4-Hour Sunset Sailing Cruise in Kennebunkport
    Saco, ME

    4-Hour Sunset Sailing Cruise in Kennebunkport

    Sail for 4 hours at sunset with room to spread out

    Sail for 4 hours at sunset with room to spread out
    5.0 • 376 reviews
    $299/ person
    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 • 376 reviews
    $801& 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
    4.7 • 1.5K reviews
    $75/ 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 • 1.2K 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 • 77 reviews
    $317
    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 • 328 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 • 253 reviews
    $557
    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 • 253 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 • 699 reviews
    $79/ 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 • 699 reviews
    $161
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