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

    Best results for Sailing

    Showing 409-432 of 497 results
    Youth Private Sailing Lesson at Jetties Beach
    Nantucket, MA

    Youth Private Sailing Lesson at Jetties Beach

    Build sailing skills with a private youth lesson for up to 3 sailors

    Build sailing skills with a private youth lesson for up to 3 sailors
    5.0 • 2 reviews
    $212
    Sail a 2-Hour Sunset Cruise in Kennebunkport
    Saco, ME

    Sail a 2-Hour Sunset Cruise in Kennebunkport

    Sail into the evening with a small-group sunset cruise

    Sail into the evening with a small-group sunset cruise
    5.0 • 402 reviews
    $138/ person
    Sail Key West on a 2-Hour Champagne Sunset Cruise
    Key West, FL

    Sail Key West on a 2-Hour Champagne Sunset Cruise

    Sail into the Key West sunset with drinks and hors d'oeuvres included

    Sail into the Key West sunset with drinks and hors d'oeuvres included
    4.9 • 593 reviews
    $123/ person
    Cruise Waikiki For Friday Fireworks & Sunset
    Honolulu, HI

    Cruise Waikiki For Friday Fireworks & Sunset

    Sail out for Waikiki’s Friday fireworks with sunset views

    Sail out for Waikiki’s Friday fireworks with sunset views
    4.8 • 1.6K reviews
    $72/ person
    St. Augustine Nights of Lights Sailing Tour
    St. Augustine, FL

    St. Augustine Nights of Lights Sailing Tour

    Sail a 35-foot yacht and admire St. Augustine's dazzling Nights of Lights

    Sail a 35-foot yacht and admire St. Augustine's dazzling Nights of Lights
    5.0 • 762 reviews
    $145/ person
    Maui Sunset Sail on a Floating Tiki Bar Catamaran
    Kihei, HI

    Maui Sunset Sail on a Floating Tiki Bar Catamaran

    Sip island cocktails and savor appetizers as you sail at sunset aboard a Hawaiian-built catamaran

    Sip island cocktails and savor appetizers as you sail at sunset aboard a Hawaiian-built catamaran
    4.8 • 1.1K reviews
    $138/ person
    The Locals Island Charter
    Pensacola, FL

    The Locals Island Charter

    Sail to a secluded beach near Fort McRee for swimming, paddleboarding, and lunch on a private 6-hour charter

    Sail to a secluded beach near Fort McRee for swimming, paddleboarding, and lunch on a private 6-hour charter
    5.0 • 17 reviews
    $1,344
    Dolphin Sightseeing Sail Aboard the Daydreams Sailboat
    Panama City, FL

    Dolphin Sightseeing Sail Aboard the Daydreams Sailboat

    Sail Grand Lagoon and Shell Island with complimentary drinks while spotting dolphins

    Sail Grand Lagoon and Shell Island with complimentary drinks while spotting dolphins
    4.9 • 3K reviews
    $88/ 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 • 2K reviews
    $501
    Sunset & Fireworks Sail in St. Augustine
    Saint Augustine, FL

    Sunset & Fireworks Sail in St. Augustine

    Sail at sunset with live music, drinks, and St. Augustine fireworks views

    Sail at sunset with live music, drinks, and St. Augustine fireworks views
    4.8 • 272 reviews
    $186/ person
    Cruise St. Augustine Nights Of Lights On A Sailboat
    St. Augustine, FL

    Cruise St. Augustine Nights Of Lights On A Sailboat

    Sail the Nights of Lights with dessert and a festive drink

    Sail the Nights of Lights with dessert and a festive drink
    5.0 • 762 reviews
    $668& up
    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
    4.4 • 477 reviews
    $530
    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 • 402 reviews
    $299/ person
    Salem Sound Sail Aboard the Schooner Fame
    Salem, MA

    Salem Sound Sail Aboard the Schooner Fame

    Hands-on 1812-style sail with engaging crew and scenic Salem Sound views

    Hands-on 1812-style sail with engaging crew and scenic Salem Sound views
    5.0 • 535 reviews
    $37/ person
    Sail Repair and Sail Making Course
    Barrington, RI

    Sail Repair and Sail Making Course

    Learn to design, build, and repair sails in a hands-on two-day class

    Learn to design, build, and repair sails in a hands-on two-day class
    4.9 • 70 reviews
    $636/ student
    Sunset Sail Cruise on the Philadelphia Waterfront
    Philadelphia, PA

    Sunset Sail Cruise on the Philadelphia Waterfront

    Sail the Delaware River at sunset with a USCG-licensed captain

    Sail the Delaware River at sunset with a USCG-licensed captain
    $113/ person
    Weekend Sailing Cruise From Barrington to Block Island
    Barrington, RI

    Weekend Sailing Cruise From Barrington to Block Island

    Sail a 42-foot boat to an island while you build skills with an instructor

    Sail a 42-foot boat to an island while you build skills with an instructor
    4.9 • 70 reviews
    $1,150/ cabin
    Hobie Cat Sailing Ride in St. Thomas
    St.Thomas, USVI

    Hobie Cat Sailing Ride in St. Thomas

    Sail Margaritaville Bay with a Hobie Cat captain in 30 or 60 minutes

    Sail Margaritaville Bay with a Hobie Cat captain in 30 or 60 minutes
    4.8 • 4.8K reviews
    $49/ person
    Sunset and Dolphin Watch Sailing Cruise on Island Time II Catamaran
    Panama City Beach, FL

    Sunset and Dolphin Watch Sailing Cruise on Island Time II Catamaran

    Sail calm waters to spot dolphins and enjoy a Gulf sunset with dancing and games

    Sail calm waters to spot dolphins and enjoy a Gulf sunset with dancing and games
    4.9 • 4.9K reviews
    $58/ person
    Sunset Sail in the Heart of the Gorge
    Cascade Locks, OR

    Sunset Sail in the Heart of the Gorge

    Sail into a Gorge sunset on a romantic 2-hour cruise aboard Wy'East

    Sail into a Gorge sunset on a romantic 2-hour cruise aboard Wy'East
    5.0 • 49 reviews
    $143/ person
    3-Hour Private Sailing Charter in Wilmington
    Chapel Hill, NC

    3-Hour Private Sailing Charter in Wilmington

    Customize a private sail with a USCG-licensed captain for up to 6 guests

    Customize a private sail with a USCG-licensed captain for up to 6 guests
    $822
    Ocean Spirit Adult Sunset Sail
    Wailuku, HI

    Ocean Spirit Adult Sunset Sail

    Sail into the sunset on an adults-only catamaran cruise with pupus and island-style music

    Sail into the sunset on an adults-only catamaran cruise with pupus and island-style music
    4.7 • 2.7K reviews
    $149/ person
    Bloodhound Daysail In Provincetown
    Provincetown, MA

    Bloodhound Daysail In Provincetown

    Sail Cape Cod Bay on a family-friendly cruise where you can help raise sails and bring a picnic aboard

    Sail Cape Cod Bay on a family-friendly cruise where you can help raise sails and bring a picnic aboard
    $66/ person
    North Shore Massachusetts Two-Day Scenic Byway Tour
    Providence, RI

    North Shore Massachusetts Two-Day Scenic Byway Tour

    Spend two days exploring charming North Shore towns with a private sunset sail and landmark stops

    Spend two days exploring charming North Shore towns with a private sunset sail and landmark stops
    4.7 • 25 reviews
    $546
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