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

    Best results for Sailing

    Showing 625-648 of 770 results
    Champagne Sunset Sailing Cruise in Key West
    Key West, FL

    Champagne Sunset Sailing Cruise in Key West

    Private sunset sailing with bubbly, wines and a gourmet cheese buffet

    Private sunset sailing with bubbly, wines and a gourmet cheese buffet
    4.9 • 635 reviews
    $1,117
    Key West 1.5-Hour Classic Day Sailing Cruise
    Key West, FL

    Key West 1.5-Hour Classic Day Sailing Cruise

    Sail Key West on Schooner America 2.0 with complimentary soft drinks

    Sail Key West on Schooner America 2.0 with complimentary soft drinks
    4.9 • 593 reviews
    Contact for pricing
    Salem Harbor Sunset Sail on 1812 Schooner
    Salem, MA

    Salem Harbor Sunset Sail on 1812 Schooner

    Watch Salem Sound glow at day’s end while you help raise the sails and toast the sunset with a relaxed drink.

    Watch Salem Sound glow at day’s end while you help raise the sails and toast the sunset with a relaxed drink.
    5.0 • 535 reviews
    $49/ person
    2-Hour Private Sailing Lesson in Nantucket
    Nantucket, MA

    2-Hour Private Sailing Lesson in Nantucket

    Build sailing skills with private coaching tailored to your goals

    Build sailing skills with private coaching tailored to your goals
    5.0 • 2 reviews
    $265
    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 to Wood Island Lighthouse Tour From Kennebunkport
    Saco, ME

    Sail to Wood Island Lighthouse Tour From Kennebunkport

    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 • 430 reviews
    $395/ person
    Sunset Sailing Cruise on Lake Erie
    Sandusky, OH

    Sunset Sailing Cruise on Lake Erie

    Sail into a Lake Erie sunset on the Black Pearl

    Sail into a Lake Erie sunset on the Black Pearl
    5.0 • 54 reviews
    $631
    Full-Day Lake Erie Sailing Charter
    Sandusky, OH

    Full-Day Lake Erie Sailing Charter

    Sail Lake Erie for about 8 hours on a private charter for up to 6 guests

    Sail Lake Erie for about 8 hours on a private charter for up to 6 guests
    5.0 • 54 reviews
    $1,691
    Sail Lake Erie on a 4-Hour Private Charter
    Sandusky, OH

    Sail Lake Erie on a 4-Hour Private Charter

    Sail around Lake Erie’s islands on the Black Pearl for 4 hours

    Sail around Lake Erie’s islands on the Black Pearl for 4 hours
    5.0 • 54 reviews
    $1,055
    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
    Waikiki Friday Fireworks Cruise
    Honolulu, HI

    Waikiki Friday Fireworks Cruise

    Sail at sunset for Waikiki Beach fireworks views

    Sail at sunset for Waikiki Beach fireworks 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 • 768 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
    $138/ person
    2-Hour Choctawhatchee Bay Sailing Charter
    Fort Walton Beach, FL

    2-Hour Choctawhatchee Bay Sailing Charter

    Sail, sightsee, and try your hand at steering a catamaran

    Sail, sightsee, and try your hand at steering a catamaran
    5.0 • 66 reviews
    $371
    Cruise Santa Rosa Island on a Private Sailboat Charter
    Fort Walton Beach, FL

    Cruise Santa Rosa Island on a Private Sailboat Charter

    Sail Santa Rosa Island on a private charter with a licensed captain

    Sail Santa Rosa Island on a private charter with a licensed captain
    5.0 • 66 reviews
    $482& up
    Sunrise Sailing Charter in Destin
    Fort Walton Beach, FL

    Sunrise Sailing Charter in Destin

    Sail Choctawhatchee Bay at dawn for Mid Bay Bridge views

    Sail Choctawhatchee Bay at dawn for Mid Bay Bridge views
    5.0 • 66 reviews
    $345
    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 • 3.3K 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 • 2.1K 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
    4.9 • 565 reviews
    $186/ person
    St. Augustine Nights of Lights Sailing Cruise
    St. Augustine, FL

    St. Augustine Nights of Lights Sailing Cruise

    Private yacht views of St. Augustine's holiday lights

    Private yacht views of St. Augustine's holiday lights
    5.0 • 768 reviews
    $669& 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 • 430 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 • 77 reviews
    $636/ student
    2-Day Sailing Cruise From Barrington
    Barrington, RI

    2-Day Sailing Cruise From Barrington

    Sail beyond Narragansett Bay as an active crewmember

    Sail beyond Narragansett Bay as an active crewmember
    4.9 • 77 reviews
    $1,150/ cabin
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