Discover Sailing Deals in Your City

$18.25 for a Boston Harbor Tall Ships Sail from Liberty Fleet of Tall Ships (Up to $42 Value)

Liberty Fleet of Tall Ships

North End

Day or evening cruises aboard replica tall ships explore the harbor with views of the Boston skyline and Boston Harbor Islands

$42 $18.25

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Schooner Sail for Two from Classic Harbor Line (Up to 31% Off). Three Options Available.

Classic Harbor Line


Flagship vessel modeled after 1890s schooners can take up to 41 passengers

$110 $85

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Two-Hour BYOB Sailing Cruise for Two or Six from Offshore Adventures Chicago (Up to 70% Off)

Offshore Adventures Chicago


Daytime or sunset Lake Michigan cruises delight with views of the Chicago skyline; passengers can bring their own drinks and playlists

$220 $69

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Sail Aboard Tall Wooden Ship Red Witch in Chicago (Up to 61% Off)

Tall Ship Red Witch

Central Chicago

Passengers relax on Chicago’s only wooden tall ship while viewing the skyline or fireworks; Readers’ Choice award winner

$40 $16

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Two-Hour Private BYOB Sunset Sailing Trip for Two or Four from Isabella's Cruises (Up to 56% Off)

Isabella's Cruises

Marina Del Ray

Sailboat crew takes couples and groups on a BYOB sunset adventure on the water

$450 $199

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Three-Hour Sailing Trip for Two or Three to Six People at Old Plank Sailing Adventures (40% Off)

Old Plank Sailing Adventures

Old Plank Sailing Adventures

Captain Matthew Mancini helms sailing trips on a luxury yacht throughout the coastal waters

$450 $270

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90-Minute Sailing Lesson or BYOB Cruise for One, Two, or Four from South Bay Sailing School (Up to 52% Off)

South Bay Sailing School

Redondo Beach

Up to six aspiring seafarers learn sailing basics or just cruise along the South Bay coastline on a 26-foot sailboat

$75 $39

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One or Three Hands-On Sailing Lessons, or Basic Membership at Sailors NYC (Up to 49% Off)

Sailors NYC

New York

Learn basic sailing skills and terminology from certified instructors aboard an 30-foot+ sloop; membership includes up to 15 sails and perks

$147 $85

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Sailboat Charter for Two or Five People from Kon-Tiki (50% Off)


City Island

Customers sail aboard a 44 ft. sailboat with a teak deck and a cheery mahogany interior

$1,000 $500

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$360 for Three-Day Basic Sailing 101 Course at True North Sailing School ($720 Value)

True North Sailing School

Newport Marina

Three-day course splits time in the classroom and on the water, teaching students the basics of sailing a small vessel

$720 $360

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Introduction Sailing Class at Afterguard Sailing Academy (Up to 50% Off). Three Options Available.

Afterguard Sailing Academy

Multiple Locations

Instructors acquaint students with sailing vernacular and basic techniques during hands-on sailing sessions

$90 $55

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3.5-Hour Sailing Lesson for Two or Four at Nautic Sailing School (Up to 50% Off)

Nautic Sailing School


3.5-hour sailing lessons for two or four people on top-of-the-line sailboats, including instructions on safety and operations

$198 $99

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$41 for a Two-Hour Public Sunset or Afternoon Cruise for Two from Bay Breeze Charters ($90 Value)

Bay Breeze Charters


A seasoned crew steers a 51-ft. yacht past Alcatraz and under Golden Gate Bridge during a festive public cruise

$90 $41

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