Discover Sailing Deals in Your City

Sail Aboard Tall Wooden Ship Red Witch in Chicago (Up to 59% Off)

Tall Ship Red Witch

Tall Ship Red Witch

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

$40 $17

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

Offshore Adventures Chicago

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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90-Minute Private BYOB Sailing Trip for Two or Four from Isabella's Cruises (Up to 51% Off)

Isabella's Cruises

Marina Del Ray

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

$450 $219

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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

Southbay Sailing

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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$342 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 $342

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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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$148 for a Day Sailing Cruise for Two from SailNOW ($390 Value)


North Bay

Expert skipper certified by US Sailing and ASA leads scenic day cruises around the bay

$390 $148

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$384 for a Learn-to-Sail Class and ASA Certification from Tradewinds Sailing School & Club ($745 Value)

Tradewinds Sailing School & Club

Marina Bay

After this course, you will be able to sail 25-foot boat in familiar waters without supervision in light to moderate wind and sea conditions

$745 $384

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