Discover Sailing Deals in Your City

Two-Hour Private Sailing Lesson or Leisurely Cruise for Up to Four from Courageous Sailing (50% Off)

Courageous Sailing

Thompson Square - Bunker Hill

$190 $95

Two-Hour BYOB Traditional Sailing Adventure on Boston Harbor from Come Sail Away Now (Up to 61% Off)

Come Sail Away Now

Boston Harbor - Fan Pier Marina

$150 $65

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

Offshore Adventures Chicago

DuSable Harbor

$220 $69

BYOB Afternoon/Evening Cruise or Fireworks Cruise for Two or Up to Six from Carefree Boat Club (Up to 67% Off)

Carefree Boat Club

South of McCormick Place

$175 $69

First-Class Sailing for Two or Six from Chicago Sailboat Charters (Up to 50% Off)

Chicago Sailboat Charters


$199 $99

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

$450 $270

Two Three-Hour Sailing Lessons for One or Two from Marina Sailing Newport Beach (Up to 59% Off)

Marina Sailing Newport Beach

Newport Beach

$600 $247

Sunset Sail for Two or Four or Day Sail for Up to Six from Pacific Sailing (Up to 72% Off)

Pacific Sailing

San Pedro

$270 $99

ASA 101 Basic Keel-Boat Certification Course or Sailing Lessons from Sailors NYC (Up to 44% Off). Four Options.

Sailors NYC

New York

$147 $89

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


City Island

$1,000 $500

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

True North Sailing School

Newport Marina

$720 $360

Sip Wine and Sail the Bay with a USCG-Licensed Captain

Wine and Cheese Sailboat Tours

The Embarcadero

$75 $75

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

Nautic Sailing School


$198 $99

$59 for Baseball Viewing Party on Boat from SF Bay Adventures ($99 Value). Three Dates Available.

SF Bay Adventures

Freda B

$99 $59