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Best results for

Sailing

Showing 937-960 of 1,004 results
Key West, FL86Honolulu, HI65San Diego, CA35St. Augustine, FL28Traverse City, MI26
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  • New York, NY24
  • Charleston, SC21
  • Chicago, IL18
  • Hilton Head Island, SC17
  • Boston, MA16
  • Newport, RI15
  • Saint Michaels, MD15
  • Pensacola Beach, FL14
  • Bluffton, SC13
  • Cocoa Beach, FL12
  • Salem, MA12
  • Destin, FL11
  • Marina del Rey, CA11
  • San Francisco, CA11
  • Irvington, VA10
  • Kennebunkport, ME10
  • Manteo, NC10
  • Oceanside, CA10
  • Boothbay Harbor, ME9
  • Camden, ME9
Sail Boston Harbor on a 2-Hour Brunch Cruise

Sail Boston Harbor on a 2-Hour Brunch Cruise

Weekend brunch sail on Boston Harbor with pastries, coffee, and tea

4.6 • 438 reviews
$73/ person
Sail Boston Harbor at Sunset on a Tall Ship

Sail Boston Harbor at Sunset on a Tall Ship

Watch the Boston skyline at twilight on a 2-hour tall ship sail

4.6 • 438 reviews
$73/ person
Sail Boston Harbor on a Tall Ship Day Cruise

Sail Boston Harbor on a Tall Ship Day Cruise

Sail Boston Harbor on the Liberty Star tall ship in 1.5 hours

4.6 • 438 reviews
$40/ person
2-Hour Boston Harbor Sunset Sail

2-Hour Boston Harbor Sunset Sail

Sail Boston Harbor at sunset on a classic schooner

4.6 • 438 reviews
$73/ person
2-Hour Historic Boston Harbor Sailing Cruise

2-Hour Historic Boston Harbor Sailing Cruise

Sail Boston Harbor with stories, skyline views, and complimentary pastries

4.6 • 438 reviews
$79/ person
2-Hour Boston Harbor Tall Ships Cruise

2-Hour Boston Harbor Tall Ships Cruise

Cruise Boston Harbor for views of the tall ships on a classic schooner

4.6 • 438 reviews
$77/ person
Boston Harbor Sunset Tall Ships Sail

Boston Harbor Sunset Tall Ships Sail

Sail Boston Harbor at sunset for views of the tall ships and skyline lights

4.6 • 438 reviews
$90/ person
Cape May Historic Afternoon Sail

Cape May Historic Afternoon Sail

Sail Delaware Bay aboard a 1928 oyster schooner

4.6 • 170 reviews
$58/ person
Cape May Family Educational Sailing Cruise

Cape May Family Educational Sailing Cruise

Sail a 1928 oyster schooner with hands-on marine activities

4.6 • 170 reviews
$58/ person
Cape May Oyster Sailing Cruise

Cape May Oyster Sailing Cruise

Sail a historic schooner while enjoying a dozen freshly shucked local oysters

4.6 • 170 reviews
$90/ person
Youth Sailing Program in Cape May

Youth Sailing Program in Cape May

Learn sailing skills and marine science aboard a historic 1928 oyster schooner

4.6 • 170 reviews
$159/ person
Atlantic Highlands 2-Hour Tall Ship Cruise

Atlantic Highlands 2-Hour Tall Ship Cruise

Sail Sandy Hook Bay aboard a restored 1928 oyster schooner

4.6 • 170 reviews
$58/ person
Youth Advanced Sailing Camp With Flying Scot

Youth Advanced Sailing Camp With Flying Scot

Build advanced sailing skills in a 5-day Flying Scot course for ages 8–15

4.6 • 110 reviews
$318/ person
Alexandria 10-Hour Sailing Course

Alexandria 10-Hour Sailing Course

Build practical sailing skills with hands-on Flying Scot instruction

4.6 • 110 reviews
$583/ person
Private Half-Day Sailing & Wildlife Tour in Friday Harbor

Private Half-Day Sailing & Wildlife Tour in Friday Harbor

Private sailing tailored to your interests in the San Juan Islands

5.0 • 4 reviews
$860
New Bern Sunset Sailing Charter

New Bern Sunset Sailing Charter

Sail the Neuse River as the sky changes color at sunset

5.0 • 4 reviews
$619/ boat
Private Sunset Sail in Friday Harbor

Private Sunset Sail in Friday Harbor

Watch daylight fade over the San Juan Islands from the Salish Sea

5.0 • 4 reviews
$573
1.5-Hour New Bern Sailing Charter

1.5-Hour New Bern Sailing Charter

Take the helm on a private Neuse River sail aboard a classic ketch

5.0 • 4 reviews
$321
Private Sailing Lesson in Natick

Private Sailing Lesson in Natick

Build sailing skills with a private instructor-led session

4.6 • 45 reviews
$174/ person
2-Hour Private Sailing Lesson in Nantucket

2-Hour Private Sailing Lesson in Nantucket

Build sailing skills with private coaching tailored to your goals

5.0 • 2 reviews
$265
1-Hour Toddler Sailing Lesson in Nantucket

1-Hour Toddler Sailing Lesson in Nantucket

Help your toddler build confidence on the water with an instructor-led sailing introduction

5.0 • 2 reviews
$133
Women’s Sailing Clinic in Nantucket

Women’s Sailing Clinic in Nantucket

Build sailing confidence with instruction tailored to your experience

5.0 • 2 reviews
$90/ person
Advanced Women's Sailing Clinic in Nantucket

Advanced Women's Sailing Clinic in Nantucket

Refine your sailing technique and build confidence on the water

5.0 • 2 reviews
$143/ person
Palm Beach Shores 4-Hour Ocean Cruise

Palm Beach Shores 4-Hour Ocean Cruise

Sail a 42-foot catamaran with refreshments and open-water views

5.0 • 2 reviews
$848& up
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