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Best results for

Sailing

Showing 1-24 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
Tall Ship Harbor Sailing Tour in Seattle

Tall Ship Harbor Sailing Tour in Seattle

Sail Puget Sound on a classic schooner with Seattle skyline views

4.8 • 417 reviews
$69/ person
Guided Hobie Cat Sail with Captain Included

Guided Hobie Cat Sail with Captain Included

Glide across Grapevine Lake on a guided 1-hour Hobie Cat sail with captain included.

4.7 • 419 reviews
$48/ person
Hobie Wave Catamaran Rental on Wai Kai Lagoon

Hobie Wave Catamaran Rental on Wai Kai Lagoon

Sail the Wai Kai Lagoon with captain-led lessons or approved self-operation

4.3 • 337 reviews
$66/ boat
2-Hour Sunset Catamaran Sail in Cocoa Beach

2-Hour Sunset Catamaran Sail in Cocoa Beach

Sail a Cocoa Beach sunset cruise with chances to spot dolphins and manatees

5.0 • 3.9K reviews
$56/ person
Blue Angels Practice Cruise in Pensacola Beach

Blue Angels Practice Cruise in Pensacola Beach

Watch Blue Angels practice from a sailboat on Pensacola Bay

5.0 • 2.1K reviews
$580
Sunset Sailboat Cruise in Beaufort, NC

Sunset Sailboat Cruise in Beaufort, NC

Unwind on a 90-minute evening cruise with coastal views and complimentary beverages

5.0 • 1.5K reviews
$78/ person
Chesapeake Bay Day Sail on a 1935 Ketch in St. Michaels

Chesapeake Bay Day Sail on a 1935 Ketch in St. Michaels

Sail a Historic 1935 Ketch on the Miles River

5.0 • 1.4K reviews
$131/ person
Sunset Sailing Cruise in South Lake Tahoe

Sunset Sailing Cruise in South Lake Tahoe

Sail Lake Tahoe at golden hour with local beer, wine, and non-alcoholic drinks included

5.0 • 492 reviews
$148/ person
1918 Schooner Day Sail on Penobscot Bay from Camden

1918 Schooner Day Sail on Penobscot Bay from Camden

Sail aboard a historic schooner with cushioned seating and crew-led local stories

5.0 • 252 reviews
$68/ person
2-Hour Charleston Harbor Daytime Sail

2-Hour Charleston Harbor Daytime Sail

Harbor sightseeing with landmark views from a spacious catamaran

4.9 • 1.3K reviews
$54/ person
1.5-Hour San Francisco Bay Catamaran Sail

1.5-Hour San Francisco Bay Catamaran Sail

Sail past Alcatraz and under the Golden Gate on a 1.5-hour catamaran cruise

4.9 • 1.1K reviews
$80/ person
Catamaran Sail & Swim with Water Slide in Fort Lauderdale

Catamaran Sail & Swim with Water Slide in Fort Lauderdale

Catamaran cruise with water toys, music, and a swim stop

4.9 • 530 reviews
$112/ person
America's Cup Yacht Sunset Sail on Hilton Head Island

America's Cup Yacht Sunset Sail on Hilton Head Island

Watch Hilton Head's vibrant sunset while relaxing or helping crew aboard the historic Stars & Stripes

4.8 • 8.1K reviews
$77/ person
Hilton Head Island Sunset Sail

Hilton Head Island Sunset Sail

Toast the evening aboard a relaxed coastal catamaran sail

4.9 • 51 reviews
$89/ person
Santa Cruz 1.5-Hour Sunset Sailing Cruise

Santa Cruz 1.5-Hour Sunset Sailing Cruise

Sail Monterey Bay's coastline as the day gives way to sunset

4.8 • 170 reviews
$69/ person
2-Hour Sunset Sail in Charleston Harbor

2-Hour Sunset Sail in Charleston Harbor

Sail the 84-foot Schooner Pride at sunset in Charleston Harbor

4.7 • 5K reviews
$61/ person
Sail to Diamond Head From Waikiki

Sail to Diamond Head From Waikiki

Diamond Head sail with snacks and unlimited nonalcohol drinks

4.7 • 211 reviews
$58/ person
1-Hour Windsurfing Lesson in Key Biscayne

1-Hour Windsurfing Lesson in Key Biscayne

Build windsurfing fundamentals in calm, shallow water

4.2 • 219 reviews
$141
Sunset Cruise in Miami

Sunset Cruise in Miami

Sail into twilight with skyline views, drinks, and light bites

4.0 • 165 reviews
$113/ person
Sail Charleston Harbor on a 90-Minute Dolphin Sail

Sail Charleston Harbor on a 90-Minute Dolphin Sail

Cruise Charleston Harbor on the 84-foot Schooner Pride and spot local wildlife

4.7 • 5K reviews
$50/ person
Waikiki Sunset Sail

Waikiki Sunset Sail

Sunset views and complimentary drinks aboard a Waikiki catamaran

$69/ person
Waikiki Sunset Cruise

Waikiki Sunset Cruise

Bring your own drinks for a sunset sail along Waikiki’s coast

5.0 • 8.5K reviews
$71/ person
Dolphin Sailing Cruise in Cocoa Beach

Dolphin Sailing Cruise in Cocoa Beach

Catamaran Sail Past Cocoa Village with Hands-On Sailing

5.0 • 3.9K reviews
$56/ person
Pensacola Beach Sunset Sail on a 27' Sailboat

Pensacola Beach Sunset Sail on a 27' Sailboat

Sail Pensacola Bay at sunset with hands-on sailing and coastal views

5.0 • 2.1K reviews
$121/ person
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