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Best results for

Sailing

Showing 385-408 of 1,008 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
Sunset Sail in Grace Bay

Sunset Sail in Grace Bay

Caribbean sunset catamaran sail with a full open bar

4.9 • 43 reviews
$194/ person
Sunset Catamaran Sail with Live Saxophone in Grace Bay

Sunset Catamaran Sail with Live Saxophone in Grace Bay

Sail into the evening with live saxophone and an open bar

4.9 • 43 reviews
$209/ person
2-Hour Afternoon Sail on Seneca Lake

2-Hour Afternoon Sail on Seneca Lake

Sail Seneca Lake aboard True Love with all ages welcome

4.8 • 178 reviews
$80/ person
2-Hour Private Sailing Charter in Buffalo

2-Hour Private Sailing Charter in Buffalo

Private sailing for celebrations and group gatherings

4.8 • 182 reviews
$345
Schooner Wedding Ceremony Sail in Watkins Glen

Schooner Wedding Ceremony Sail in Watkins Glen

Pair your wedding ceremony with a custom sail

4.8 • 178 reviews
$2,034
Santa Cruz 1-Hour Daytime Sailing Cruise

Santa Cruz 1-Hour Daytime Sailing Cruise

See Santa Cruz’s coastline from a smooth, stable 65-foot catamaran

4.8 • 170 reviews
$47/ person
Santa Cruz 1.5-Hour Beer Tasting Sail

Santa Cruz 1.5-Hour Beer Tasting Sail

Local beer, gourmet pizza, and Monterey Bay views from a 65-foot catamaran

4.8 • 170 reviews
$81/ person
Santa Cruz Daytime Sailing Cruise

Santa Cruz Daytime Sailing Cruise

A relaxed catamaran sail for coastal views and Monterey Bay wildlife

4.8 • 170 reviews
$69/ person
Sunset Catamaran Sail on Monterey Bay in Santa Cruz

Sunset Catamaran Sail on Monterey Bay in Santa Cruz

Ease into the evening with sunset views from a smooth, stable catamaran

4.8 • 170 reviews
$81/ person
Waikiki Sunset Catamaran Sail

Waikiki Sunset Catamaran Sail

Sail off Waikiki at sunset with a pupu platter and skyline views

4.8 • 160 reviews
$95/ person
Sunset Sailing Charter in Harwich

Sunset Sailing Charter in Harwich

A private evening sail with room for your own refreshments

4.8 • 134 reviews
$1,650
Private 2-Hour Sailing Charter in Harwich

Private 2-Hour Sailing Charter in Harwich

Set sail privately with your group on Pleasant Bay

4.8 • 134 reviews
$1,350
Hernando Beach Sunset Cruise

Hernando Beach Sunset Cruise

Watch Gulf Coast skies change color from a 28-foot catamaran

5.0 • 20 reviews
$56/ person
Manteo Sunset Sailing Cruise

Manteo Sunset Sailing Cruise

Sail into a Roanoke Sound sunset aboard an all-electric catamaran

5.0 • 19 reviews
$108/ person
Roanoke Sound Brunch Sailing Cruise

Roanoke Sound Brunch Sailing Cruise

Sail Roanoke Sound aboard a zero-emissions electric catamaran

5.0 • 19 reviews
$918
Afternoon Sailing Cruise in Manteo

Afternoon Sailing Cruise in Manteo

Sail the Roanoke Sound aboard a zero-emissions electric catamaran

5.0 • 19 reviews
$97/ person
Manteo Brunch Cruise

Manteo Brunch Cruise

Sail Roanoke Sound aboard a zero-emissions electric catamaran

5.0 • 19 reviews
$97/ person
Sunset Sailing Charter in Manteo

Sunset Sailing Charter in Manteo

Sail a renewable-energy catamaran into a Roanoke Sound sunset

5.0 • 19 reviews
$1,058
Key West Full-Day Sail & Snorkel Charter

Key West Full-Day Sail & Snorkel Charter

Customize a private day on the water with snorkeling and onboard lunch

5.0 • 18 reviews
$1,060
2-Hour Private Sailing Charter in Key West

2-Hour Private Sailing Charter in Key West

Sail Key West waters with drinks, onboard gear, and a freshwater rinse

5.0 • 18 reviews
$477
Key West Sunset Cruise

Key West Sunset Cruise

Toast the sunset with champagne aboard a private 47-foot sloop

5.0 • 18 reviews
$477
3-Hour Private Sunset Sail In Key West

3-Hour Private Sunset Sail In Key West

Private Key West sunset sail with your music and a flexible start time

4.8 • 71 reviews
$1,634& up
Private Half-Day Catamaran Sail & Snorkel in Key West

Private Half-Day Catamaran Sail & Snorkel in Key West

Sail Key West waters on a private 4-hour charter for up to six guests

4.8 • 71 reviews
$1,907& up
Private Full-Day Catamaran Sail in Key West

Private Full-Day Catamaran Sail in Key West

Spend a full day sailing from Key West with up to 6 guests

4.8 • 71 reviews
$3,677& up
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