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Best results for

Sailing

Showing 73-96 of 1,004 results
Key West, FL86Honolulu, HI65San Diego, CA35St. Augustine, FL28Traverse City, MI26
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  • New York, NY24
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  • Hilton Head Island, SC17
  • Boston, MA16
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  • Saint Michaels, MD15
  • Pensacola Beach, FL14
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2.5-Hour Daytime Sail Charter in Charleston Harbor

2.5-Hour Daytime Sail Charter in Charleston Harbor

Sail Charleston Harbor on a private 36 ft Beneteau—up to 6 guests

5.0 • 297 reviews
$557
Private Sunset Sail & Dolphin Watch in Bluffton

Private Sunset Sail & Dolphin Watch in Bluffton

An evening sail for sunset views and wildlife watching

5.0 • 390 reviews
$472
Private Half-Day Sail on a 1935 Ketch in St. Michaels

Private Half-Day Sail on a 1935 Ketch in St. Michaels

Sail the Miles River aboard a historic 1935 ketch

5.0 • 1.4K reviews
$2,623
Morning Sailing Charter in San Diego

Morning Sailing Charter in San Diego

Private bay sailing with Point Loma or Coronado routes

5.0 • 323 reviews
$525& up
Private Day Sail on a 35' Sailboat in St. Augustine

Private Day Sail on a 35' Sailboat in St. Augustine

Private 2-hour sunset sail for up to 6 in St. Augustine

5.0 • 768 reviews
$894
Sunset Sailing Cruise in Wrightsville Beach

Sunset Sailing Cruise in Wrightsville Beach

Sail into the evening with waterfowl views and possible dolphin sightings

5.0 • 280 reviews
$133/ person
Fort Myers Beach Sunset Sailing Charter

Fort Myers Beach Sunset Sailing Charter

Watch the Gulf sunset from your own private boat

5.0 • 575 reviews
$1,350
Private Pirate Costume Sail on Lake Pontchartrain

Private Pirate Costume Sail on Lake Pontchartrain

Take your pirate celebration onto the water with a private yacht sail

5.0 • 282 reviews
$679
Cruise New York Harbor on a 3-Hour Private Sail

Cruise New York Harbor on a 3-Hour Private Sail

Private 3-hour sail past the Statue of Liberty from Jersey City

5.0 • 516 reviews
$875& up
Private Sail & Swim Charter With Paddle Boards in San Diego

Private Sail & Swim Charter With Paddle Boards in San Diego

Enjoy sailing and time in the water without choosing between them

5.0 • 284 reviews
$1,309
Private Catamaran Charter in Cocoa Beach

Private Catamaran Charter in Cocoa Beach

Sail privately with your group aboard S/V Endless Summer

5.0 • 3.9K reviews
$339
Private New York Harbor Sail Past the Statue of Liberty

Private New York Harbor Sail Past the Statue of Liberty

Set sail on a private New York Harbor cruise with skyline views

5.0 • 265 reviews
$557
Charleston Sunset Sailing Charter

Charleston Sunset Sailing Charter

Sail into the Charleston sunset on a 2.5-hour private charter for up to 6

5.0 • 297 reviews
$635
Shared Afternoon Sailing Charter in Bluffton

Shared Afternoon Sailing Charter in Bluffton

Share a small-group sail and take the helm if you like

5.0 • 390 reviews
$101/ person
Sunset Champagne Cruise in St. Michaels

Sunset Champagne Cruise in St. Michaels

Sail a historic ketch at sunset with champagne and Chesapeake Bay views

5.0 • 1.4K reviews
$159/ person
San Diego 4-Hour Sail & Swim Charter

San Diego 4-Hour Sail & Swim Charter

Cruise San Diego Bay, swim in Glorietta Bay, and explore your preferred route

5.0 • 323 reviews
$795& up
Sail on a Shared Day Charter in St Augustine

Sail on a Shared Day Charter in St Augustine

Sail past St Augustine landmarks on a 2-hour small-group charter

5.0 • 768 reviews
$201/ person
Private 45' Sailing Yacht Charter in Destin

Private 45' Sailing Yacht Charter in Destin

Private daytime sailing cruise with optional hands-on instruction

5.0 • 251 reviews
$456& up
Amelia Island Sunset Sightseeing Cruise

Amelia Island Sunset Sightseeing Cruise

Watch for coastal wildlife and view Fort Clinch from a catamaran

5.0 • 236 reviews
$631
Sailing Charter in Destin on a Stiletto 30 Catamaran

Sailing Charter in Destin on a Stiletto 30 Catamaran

Private catamaran sailing with dolphin watching, snorkeling, and Crab Island

5.0 • 223 reviews
$372
Learn to Sail in New York Harbor for 4 Hours

Learn to Sail in New York Harbor for 4 Hours

Take the helm for hands-on sailing beneath the Manhattan skyline

5.0 • 516 reviews
$2,120
Private Sailing Charter to Point Loma in San Diego

Private Sailing Charter to Point Loma in San Diego

Relax at sea with your own crew and views of the California coast and Mexico

5.0 • 284 reviews
$1,091
Cocoa Beach Private Island Sail Charter

Cocoa Beach Private Island Sail Charter

Private catamaran sailing with a flexible, crew-led escape

5.0 • 3.9K reviews
$452/ boat
Shared New York Harbor Sail with Statue of Liberty Views

Shared New York Harbor Sail with Statue of Liberty Views

Sail New York Harbor in a small group, with skyline and Statue of Liberty views

5.0 • 265 reviews
$94/ person
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