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Best results for

Sailing

Showing 97-120 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
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Private Sunset Sailboat Charter in Charleston

Private Sunset Sailboat Charter in Charleston

Sail into the Charleston sunset on a private 32 ft boat for up to 6 guests

5.0 • 297 reviews
$635
Private Sunset Sail in Hilton Head Island

Private Sunset Sail in Hilton Head Island

Sail into sunset views with your private group

5.0 • 390 reviews
$535& up
Full-Day Private Sailing Charter in St. Michaels

Full-Day Private Sailing Charter in St. Michaels

Private catamaran sailing with harbor views and Miles River breezes

5.0 • 1.4K reviews
$3,453
San Diego Rady Shell Concert Sailing Experience

San Diego Rady Shell Concert Sailing Experience

Sail to a Rady Shell concert and watch from the water

5.0 • 323 reviews
$795& up
Sunset Sailing Cruise in St Augustine

Sunset Sailing Cruise in St Augustine

Sail into sunset views of St Augustine landmarks on a small-group charter

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

Private Sunset Sailing Charter on a 45' Yacht in Destin

Sail into the Destin sunset on a private, quiet cruise

5.0 • 251 reviews
$513& up
2-Hour Private Sailing Charter in Newport

2-Hour Private Sailing Charter in Newport

Sail Narragansett Bay on a private 36-foot sloop with your captain

5.0 • 210 reviews
$419
Sail & Swim Charter in Destin on a Stiletto 30

Sail & Swim Charter in Destin on a Stiletto 30

Sail, snorkel, and explore Crab Island from Destin

5.0 • 223 reviews
$509
2-Hour New York Harbor Sailing Charter

2-Hour New York Harbor Sailing Charter

Private sail past the Statue of Liberty and New York Harbor landmarks

5.0 • 516 reviews
$742& up
2-Hour Private Sailing Cruise in Folly Beach

2-Hour Private Sailing Cruise in Folly Beach

Sail the Folly River on a private 2-hour cruise for up to 6 guests

5.0 • 214 reviews
$477
Private Catamaran Sail & Dolphin Watching in Cocoa Beach

Private Catamaran Sail & Dolphin Watching in Cocoa Beach

Celebrate or unwind on a private coastal sail

5.0 • 3.9K reviews
$339
Private Apostle Islands Sail & Sea Cave Exploration

Private Apostle Islands Sail & Sea Cave Exploration

Explore smaller sea caves on a private sail through sheltered island waters

5.0 • 203 reviews
$891
Sail a Catered Sunset Cruise in Charleston

Sail a Catered Sunset Cruise in Charleston

Catered 2.5-hour sunset sail for up to 6 guests

5.0 • 297 reviews
$1,022
Shared Afternoon Sailing Tour in Bluffton

Shared Afternoon Sailing Tour in Bluffton

Take the helm or relax on a motor-free public afternoon sail

5.0 • 390 reviews
$127/ person
2-Hour Chesapeake Bay Sailing Cruise

2-Hour Chesapeake Bay Sailing Cruise

Sail the Miles River aboard a spacious catamaran

5.0 • 1.4K reviews
$242/ person
Private San Francisco Bay Sailing Charter From Sausalito

Private San Francisco Bay Sailing Charter From Sausalito

Sail San Francisco Bay your way, with time to take the helm or relax aboard

5.0 • 199 reviews
$636& up
Cruise St. Augustine Bayfront on a Private 2-Hour Sail

Cruise St. Augustine Bayfront on a Private 2-Hour Sail

Private 2-hour sail past St. Augustine’s historic bayfront sites

5.0 • 768 reviews
$797& up
Private Sunset Catamaran Sail in Folly Beach

Private Sunset Catamaran Sail in Folly Beach

Sail into the Folly River marsh at sunset on a private catamaran

5.0 • 190 reviews
$398
Private 3.5-Hour Sailing Cruise in Newport

Private 3.5-Hour Sailing Cruise in Newport

Sail Narragansett Bay on a private 3.5-hour cruise aboard the 36' sloop Hurrah

5.0 • 210 reviews
$843
Destin Sunset Sailing Charter

Destin Sunset Sailing Charter

Sail Destin Harbor aboard a private Stiletto 30 catamaran at sunset

5.0 • 223 reviews
$412
Jersey City Sunset Sailing Charter

Jersey City Sunset Sailing Charter

Golden-hour harbor views from a private classic sailboat

5.0 • 516 reviews
$790& up
Salem 2-Hour Classic Yacht Sail

Salem 2-Hour Classic Yacht Sail

Take the helm or relax aboard a historic wooden schooner

5.0 • 180 reviews
$73/ person
Swim & Sail on a Waikiki 2.5-Hour Cruise

Swim & Sail on a Waikiki 2.5-Hour Cruise

Swim, relax, and sail past Waikiki and Diamond Head

5.0 • 176 reviews
$134/ person
Private Apostle Islands Sailing Charter from Bayfield

Private Apostle Islands Sailing Charter from Bayfield

Take the wheel or relax on a private sail through island-sheltered waters

5.0 • 203 reviews
$513
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