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Best results for

Sailing

Showing 457-480 of 1,017 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
  • Bluffton, SC13
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4-Hour Sailing Catamaran Charter in Key West

4-Hour Sailing Catamaran Charter in Key West

Private sailing with an onboard bathroom and kitchen

5.0 • 4 reviews
$1,219
6-Hour Private Sailing Charter in Key West

6-Hour Private Sailing Charter in Key West

Private catamaran sailing with ocean serenity

5.0 • 4 reviews
$1,590
4-Hour Sailing Catamaran Charter in Key West

4-Hour Sailing Catamaran Charter in Key West

Private catamaran sailing with a full bathroom and kitchen

5.0 • 4 reviews
$1,219
Full-Day Private Sailing & Wildlife Tour in Friday Harbor

Full-Day Private Sailing & Wildlife Tour in Friday Harbor

Sail the San Juan Islands with a captain-naturalist and shape the day around your interests

5.0 • 4 reviews
$1,261
Private Sunset Sailing Charter in Murrells Inlet

Private Sunset Sailing Charter in Murrells Inlet

Sail Murrells Inlet aboard Miss Adventure with your private group

5.0 • 4 reviews
$265
Naturist Sailing Catamaran Charter in Key West

Naturist Sailing Catamaran Charter in Key West

Sail privately in a clothing-optional setting shaped around your comfort

5.0 • 4 reviews
$1,590
Naturist Catamaran Charter in Key West

Naturist Catamaran Charter in Key West

Spend a private day on a clothing-optional sailing catamaran

5.0 • 4 reviews
$1,855
Murrells Inlet Private 1.5-Hour Sailing Charter

Murrells Inlet Private 1.5-Hour Sailing Charter

Cruise Murrells Inlet with a captain and crew aboard Miss Adventure

5.0 • 4 reviews
$212
Private Naples Day Sailing Charter From Naples City Dock

Private Naples Day Sailing Charter From Naples City Dock

Private Naples day sail for up to 6 guests on a 47' Beneteau

5.0 • 3 reviews
$424& up
Private Naples Day Sailing Charter From City Dock

Private Naples Day Sailing Charter From City Dock

Private sail from Naples City Dock on a 31' Catalina for up to 6 guests

5.0 • 3 reviews
$371& up
Sunset Sailing Cruise From Naples City Dock

Sunset Sailing Cruise From Naples City Dock

Private sunset sail for up to 6 on a 31' Catalina from Naples City Dock

5.0 • 3 reviews
$530
Sunset Sailing Cruise From Naples City Dock

Sunset Sailing Cruise From Naples City Dock

Sail the Naples coastline at sunset on a 47' Beneteau yacht

5.0 • 3 reviews
$610
Private Sea of Cortez Sailing Charter

Private Sea of Cortez Sailing Charter

Sail Cabo San Lucas’ shoreline with your private group

5.0 • 2 reviews
$5,088/ boat
Private 40' Sailing Catamaran Charter in Marina del Rey

Private 40' Sailing Catamaran Charter in Marina del Rey

Relax on bow sailing nets with space to unwind indoors and on deck

5.0 • 1 reviews
$2,541/ boat
Full-Day Sailing & Snorkeling Charter in Red Hook

Full-Day Sailing & Snorkeling Charter in Red Hook

Customize a Caribbean catamaran day with snorkeling, beach stops and onboard comforts

4.5 • 272 reviews
$1,674
Sunset Catamaran Charter in St. Thomas

Sunset Catamaran Charter in St. Thomas

Sail into sunset aboard a spacious luxury catamaran with champagne and music

4.5 • 272 reviews
$1,134
2.5-Hour Private Sailing Charter in San Diego Bay

2.5-Hour Private Sailing Charter in San Diego Bay

Sail, swim, and toast aboard a private yacht

$1,018
4-Hour Sailing Charter in San Diego

4-Hour Sailing Charter in San Diego

Sail the coastline, swim in a calm bay, and relax on the water

$1,479
Small-Group Sailing Yacht Cruise on San Diego Bay

Small-Group Sailing Yacht Cruise on San Diego Bay

Share a relaxed yacht sail with coastal views and a group toast

$253/ person
Private 3-Hour Sailing Cruise in Key West

Private 3-Hour Sailing Cruise in Key West

Sail the Florida Keys privately aboard a classic sailboat

$635
Private Vineyard Sound Sailing Charter

Private Vineyard Sound Sailing Charter

Feel the power of sailing on Martha's Vineyard waters

$1,268
3-Hour Vineyard Sound Sailing Charter

3-Hour Vineyard Sound Sailing Charter

Sail Vineyard Sound with lighthouse views and secluded swim options

$2,113
3.5-Hour Sailing Charter in St. Thomas

3.5-Hour Sailing Charter in St. Thomas

Private sailing with snorkeling, open bar, and a Christmas Cove option

$795
Private Sunset Sail on a Classic Yacht in St. Thomas

Private Sunset Sail on a Classic Yacht in St. Thomas

Sail into sunset colors with sparkling wine and coastal bites

$795
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