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Best results for

Sailing

Showing 25-48 of 1,004 results
Key West, FL86Honolulu, HI65San Diego, CA35St. Augustine, FL28Traverse City, MI26
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  • New York, NY24
  • Charleston, SC21
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  • Hilton Head Island, SC17
  • Boston, MA16
  • Newport, RI15
  • Saint Michaels, MD15
  • Pensacola Beach, FL14
  • Bluffton, SC13
  • Cocoa Beach, FL12
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  • Destin, FL11
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Sail & Snorkel Jost Van Dyke 9-Hour Cruise

Sail & Snorkel Jost Van Dyke 9-Hour Cruise

Catamaran sail to Jost Van Dyke with snorkeling, breakfast and an open bar

5.0 • 1.7K reviews
$307/ person
Sail to Cape Lookout for Beach Time & Lunch

Sail to Cape Lookout for Beach Time & Lunch

Sail to Cape Lookout for beach time, catered lunch, and lighthouse views on a stable catamaran

5.0 • 1.5K reviews
$168/ person
Private Sailing Catamaran Charter in St. Michaels

Private Sailing Catamaran Charter in St. Michaels

Sail the Miles River with room to relax aboard Epiphany

5.0 • 1.4K reviews
$1,237& up
Private Sunset Catamaran Cruise & Snorkel in Honolulu

Private Sunset Catamaran Cruise & Snorkel in Honolulu

A private evening sail with your own music, food, and drinks

5.0 • 803 reviews
$1,058
Sunset Sail in St. Augustine

Sunset Sail in St. Augustine

Sail St. Augustine’s historic bayfront as the sun sets from a private yacht

5.0 • 768 reviews
$797& up
Private Morning Sailing Charter in Charleston Harbor

Private Morning Sailing Charter in Charleston Harbor

Private morning sail in Charleston Harbor for up to 6 guests

5.0 • 730 reviews
$579
Private 4-Hour Sailing Charter in Fort Myers Beach

Private 4-Hour Sailing Charter in Fort Myers Beach

Sail a private catamaran to Lovers Key with time to swim and shell

5.0 • 575 reviews
$1,631
Sail a Private Waikiki Charter

Sail a Private Waikiki Charter

Set your own agenda on a private Waikiki sail for up to 6 guests

5.0 • 493 reviews
$1,777& up
3-Hour Private Sailing Charter in New York Harbor

3-Hour Private Sailing Charter in New York Harbor

Private New York Harbor sail with views of the Statue of Liberty

5.0 • 516 reviews
$769& up
Sunset Sail Charter in South Lake Tahoe

Sunset Sail Charter in South Lake Tahoe

Private Lake Tahoe sailing with complimentary drinks and a dedicated crew

5.0 • 492 reviews
$2,251
Cocoa Beach Dolphin Sailing Charter

Cocoa Beach Dolphin Sailing Charter

Private catamaran sailing with Indian River Lagoon wildlife views

5.0 • 3.9K reviews
$339
Half-Day Sailing Tour on Saco Bay

Half-Day Sailing Tour on Saco Bay

Sail longer and see more of Saco Bay on a half-day trip

5.0 • 430 reviews
$256/ person
Private Sailing Catamaran Charter from St Thomas

Private Sailing Catamaran Charter from St Thomas

Sail the US Virgin Islands with a private crew and open bar

5.0 • 1.7K reviews
$2,014& up
Afternoon Sailing Charter in Hilton Head Island

Afternoon Sailing Charter in Hilton Head Island

A breezy private sail with island insights and room to unwind

5.0 • 390 reviews
$429
Chesapeake Bay Sunset Champagne Sail in St. Michaels

Chesapeake Bay Sunset Champagne Sail in St. Michaels

Sail Chesapeake Bay at sunset with champagne and light bites

5.0 • 1.4K reviews
$270/ person
Bottomless Mimosa Brunch Sail & Swim in Key West

Bottomless Mimosa Brunch Sail & Swim in Key West

Brunch, drinks, and a swim stop aboard a Key West sail

5.0 • 375 reviews
$153/ person
Sail On a Private Brunch Cruise in St. Augustine

Sail On a Private Brunch Cruise in St. Augustine

Charter a luxury catamaran and enjoy a family-style brunch with bottomless mimosas

5.0 • 768 reviews
$1,815
Private Afternoon Sailboat Charter in Charleston Harbor

Private Afternoon Sailboat Charter in Charleston Harbor

Sail Charleston Harbor on a private afternoon charter for up to 6 guests

5.0 • 730 reviews
$579
Sunset Sail in Southwest Florida

Sunset Sail in Southwest Florida

Sail into golden-hour views on a 2-hour sunset cruise

5.0 • 575 reviews
$68/ person
Overnight Sailing Charter to Kiawah Island

Overnight Sailing Charter to Kiawah Island

Sail offshore from Charleston and anchor overnight near Kiawah Island

5.0 • 328 reviews
$1,712& up
Private Night Sail Past Statue of Liberty in New York City

Private Night Sail Past Statue of Liberty in New York City

Private moonlight sail past the Manhattan skyline and Statue of Liberty

5.0 • 516 reviews
$610& up
Afternoon Sailing Cruise on Lake Tahoe

Afternoon Sailing Cruise on Lake Tahoe

Late-afternoon Lake Tahoe sail with complimentary drinks

5.0 • 492 reviews
$148/ person
Wildlife Sailing Cruise in Cocoa Beach

Wildlife Sailing Cruise in Cocoa Beach

Hands-On Catamaran Sailing for All Ages

5.0 • 3.9K reviews
$56/ person
Cruise the Saco River & Saco Bay on a 2-Hour Sail

Cruise the Saco River & Saco Bay on a 2-Hour Sail

Sail Maine’s coast in a small group of 6 or fewer

5.0 • 430 reviews
$127/ person
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