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Best results for

Sailing

Showing 265-288 of 1,008 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
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  • Pensacola Beach, FL14
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Private 42' Sailing Catamaran Charter in Sarasota

Private 42' Sailing Catamaran Charter in Sarasota

Private sailing with spacious lounges, swim access, and Sarasota Bay views

4.9 • 517 reviews
$1,844
Private 48' Sailing Yacht Charter in St. Petersburg

Private 48' Sailing Yacht Charter in St. Petersburg

Sail Tampa Bay aboard a private 48-foot Jeanneau yacht

4.9 • 517 reviews
$1,211
Private 42' Sailing Catamaran Sunset Charter in Sarasota

Private 42' Sailing Catamaran Sunset Charter in Sarasota

Sail into golden hour with four spacious places to gather aboard

4.9 • 517 reviews
$1,844
Key West Sunset Sail on an 80' Pirate-Style Schooner

Key West Sunset Sail on an 80' Pirate-Style Schooner

Take in Key West's sunset from the water with a hint of piracy

4.9 • 487 reviews
$108/ person
St. Augustine 2-Hour Guided Sailing Excursion

St. Augustine 2-Hour Guided Sailing Excursion

Sail St. Augustine's estuary aboard a stable catamaran

4.9 • 456 reviews
$82/ person
Private Kayak, Snorkel & Sail Charter in Key West

Private Kayak, Snorkel & Sail Charter in Key West

Sail, kayak, and snorkel Key West's shallow waters on a private cruise

4.9 • 414 reviews
$847
Men's Sailing Cruise in Key West

Men's Sailing Cruise in Key West

A clothing-optional all-male sailing trip with snorkeling, sandbar, or kayaking

4.9 • 414 reviews
$146/ person
Seattle Day Sailing Adventure

Seattle Day Sailing Adventure

Build day-sailing skills on a skipper-led voyage beyond the bay

4.9 • 342 reviews
$140/ person
Sail a Private Charter on Oahu's North Shore

Sail a Private Charter on Oahu's North Shore

Private sailing charter on Oahu’s North Shore for up to 6 people

5.0 • 59 reviews
$1,147& up
Full-Day Private Sailing Charter to Waimea Bay

Full-Day Private Sailing Charter to Waimea Bay

Private 6-hour sail to Waimea Bay for up to 6 people

5.0 • 59 reviews
$1,937
Half-Day Private Sailing Charter on Oahu's North Shore

Half-Day Private Sailing Charter on Oahu's North Shore

Sail the North Shore with a naturalist and seasonal whale listening

5.0 • 59 reviews
$1,661
Daytime Catamaran Sailing Cruise

Daytime Catamaran Sailing Cruise

Relax on a 35-minute Monterey Bay sail with included drink and snacks

4.9 • 246 reviews
$63/ person
Private Sailing Cruise on Monterey Bay

Private Sailing Cruise on Monterey Bay

Private keelboat sailing for up to 6 from Old Fisherman’s Wharf

4.9 • 246 reviews
$996
Private Sunset Cruise from Baytowne Wharf in Sandestin

Private Sunset Cruise from Baytowne Wharf in Sandestin

Sail into sunset views on a private captained catamaran

4.9 • 245 reviews
$786
Sunset Cruise in Miramar Beach

Sunset Cruise in Miramar Beach

Sail into a Gulf sunset aboard a private captained catamaran

4.9 • 245 reviews
$787
Sunset Catamaran Sailing Cruise in Monterey

Sunset Catamaran Sailing Cruise in Monterey

Sail Monterey Bay at sunset with a drink and snacks included

4.9 • 246 reviews
$94/ person
Intro to Sailing Lesson at Old Fisherman's Wharf Monterey

Intro to Sailing Lesson at Old Fisherman's Wharf Monterey

Learn sailing basics in a 2-hour class from Old Fisherman’s Wharf

4.9 • 246 reviews
$169/ person
Coastal Navigation Course in Monterey

Coastal Navigation Course in Monterey

Practice coastal navigation skills on the water in Monterey

4.9 • 246 reviews
$550/ person
Sail San Diego Bay Catamaran Cruise With Drinks

Sail San Diego Bay Catamaran Cruise With Drinks

Sail San Diego Bay on a small-group catamaran with drinks included

4.9 • 251 reviews
$660
Private Catamaran Sailing Charter on San Diego Bay

Private Catamaran Sailing Charter on San Diego Bay

Charter a private catamaran for your special occasion on San Diego Bay

4.9 • 251 reviews
$660
Sunset Sailing Cruise in San Diego

Sunset Sailing Cruise in San Diego

Unwind on an evening sail with drinks and skyline views

4.9 • 251 reviews
$119/ person
Naples 2-Hour Sailing Charter

Naples 2-Hour Sailing Charter

Private catamaran sailing around the Ten Thousands Islands

5.0 • 55 reviews
$316
Naples 4-Hour Sailing Charter

Naples 4-Hour Sailing Charter

Sail to barrier islands on a private morning or afternoon outing

5.0 • 55 reviews
$672
Private Sailing Charter in Long Beach

Private Sailing Charter in Long Beach

Shape your own coastal adventure, from a lively sail to a mellow outing

5.0 • 55 reviews
$476
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