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Best results for

Sailing

Showing 313-336 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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40' Sailing Charter in Marina del Rey

40' Sailing Charter in Marina del Rey

Sail the coast or cruise to Catalina aboard a 2023 Beneteau

4.9 • 133 reviews
$1,403/ boat
Instructor-Led Night Sailing Class in Marina del Rey

Instructor-Led Night Sailing Class in Marina del Rey

Learn the basics of sailing after dark

4.9 • 133 reviews
$530& up
Private Diamond Head Sailing Charter in Honolulu

Private Diamond Head Sailing Charter in Honolulu

Private sailing with Diamond Head views and room to celebrate

5.0 • 44 reviews
$769& up
Honolulu Sunset Sailing Charter

Honolulu Sunset Sailing Charter

Private late-afternoon sail with sunset views of Honolulu and Oahu’s shores

5.0 • 44 reviews
$769
Honolulu Fireworks Private Sailing Charter

Honolulu Fireworks Private Sailing Charter

Sail into Friday night for Waikīkī fireworks views from the water

5.0 • 44 reviews
$619& up
Honolulu Special Occasion Sailing Charter

Honolulu Special Occasion Sailing Charter

Celebrate on a private sail along Oʻahu’s coast with views of Diamond Head

5.0 • 44 reviews
$769& up
Private Proposal Sailing Charter in Honolulu

Private Proposal Sailing Charter in Honolulu

Set the scene for your proposal with an ocean backdrop

5.0 • 44 reviews
$769/ boat
Private Wedding & Elopement Sailing Charter in Honolulu

Private Wedding & Elopement Sailing Charter in Honolulu

Exchange vows at sea with an officiant included and Oʻahu’s coastline as your backdrop

5.0 • 44 reviews
$769/ boat
Private Sunset Sail in Pensacola Beach

Private Sunset Sail in Pensacola Beach

Sail into the evening with charcuterie and sparkling wine

5.0 • 44 reviews
$477
Private Sailing Charter in Pensacola Beach

Private Sailing Charter in Pensacola Beach

Relax on board or make a splash on your own private sail

5.0 • 44 reviews
$742& up
Private Brunch Sailing Cruise on Pensacola Bay

Private Brunch Sailing Cruise on Pensacola Bay

Ease into the day with seasonal fruit and fresh-squeezed orange juice mimosas

5.0 • 44 reviews
$398
Private Ash Scattering Sailing Charter in Honolulu

Private Ash Scattering Sailing Charter in Honolulu

Honor your loved one at sea with an experienced ceremony captain

5.0 • 44 reviews
$989/ boat
Private Dolphin Sailing Tour in Hilton Head Island

Private Dolphin Sailing Tour in Hilton Head Island

Private 2-hour sail to learn the salt marsh and watch for dolphins

4.9 • 118 reviews
$397
Hilton Head Sunset Dolphin Sailing Charter

Hilton Head Sunset Dolphin Sailing Charter

Sail into sunset with coastal wildlife and ecology insights

4.9 • 118 reviews
$442
Classic Yacht Afternoon Sail on San Diego Bay

Classic Yacht Afternoon Sail on San Diego Bay

Sail a classic yacht past San Diego Bay landmarks with drinks and snacks

4.9 • 113 reviews
$125/ person
Sunset Sail on a Classic Yacht in San Diego Bay

Sunset Sail on a Classic Yacht in San Diego Bay

A classic-yacht sunset sail with drinks and San Diego Bay views

4.9 • 113 reviews
$125/ person
Sunset Sail Charter With Dinner In Honolulu

Sunset Sail Charter With Dinner In Honolulu

Private 2-hour Honolulu sunset sail with voyaging dinner and cultural activities

4.9 • 107 reviews
$1,218
Morning Sail on Oahu's Kona Coast

Morning Sail on Oahu's Kona Coast

A weekday sail with Hawaiian cultural activities and refreshments

4.9 • 107 reviews
$221/ person
Hawaiian Cultural Sail on O'ahu's Kona Coast

Hawaiian Cultural Sail on O'ahu's Kona Coast

Sail into Hawaiian culture with music, activities, and refreshments

4.9 • 107 reviews
$221/ person
Morning Sail Charter on O'ahu's Kona Coast

Morning Sail Charter on O'ahu's Kona Coast

Explore Hawaiian culture and ocean landscapes on a family-friendly morning sail

4.9 • 107 reviews
$1,107
Cultural Sail Charter on O'ahu

Cultural Sail Charter on O'ahu

Sail O'ahu's Kona coast with Hawaiian stories, activities, and deckside relaxation

4.9 • 107 reviews
$1,107
Private 35' Catamaran Sailing Charter in Savannah

Private 35' Catamaran Sailing Charter in Savannah

Private 2-hour catamaran sail with champagne for up to 6

4.9 • 105 reviews
$525
Sail on a 2-Hour Private Charter in Savannah

Sail on a 2-Hour Private Charter in Savannah

Sail from Wilmington Island on a private 2-hour charter for up to 6 guests

4.9 • 105 reviews
$423
Private Catamaran Party & Snorkel Cruise in Montego Bay

Private Catamaran Party & Snorkel Cruise in Montego Bay

Private Caribbean sailing with an open bar, snacks, snorkeling, and music

5.0 • 41 reviews
$2,109& up
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