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Best results for

Sailing

Showing 769-792 of 1,004 results
Key West, FL86Honolulu, HI65San Diego, CA35St. Augustine, FL28Traverse City, MI26
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  • New York, NY24
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  • Boston, MA16
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  • Saint Michaels, MD15
  • Pensacola Beach, FL14
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Waikiki Friday Night Fireworks Sail with Drinks and Bento

Waikiki Friday Night Fireworks Sail with Drinks and Bento

Sail at sunset for front-row views of Waikiki’s Friday fireworks, with drinks and a bento included

4.9 • 926 reviews
$183/ person
Afternoon Waikiki Coast Sail

Afternoon Waikiki Coast Sail

Relax along Oʻahu’s south shore with Waikiki views, Diamond Head, snacks, and drinks

4.9 • 926 reviews
$86/ person
Private 1.5-Hour Sunset Sail in Honolulu

Private 1.5-Hour Sunset Sail in Honolulu

1.5-hour private sunset sail with wine, beer, and non-alcoholic drinks

4.9 • 917 reviews
$4,314
Private Afternoon Sail in Waikiki

Private Afternoon Sail in Waikiki

Private beach-boarded sail with Diamond Head Lighthouse views

4.9 • 917 reviews
$2,259
1-Hour Fireworks Sail in Honolulu

1-Hour Fireworks Sail in Honolulu

Watch Honolulu’s Friday-night fireworks from a private sail

4.9 • 917 reviews
$3,514
Birthday Sailing Charter in San Diego

Birthday Sailing Charter in San Diego

Celebrate your birthday with a private sail on San Diego Bay

4.9 • 877 reviews
$631& up
2-Hour Morning Sail in San Diego

2-Hour Morning Sail in San Diego

Enjoy a relaxed San Diego Bay sail with snacks, drinks and family-friendly fun

4.9 • 877 reviews
$94/ person
Private Morning Sail in San Diego

Private Morning Sail in San Diego

Set sail through historic San Diego with complimentary drinks and snacks

4.9 • 877 reviews
$477& up
San Diego 3-Hour Bachelor Sailing Charter

San Diego 3-Hour Bachelor Sailing Charter

Private bachelor sail with drinks, snacks, and daytime or sunset departures

4.9 • 877 reviews
$583& up
Sunset Sailboat Cruise in Little River

Sunset Sailboat Cruise in Little River

Private evening sailing with sunset shoreline views and a customizable route

5.0 • 71 reviews
$504
7-Hour Private Sailing Charter in Little River

7-Hour Private Sailing Charter in Little River

Sail to Bird Island, explore the shore, and take the helm on Freedom

5.0 • 71 reviews
$1,484
Cruise Grand Traverse Bay on a 6-Hour Private Sail

Cruise Grand Traverse Bay on a 6-Hour Private Sail

Private 6-hour sail for up to 6, with time to raise sails and take the wheel

4.9 • 675 reviews
$812
Sail Grand Traverse Bay Fall Flavors Cruise

Sail Grand Traverse Bay Fall Flavors Cruise

Sail Grand Traverse Bay and enjoy Moomers ice cream on a 2-hour fall cruise

4.9 • 675 reviews
$60/ person
Sail Traverse City With Moomers Ice Cream

Sail Traverse City With Moomers Ice Cream

Sail Traverse City and enjoy two scoops of Moomers ice cream

4.9 • 675 reviews
$60/ person
Brunch Cruise in Traverse City

Brunch Cruise in Traverse City

Sail the bay on a 2-hour brunch cruise with your first drink included

4.9 • 675 reviews
$88/ person
Sail a 2-Hour Private Cruise in Traverse City

Sail a 2-Hour Private Cruise in Traverse City

Private 2-hour sail on Grand Traverse Bay with hands-on sailing options

4.9 • 675 reviews
$349
Cruise Traverse City on a 2-Hour Live Music Sail

Cruise Traverse City on a 2-Hour Live Music Sail

Dance to live music on a 2-hour evening sail on Grand Traverse Bay

4.9 • 675 reviews
$86/ person
Private Sunset Sailing Cruise in Traverse City

Private Sunset Sailing Cruise in Traverse City

Private sunset sail on Grand Traverse Bay with hands-on sailing options

4.9 • 675 reviews
$370
Traverse City Fall Evening Sail

Traverse City Fall Evening Sail

Hoist the sails and cruise Grand Traverse Bay aboard a historic tall ship

4.9 • 675 reviews
$64/ person
Holiday Party Sailing Charter Key West

Holiday Party Sailing Charter Key West

Private catamaran celebration with bubbly, wines, and party platters

4.9 • 635 reviews
$1,340
Key West 1.5-Hour Classic Day Sailing Cruise

Key West 1.5-Hour Classic Day Sailing Cruise

Sail Key West on Schooner America 2.0 with complimentary soft drinks

4.9 • 593 reviews
Contact for pricing
Sail Key West on a 2-Hour Champagne Sunset Cruise

Sail Key West on a 2-Hour Champagne Sunset Cruise

Sail into the Key West sunset with drinks and hors d'oeuvres included

4.9 • 593 reviews
$127/ person
Key West Full Moon Sailing Cruise

Key West Full Moon Sailing Cruise

Sail Key West's night waters beneath the full moon aboard a 105-foot schooner

4.9 • 593 reviews
$73/ person
Key West Wrecker's Race Sailing Cruise

Key West Wrecker's Race Sailing Cruise

Join Key West schooners in a monthly race to Sand Key Lighthouse

4.9 • 593 reviews
$127/ person
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