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Best results for

Sailing

Showing 217-240 of 1,004 results
Key West, FL86Honolulu, HI65San Diego, CA35St. Augustine, FL28Traverse City, MI26
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  • New York, NY24
  • Charleston, SC21
  • Chicago, IL18
  • Hilton Head Island, SC17
  • Boston, MA16
  • Newport, RI15
  • Saint Michaels, MD15
  • Pensacola Beach, FL14
  • Bluffton, SC13
  • Cocoa Beach, FL12
  • Salem, MA12
  • Destin, FL11
  • Marina del Rey, CA11
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  • Irvington, VA10
  • Kennebunkport, ME10
  • Manteo, NC10
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Sunset Sail in Maui's Au'Au Channel

Sunset Sail in Maui's Au'Au Channel

Sail Lahaina’s sunset with food, drinks, and space to relax

4.9 • 1.3K reviews
$131/ person
2-Hour Maui Sunset Catamaran Cruise From Lahaina

2-Hour Maui Sunset Catamaran Cruise From Lahaina

Sail Lahaina’s sunset with appetizers and an open bar

4.9 • 1.3K reviews
$131/ person
Maui Sunset Sail

Maui Sunset Sail

Golden-hour catamaran sailing with cocktails, island bites, and open-ocean views

4.9 • 1.3K reviews
$240/ person
NFL Sunday Pregame Sail on Charleston Harbor

NFL Sunday Pregame Sail on Charleston Harbor

Start game day with fellow football fans aboard a spacious catamaran

4.9 • 1.3K reviews
$55/ person
San Francisco Bay Sunset Catamaran Sail From Pier 39

San Francisco Bay Sunset Catamaran Sail From Pier 39

Cruise the Bay at sunset with 1 beer or wine included

4.9 • 1.1K reviews
$95/ person
West Oahu Dolphin Sail with Lunch & Snorkeling

West Oahu Dolphin Sail with Lunch & Snorkeling

See wild dolphins, snorkel with turtles, and enjoy lunch on a 3-hour West Oahu sail

4.9 • 926 reviews
$172/ person
West Oahu Sunset Sail with Drinks & Appetizers

West Oahu Sunset Sail with Drinks & Appetizers

Unwind on a West O‘ahu sunset cruise with panoramic views, drinks, and light bites included

4.9 • 926 reviews
$115/ person
Ko Olina Sunset Sail With Hawaiian Music

Ko Olina Sunset Sail With Hawaiian Music

Toast the evening with coastal views and a full open bar

4.9 • 926 reviews
$160/ person
Ko Olina Sunset Sail & Luau

Ko Olina Sunset Sail & Luau

Sail Oʻahu’s coast before an evening of island dining and culture

4.9 • 926 reviews
$342/ person
Private Midday Sailing Charter in San Diego

Private Midday Sailing Charter in San Diego

See San Diego’s historic waterfront on a private daytime sail

4.9 • 877 reviews
$631& up
Private 3-Hour Sailing Lesson in San Diego

Private 3-Hour Sailing Lesson in San Diego

Learn to sail in a private 3-hour lesson with a US Coast Guard certified captain

4.9 • 877 reviews
$689
Sail Waikiki to Diamond Head on a 1.5-Hour Cruise

Sail Waikiki to Diamond Head on a 1.5-Hour Cruise

Sail Waikiki’s south shore with Diamond Head views and beach boarding

4.9 • 917 reviews
$57/ person
Sunset Catamaran Sail with Open Bar in Waikiki

Sunset Catamaran Sail with Open Bar in Waikiki

Sail Waikiki at sunset with drinks included on a 1.5-hour happy hour cruise

4.9 • 917 reviews
$90/ person
Private Sailing Charter in San Diego

Private Sailing Charter in San Diego

Customize a private sail with your own captain and crew

4.9 • 877 reviews
$1,198& up
Watch Friday Night Fireworks on a Honolulu Sail

Watch Friday Night Fireworks on a Honolulu Sail

Sail Friday night and watch Honolulu fireworks from the water

4.9 • 917 reviews
$96& up
3-Hour Private Sunset Sailing Cruise in San Diego

3-Hour Private Sunset Sailing Cruise in San Diego

Sail the San Diego coast at sunset with complimentary drinks and snacks

4.9 • 877 reviews
$631
Bottomless Mimosa Sailing Cruise in San Diego

Bottomless Mimosa Sailing Cruise in San Diego

Sail San Diego Bay with bottomless mimosas on a 2-hour morning cruise

4.9 • 877 reviews
$80/ person
Private Midday Sailing Charter in San Diego Bay

Private Midday Sailing Charter in San Diego Bay

Private coastal views with complimentary drinks and snacks

4.9 • 877 reviews
$631
Private Bachelorette Sailing Charter in San Diego

Private Bachelorette Sailing Charter in San Diego

Book a 3-hour private bachelorette sail in San Diego, with daytime or sunset departures

4.9 • 877 reviews
$583& up
Private Sunset Sailing Charter in San Diego

Private Sunset Sailing Charter in San Diego

Sail San Diego at sunset on a private 3-hour cruise

4.9 • 877 reviews
$631& up
Private Romantic Sail for Proposals in San Diego

Private Romantic Sail for Proposals in San Diego

Sail privately in San Diego Bay with drinks and snacks included

4.9 • 877 reviews
$631& up
Private 6-Hour Sailing Charter in San Diego

Private 6-Hour Sailing Charter in San Diego

Sail San Diego Bay on a private 6-hour charter for up to 12 guests

4.9 • 877 reviews
$954& up
3-Hour Midday Sailing Cruise In San Diego

3-Hour Midday Sailing Cruise In San Diego

Midday sail in San Diego with drinks and snacks included

4.9 • 877 reviews
$116/ person
Sunset Sail on a 40' Sailboat in San Diego

Sunset Sail on a 40' Sailboat in San Diego

3-hour sunset sail on a 40-foot boat with drinks and snacks included

4.9 • 877 reviews
$126/ person
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