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Best results for

Sailing

Showing 409-432 of 1,020 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
  • Boston, MA16
  • Newport, RI15
  • Saint Michaels, MD15
  • Pensacola Beach, FL14
  • Bluffton, SC13
  • Cocoa Beach, FL12
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  • Destin, FL11
  • Marina del Rey, CA11
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3-Hour Sailing Lesson in Honolulu

3-Hour Sailing Lesson in Honolulu

Learn foundational sailing skills with professional captains in Hawaii

4.9 • 28 reviews
$663/ person
Beginner Sailing Lesson in Chelsea

Beginner Sailing Lesson in Chelsea

Learn sailing basics and take the helm on the Hudson River

4.8 • 66 reviews
$133/ person
Private Intracoastal Sailing Charter in Little River, SC

Private Intracoastal Sailing Charter in Little River, SC

Ease into sailing on a private midday outing

4.8 • 54 reviews
$610
Private Sunset Ocean & Inlet Sail in Little River

Private Sunset Ocean & Inlet Sail in Little River

Take in the Carolina coastline at sunset on a sail reserved for your group

4.8 • 54 reviews
$663
Key West Champagne Sunset Sail

Key West Champagne Sunset Sail

Sail into Key West’s sunset with complimentary drinks on board

4.7 • 8.1K reviews
$63/ person
Maui Sunset Sailing Cruise

Maui Sunset Sailing Cruise

Island music, appetizers, and Pacific views at sunset

4.7 • 2.9K reviews
$149/ person
4-Hour Sailing & Snorkeling Charter in Oranjestad

4-Hour Sailing & Snorkeling Charter in Oranjestad

Sail, snorkel, and enjoy a barbecue meal with an open bar

4.7 • 539 reviews
$153/ person
Key West Sunset Cocktail Cruise

Key West Sunset Cocktail Cruise

Evening catamaran cruise with craft drinks and island music

4.7 • 405 reviews
$95/ person
St. Thomas Champagne Sunset Sail

St. Thomas Champagne Sunset Sail

Evening catamaran cruise with drinks, appetizers, and Caribbean views

4.7 • 356 reviews
$117/ person
Soufriere Catamaran Cruise & Tet Paul Hike

Soufriere Catamaran Cruise & Tet Paul Hike

Sail St. Lucia’s coast, hike Tet Paul Nature Trail, and snorkel in a protected bay

4.7 • 293 reviews
$195/ person
Soufriere Catamaran Cruise With Tet Paul Hike

Soufriere Catamaran Cruise With Tet Paul Hike

Sail St. Lucia’s west coast, hike Tet Paul, and snorkel in protected coves

4.7 • 293 reviews
$178/ person
Private Sunset Catamaran Cruise in St. Lucia

Private Sunset Catamaran Cruise in St. Lucia

Private catamaran sailing at sunset with drinks and finger foods

4.7 • 293 reviews
$1,079& up
Private Sunset Cruise From Soufriere

Private Sunset Cruise From Soufriere

Sail the St. Lucia coast as the sun sets behind the Pitons

4.7 • 293 reviews
$1,483
Soufriere Catamaran Cruise With Rum & Chocolate Tasting

Soufriere Catamaran Cruise With Rum & Chocolate Tasting

Sail to the Pitons with snorkeling, local lunch, and tastings

4.7 • 293 reviews
$211/ person
Soufriere, St. Lucia Day Trip with Rum & Chocolate Tasting

Soufriere, St. Lucia Day Trip with Rum & Chocolate Tasting

Sail to Soufriere for rum and chocolate tastings

4.7 • 293 reviews
$211/ person
2-Hour Sandbar Sailing Charter in Marathon

2-Hour Sandbar Sailing Charter in Marathon

Sail to a local sandbar aboard a captained Hobie Cat

4.7 • 235 reviews
$283
Private Snorkel & Beach Sailing Charter in Fajardo

Private Snorkel & Beach Sailing Charter in Fajardo

Enjoy an island beach day at your own pace, with snorkeling and lunch included

4.7 • 199 reviews
$1,171
Honolulu Sunrise Private Cruise

Honolulu Sunrise Private Cruise

Private morning sailing with mimosas and open-water views

4.7 • 164 reviews
$2,041& up
Honolulu 3-Hour Sailing Lesson

Honolulu 3-Hour Sailing Lesson

Take the Helm With Private Sailing Instruction

4.7 • 164 reviews
$1,358
Private Waikiki Fireworks Sailing Catamaran Cruise

Private Waikiki Fireworks Sailing Catamaran Cruise

Sail aboard Sea Scape for private ocean views and Friday night fireworks

4.7 • 164 reviews
$2,041& up
Private Daytime Sailing Charter in Honolulu

Private Daytime Sailing Charter in Honolulu

Sail Waikiki’s coast privately with a captain and room to relax on deck

4.7 • 164 reviews
$949& up
Sunset Sail Around Charlotte Amalie Harbour

Sunset Sail Around Charlotte Amalie Harbour

Sunset sailing with appetizers, drinks and pirate tattoos

4.7 • 128 reviews
$94/ person
90-Minute San Francisco Bay Sailing Cruise

90-Minute San Francisco Bay Sailing Cruise

Sail San Francisco Bay from Pier 39 with 2 drinks included

4.7 • 112 reviews
$99/ person
San Francisco Bay Sunset Sailing Cruise

San Francisco Bay Sunset Sailing Cruise

Sail past landmark views as the San Francisco Bay shifts into sunset

4.7 • 112 reviews
$129/ person
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