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Best results for

Sailing

Showing 241-264 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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Honolulu Sunset Cruise

Honolulu Sunset Cruise

Unwind on the water as the sun sets over the horizon

5.0 • 72 reviews
$108/ person
Sail & Swim on a Waikiki Sunset Cruise

Sail & Swim on a Waikiki Sunset Cruise

Bring your own drinks on a Waikīkī sunset sail with a swim stop

4.9 • 790 reviews
$81/ person
Private Event Sailing Charter in Honolulu

Private Event Sailing Charter in Honolulu

Customize your private Waikiki charter for groups up to 40

4.9 • 790 reviews
$1,826& up
3-Hour Private Sailing Cruise in Little River

3-Hour Private Sailing Cruise in Little River

Customize a private sail with hands-on options and coastal views

5.0 • 71 reviews
$737
Sunset Marriage Proposal Cruise in Little River

Sunset Marriage Proposal Cruise in Little River

Plan a private sunset proposal sail with a captain and mate

5.0 • 71 reviews
$795
Private Introduction to Sailing Lesson in Little River

Private Introduction to Sailing Lesson in Little River

Try private sailing with hands-on instruction, lunch, and time on the water

5.0 • 71 reviews
$525/ person
Day Sailing Cruise in Little River

Day Sailing Cruise in Little River

Customize a private sail with time at the helm or room to relax

5.0 • 71 reviews
$477
Sunset Sailboat Cruise in Little River

Sunset Sailboat Cruise in Little River

Sail the Little River Inlet and Atlantic coastline at sunset on a private charter

5.0 • 71 reviews
$689
Waikoloa Sunset Sail

Waikoloa Sunset Sail

Sunset views, drinks, and light bites aboard the Spirit of Aloha

4.9 • 666 reviews
$160/ person
Kona Coast Sunset Sail

Kona Coast Sunset Sail

Sunset views, light bites, and drinks aboard a Kona Coast catamaran

4.9 • 666 reviews
$115/ person
Kona 1.5-Hour Tradewind Sailing Cruise

Kona 1.5-Hour Tradewind Sailing Cruise

Unwind under sail with ocean air, shaded space and marine-life viewing

4.9 • 666 reviews
$92/ person
Adults-Only Champagne Sunset Sail in Key West

Adults-Only Champagne Sunset Sail in Key West

Adults-only Key West sunset sail with champagne and gourmet cheese

4.9 • 635 reviews
$112/ person
Key West Adults-Only Champagne Sunset Sail

Key West Adults-Only Champagne Sunset Sail

Sip bubbly and sail into the Key West sunset aboard a spacious catamaran

4.9 • 635 reviews
$112/ person
Private Champagne Sunset Catamaran Sail in Key West

Private Champagne Sunset Catamaran Sail in Key West

Private catamaran sailing with champagne, wines and a gourmet cheese buffet

4.9 • 635 reviews
$1,470
Key West Private Sailing Charter

Key West Private Sailing Charter

Sail, snorkel, and seek sandbars aboard a private catamaran

4.9 • 635 reviews
$1,470& up
Key West Private Day Sailing Charter

Key West Private Day Sailing Charter

Private Key West sailing with snorkeling, sandbars, and dolphin searches

4.9 • 635 reviews
$1,356& up
Champagne Sunset Sailing Cruise in Key West

Champagne Sunset Sailing Cruise in Key West

Private sunset sailing with bubbly, wines and a gourmet cheese buffet

4.9 • 635 reviews
$1,016
Enjoy a Live Music Sunset Sail in Saint Augustine

Enjoy a Live Music Sunset Sail in Saint Augustine

Sail Saint Augustine at sunset with live music and complimentary drinks

4.9 • 565 reviews
$66/ person
Santa Barbara Sunset Sailing Charter

Santa Barbara Sunset Sailing Charter

Sail into sunset views of the Pacific and Santa Ynez Mountains

5.0 • 68 reviews
$1,058
Santa Barbara Private Sailing Charter

Santa Barbara Private Sailing Charter

Set sail past Santa Barbara and Montecito on a classic yacht

5.0 • 68 reviews
$676& up
Santa Barbara Harbor Private Sailing Charter

Santa Barbara Harbor Private Sailing Charter

Sail Santa Barbara’s harbor and waterfront with coastal views and onboard narration

5.0 • 68 reviews
$411& up
Sunset Sailing Cruise on Banderas Bay

Sunset Sailing Cruise on Banderas Bay

Sail Banderas Bay at sunset with snacks and an open bar

4.9 • 539 reviews
$105/ person
Private 40' Sailing Catamaran Charter in St. Petersburg

Private 40' Sailing Catamaran Charter in St. Petersburg

Private catamaran sailing with space to swim, paddle, and unwind

4.9 • 517 reviews
$2,916
Sunset Sailing Charter in St. Pete

Sunset Sailing Charter in St. Pete

Sail Tampa Bay at golden hour aboard a 40-foot luxury catamaran

4.9 • 517 reviews
$1,744
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