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Best results for

Sailing

Showing 481-504 of 1,016 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
  • San Francisco, CA11
  • Irvington, VA10
  • Kennebunkport, ME10
  • Manteo, NC10
  • Oceanside, CA10
  • Boothbay Harbor, ME9
  • Camden, ME9
Sunset San Juan Bay Cruise

Sunset San Juan Bay Cruise

Sail past Old San Juan landmarks with drinks and appetizers at sunset

4.5 • 111 reviews
$116/ person
Sunset Sail Charter on Martha's Vineyard

Sunset Sail Charter on Martha's Vineyard

Relax on deck as the sun sets over the water

$3,169
4-Hour Sailing Charter on Pamlico Sound

4-Hour Sailing Charter on Pamlico Sound

A captain-led Pamlico Sound outing with your choice of classic vessel

4.5 • 4 reviews
$525& up
4-Hour Sailboat Rental in Buxton

4-Hour Sailboat Rental in Buxton

Take the helm on sailboats used by Buxton's local sailing team

4.5 • 4 reviews
$212/ boat
Sailing Charter on Casco Bay Aboard 36' Sailboat

Sailing Charter on Casco Bay Aboard 36' Sailboat

Enjoy a private sail aboard Endurance with views of Casco Bay’s islands and lighthouses

$89/ person
2-6 Hour Sailing Cruise in South Portland

2-6 Hour Sailing Cruise in South Portland

Celebrate or unwind aboard Endurance on a custom sail

$500& up
Sunset Sailing Cruise in Casco Bay

Sunset Sailing Cruise in Casco Bay

Sail Casco Bay at sunset past islands, lighthouses, and local wildlife

$100/ person
Pamlico Sound Sunset Sail on Hatteras Island

Pamlico Sound Sunset Sail on Hatteras Island

Fit an evening on the water around your dinner plans

4.5 • 4 reviews
$419/ boat
Private Catamaran Sailing Lesson on Hatteras Island

Private Catamaran Sailing Lesson on Hatteras Island

Take an active role in sailing a catamaran

4.5 • 4 reviews
$313& up
Full-Day Captained Sailing on Pamlico Sound in Buxton

Full-Day Captained Sailing on Pamlico Sound in Buxton

Explore Cape Hatteras waters aboard a catamaran, classic sloop, or powerboat

4.5 • 4 reviews
$896/ boat
Private Intro to Keelboat Sailing on Hatteras Island

Private Intro to Keelboat Sailing on Hatteras Island

Build sailing skills by taking an active role on the water

4.5 • 4 reviews
$313& up
Private Morning Sailing Charter in Carolina Beach

Private Morning Sailing Charter in Carolina Beach

Enjoy a morning on the water at your own pace

$400
Private Sunset Sailing Cruise in Carolina Beach

Private Sunset Sailing Cruise in Carolina Beach

Slow down and connect as the day fades

$400
Private Sunset Catamaran Sail in Galveston

Private Sunset Catamaran Sail in Galveston

Ease into the evening with a licensed captain and experienced sailing crew

$445
Private Afternoon Catamaran Sail in Galveston

Private Afternoon Catamaran Sail in Galveston

Enjoy a relaxed sail aboard a stable catamaran

$413
Private 42' Catamaran Sunset Sail in St. Thomas

Private 42' Catamaran Sunset Sail in St. Thomas

Wind down with a private evening sail, island views, and drinks on deck

$1,373
Private Boot Key Harbor Sailing Charter in Marathon

Private Boot Key Harbor Sailing Charter in Marathon

Enjoy the Florida Keys with a sailboat all to yourselves

$530
Private 50' Yacht Sunset Sail in Marathon, Florida Keys

Private 50' Yacht Sunset Sail in Marathon, Florida Keys

Unwind on the water with a sail reserved just for your group

$530
Custom Private Sailing Charter in Boothbay Harbor

Custom Private Sailing Charter in Boothbay Harbor

Make your time on the water your own

$558& up
Private Sunset Sailing Charter in Boothbay Harbor

Private Sunset Sailing Charter in Boothbay Harbor

Unwind on the water as evening settles over the coast

$558
Private Full-Day Island & Cove Sailing Charter in Boothbay Harbor

Private Full-Day Island & Cove Sailing Charter in Boothbay Harbor

More time to sail, relax, and explore the Maine coast

$1,115
Private Half-Day Sailing Charter in Boothbay Harbor

Private Half-Day Sailing Charter in Boothbay Harbor

See Maine's lighthouses and islands from the water

$558
Beginner Sailing Lesson on Buttonwood Sound in Key Largo

Beginner Sailing Lesson on Buttonwood Sound in Key Largo

Discover how sailing works with a licensed captain by your side

$221/ person
Private 42' Sailing Catamaran Charter in Key West

Private 42' Sailing Catamaran Charter in Key West

Stretch out and relax on a private sail

$224/ boat
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