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Best results for

Sailing

Showing 673-696 of 1,008 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
  • Salem, MA12
  • Destin, FL11
  • Marina del Rey, CA11
  • San Francisco, CA11
  • Irvington, VA10
  • Kennebunkport, ME10
  • Manteo, NC10
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  • Boothbay Harbor, ME9
  • Camden, ME9
Sunset Catamaran Cruise in South Lake Tahoe

Sunset Catamaran Cruise in South Lake Tahoe

Sail into golden hour aboard a 50-foot catamaran

5.0 • 492 reviews
$138/ person
Half-Day Sailing Tour on Saco Bay

Half-Day Sailing Tour on Saco Bay

Sail longer and see more of Saco Bay on a half-day trip

5.0 • 430 reviews
$256/ person
Sail a 2-Hour Sunset Cruise in Kennebunkport

Sail a 2-Hour Sunset Cruise in Kennebunkport

Sail into the evening with a small-group sunset cruise

5.0 • 430 reviews
$138/ person
Sail to Wood Island Lighthouse Tour From Kennebunkport

Sail to Wood Island Lighthouse Tour From Kennebunkport

Sail to Wood Island and tour inside the lighthouse and keeper’s house

5.0 • 430 reviews
$395/ person
Cruise the Saco River & Saco Bay on a 2-Hour Sail

Cruise the Saco River & Saco Bay on a 2-Hour Sail

Sail Maine’s coast in a small group of 6 or fewer

5.0 • 430 reviews
$127/ person
4-Hour Sunset Sailing Cruise in Kennebunkport

4-Hour Sunset Sailing Cruise in Kennebunkport

Sail for 4 hours at sunset with room to spread out

5.0 • 430 reviews
$299/ person
2-Hour Sailing Lesson in Saco

2-Hour Sailing Lesson in Saco

Build confidence on the water with a lesson shaped around your goals

5.0 • 430 reviews
$801& up
Private Sailing Tour of Wood Island Lighthouse

Private Sailing Tour of Wood Island Lighthouse

Sail Saco Bay and tour Wood Island Lighthouse from tower to Keeper's House

5.0 • 430 reviews
$1,707& up
Private Sailing Charter on Saco Bay, Maine

Private Sailing Charter on Saco Bay, Maine

Sail the Saco River and Maine coast on your own private boat

5.0 • 430 reviews
$941& up
3-Hour Guided Sailing Cruise in Kennebunkport

3-Hour Guided Sailing Cruise in Kennebunkport

Sail the Saco River and Saco Bay in a small group

5.0 • 430 reviews
$192/ person
Sunset Sailing Charter in Kennebunkport

Sunset Sailing Charter in Kennebunkport

A private evening sail with ocean sunset views

5.0 • 430 reviews
$801/ boat
4-Hour Sailing Lesson in Saco

4-Hour Sailing Lesson in Saco

Build sailing confidence with a lesson tailored to your experience and goals

5.0 • 430 reviews
$1,279& up
Private 6-Hour Sailing Charter in Saco

Private 6-Hour Sailing Charter in Saco

More time to explore the Saco Bay coastline by private sailboat

5.0 • 430 reviews
$1,921& up
Private Sunset Sail in Kennebunkport

Private Sunset Sail in Kennebunkport

Set sail for an extended evening on the ocean

5.0 • 430 reviews
$1,493& up
Private Morning Sail & Dolphin Watch in Bluffton

Private Morning Sail & Dolphin Watch in Bluffton

A calm morning sail for coastal views and wildlife watching

5.0 • 390 reviews
$472& up
Morning Sailing Charter in Hilton Head Island

Morning Sailing Charter in Hilton Head Island

Sail Hilton Head’s morning waters and look for coastal wildlife

5.0 • 390 reviews
$419
Key West Sunday Brunch Sail

Key West Sunday Brunch Sail

Sunday sailing with brunch bites and bottomless mimosas

5.0 • 375 reviews
$124/ person
Christmas Brunch Sail in Key West

Christmas Brunch Sail in Key West

Sail into Christmas morning with brunch, mimosas, and Key West views

5.0 • 375 reviews
$227/ person
Skagway E-Bike Tour & Sail

Skagway E-Bike Tour & Sail

Cycle past Gold Rush landmarks, then sail Skagway's Taiya Inlet

5.0 • 371 reviews
$332/ person
Rockland Harbor Sailing Tour Past Breakwater Lighthouse

Rockland Harbor Sailing Tour Past Breakwater Lighthouse

Help raise the sails and try steering along Maine's rugged coast

5.0 • 306 reviews
$75/ person
Private Half-Day Sailing Charter in Rockland, Maine

Private Half-Day Sailing Charter in Rockland, Maine

Explore Penobscot Bay on a private sail shaped around you

5.0 • 306 reviews
$2,247/ boat
Private 55' Ketch Sailing Charter in Rockland

Private 55' Ketch Sailing Charter in Rockland

Set your own course across Penobscot Bay, with the option to explore an island preserve

5.0 • 306 reviews
$3,157
Private Penobscot Bay Sailing Charter from Rockland

Private Penobscot Bay Sailing Charter from Rockland

Relax on your own private ketch or lend a hand with the sailing

5.0 • 306 reviews
$1,284/ boat
3-Hour Private Sailing Charter in Wilmington

3-Hour Private Sailing Charter in Wilmington

Customize a private sail with a USCG-licensed captain for up to 6 guests

5.0 • 280 reviews
$822
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