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Best results for

Sailing

Showing 505-528 of 1,008 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
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
Group Day Sailing Tour in Newport, Rhode Island

Group Day Sailing Tour in Newport, Rhode Island

Take in Newport's sights from the water

$80/ person
Private Day Sailing Tour in Newport, Rhode Island

Private Day Sailing Tour in Newport, Rhode Island

Take in Newport's sights on a sail reserved for your group

$431
Sunset Sailing Tour in Newport, Rhode Island

Sunset Sailing Tour in Newport, Rhode Island

Head onto the water for a shared sunset sail

$82/ person
Private Sunset Sail in Newport, Rhode Island

Private Sunset Sail in Newport, Rhode Island

Enjoy sunset on the water with just your own group

$491
Private Afternoon Sailing Charter in Oceanside

Private Afternoon Sailing Charter in Oceanside

Let the wind carry you aboard your own private sailing yacht

$477
Private Sunset Sail on 36' Catalina Yacht in Oceanside

Private Sunset Sail on 36' Catalina Yacht in Oceanside

Let the wind carry you into the evening on your own private yacht

$318
Private Morning Sailing Charter on a 36' Yacht in Oceanside

Private Morning Sailing Charter on a 36' Yacht in Oceanside

Let the wind carry you on a private morning sail

$318
Private Luxury Sailboat Charter in Marina del Rey

Private Luxury Sailboat Charter in Marina del Rey

Unwind at sea with gourmet hors d'oeuvres and rosé

$475
Private Santa Monica Bay Sail from Marina del Rey

Private Santa Monica Bay Sail from Marina del Rey

Pair a private ocean escape with gourmet hors d'oeuvres and rosé

$682
Private Santa Monica Bay Sailing Tour from Marina del Rey

Private Santa Monica Bay Sailing Tour from Marina del Rey

Unwind on a private sail with gourmet bites and rosé

$890
Private Full-Day Sailing Charter in Orange Beach

Private Full-Day Sailing Charter in Orange Beach

Pair a boat-only island escape with a sunset sail

$1,994
Private Sunset Sailing Charter in Orange Beach

Private Sunset Sailing Charter in Orange Beach

Share sunset views of coastal Alabama with someone you love

$532
Private Sailing Charter Through Perdido Pass in Orange Beach

Private Sailing Charter Through Perdido Pass in Orange Beach

Take a break from shore with a relaxing escape under sail

$399
Introductory Sailing Lesson on Monterey Bay in Santa Cruz

Introductory Sailing Lesson on Monterey Bay in Santa Cruz

Take the helm or sit back and enjoy the sail

$167/ person
Isla Mujeres Catamaran & Snorkel Tour from Cancún

Isla Mujeres Catamaran & Snorkel Tour from Cancún

Set sail with an unlimited open bar and round-trip transportation included

$147/ person
Private 39' Sailboat Charter Near Mystic

Private 39' Sailboat Charter Near Mystic

Sail straight into Fishers Island Sound, with room to relax or take the wheel

$462/ boat
Private Full-Day Boston Harbor Islands Sailing Charter

Private Full-Day Boston Harbor Islands Sailing Charter

Make the day your own with island hopping, lighthouse views and a swim

$1,585
Private Half-Day Sailing Charter to Boston Harbor Islands

Private Half-Day Sailing Charter to Boston Harbor Islands

Shape your own sailing adventure, with the option to swim

$1,055
Private Boston Harbor Sailing Charter from Seaport

Private Boston Harbor Sailing Charter from Seaport

Take in Boston's waterfront with harbor history or music on a leisurely private sail

$599
Private Sunset Sail Past El Morro in San Juan

Private Sunset Sail Past El Morro in San Juan

Enjoy a classic sailboat all to yourselves, with a licensed captain at the helm

$689/ boat
Private Sailing Tour of San Juan's Old Spanish Forts

Private Sailing Tour of San Juan's Old Spanish Forts

Discover San Juan's historic defenses from the water

$631
Private Sailboat Charter Around Old San Juan Bay

Private Sailboat Charter Around Old San Juan Bay

Help sail or sit back on a private outing

$504/ boat
Burial at Sea Ash Scattering Sail in Oceanside

Burial at Sea Ash Scattering Sail in Oceanside

Share a farewell at sea with your family beside you

$954
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