Waterpoint Marina Party Boats and Lakeside Venue | Houston, Texas | Sailing

Waterpoint Marina Party Boats and Lakeside Venue

Houston, Texas
Sailing Classes in Vancouver | Vancouver, British Columbia | Sailing

Sailing Classes in Vancouver

Vancouver, British Columbia
From $79
Wild Island Tours | Amelia Island, Florida | Sailing

Wild Island Tours

Amelia Island, Florida
Luxury Yacht Charter Cancun Playa Mujeres Mexico | Cancun, Mexico | Sailing

Luxury Yacht Charter Cancun Playa Mujeres Mexico

Cancun, Mexico
From $700
Yacht Charter Holidays in the Greek islands | North Miami Beach, Florida | Sailing

Yacht Charter Holidays in the Greek islands

North Miami Beach, Florida
The Advantaged Yacht Charters & Sales | Miami Beach, Florida | Sailing

The Advantaged Yacht Charters & Sales

Miami Beach, Florida
From $1,200
Nancy Anne Sailing Charters | Holland, Michigan | Sailing

Nancy Anne Sailing Charters

Holland, Michigan
From $300
Cinderella Sailing Charters | Wailuku, Hawaii | Sailing

Cinderella Sailing Charters

Wailuku, Hawaii
Honolul Sailing Company | Honolulu, Hawaii | Sailing

Honolul Sailing Company

Honolulu, Hawaii
From $60
Hawaii Glass Bottom Boat | Honolulu, Hawaii | Sailing

Hawaii Glass Bottom Boat

Honolulu, Hawaii
From $35
Pacific Northwest Yacht Charters | Seattle, Washington | Sailing

Pacific Northwest Yacht Charters

Seattle, Washington
Seattle Yacht Charters Daily | Pahrump, Nevada | Sailing

Seattle Yacht Charters Daily

Pahrump, Nevada
Yankee Schooner Cruises | Camden, Maine | Sailing

Yankee Schooner Cruises

Camden, Maine
Adventure Cat Sailing Charters | San Francisco, California | Sailing

Adventure Cat Sailing Charters

San Francisco, California
Executive Get-A-Way Yacht Charters | Boca Raton, Florida | Sailing

Executive Get-A-Way Yacht Charters

Boca Raton, Florida
Land's End Sailing School | Vancouver, British Columbia | Sailing

Land's End Sailing School

Vancouver, British Columbia
Alaska Good Time Charters | Wasilla, Alaska | Sailing

Alaska Good Time Charters

Wasilla, Alaska

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More Sailing Around the World (show all)
Tum Tour Gulet Motor Yacht Charter & Blue Cruise | Mugla, Turkey | Sailing

Tum Tour Gulet Motor Yacht Charter & Blue Cruise

Mugla, Turkey
From $385
Halkidiki Sailing Boat Day Trips & Tours | Neos Marmaras, Greece | Sailing

Halkidiki Sailing Boat Day Trips & Tours

Neos Marmaras, Greece
From $439
Medsail Holidays AB | Mugla, Turkey | Sailing

Medsail Holidays AB

Mugla, Turkey
From $330
Sail Selina Ii | Saint Michaels, Maryland | Sailing

Sail Selina Ii

Saint Michaels, Maryland
From $75
Sailing in Arizona | Peoria, Arizona | Sailing

Sailing in Arizona

Peoria, Arizona
From $185
Unique Southern Adriatic Cruising | Split, Croatia | Sailing

Unique Southern Adriatic Cruising

Split, Croatia
From $188
Sailing Orlando | Orlando, Florida | Sailing

Sailing Orlando

Orlando, Florida
From $69
Capri Boat Excursions | Sorrento, Italy | Sailing

Capri Boat Excursions

Sorrento, Italy
From $88
Duchess Sailing Charters | Grosse Pointe, Michigan | Sailing

Duchess Sailing Charters

Grosse Pointe, Michigan
From $250
Joy Ride Charters | Westbrook, Connecticut | Sailing

Joy Ride Charters

Westbrook, Connecticut
From $110
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Sound Sailing- Crewed Sailboat Charters in Alaska | Sitka, Alaska | Sailing

Sound Sailing- Crewed Sailboat Charters in Alaska

Sitka, Alaska
From $300
Luxury Yacht Charters from Granville Island | Vancouver, British Columbia | Sailing

Luxury Yacht Charters from Granville Island

Vancouver, British Columbia
From $251
Adventure Cat Sailing Charters | San Francisco, California | Sailing

Adventure Cat Sailing Charters

San Francisco, California
From $40
Alaska Charter Yachts | Petersburg, Alaska | Sailing

Alaska Charter Yachts

Petersburg, Alaska
From $4,000
Pacific Yellowfin Private Charters | Vancouver, British Columbia | Sailing

Pacific Yellowfin Private Charters

Vancouver, British Columbia
From $8,978
Classic Harbor Line | Key West, Florida | Sailing

Classic Harbor Line

Key West, Florida
From $55
Vancouver Island Sailing School, lessons & courses | Island, British Columbia | Sailing

Vancouver Island Sailing School, lessons & courses

Island, British Columbia
Sail the Maine Coast on the Schooner Stephen Taber | Rockland, Maine | Sailing

Sail the Maine Coast on the Schooner Stephen Taber

Rockland, Maine
From $550
Adventure Charters and Dive | Moss Point, Mississippi | Sailing

Adventure Charters and Dive

Moss Point, Mississippi
From $100
Top Listings in North America (show all)
Mayfield Country Cottages | Cavendish, Prince Edward Island | Vacation Rentals

Mayfield Country Cottages

Cavendish, Prince Edward Island
Vacation Rentals
From $79
Alberta Fishing Charters | Calgary, Alberta | Fishing Trips

Alberta Fishing Charters

Calgary, Alberta
Fishing Trips
From $278
South Louisiana Red Fishing Charters | Lafayette, Louisiana | Fishing Trips

South Louisiana Red Fishing Charters

Lafayette, Louisiana
Fishing Trips
From $250
Romantic Oceanfront Cottage Nova Scotia | Shelburne, Nova Scotia | Vacation Rentals

Romantic Oceanfront Cottage Nova Scotia

Shelburne, Nova Scotia
Vacation Rentals
From $119
Family Friendly Disney Villa W/ Pool & Playground | Orlando, Florida | Vacation Rentals

Family Friendly Disney Villa W/ Pool & Playground

Orlando, Florida
Vacation Rentals
From $114
Maui Condo Rental By Beach From $165nt -kihei Maui | Kihei, Hawaii | Vacation Rentals

Maui Condo Rental By Beach From $165nt -kihei Maui

Kihei, Hawaii
Vacation Rentals
From $165
The Pines Motel & Cottages | Rustico, Prince Edward Island | Vacation Rentals

The Pines Motel & Cottages

Rustico, Prince Edward Island
Vacation Rentals
From $80
Romantic Bar Harbor Waterfront B & B | Bar Harbor, Maine | Bed & Breakfasts

Romantic Bar Harbor Waterfront B & B

Bar Harbor, Maine
Bed & Breakfasts
From $155
Ez Campin' Rentals | Bass Lake , California | RV Rentals

Ez Campin' Rentals

Bass Lake , California
RV Rentals
Alberta Sturgeon Fishing Trips | Medicine Hat, Alberta | Fishing Trips

Alberta Sturgeon Fishing Trips

Medicine Hat, Alberta
Fishing Trips
From $585
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North America Sailing Vacations | Trips, Rentals & Lessons

Browse incredible North America sailing vacations & trips, take a lesson or rent your own sail boat. Browse our North America sailing options and plan your vacation. Also of Interest: boat charter | charter sailing | charter yacht | private sail | private sailing |