Day Sailing & Custom Charters On The Schooner Olad | Camden, Maine | Sailing

Day Sailing & Custom Charters On The Schooner Olad

Camden, Maine
From $57
Rainy Lake Houseboats premier houseboat rentals | International Falls, Minnesota | Sailing

Rainy Lake Houseboats premier houseboat rentals

International Falls, Minnesota
From $260
Custom Sailing Charters from Rockland, Maine | Rockland, Maine | Sailing

Custom Sailing Charters from Rockland, Maine

Rockland, Maine
From $30
Emerald Isle Sailing Charters | Deer Harbor, Washington | Sailing

Emerald Isle Sailing Charters

Deer Harbor, Washington
From $229
Hawaii Sailing Adventures | Honolulu, Hawaii | Sailing

Hawaii Sailing Adventures

Honolulu, Hawaii
From $600
Sailing Charters At Compass Sailing, Llc | Savannah, Georgia | Sailing

Sailing Charters At Compass Sailing, Llc

Savannah, Georgia
From $499
Sail Channel Islands | Oxnard, California | Sailing

Sail Channel Islands

Oxnard, California
From $195
Delaune Sailing Charters | Mandeville, Louisiana | Sailing

Delaune Sailing Charters

Mandeville, Louisiana
From $450
Sailing Alaska | Auke Bay, Alaska | Sailing

Sailing Alaska

Auke Bay, Alaska
From $440
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
Sailing Orlando | Orlando, Florida | Sailing

Sailing Orlando

Orlando, Florida
From $69
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
Newport Beach Sailing Charters | Newport Beach, California | Sailing

Newport Beach Sailing Charters

Newport Beach, California
From $700
Florida Yachts Charter | Saint Petersburg, Florida | Sailing

Florida Yachts Charter

Saint Petersburg, Florida
From $1,300
Chardonnay Sailing Charters | Santa Cruz, California | Sailing

Chardonnay Sailing Charters

Santa Cruz, California
From $60

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More Sailing in North America (show all)
Vancouver Luxury Yacht Charters | Vancouver, British Columbia | Sailing

Vancouver Luxury Yacht Charters

Vancouver, British Columbia
From $3,243
Kootenay Lake Sailing Charters Canada | Crawford Bay, British Columbia | Sailing

Kootenay Lake Sailing Charters Canada

Crawford Bay, British Columbia
From $79
Bareboat yacht charters Pacific North West, Canada | Nanaimo, British Columbia | Sailing

Bareboat yacht charters Pacific North West, Canada

Nanaimo, British Columbia
From $186
Empowerment Adventures For Women | Nanaimo, British Columbia | Sailing

Empowerment Adventures For Women

Nanaimo, British Columbia
From $2,195
Discovery Sailing RYA Sail Training Centre | Chester Basin, Nova Scotia | Sailing

Discovery Sailing RYA Sail Training Centre

Chester Basin, Nova Scotia
8 days cruise - Small island's jewels | Split, Alabama | Sailing

8 days cruise - Small island's jewels

Split, Alabama
From $102
Nova Scotia Sea School | Halifax, Nova Scotia | Sailing

Nova Scotia Sea School

Halifax, Nova Scotia
3-Hour sail Ltd. | Victoria, British Columbia | Sailing

3-Hour sail Ltd.

Victoria, British Columbia
From $52
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
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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
Classic Harbor Line | Key West, Florida | Sailing

Classic Harbor Line

Key West, Florida
From $55
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
Waterpoint Marina Party Boats and Lakeside Venue | Houston, Texas | Sailing

Waterpoint Marina Party Boats and Lakeside Venue

Houston, Texas
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Mt. Baker Lodging Cabins At Mount Baker Washington | Maple Falls, Washington | Vacation Rentals

Mt. Baker Lodging Cabins At Mount Baker Washington

Maple Falls, Washington
Vacation Rentals
From $99
Africa Tours | Philadelphia, Pennsylvania | Sight-Seeing Tours

Africa Tours

Philadelphia, Pennsylvania
Sight-Seeing Tours
From $1,475
Cruzan Yacht Charters, Inc. | Miami, Florida | Yacht Charters

Cruzan Yacht Charters, Inc.

Miami, Florida
Yacht Charters
From $950
Timberpine Lodge | Adel, Iowa | Vacation Rentals

Timberpine Lodge

Adel, Iowa
Vacation Rentals
From $375
Maine's Best Vacation Value Poland Spring Resort | Poland Spring , Maine | Hotels & Resorts

Maine's Best Vacation Value Poland Spring Resort

Poland Spring , Maine
Hotels & Resorts
From $145
Everglades Day Safari | Fort Myers, Florida | Eco Tours

Everglades Day Safari

Fort Myers, Florida
Eco Tours
From $199
Cielito Lindo Travel Agency Llc | Indio, California | Car & Van Shuttle Service

Cielito Lindo Travel Agency Llc

Indio, California
Car & Van Shuttle Service
From $65
Florida Van Rentals - Passenger & Wheelchair Vans | Orlando, Florida | Car Rentals

Florida Van Rentals - Passenger & Wheelchair Vans

Orlando, Florida
Car Rentals
From $71
Fun fishing Charter Williamsburg Virginia | Williamsburg, Virginia | Fishing Trips

Fun fishing Charter Williamsburg Virginia

Williamsburg, Virginia
Fishing Trips
From $300
The Isle au Haut Mail Boat - Puffin Cruises | Stonington, Maine | Cruises

The Isle au Haut Mail Boat - Puffin Cruises

Stonington, Maine
Cruises
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Top United States Sailing Vacations | Trips, Rentals & Lessons

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