Joy Ride Charters | Westbrook, Connecticut | Sailing

Joy Ride Charters

Westbrook, Connecticut
From $110
Discovery Sailing RYA Sail Training Centre | Chester Basin, Nova Scotia | Sailing

Discovery Sailing RYA Sail Training Centre

Chester Basin, Nova Scotia
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
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
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

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Sailing In Mediterranean With Medsail Holidays | Aegean Islands, Greece | Sailing

Sailing In Mediterranean With Medsail Holidays

Aegean Islands, Greece
From $164
Empowerment Adventures For Women | Nanaimo, British Columbia | Sailing

Empowerment Adventures For Women

Nanaimo, British Columbia
From $2,195
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
CYCLADES REGATA 2015 on a DUFOUR 30 Classic | Athens, Greece | Sailing

CYCLADES REGATA 2015 on a DUFOUR 30 Classic

Athens, Greece
From $550
SAIL aboard AUTHENTIC 1875 Schooner & in the Med | Prevesa, Greece, Greece | Sailing

SAIL aboard AUTHENTIC 1875 Schooner & in the Med

Prevesa, Greece, Greece
From $87
Delaune Sailing Charters | Mandeville, Louisiana | Sailing

Delaune Sailing Charters

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

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Auke Bay, Alaska
From $440
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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
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Ayahuasca Hawaii? Enjoy Our Hawaiaka Brew, Kona | Kealakekua, Hawaii | Health Spas & Retreats

Ayahuasca Hawaii? Enjoy Our Hawaiaka Brew, Kona

Kealakekua, Hawaii
Health Spas & Retreats
Helicopter Sightseeing Tours - Halifax, Ns | Enfield, Nova Scotia | Sight-Seeing Tours

Helicopter Sightseeing Tours - Halifax, Ns

Enfield, Nova Scotia
Sight-Seeing Tours
From $1,193
Secluded Cabin in Texas Hill Country on Frio River | Leakey, Texas | Vacation Rentals

Secluded Cabin in Texas Hill Country on Frio River

Leakey, Texas
Vacation Rentals
From $95
Ride a dogsled through a forest white with snow | Moonstone, Ontario | Dog Sledding

Ride a dogsled through a forest white with snow

Moonstone, Ontario
Dog Sledding
From $48
Redfish Capital Of The World | Delacroix, Louisiana | Fishing Trips

Redfish Capital Of The World

Delacroix, Louisiana
Fishing Trips
From $150
Whales and Wildlife Catamaran Style | St. Andrews, New Brunswick | Whale Watching

Whales and Wildlife Catamaran Style

St. Andrews, New Brunswick
Whale Watching
From $30
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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 |