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

Custom Sailing Charters from Rockland, Maine

Rockland, Maine - 55.2 mi away
Sail the Maine Coast on the Schooner Stephen Taber | Rockland, Maine | Sailing
Yankee Schooner Cruises | Camden, Maine | Sailing

Yankee Schooner Cruises

Camden, Maine - 51.1 mi away

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Rainy Lake Houseboats  premier houseboat rentals | International Falls, Minnesota | Sailing

Rainy Lake Houseboats premier houseboat rentals

International Falls, Minnesota
Joy Ride Charters | Westbrook, Connecticut | Sailing

Joy Ride Charters

Westbrook, Connecticut
Emerald Isle Sailing Charters | Deer Harbor, Washington | Sailing

Emerald Isle Sailing Charters

Deer Harbor, Washington
Hawaii Sailing Adventures | Honolulu, Hawaii | Sailing

Hawaii Sailing Adventures

Honolulu, Hawaii
Sailing Charters At Compass Sailing, Llc | Savannah, Georgia | Sailing
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Sail Channel Islands

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Delaune Sailing Charters | Mandeville, Louisiana | Sailing

Delaune Sailing Charters

Mandeville, Louisiana
Sailing Alaska | Auke Bay, Alaska | Sailing

Sailing Alaska

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Sail Selina Ii | Saint Michaels, Maryland | Sailing

Sail Selina Ii

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Sailing in Arizona | Peoria, Arizona | Sailing

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Top Listings in Maine (show all)
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
Romantic Bar Harbor Waterfront B & B | Bar Harbor, Maine | Bed & Breakfasts

Romantic Bar Harbor Waterfront B & B

Bar Harbor, Maine
Bed & Breakfasts
New England Outdoor Center | Millinocket, Maine | Hotels & Resorts

New England Outdoor Center

Millinocket, Maine
Hotels & Resorts
New England Outdoor Center | Millinocket, Maine | Snowmobiling

New England Outdoor Center

Millinocket, Maine
Snowmobiling
Bill Laflamme | Sidney , Maine | Fishing Trips

Bill Laflamme

Sidney , Maine
Fishing Trips
Eco Sailing Expeditions | Belfast, Maine | Eco Tours

Eco Sailing Expeditions

Belfast, Maine
Eco Tours
Ocean Walk Hotel | Old Orchard Beach, Maine | Hotels & Resorts

Ocean Walk Hotel

Old Orchard Beach, Maine
Hotels & Resorts
Damariscotta River Cruises | Damariscotta, Maine | Cruises

Damariscotta River Cruises

Damariscotta, Maine
Cruises
Getaway to the Coast at the Tugboat Inn | Boothbay Harbor, Maine | Hotels & Resorts

Getaway to the Coast at the Tugboat Inn

Boothbay Harbor, Maine
Hotels & Resorts

Explore Over 100 Travel Categories To Find Your Next Amazing Vacation

With a diverse array of more than 100 travel categories and options, finding the ideal vacation is a breeze. Whether you are looking for a cozy cabins, luxurious resorts, thrilling adventure tours, or tranquil beach getaways, we have the perfect travel option waiting for you.

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Top Winter Harbor, Maine Sailing Vacations | Trips, Rentals & Lessons

Browse incredible Winter Harbor, Maine sailing vacations & trips, take a lesson or rent your own sail boat. Browse our Winter Harbor, Maine sailing options and plan your vacation. Also of Interest: boat charter | charter sailing | charter yacht | private sail | private sailing |
More Within 5 mi, 10 mi, 25 mi, 50 mi, 100 mi, 250 mi, 500 mi, 1000 mi of Winter Harbor, Maine