Best results for
Sailing in Wiscasset, ME
Showing 1-16 of 16 results
Lobstering Sail Past Rockland Breakwater Lighthouse
Help haul lobster traps aboard one of Maine's last sailing lobster boats
Private Sunset Sailing Charter in Boothbay Harbor
Unwind on the water as evening settles over the coast
Private Full-Day Island & Cove Sailing Charter in Boothbay Harbor
More time to sail, relax, and explore the Maine coast
Private Half-Day Sailing Charter in Boothbay Harbor
See Maine's lighthouses and islands from the water
Fall Foliage Cruise in Rockland
Sail through fall colors and search for an island lobster-feast setting
4.9 • 133 reviews
Sail Boothbay Harbor on a 1.5-Hour Guided Cruise
Sail Boothbay Harbor aboard the Friendship Sloop Bay Lady on a 1.5-hour trip
4.7 • 190 reviews
Rockland Harbor Sailing Tour Past Breakwater Lighthouse
Help raise the sails and try steering along Maine's rugged coast
Schooner Sail Past Burnt Island Light in Boothbay Harbor
Help sail Boothbay Harbor’s oldest windjammer
Fall Foliage Sailing Cruise From Rockland
Sail through fall color toward an island lobster feast
4.9 • 133 reviews
Private Half-Day Sailing Charter in Rockland, Maine
Explore Penobscot Bay on a private sail shaped around you
Classic Schooner Sail in Boothbay Harbor
Take in Maine’s rugged coastline with open views from every seat
Private 55' Ketch Sailing Charter in Rockland
Set your own course across Penobscot Bay, with the option to explore an island preserve
Sunset Schooner Sail in Boothbay Harbor
Take in Maine's rugged coast with 360-degree views from your seat
Private Penobscot Bay Sailing Charter from Rockland
Relax on your own private ketch or lend a hand with the sailing
Boothbay Harbor Sunset Schooner Sail Past Burnt Island Light
Take in Maine's rocky coast with 360-degree views from your seat