Written by Missy Johnston

Portland Maine Headlands

Portland Head Lighthouse

From Portland to Camden, explore the coast of the state of Maine on a crewed yacht charter when cruising in Maine.   Start in Portland, Maine heading “Down East” gunk holing from port to port, bay to bay and island to island on this great yacht charter itinerary cruising in Maine.


7 Days: Portland – Rockland


Maine Landscape


Fly into Portland to meet your yacht. Relax and unwind while you head into Casco Bay, cruising by picturesque 18th century Portland Head Lighthouse, one of the many historic lighthouses you’ll see along Maine’s dramatic coast when cruising in Maine. Continue to Boothbay Harbor to dine on fresh-caught native Maine lobster.

Maine Lobsters Grilling

Lobsters Grilling

After enjoying breakfast, cruise to quiet Tenants Harbor. Take a taxi to nearby Cushing to visit the Olson House, scene of Andrew Wyeth’s famous painting “Christina’s World”. Today, the Olson House belongs to the Farnsworth Museum in nearby Rockland. If time permits, continue to Rockland, by taxi, to visit the Farnsworth, with its Wyeth Center, featuring the work of N.C., Andrew, and Jamie Wyeth.

Maine Coast

Maine Coast 

Cruise along Penobscot Bay with a stop in Vinalhaven.  Once a granite-quarrying capital, the island provided stone for the huge columns of St. John the Divine in New York. Later, stroll the Victorian town of Carver’s Harbor, home to Maine’s largest lobster boat fleet.


Bass Harbor Headlight - Maine Photo Credit Chantal Maxwell

Bass Harbor Headlight

Stop in the Cranberry Isles to view marine memorabilia at the Islesford Historical Museum. This group of isles is also an ideal area to tour with kayaks. Continue on to near-by Swan’s Island, which cyclists will especially enjoy with its miles of scenic roads. Bass Harbor Light provides a picturesque destination.

Bar Harbor Maine, Docks

Bar Harbor Maine, Docks

After breakfast sail to Bar Harbor on Mount Desert Island. Stroll the charming streets or, for the more adventurous, make an afternoon of hiking in Arcadia National Park, where spectacular views await from the top of Cadillac Mountain. In the evening, dine aboard or at “George’s” before seeing a show at the historic Criterion Theatre.

Camden Maine Overview


Cruise along dramatic Eggermoggin Reach to the quiet village of Castine, home to the Maine Maritime Academy and its 499-foot training ship. Continue to Camden for a cocktail at the Camden Yacht Club. In the morning head to Rocklandto disembark, ending your cruising in Maine adventure.