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Seafaring Splendors | A Maine Sailing Itinerary

Explore Maine’s rugged and beautiful coast, with hundreds of picturesque islands, coves, and harbors. The next New England sailing vacation offers visits to out-of-the-way fishing villages accessible only by boat and seacoast towns with restaurants and shops. Allow the yacht charter brokers at Luxury Yacht Charters to plan every detail of your Maine Sailing Itinerary. All you have to do is relax and enjoy the ride.

maine sailing itinerary
Sailing Yacht August Maverick

7-Day Maine Sailing Itinerary from Mid-Coast and Downeast Maine

Day 1

Meet your yacht charter in Southwest Harbor and enjoy lunch while watching the harbor activity. Sail through the famous Hinckley Yacht moorings and view some of the prettiest sailboats ever. Then, set sail for Frenchboro, Long Island, passing Placentia, Black, and Gott’s Island. If the tide is low, you can see seals on rocky ledges along the way.

Frenchboro is a traditional offshore Maine fishing village with a 200+ year commercial history. Take a leisurely walk ashore on paths through the woods. Then, enjoy a traditional Maine lobster feast onboard with freshly caught lobsters purchased from local fishing boats.

Day 2

Sail up Blue Hill Bay and into the Eggemoggin Reach, stopping at Wooden Boat Harbor, home to Wooden Boat Magazine and the Wooden Boat School. Enjoy the view from the cockpit or a dinghy tour of some of the most beautiful wooden boats in the world.

The various student projects underway at the Wooden Boat School may be of interest, as well as the gift shop, which has an exciting assortment of nautical memorabilia and books. It’s an excellent place to stretch your legs before returning to the boat for dinner. Another option is to go to Brooklyn for fine dining ashore.

Day 3

After breakfast, continue up the Eggemoggin Reach, under the Deer Isle Bridge, around Cape Rosier, and into the eastern side of Penobscot Bay. The scenery in the Reach is stunning, the water is protected, and the sailing is smooth.

Then, continue up Penobscot Bay enjoying the scenery along the Cape Rosier coast and a cup of chowder. Enter the Bagaduce River, sail past the Maine Maritime Academy, and pick up a mooring at Eaton’s Boatyard in Castine.

Enjoy a stroll in this historic town, pausing to admire the traditional black shuttered white framed captain’s homes. Four nations governed Castine in revolutionary war times, and each left its mark. There are multiple options for eating ashore, ranging from fine dining at historic inns to on-the-water seafood restaurants.

Day 4

Continue your Maine Sailing Itinerary and enjoy the waters in northern Penobscot Bay. Have a sailor’s lunch aboard or a stop in Belfast for a meal ashore. Several shops in Belfast may be of interest.

After lunch, sail down the western side of Penobscot Bay along the scenic coast of Isleboro and pick up a mooring or anchor in Gilkey Harbor off Seven Hundred Acre Island.

A small boatyard on this island often offers homemade jams from local berries. There is a small dirt road (no cars) for hiking ashore through mossy woods and meadows where you may see wild turkeys. Return to the boat with a hearty appetite for drinks, snacks, and dinner. Enjoy the sunset.

Day 5

Hoist the sail and head down the west side of Penobscot Bay, past Camden, Rockport, the Rockland Breakwater and Light, and into Rockland Harbor. While sailing Penobscot Bay, you will likely see the famous Maine windjammers. With their many sails, these grand schooners are a sight right out of the 19th century.

Pick up a mooring in Rockland and, at your option, eat ashore with many choices and enjoy the shops and waterfront attractions. An option here is a layover to explore the Farnsworth Art Museum and its famous Wyeth collection. It is also a short hop by taxi to bustling Camden with its picturesque harbor.

Day 6

Head east across Lower Penobscot Bay to the picturesque Deer Island Thoroughfare as you enter one of the world’s most famous sailboat cruising grounds. Sail past North Haven, across Isle Au Haute Bay, Stonington, and through the Fox Island Thoroughfare and Jericho and Toothacher Bays.

You’ll see granite quarrying, picturesque villages, working lobster boats, and grand estates. If the Rockland layover option has been taken, you will sail directly to Bass Harbor. Otherwise, you will enter Burnt Coat Harbor on Swan’s Island, a protected working harbor and an excellent place to relax last night aboard.

It is a short walk to a restored lighthouse at the entrance to the harbor. It has a spectacular view of the West and South. Return to the boat for dinner aboard. An option here is “fresh off the boat” local lobster.

Day 7

As the colorful lobster boats head out to fish, have breakfast in the cockpit and enjoy your coffee while watching a Maine fishing harbor at work. Sail north along the eastern shore of Swan’s Island, east through the Casco Passage, and past the Bass Harbor Light, the most photographed light on the US eastern coast. Enter Bass Harbor and pick up Fiona’s mooring and dinghy ashore or tie up at a pier.

In addition to the picturesque lighthouses, beautiful boats, and quaint island villages, you likely have seen seals, porpoises, loons, ospreys, and bald eagles during your cruise. And since you have tasted Maine, we hope you will want to return and experience more of it.

The more adventuresome may wish to explore Downeast Maine more extensively. And the Canadian Maritime Provinces, including the Bay of Fundy, the South coast of Nova Scotia, and Cape Breton.

The above sample itinerary is from the sailing yacht “Fiona Rois.”