Maine Cruising Itinerary

Maine Cruising Itinerary

Take a week to explore the coastal life from Portland to Camden with this Maine cruising itinerary.

Who wouldn’t want a chance to get a taste of cosmopolitan Portland, Maine’s mid-coast and Downeast areas, and explore its working watermen villages? Missy Johnston, owner, president and senior yacht charter specialist at Northrop-Johnson Yacht Charters Newport, recommends the following weeklong Portland to Camden Maine cruising itinerary for any sailor looking to experience all of the fantastic amenities and attractions along the coast of Maine.

Maine’s rocky, rugged coastline is resplendent with islands, coves, bays, anchorages, and wildlife (harbor seals, minke and finback whales, Atlantic puffins, and more), while its coastal towns and villages lure visitors with their working harbors, art galleries, historic theaters, and restaurants serving up fresh Maine lobster.

Capt. Brian Warner of the 86-foot, Custom Line Navetta 26 Slainte III has cruised this route multiple times and praises its natural beauty; however, he warns captains that morning fog (which usually lifts but sometimes persists throughout the day), lobster pots and rocks are a few of the challenges, and adds, “The most popular anchorages have good holding in a muddy bottom, but you need to be aware of rocks, which can sometimes hang you up.”

If you’re planning to explore on your own, Warner advises that you “read as many
area cruising guides as possible, use good charts and look out the window instead of
at your chartplotter all the time.”

DAY 1: Portland to Boothbay Harbor

Start your week at DiMillo’s Marina in the heart of Portland’s revitalized warehouse

district, Old Port. Full provisioning and marine services are available. It’s also worth spending a night or two here before your cruise to explore the area’s nightlife, microbreweries, farm/ocean-to-table restaurants, 19th, and 20th-century architecture, markets, museums, and boutique shopping.

maine cruising itinerary
Booth Bay Harbor is worth the trip.

A few blocks from the waterfront is the Arts District, home to the Portland Museum of Art, the Wadsworth-Longfellow House (poet Henry Wadsworth Longfellow’s (1807-1882) childhood home) and more.

Casco Bay and its many islands border Portland to the east. After a short cruise southeast, you’ll be treated to a view of the Portland Head Light, Maine’s oldest lighthouse.

Take a turn to the northeast and continue 32 nautical miles through Casco Bay past Halfway Rock and Sequin Island before rounding the Cuckolds to head north into well-protected Boothbay Harbor. The region has a lengthy shipbuilding history, which continues today, with shipyards building luxury yachts, tugboats, modern lobster boats, and more.

Dock or moor at one of the marinas, or anchor on the west side of the harbor near Mill Cove. Then, wander around town, seeking out the perfect dinner and possibly catching a performance at the prestigious Opera House.

DAY 2: Boothbay Harbor to Monhegan Island

Maine Cruising Itinerary
Classic lobster boats fill the harbors.

Today’s destination, following a 17.5-nautical mile cruise south and then east, is car-free Monhegan Island, a small, hilly, rocky island 10 miles from the nearest mainland and a longtime haven for artists. Peruse its art studios and hike some of its often steep and strenuous trails, which lead through woodlands and up to high cliffs such as Whitehead and Burnt Head. Guest moorings and anchorages are first-come, first-served. Contact
the harbormaster when you’re near the island for suggestions.

DAY 3: Monhegan Island to Tenants Harbor

Today’s stop in the Maine cruising itinerary takes you fifteen nautical miles to the northeast past Mosquito Island and back along the fingers of the Maine coast. You’ll cruise into Tenants Harbor. Moor in the harbor (contact the  Tenants Harbor Boatyard,, for a rental), then come ashore to stretch your legs and browse the village shops.

For the true art historian, catch a taxi to the Olson House in Cushing, a 30-minute country ride up through Thomaston and back south to see the colonial farmhouse that was the
subject of numerous works by American painter Andrew Wyeth, including Christina’s World (1948). Lighthouse lovers can taxi south from Tenants Harbor to Marshall Point
Lighthouse which sits on a rocky point with a long wooden runway connecting it to the house. It’s the spot where Tom Hanks ended a leg of his cross-country run in the 1994 film Forrest Gump.

DAY 4: Tenants Harbor to Vinalhaven

Vinalhaven has one of the world’s largest fleets of lobster boats.

Head out on today’s 19.5-nautical mile cruise east then northeast passing south of the Muscle Ridge islands then sail up across southern Penobscot Bay to Vinalhaven, Maine’s largest offshore island community. Carvers Harbor, on Vinalhaven’s southern end, is home to one of the world’s largest lobster fishing fleets.

Anchor or moor in the inside of the harbor, says Warner, then “relax and take in the sights of a town that doesn’t want to be found.” One such sight is Lane’s Island, a land preserve south of town, with a couple miles of trails and a few different species of birds for birdwatching.

DAY 5: Vinalhaven to Swan’s Island (via Cranberry Isles)

Venture into Maine’s Downeast, cruising 31 nautical miles east/northeast to the Cranberry Isles. The five islands are named for their low-bush cranberries and boasting views of nearby Acadia National Park’s mountains. Moor if your yacht is less than 50 feet. Or anchor in small, lobster buoy-filled Islesford Harbor on Little Cranberry Island. Definitely visit the  Islesford Historical Museum and art galleries.

Afterward, backtrack 11 nautical miles to Swan’s Island and moor along Burnt Coat  Harbor’s southwest side north of the Burnt Coat Harbor Lighthouse. Spend the afternoon visiting one or more of this lobstering island’s three small villages. Be sure to catch the sunset from the lighthouse on Hockamock Head. Or, take an adventure to find Fine Sand Beach.

DAY 6: Swan’s Island to Bar Harbor

maine cruising itinerary
Wander the scenic streets of Bar Harbor, ME.

Today, cruise 25 nautical miles northeast past the Cranberrys. Take in the rocky, forested shores of Acadia National Park on Mount Desert Island. Arrive in Bar Harbor, a
popular vacation destination and the gateway to the Park. After docking at Harborside Marina on Frenchman Bay, set off for a hike in the national park. Perhaps you’ll summit Cadillac Mountain on a 7.1-mile return adventure. After dinner, if you’re still awake, see a show at the 1932 Criterion Theatre.

DAY 7: Bar Harbor to Camden

Don’t stuff yourself at breakfast. The highlight today is a lunchtime lobster boil (lobster, clams, chorizo or Kielbasa, red boiling potatoes, and corn), which is a fun way to take a break on your voyage to Camden. Cruise south from Bar Harbor back around the  Cranberrys, past the Bass Harbor Head Lighthouse and up through the dramatic Eggemoggin Reach. You’ll have Little Deer Isle to port and pass under the Deer Isle Bridge. Once around Eggemoggin on the northern tip of the island, head southwest to tiny Barred Island, just past Hog Island. It’s an uninhabited island split by a beach.

With a full belly, cruise 45 nautical miles through the islands of Islesboro and into West
Penobscot Bay to Camden, a harbor at the foot of the Camden Hills. (Call the Camden harbormaster for a dock in town.) Then make the most of your remaining Maine moments. Peruse the downtown shops. Maybe check out the views over Camden Harbor and Penobscot Bay from the Mount Battie trail in Camden Hills State Park. Or, attend a performance at the historic Camden Opera House.

Your heart may yearn for another week of exploration on this Maine cruising itinerary. But rest assured, Camden is a picturesque place to finish, evoking a sense of the area’s rich maritime history. “In the evening,” says Johnston, “with all the wooden schooners home at the docks and on mooring balls, one can envision what a Maine harbor looked like in the 1800s.”

Charming? Absolutely.

By Kara Murphy, Southern Boating July 2019

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