Sailing Adventure: Windjammer Cruise in Maine

Cruising in Maine is a unique experience. Instead of massive cruise ships, a small fleet of historic wooden tall ships plies these waters.

Sailing through the islands of Maine. Photo by Janna Graber
Sailing through the islands of Maine. Photo by Janna Graber

The Island Life

Maine has more than 7,000 islands. While most are uninhabited, some of the islands are dotted with million dollar (and up) summer vacation homes; others are home to a few year-round locals. A few of the islands even have farms, their own power, including wind turbines. Maine’s ferry system provides transportation to several islands, providing a range of daily or even just monthly service.

Sailing in Penobscot Bay is like a front row seat to Mother Nature. In addition to the island scenery, these waters are home to puffins, seals, and even whales. Without the light pollution of the city, the night skies are covered with stars. Every once in a while, you can even see the colorful, undulating Northern Lights.

Every Windjammer cruise is a different experience because there is no set itinerary. The winds and the weather help the captain determine our course. Though most of our time is spent sailing, each day, we go ashore somewhere to stretch our legs and explore. Windjammer cruises may stop at fishing villages, bustling towns, or even Acadia National Park.

Our first stop is at Stonington, a small town on a bridged island in Penobscot Bay. A true lobster town, the waters of Stonington and nearby Deer Isle are home to a working fleet of more than 300 lobster boats. Colorful lobster buoys dot the water like candy, and lobster boats fill the harbor.

Though there are shops and cafes to visit, I’m more curious about what it’s like to live in Stonington. We meander the streets, walking past historic homes that range from grand colonial-style houses to country cottages. Lobster traps sit stacked in backyards or in shingled sheds. Here and there a boat sits out back, waiting to return to the water.

Over the next few days, time seems to slow down. My cell phone rarely get signal, so I happily put it away and forget about the office. The days are warm, and the nights cool. I can feel the stress leaving my body.

On our last evening, we drop anchor in quiet Pulpit Harbor off the coast of North Haven. The sun is starting to set as we finish our meal.

“Who wants to go rowing?” one of the crew calls. Within minutes, Ben and I are in a rowboat exploring the harbor. (In truth, Ben is rowing, while I’m enjoying the ride.)

As the sky darkens, tiny lights illuminate the other boats anchored in the harbor. Everything is absolutely quiet; all I hear is the sound of Ben’s rowing and the gentle sound of laughter coming from the American Eagle, which is now in the distance.

The American Eagle looks tall and majestic, silhouetted in the sunset. Ben stops rowing and we coast silently, savoring this moment. Then we grin at each other, and head back to the ship.

If You Go

Getting There

The American Eagle sails out of Rockland, which is located in mid-coast Maine. It is a four-hour drive from Boston and a two-hour drive from Portland.

The Maine Windjammer Association offers an Air & Sea Package for an additional $150/person, which includes air transportation from Boston to Rockland via Cape Air, and ground transportation from the airport to the harbor. Cape Air has several flights daily from Boston, and offers friendly, efficient service.

Cape Air

American Eagle
The American Eagle offers three to seven-day cruises from late May to mid-October

Where to Stay in Rockland
Many guests prefer to go a day early and stay at one of Rockland’s unique Bed & Breakfasts. We stayed at the Old Granite Inn. The 8-room inn is located in beautiful stone building on Main Street overlooking Rockland Harbor, and its only a quick walk down the street to the town shops and restaurants. The rooms are large and comfortable. Innkeeper Ed Hantz is known for his incredible breakfasts — and he doesn’t disappoint.

Granite Inn

Maine Windjammer Cruises
Cruises run from mid-May to mid-October, and last from three to seven days.
Windjammer cruises are good for older children and on up. Prices average around $160/day include all meals. Some guests come alone; others come in families, couples or even groups.

Maine Windjammer Association



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