There is a reason the name of this company is Sail Away Maine. Penobscot Bay is one of the great sailing grounds of the entire eastern seaboard, a vast and island-studded body of water that has shaped the life and culture of this coast for centuries. Dennis and Kami of our own team sail the bay aboard their Pearson 31 foot sailboat, and they will tell you that there is no better way to understand Mid-Coast Maine than from the water.
For guests staying in the Samoset Village oceanview cottages we manage in Rockport, the bay is not a distant attraction. It is right there, visible from the porch, and the harbors that launch you onto it are minutes away. Whether you have sailed your whole life or have never set foot on a boat, a week in a Rockport cottage puts you at the center of one of the finest cruising grounds in North America. Here is how to make the most of it.
Why Penobscot Bay Is One of America’s Great Sailing Grounds
Penobscot Bay earns its reputation. It is large enough to offer serious, multi-day cruising and yet sheltered enough, with countless coves, harbors, and islands, to give paddlers and day sailors calm water when they want it. Scattered across the bay are dozens of islands, from the year-round communities of Vinalhaven and North Haven to uninhabited rocks where seals haul out and ospreys nest. The wind tends to fill in reliably on summer afternoons, the scenery is extraordinary in every direction, and the harbors of Rockland, Camden, and Rockport sit within a few miles of one another along the western shore. For sailors, this combination of protected water, dependable wind, abundant destinations, and genuine beauty is close to ideal.
Sail Aboard a Historic Windjammer
The signature Penobscot Bay sailing experience is a voyage aboard a windjammer, one of the traditional tall-masted schooners that once worked these waters carrying cargo and now carry passengers under sail. The Maine Windjammer Association operates a fleet of about nine vessels out of Camden and Rockland, and it is the oldest and largest fleet of working sailing vessels in North America. Several of the schooners are designated National Historic Landmarks, which means a sail aboard one is a passage through living maritime history.
These ships offer multi-day cruises, typically ranging from three to ten days, from late spring through the middle of fall. On a windjammer trip, the captain follows the wind and weather to wherever the bay is most beautiful that day, anchoring in quiet coves, putting ashore on islands, and serving meals cooked on a wood-fired galley stove. For visitors who want to immerse themselves fully, a windjammer cruise is unforgettable. For those keeping a cottage as a base, many operators also offer shorter day sails that capture the spirit of the experience in an afternoon.
Day Sails and Charters from Camden, Rockland, and Rockport
If your week is built around your Rockport cottage, day sails and private charters are the easiest way onto the water, and the options are excellent. From Camden Harbor, a short drive north, classic vessels such as the schooner Olad and the cutter Owl run public day sails and private charters throughout the summer and into the fall, and the 57-foot schooner Surprise offers tours of Penobscot Bay from the same harbor. Sunset sails are a particular pleasure, with the light going golden over the Camden Hills and the water turning still.
Closer still, from Rockport Harbor itself, the lobster cruiser Harvest Moon runs tours that combine sailing the bay with hauling lobster traps, watching for wildlife, and learning how the fishery that defines this coast actually works. It’s a wonderful outing for families and for anyone curious about the working life of the bay. Across all three harbors, you’ll find options ranging from two-hour public sails to full-day private charters, so you can match the trip to your group and your mood.
Learn to Sail While You’re Here
A cottage week is also a fine time to learn the ropes, literally. The Mid-Coast supports several sailing schools, including instruction based on the protected waters of Rockland Harbor, where US Sailing courses welcome students of every level. Beginners can take their first lessons in a sheltered harbor and progress, as their skills grow, to sailing out into the bay and along the islands. Programs exist for children as well as adults, which makes a learn-to-sail week a memorable family project. There are few better classrooms than Penobscot Bay on a bright summer morning.
Kayaking and Paddling the Coves and Islands
Not every day on the water needs a sail or a captain. Sea kayaking is one of the most rewarding and accessible ways to explore the Mid-Coast shoreline, and outfitters in Rockport and Camden, including Maine Sport Outfitters, rent kayaks, canoes, and standup paddleboards along with guidance on where to go. Rockport Harbor and the sheltered coves nearby offer calm, scenic paddling close to your cottage, while more experienced paddlers can venture farther along the coast.
Serious paddlers should know about the Maine Island Trail, a water trail linking more than 200 islands and mainland sites along the coast, many of them open for day visits or primitive camping. It is one of the finest paddling resources in the country and a magnificent way to experience the bay at water level. A word of respect is in order, though: Maine’s waters are cold even in summer, tides and currents are significant, and fog can roll in quickly, so check the forecast, mind the tides, and stay close to shore unless you are experienced or with a guide.
Bring or Rent a Powerboat
For visitors who prefer a motor, Penobscot Bay is equally welcoming. The harbors at Rockland, Rockport, and Camden offer launches, moorings, and marina services, and a powerboat opens up easy day trips to the islands, productive fishing, and the simple pleasure of cruising the shoreline with a picnic aboard. Whether you trailer your own boat north or arrange a rental once you arrive, the bay is yours to explore at whatever pace you like.
Your Cottage as the Perfect Base
What ties all of this together is location. The Samoset Village cottages sit in Rockport, directly between Rockland to the south and Camden to the north, which places every one of these boating options within a short drive. You can take a sunrise paddle in Rockport Harbor, drive to Camden for an afternoon day sail, and be back on your own porch above Penobscot Bay in time to watch the sunset, grilling the day’s catch in a full kitchen that is yours for the week. The cottage is where the day begins and ends; the bay is the wide-open middle. Pair your time on the water with a round on the oceanfront course next door and a walk on the Rockland Breakwater, and you have the shape of a truly great Mid-Coast week. Our guide to using a Rockport cottage as your home base covers the land-side adventures in more detail.
A Few Practical Notes
The boating season on Penobscot Bay runs roughly from late spring through the middle of October, with peak conditions in July and August. Those peak weeks are also when day sails, charters, and the cottages themselves book up fastest, so reserve early. Dress in layers even on warm days, since it is always cooler on the water, and build a little flexibility into your plans, because the weather and the famous Maine fog write their own schedule. Embrace that unpredictability rather than fight it, and the bay will reward you.
Reserve Your Cottage on Penobscot Bay
A week in a Samoset Village cottage puts the best sailing and boating in New England right outside your door, with the comfort of a fully equipped oceanview home to return to each evening. Availability moves quickly, especially for peak summer weeks, so reach out early to secure your dates. Contact Judy Evans at Sail Away Maine to inquire about availability and rates.
Sail Away Maine Realty and Property Management. Call (207) 593-7065. Our offices are located in Rockport at 89 Village Way and Rockland at 66B Maverick Street. View current cottage listings and learn more at sailawaymaine.com.