Your Maine Sailing Vacation Begins Here...

Sailing aboard the Schooner Timberwind for a 3, 4, and 6-day windjammer cruise may be one of the smartest vacation decisions you will ever make! Your adventure begins in beautiful Rockport Harbor with the sounds of sea birds, and the scent of fresh salt air.  From the moment you are welcomed aboard, there is nothing else for you to plan or organize. Away from the phones, faxes, emails, and traffic, you are invited to step back in time aboard this National Historic Landmark Vessel, as she sails along the sheltered waters and Islands of Penobscot Bay.  An all-inclusive sailing adventure, your meals are lovingly prepared on a wood burning cook stove by chef and co-owner (Dawn), who delights in treating you to feasts of memorable proportions; delicious foods presented with a passion for detail, and a traditional Maine lobster bake are a feature on every cruise!  A native Maine windjammer, the Timberwind is the only pilot schooner sailing the coast of Maine. With no inboard engine, she sails in harmony with the winds and tides ... and as the saying goes, “Wherever we end up, its right where we want to be, and whenever we get there, we’re right on time” Capt. O.K. Barnes

Why Choose the Timberwind?

We started our adventure into the Windjammer business as passengers, and just like you, didn’t know exactly what to expect. We have worked in every level of this business from shore support to ownership, and this unique perspective enables us to offer you a cruise experience that is welcoming, personal, fun, and worry free!

We specialize in Family Cruises:

Family owned and operated, the Timberwind specializes in bringing every kind of family together in a safe, friendly, relaxing, and nurturing environment. With special Charter rates available, the Timberwind is the perfect platform for reunions, retreats, workshops, or school and scouting trips.    “We have an abiding love for family, nature, the cruising grounds we sail, and our vessels place in history, and we are eager to share our beautiful schooner with you.”

Capt. Bob, Dawn, Will, and Emily!

 *The Timberwind welcomes children ages 5 and up.

Click here for more information on our "Sail Inn" land and sea package