The Schooner Gam is an annual, spirited raft-up of the fleet — a time when traditional schooners come together under sail, guests hop from boat to boat, live music drifts across the decks, and captains raise a toast to the season. Book now.

Boothbay Windjammer Days is a spectacular journey along Maine’s coastline, culminating in the lively charm of Boothbay Harbor. Here, a large fleet of schooners and traditionally rigged vessels gathers in a celebration of maritime heritage. Guests come together for a classic lobster bake on Cabbage Island, then sail into the inner harbor in unison, joining the annual festival where the sights, sounds, and spirit of Maine’s seafaring tradition fill the air. Book now.

These offshore voyages are not for everyone. This year’s selection includes a passage from Rockland, ME to New York City, and the return journey from New York City back to Rockland. These are true offshore trips, with continuous sailing day and night until we reach our destination. While crossing the Gulf of Maine, we may be up to 60 miles from the nearest point of land, covering approximately 350 miles in a single passage. Guests should be prepared for challenging sea conditions and potentially heavy winds.

Due to the nature of these voyages, a personal conversation with Captain Josh is required for all guests prior to booking. In the days leading up to departure, Captain Josh will reach out again to review the weather forecast. At that time, you may cancel your trip for a full refund if you do not feel comfortable making the passage. Likewise, Captain Josh reserves the right to cancel the trip entirely if conditions are deemed unsafe for the guests. These journeys are extraordinary, but safety and confidence aboard the vessel are paramount. Inquire.

A six-night voyage aboard the Tree of Life participating in the Eggemoggin Reach Regatta is a true celebration of Maine’s sailing tradition. Guests experience the thrill of racing under full sail alongside a fleet of classic schooners, navigating the sparkling waters of Penobscot Bay and Eggemoggin Reach. Days are filled with the rhythm of the wind, breathtaking coastal scenery, and lively camaraderie among fellow sailors, while evenings are spent anchored in quiet coves, savoring meals prepared aboard and the gentle lull of the water beneath the hull. This journey blends the exhilaration of a historic regatta with the intimate luxury and comfort of life aboard a traditional Maine windjammer. Book Now.

A voyage aboard the Tree of Life during Camden Windjammer Festival is a celebration of Maine’s maritime heritage at its most lively and picturesque. Guests sail through the sparkling waters of Penobscot Bay alongside a fleet of classic schooners under full sail, then dock in Camden with the fleet to join in the festivities onshore. Guests and crew are welcome to participate in the lively talent show, adding a personal touch to the celebration. Book Now.

On our final gathering with the fleet for the season, we gather at the stunning Wooden Boat School campus in beautiful Brooklin Maine, where the art of boatbuilding and maritime craftsmanship is taught and preserved. Ashore, guests are welcomed with refreshments, live music, and guided tours of the facilities, offering a glimpse into Maine’s rich nautical heritage. Book Now.