Late-spring breezes, long golden evenings, and the first warmth of the season. Starting at $1,950/ person. Book here.

Between spring’s close and summer’s dawn — tranquil seas and soft light over the bay. Starting at $1,950/ person. Book here.

Calm waters, pine trees, and wild roses along the coast. Starting at $1,950/ person.Book here.

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. Starting at $1,950/ person.Book here.

Aligns with the Strawberry Full Moon (June 11) — a voyage of light and renewal. Starting at $2,600/ person. Book here.

Gentle winds and the longest days of the year, sailing toward midsummer’s glow. Starting at $3,000/ person. Book here.

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. Starting at $3,750/ person. Book here.

A shorter escape for those seeking luxury in simplicity — sailing between the tides. Starting at $1,500/ person. Book here.

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. Starting at $2,250/ person.Book here.

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. Starting at $2,250/ person. Book here.

Aligned with the Capricorn Full Moon (July 10) — evenings of moonlit sailing and refined dining on deck. Starting at $3,000/ person. Book here.

Mid-summer ease — warm winds, remote islands, and quiet anchorages perfect for repose. Starting at $2,250/ person. Book here.

Long, sunlit afternoons and starlit nights; the height of Maine’s summer luxury. Starting at $2,250/ person. Book here.

Calm seas and luminous skies before the midsummer waning moon. Starting at $2,250/ person. Book here.

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. Starting at $4,500/ person. Book here.

Long, luminous days — ideal for exploring quiet anchorages beneath endless sky. Starting at $2,250/ person. Book here.

Aligned with the Sturgeon Full Moon (August 8–9) — luminous nights and deep tranquility. Starting at $3,000/ person. Book here.

Sailing under the Perseid Meteor Shower (peaks August 12–13) — celestial spectacle at sea. Starting at $3,000/ person. Book here.

Late-summer calm and the first whisper of autumn. Starting at $2,250/ person. Book here.

Golden light, warm tides, and elegant simplicity as summer begins to turn. Starting at $2,250/ person. Book here.

Between the moon’s phases — perfect balance of daylight and stillness. Starting at $2,250/ person. Book here.

Sail into the season’s close with refined leisure and coastal charm. Starting at $2,250/ person. Book here.

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. Starting at $3,000/ person.Book here.

Crisp mornings, clear skies, and the first notes of fall in the air. Starting at $1,950/ person. Book here.

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. Starting at $3,250/ person.Book here.

Aligns with the Partial Solar Eclipse (September 21) — a rare and radiant passage beneath the shifting light. Starting at $1,950/ person. Book here.

The glow of early fall — warm days, crisp evenings, and soft, amber light. Starting at $2,600/ person. Book here.

Late-season calm — intimate sailing and serene anchorages. Starting at $1,950/ person. Book here.

Sail into autumn’s quiet — the final voyage of the year beneath a canopy of stars. Starting at $2,600/ person. Book here.