Specialty Cruises


Wine Tasting


Wine-Tasting Cruise

Each day will culminate in a wine journey led by the talented Jane Barrett Barnes. We’ll visit a different country each evening with a wine tasting and a discussion of its varietals and viticultural history. The evening’s meal will include wine pairings which perfectly complement the menu that Jane and our chef have created.

  • Jun 11–14, 3 nights ($818/$777 before Mar 1)

  • Jul 5–9, 4 nights ($1,088/$1,034 before Mar 1)

  • Aug 24–28, 4 nights ($1,088/$1,034 before Mar 1)

  • Sep 20–26, 6 nights ($1,318/$1,252 before Mar 1)


Gourmet Gastropub Cruise

If the idea of elevated comfort food and classic bistro fare has your mouth watering, then sail with Chef James Tranchemontagne. Owner of gastropub Frog and Turtle, Chef James will not only cook for us but also be on hand to discuss techniques, inspirations, and his passion for housemade charcuterie.

  • Jun 24–27, 3 nights ($768/ $730 before Mar 1)


Live, Acoustic Music

Live Music and Fleet Rendezvous

This cruise features a "gam," a festive gathering of Maine's magnificent schooner fleet to celebrate America's maritime heritage. By day we'll sail in company. Each evening, we'll raft up together and our onboard house band, the Charlie Nobles, will add an upbeat note of jazz, blues, and Americana to the air.

  • Jun 6–11, 5 nights ($918/872 before Mar 1)

Summer Solstice + Music Cruise

We’ll raft up each evening alongside sister ship Ladona to unwind with an informal yet intimate concert provided by Jenn Schott and Melissa Peirce. These two accomplished Nashville-based recording artists will be joined by the musically gifted captains of both ships.


Fleet Racing + Rendezvous


The Great Schooner Race

Our week of sailing will culminate in one of the most exciting days of the season. Known as North America’s largest annual gathering of tall ships, the Great Schooner Race attracts more than two dozen windjammers. The Taber looks to defend her title as 2017’s fastest ship. Sailing experience not necessary.

Parade of Tall Ships

On our first full day, you’ll get a close-up view of Maine’s entire windjammer fleet in the annual Parade of Sail in our home port of Rockland. This event alone is a photographer’s paradise, so don’t leave home without your camera!

Yacht Racing Regatta

4 nights (Thu–Tue) ‧ $1,128/$1,072 before Mar 1
Set your eyes on a beautiful fleet of classic yachts as we join the annual Camden Classics Cup. A parade of sail and the big race will set a festive and exciting tone to the beginning of our trip.

Eggemoggin Reach Regatta

5 nights (Wed–Mon) ‧ $1,128/$1,072 before Mar 1
The Eggemoggin Reach Regatta promises good sailing, sportsmanship, and camaraderie. What began in 1985 with 13 wooden boats has grown to an internationally known gentlemen’s race with 125 classic yachts of varying sizes and classes. Catching sight of the grand fleet is breathtaking, and being aboard is a rare opportunity indeed.

Camden Windjammer Festival

We’ll gather with the fleet on the final full day of the cruise in picturesque Camden Harbor for the Camden Windjammer Festival, its festivities reminiscent of the days when hundreds of coastal schooners lined the waterfront. A parade of sail, flag-raising ceremonies, live music, dancing, fireworks – there’s something for everyone.

Final Fleet Gathering at WoodenBoat

On our last rendezvous with the fleet for the season, we’ll gather at the beautiful campus headquarters of WoodenBoat School where boat building and craftsmanship are taught and preserved. Ashore, you’ll be treated to refreshments, live music, and facility tours. Bring your camera for a spectacular sunset at Eggemoggin Reach.


Lighthouses + Photography


Lighthouse Cruise

4 nights (Tue–Sat) ‧ $968/$920 before Mar 1
Maine is home to well over 50 unique and picturesque lighthouses. We’ll attempt to visit as many as possible. If photography is your thing, you won’t want to miss this opportunity.

Photography + Lighthouse Cruise

6 nights (Sun–Sat) ‧ $1,198/$1,138 before Mar 1Award-winning photographer John L. Shipman will be on board to give informal classes. Whether you’re looking to hone your photography skills or learn the basics of good composition, you’ll have plenty of beautiful scenery to capture as we attempt to visit as many lighthouses as possible.


Fall Colors

If you’ve never seen the fiery landscape of Maine from the water, then you’re in for a treat. Coastal hardwoods begin to show in late September; by our last cruise, the hillsides are crimson, yellow, and orange. The weather is crisp, the breeze is strong, and we’ll have the entire bay to ourselves.

  • Sep 27–Oct 1, 4 nights ($888/$844 before Mar 1)

  • Oct 2–6, 4 nights ($868/$825 before Mar 1)

  • Oct 8–12, 4 nights ($898/$853 before Mar 1)

  • Oct 13–16, 3 nights ($698/$663 before Mar 1)