Skip to content or footer

Windjammer cruises for music lovers

Music has long been a tradition at sea. From work shanties to ballads to boisterous sing-alongs, sailors have filled the salt air with melodies capturing life at sea. Our Windjammer captains and crew are a pretty musically-talented lot as well. Don’t be surprised if the crew breaks out instruments in the evening. (You’re welcome to bring your own, too!) Additionally, some of our boats offer specialty music cruises which feature guest musicians or a visit to a local music festival. Here’s a rundown of our 2023 music cruise offerings.

Bennett Konesni and Gawler Family Band aboard Schooner J.& E. Riggin, May 26-30 (5-nights)

These talented musicians brighten the world with their fiddle, banjo, and guitar music steeped in the traditions of American work songs, bluegrass, and Americana.

The Gawler Family band. photo courtesy Schooner J&E Riggin

Lobsters, Sailing, and Music aboard Schooner Heritage, June 6-9 (3-nights), June 15-18 (3-nights), July 12-15 (3-nights)

Evenings full of music performed by Captains Ben Welzenbach and Sean Grimes.

Trio Cattails aboard Schooner Ladona, June 10-14 (4-nights) or Schooner Stephen Taber, June 9-14 (5-nights)

The vessels join together in the evenings to enjoy the music of this female trio as they enchant us with their three-part harmony and old-timey country covers.

Tim Grimm aboard Schooner Grace Bailey,  June 20-24 (4-nights)

Tim’s folk, roots, and Americana music has topped the folk music charts. Aboard he performs casually in the evenings creating a wonderful backdrop to the evening.

Jenn Schott and Melissa Peirce aboard Schooner Ladona, June 20-24 (4-nights)  and Schooner Stephen Taber, June 20-24 (4-nights)

 he two schooners join together in the evening to enjoy music from these accomplished Nashville recording artists.

The Charlie Nobles aboard Schooner Stephen Taber, June 25-30 (5-nights)

The Charlie Nobles, also known as the Taber’s house band, are back by popular demand. You can expect this hat-wearing trio to break out the instruments for casual impromptu jams throughout the day. After dinner, they turn it up a notch with a set of folk, blues, and Americana that’ll have you hollerin’ for more.

The Charlie Nobles. photo Kat Singer

Geoff Kaufman aboard J.& E. Riggin, July 23-29 (7-nights)

Geoff calls his music “acoustic music with a pinch of salt!” He’ll be on board to entertain guests with his songs of the sea, the earth, the heart and the spirit.

Bennett Konesni and Co. aboard Schooner J. & E. Riggin, July 30-August 4 (6-nights)

These talented musicians brighten the world with their fiddle, banjo and guitar music steeped in the traditions of American work songs, bluegrass and Americana.

Sweet Chariot Music Festival: an eclectic gathering of folk and indie performers from around New England on Swan’s island. Schooners attend the festival one evening of the cruise.

aboard Schooner Lewis R. French, July 30-August 5 (6-nights)

aboard Schooner American Eagle, August 1-5 (4-nights)

Darlin’Corey, aboard Schooner American Eagle, August 21-24 (3-nights)

This North American folk duo hailing from Portland, Maine joins the cruise to share their songs calling on the bluegrass, old-time and Franco-American traditions.

Guitarist Bill Barnes aboard Schooner Stephen Taber, Sept 3-5 (3-nights)

Starry nights and smooth tunes with Bill Barnes, who adds a musical backdrop to each evening as the schooner lies anchored in a peaceful harbor or secluded cove.

Mike and Amy Aiken aboard Schooner Grace Bailey, Sept 3-9 (6-nights)

Back for a third time this duo combines their love of sailing with their love of Americana music.

Categories: Fleet, Music Cruises, Specialty cruises

Stay in the Know

With our monthly newsletter, you’ll receive tips and hints from folks who have sailed as well as information about the best dining and attractions the area has to offer, special packages, windjammer history, events, and more!

Monthly Newsletter Signup


You can request a mailed or digital packet of brochures, or you can find individual ships’ brochures under each listing on the fleet page.

Request a Packet Visit the Fleet Page

You are using an outdated browser. Please upgrade your browser to improve your experience. We recommend Google Chrome.