Cruising Fleet Membership




For some of us, it’s all about the big boats and thoughts of sailing around the world. Our cruising fleet won’t take you quite that far, but it will take you around Boston Harbor and then some. Whether you want to invite friends for a trip around the Harbor Islands, spend a night anchored under the stars, or practice your big boat skills in preparation for a weekend overnight in Gloucester, our cruising membership has you covered. The Courageous Cruising Fleet provides an excellent platform to learn, gain confidence and experience as a cruiser, and enjoy simple daysails and overnights in and around Boston Harbor, albeit without some of the bells, whistles, and creature comforts of more expensive charter boats.

Cruising memberships are available in full (7-day) or weekday (Monday-Thursday) options. Both include guest privileges and access to the Rhodes 19 and J80 fleets (after passing on-the-water checkouts). The number of guests is limited to 5 or 7 depending on the size of the vessel. Cruising members enjoy all the Courageous membership perks: barbecues, racing, moonlight sails, Harbor Island camping trips, and discounts on courses, and private lessons (50% off!). Cruising members may take overnight trips for up to 2 days / 1 night. We limit all members to two standing reservations at any one time to ensure fair and equal access. 

Please note: memberships are limited to a single sailing season (May 1 through October 31) and don’t “roll over” to the following year.


Prerequisites are recommended to better prepare members for our Cruising membership check-out

Recommended Supplements

Recommended Next Steps

An Evolving Fleet, Getting Better with Time

As a nonprofit supporting a great mission, we are extremely fortunate to receive boats as donations. Due to our limited dock and storage, we only accept boats in good condition that enhance the fleet – and this has resulted in a fleet that is improving steadily over time. 

  • Ark En Ciel, a beautiful, easy-to-handle 34’ Beneteau 331
  • Watermark, a comfy Pearson 34
  • Traveler II, a fun Saber 33
  • Tashtego, a solid Tartan 30
  • Dolce Vento, a “new to us” Tartan 34
  • Storm Warning, a seasoned Raider 32

A Shared Fleet

Note that we carefully limit our available full cruising memberships to a ratio of just six memberships per cruiser in our fleet to ensure that everyone has plenty of access. In order to meet the needs of cruising members and students for ongoing instruction, approximately one cruiser may be used for teaching most weekends of the season. The teaching boat will rotate through different boats in the fleet. By adhering to these ratios – unchanged from 2018 levels – and limiting reservations to two per membership at any given time, we ensure ample access for all members.

Cruising memberships are valid for the 2023 season; May 1-October 31. For information on our refund policy, click here.

*Membership policies are updated regularly

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