Cruising Fleet Membership


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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 and family for trips around the Harbor Islands, anchor for a picnic lunch, spend a night moored or at anchor under the stars, or practice your big boat skills in preparation for a bareboat trip in the Caribbean, 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 J/80 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, fireworks-watching parties, moonlight sails, Harbor Island camping trips, and discounts on courses, 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 that all cruising 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

  • Basic Cruising or equivalent
  • Navigation Assessment- Beginning with the 2022 season, all cruising members will be asked to complete an online assessment covering basic navigation.

Recommended Supplements

Covid-19 Updates
Guidelines for member use, boat availability, and guest privileges are subject to change and will reflect the most up to date CDC and Massachusetts guidelines with respect to Covid-19. Please continue to check our Covid-19 Updates page for more direct guidance.

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 are only able to accept boats in good condition that enhance the fleet – and this has resulted in a fleet that is improving steadily over time. In 2018 we were thrilled to add Ark En Ciel, a beautiful, easy to handle 34’ Beneteau 331 in terrific condition. Ark joins  Watermark, a comfy Pearson 34; Traveler II, a fun Saber 33, and Tashtego, a solid Tartan 30. For the 2022 season, a smaller Tanzer has been added to the site and will be available to any of our cruising members. The exact composition of the fleet will continue to change – for the better, we expect – in the coming years.

A Shared Fleet

Take a quick short-handed spin around Spectacle in a 30-footer, or bring a group of friends or family out to Peddocks Island for a more spacious overnight on a 34-footer – if you’re a cruising member, each boat is yours to reserve.

Note that we carefully limit our available full cruising memberships to just six per boat to ensure that everyone has plenty of access. Also, 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.

Cancellation and Refund Policy: Please note that in an effort to keep our courses and memberships as affordable as possible, we must limit changes in schedule and membership. Because staff and instructors are hired and scheduled in advance, Courageous memberships, lessons, and/or other program fees are not refundable for any reason, including cancellation due to weather, or the participant’s inability to utilize the membership, lesson, or program. That said, we do understand that sometimes life gets in the way of sailing plans and, if necessary, we will work with you to reschedule for a later date. We cannot reschedule lessons within two weeks of their start date unless we are able to fill the spot with another student. All rescheduled lessons purchased before September 1 must be completed before the end of the season for which they were purchased; if purchased between September 1 and October 31, rescheduled lessons must be completed before June 30 of the following year.

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