Caribbean Courses

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Maybe you are up for your next cruising adventure but can’t wait for summer. Or perhaps you are ready to be underway and under sail in one of the best cruising grounds on the planet, where the air is warm, the water is clear turquoise and the breeze is strong and steady. Either way, Courageous’s new cruising courses in the Caribbean have you covered.

Over three weeks, we will run at least three courses: Bareboats  (5 days, 4 nights). The Bareboats will likely stay within the US Virgin Islands. The curriculum is the same as courses run in Boston, but oh, how sweet it will be to cover the material in the Virgin Islands, instead.

Things to note:

In order to remove a leg of travel for students, we will be departing from St. Thomas for all courses, but still sailing over to the SVIs.  This move cuts down on the cost and time of traveling to the boat. The course will be run on a J/130. The course fee includes the cost of provisions for the week, along with dockage, moorings, and operational costs.  Transportation and pre-course accommodations are not included. US Sailing certification is available at both the Bareboat and Coastal Passage Making levels.

IMPORTANT: We must reach a minimum capacity of at least 3 participants per course. Please contact us following your course purchase before buying your flight so we can be sure we have reached capacity. Please feel free to contact Emilio with any questions.

Covid Requirements

  • Travel insurance is strongly recommended
  • All students must show proof of vaccination
  • All students must acquire a negative covid test before arriving on the island
  • Students will also have to follow all guidelines for leaving and departing the SVI’s, requirements are ever-changing and more information will be shared with students at least 2 weeks prior to departure.


  • Basic Cruising or equivalent for the Caribbean Bareboat Course
  • Basic Cruising + Bareboat Cruising or equivalent for the Caribbean Coastal Passage Making course

Note: Students may enroll for Bareboat and Coastal Passage Making back to back.

Next steps and additional courses include:


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.