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Mile Building Passages

The goal of First Reef Sailing’s mile-building passages is to provide our students the first hand experience of sailing a multi-day offshore passage as we deliver our training boats from our summer location in Boston, MA to our winter location in the US Virgin Islands and back. This provides an opportunity to gain experience in coastal and offshore passage-making. These are not certification courses, they are real world passages and provide valuable insight into the actual cruising experience. Many of our students go on to sail these routes in their own sailboats using the knowledge and experience they gain with us. In fact, we often have former students join with their own boats and sail alongside us as we make these annual migrations.


Each passage is five to seven days total giving students the opportunity to experience the routine of actual offshore passage-making, including watch-standing, navigation, weather, ship detection and more. We make stops in Bermuda and St. Thomas allowing the sailors to explore new ports and cities and provides students with the opportunity to practice their seamanship and navigation skills as we sail into unfamiliar ports.

We typically require students to have attained the ASA 104 - Bareboat Cruising certification or have the commensurate experience. After booking with a refundable deposit, we have a comprehensive conversation with each potential crewmember to ensure they have the appropriate experience and will contribute to a safe and enjoyable voyage! If you are unsure whether you qualify to join a passage don't hesitate to give us a call.

Read the "Debriefs" from our prior mile building passages on our Blog!

Spring 2024 Passages


The Northern Passage

Est. 4/24/2024 - 4/29/2024

Depart: St. George's, Bermuda

Arrive: Boston, MA

700 nautical miles

5 days


The Tradewinds Passage

Est. 4/15/2024 - 4/22/2024

Depart: St. Thomas, USVI

Arrive: St. George's, Bermuda

850 nautical miles

7 days

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