Caribbean Mile Builder

March 9-16 2024
April 13-20 2024

Performance Training and Cruising

Itinerary - In/out Simpson Bay, St. Maarten,

500+nm around the Caribbean islands

Overnight sailing in watches, mixed with beautiful Caribbean anchorages


Gain miles towards your Master of Yachts, or just hone your offshore skills on a practical, fast and fun Caribbean mile-builder onboard S/V Hermes.

Our Pogo 12.50 Hermes is designed for fast cruising with style and confidence. While the boat resembles her Class40 cousin on deck, down below the interior is thoughtfully designed with modern minimalism. Expect racing speeds with cruising comforts as you chart your own course through the Caribbean.

The traditional Caribbean tradewinds offer exquisite sailing conditions, with plenty of islands to explore, while also plenty of pure-blue ocean to cover between them. Together as a team, the crew will investigate weather forecasts, nearby harbors, and chart your own course to determine how far your week of adventures through the islands will take you. 

Itinerary starts and ends in Simpson Bay, St. Maarten, with each mile-builder trip being unique to the weather and crew. The target will be 500+ NM, which will be weather-dependent, while balancing a mix of overnights offshore and in destination ports around the Caribbean.


Prepare to become a Master of Yachts, or a master of your own yacht as a confident boat owner or bareboat charterer. Learn about cruising the Caribbean, exploring the liveaboard lifestyle, or tracking to become a professional Ocean Racer from our expert crew who have done it all! 

More about MSWI Master of Yachts ITY certification course:

In partnership with the Maritime School of the West Indies, we offer mile-builders in alignment with MSWI’s IYT Master of Yachts courses in St. Maarten. For those looking to pursue professional careers in the industry and still in need of some additional sea miles or training, you may also combine your mile-builder in a 3-week course package to include Master of Yachts Theory and Practical courses. At the conclusion of the 3 weeks, eligible and successful students will earn a Master of Yachts certification from IYT.  If you are interested in our Ocean Racers MSWI Master of Yachts program, please inquire.

Caribbean Mile Builder
$2950 USD
Per crew spot

Bunk onboard

Meals while sailing

Professional Coach