Sailing to Cuba: one for the Sailing Bucket List

When the book 50 Places to Sail Before You Die hit the stands in 2007, Cuba – the largest island in the Caribbean, notable for its sugar-white beaches and unique architecture – was not included. One of the reasons, no doubt, was because of strict sanctions against travel there by Americans, but now that those have been relaxed, the 2017 Conch Republic Cup, a.k.a. Key West Cuba Race Week, can and should be at the top of every U.S. sailor’s bucket list.

Mirroring the restoration of Cuban-American diplomatic relations in 2015, the Conch Republic Cup re-emerged in early 2016 after what was effectively a 13-year shut-down of its activities by the U.S. government, and next year’s January 22-February 3 edition promises to build on the success of that event with an expected 60 teams in divisions for cruising and racing monohulls and schooners.

“Initially I wanted to join in for the thrill of visiting Cuba,” said this year’s overall winner Eddie Evans (Charleston, S.C.), who had competed for many years in the Regatta Time in Abaco because of the spirited competition and fun-loving attitudes of its organizers and participants, “but I found the Conch Republic Cup to share the recipe of fun and competition that my crew and I find so appealing.”

Evans used to manage single-family rentals while his wife worked – sometimes “on call” – in the medical field. One night during dinner with friends, Evans’ phone rang continually and he noted that he seemed more on call than she, a remark that ultimately led to the naming of their then-new Oceanis 381 Naut-On Call. He has been sailing for 40 years, and while he used to average 200 ocean miles a year aboard Naut-On Call, he now averages closer to 5,000 nautical miles when he includes the Conch Republic Cup on his schedule, which he is planning to do again in 2017.

“While we enjoy being competitive, our boat’s ultimate goal is making friendships and sharing our passion of sailing and adventure with like-minded individuals,” said Evans.

The Conch Republic Cup is not just another race to Cuba but a four-part series with several scheduled lay days designed to make the most of “a cultural exchange through sport.” The Race Week starts with a 110-mile race from Key West to Varadero, Cuba, followed by a 100-mile race from Varadero to Havana. In Havana, the fleet stays at Hemingway International Marina (a co-host of the event with Key West Community Sailing Center) and participates in the around-the-marks Castillo del Morro Race and Parade of Sail before racing back from Havana to Key West for an additional distance of 90 miles.

“The winner of the Conch Republic Cup is the team with the best combined overall performance in the four races that comprise Key West Cuba Race Week,” said Conch Republic Cup Executive Director Karen Angle. “Balancing race days with lay days gives participants time to enjoy the sights and adventures Key West and Cuba have to offer, and the event timing is designed to allow sailors who follow the racing calendar to continue on to the Caribbean racing circuit.”

Entries for the Conch Republic Cup are limited. Register at by December 15. For more information, including the newly posted Notice of Race and full schedule, visit or email [email protected].