Gliding out of Key West, FL as the sun set, bound for Marina Hemingway in Cuba, we hoisted sails, put the throttles at 1600 RPM, set a course a bit west of the rhumb line to Havana in anticipation of the current to come and watched the half-moon rise. With 14-18 knots of east wind building throughout early morning of the next day, we cleared customs before noon and took our slip in Canal 2 the for week-long visit.

We were underway for Waterway Guide Media’s inaugural rally to Cuba and to join in the celebration of Hemingway International Yacht Club of Cuba’s 25th anniversary. Four of our team boarded a Fountaine Pagot SABA catamaran at Stock Island Village Marina on May 15 and crossed the Straits of Florida in 14 hours, arriving at Marina Hemingway the next morning. 

This event was the crown jewel of Waterway Guide’s commemoration of our 70th anniversary this year. The event also celebrated our recently added Cuba title to our series of six other guidebooks.

The rally was designed to promote our anniversary year and the new book. Ten boats and over 40 crew arrived throughout the day and settled in for the people-to-people exchanges and sailing events scheduled at the club.

Upon making landfall, we all quickly fell into ‘Cuba-time’ and began our planned activities.  

There were scores of boats in the canals at Marina Hemingway, with owners and guests fulfilling long-held ambitions of seeing Cuba. The largest unexplored cruising destination in the Caribbean, for most American boaters, is slowly coming into focus.

As U.S. regulations continue to relax and more and more vessels make the 90+ mile trip south to Havana and Varadero, the word is out. Trawlers, sailors and sport boats are filing the paperwork with the U.S. Coast Guard and going to Cuba.

As on most trips, we met old friends who had arrived for the festivities at the yacht club and to take advantage of spring weather. Throughout the week the yacht club held races, parades of sail and dedicated events designed to spotlight its 25 years under the guidance of Commodore Jose Escrich, a retired Cuban Naval officer who has shepherded the club through a tumultuous progression in a country that hasn’t embraced recreational boating for over a half century.

I began my travels to Cuba 20 years ago while working with the University of Richmond on a multi-year project documenting the evolution of Cuban and American music. I’m often asked what has changed? Or hear the lament that, “I better get there before the Americans ruin it.” Based on my experiences, then and now, I believe that change will come slowly, at least under the current political and social climate. Don’t expect to see a McDonald’s or Wendy’s anytime soon.

Since 1997 I’ve experienced the evolution of the American dollar from legal tender in Cuba to now not being accepted on the street. Prices have tripled on many items such as beer, hotel rooms and some meals. But, that means that $1 mojitos are now $3. Meals that were once $4 are now $9. There are many more restaurants and Casa Particulars than ever, so prices for food and lodging remain reasonable. You can find bargains everywhere, especially in the countryside.

Outwardly, little has changed over the past 20 years, although WiFi hotspots are now obvious with young Cubans sitting in groups on the curbs, thumbing their cell phones. The same streets, bars and hotels beckon, albeit with waiters and waitresses a little more aloof, perhaps now jaded by so many cameras and obligatory mojitos.

Many barrios remain decrepit. Spanish colonial architecture is under constant renovation. There are more tourists in Havana than ever as cruise ships continue to disgorge their passengers at San Francisco Terminal. The old American cars appear to be in better shape than ever due to higher quality paint and better access to parts for repairs. Cab rides are more expensive and traditional music still peals from the clubs and cafes.

Following the Hemingway International Yacht Club of Cuba’s gala on Sunday night, May 21, the 11-hour crossing home to Key West on Monday was a joy, if not a bit sporty for the 4 hours, or so, we spent in the axis of the Gulf Stream. Winds from the E-ENE at 17-20 knots kept us on a close reach the entire trip. Making several adjustments for commercial traffic throughout the day, we maintained course and speed and tied up at Stock Island Village Marina flying our Q flag as the sun set.

Several of our rally participants had preceded us, and several more pulled in over the next few hours. All arrived home safely.  

In  anticipation of another rally in 2018, we are working toward making next year’s event bigger and better.

Revisions to our guidebook, Cuba, are in the works and the new edition should be ready in a couple of months. If you are going, please take time to study the guidebook. Nuances associated with customs, money, facilities and local knowledge are presented in detail throughout the book and will assist your planning for traveling there.

This is a time of change, so be patient, take cash, remain flexible and enjoy! It’s Cuba.