I had a very last minute opportunity to hop aboard my neighbor’s sailboat to Marina Hemingway from Key West. This particular trip is not for the fainthearted: we left at sunset and sailed overnight into some extremely windy conditions with 12-foot waves in the Gulf Stream.
Despite the rough ride (I definitely got seasick despite the fact that I live on a sailboat), I would do it again (preferably in calmer weather conditions).
Marina Hemingway is located in Jaimanitas, a local neighborhood that I preferred to downtown Havana, so staying in this area has an added advantage of dodging the usual tourist traps. A stunning neighborhood of art reminiscent of Park Gruel in Barcelona was just around the corner from where we stayed.
Cuba had just lost Fidel Castro, so our trip was quiet: no music or alcohol was allowed, and we were able to visit Revolution Square with thousands of others who were paying their respects. It was a very solemn time to visit, but also a historic time.
Many of our guests ask about visiting Cuba, and if interested I can help arrange a budget sailing trip (not the luxurious expensive catamarans) – which is a pretty bad ass way to go. You can stay on the boat in Cuba, or opt for a guesthouse/hotel (around $30 a night). Taxis in the old cars are less than a dollar with a shared ride to old Havana, and the trip also includes day trips to a nearby countryside town (which I had to miss this time around unfortunately).
Sailing takes 16 to 19 hours depending on weather, and a minimum of two weeks in advance are needed to arrange the VISA. If you are interested, please talk to Amber as soon as you can to get the ball rolling. The boat holds about eight people at the most. The cost is around $500 round-trip.