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Lucy Newman

Rally to Cuba!

Untouched, unspoiled

Tantalizingly close but frozen in a bygone era, Cuba’s cobble stone streets and deep-rooted culture are as inviting as the people. Experience this special moment in history where you can still explore a place that has remained isolated and untouched by the mass tourism and foreign involvement. South Coast Sailing Adventures joins Waterway Guide’s Rally to Cuba on a unique people-to-people rally with round-trip sailing from Key West, Florida to Havana, Cuba this May! Experience Cuba both from land and sea!

Be an Ambassador

People-to-people travel is an initiative allowing U.S. citizens to legally travel to Cuba as “true ambassadors” to:

  • participate in cultural experiences;
  • have direct contact with the Cuban people to learn about their way of life;
  • teach Cubans about the American way of life; and yes – enjoy beautiful sights, sounds and flavors of this unspoiled Caribbean gem.

Sailing experience at its best!

What a fantastic opportunity to make two 100-mile Gulf Stream crossings and add excellent experience to your resume by sailing round trip from Key West to Havana! You will gain valuable open ocean experience, practice night sailing, fine-tune your navigation skills and sail in potentially new conditions for your skill set. Plus, ambassadors on this trip will enjoy opportunities to:

  • experience the fun and excitement of Key West;
  • participate in a tour of Havana;
  • visit a Cuban tobacco field and/or Cuban rum factory;
  • interact with Cuban locals. explore Hemmingway House, and visit the farmers market and many other beautiful places in Cuba.

We’ve reserved a new 50 ft Fountaine Pajot Saba with 5 cabins and 5 heads with lots of amenities and fun extras!


Trip costs are approximately $2,500 per person, double occupancy, plus optional excursions, meals ashore and other miscellaneous personal expenditures such as shopping or souvenirs. Space is limited and expected to sell out quickly. Reserve your spot and cabin priority preference with a $200 deposit.

Tentative Schedule

  • Thursday, April 19th – Arrive in Key West, provisioning, evening departure, night sail across the Gulf Stream
  • Friday, April 20th – Arrive at Hemingway Marina, Cuba
  • Saturday — Thursday – Land-based activities in Cuba
  • Friday, April 27th – Early morning departure from Hemingway Marina, Cuba
  • Friday, April 27th – Arrive in Key West before sunset
  • Saturday, April 28th – Disembark before noon, clear customs
  • Saturday, April 28th – Optional overnight in Key West