Thursday, April 19, 2018 at 8:00 AM CDT
Saturday, April 28, 2018 at 5:00 PM CDT

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Stock Island Marina 
7005 Shrimp Road
Key West, FL 33040

Driving Directions 


South Coast Sailing Club 
South Coast Sailing Adventures 

Rally to Cuba

April 19-28, 2018

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. Join South Coast Sailing Adventures on this Rally to Cuba! This is a unique people-to-people flotilla with round-trip sailing from Key West, Florida to Havana, Cuba. Experience Cuba both from land and sea!

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.

Experience sailing at its best!  This trip is a fantastic opportunity to make two 100-mile Gulf Stream crossings and add excellent offshore experience to your resume. You will gain valuable passagemaking experience, practice night sailing and watch keeping, 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
  • take salsa lessons
  • visit the farmers market as well as many other beautiful places in Cuba.

Trip costs are approximately $2500 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 $500 deposit.

Contact Flotilla Leader, Captain Lucy Newman, for more information.

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