Wednesday, November 1, 2017 at 12:00 PM CDT
Wednesday, November 8, 2017 at 12:00 PM CST

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Stock Island Marina 
7005 shrimp road
Key West, FL 33040

Driving Directions 


South Coast Sailing Club 
South Coast Sailing Adventures 

Cuba Flotilla

November 1-8, 2017

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.

We've reserved a brand new Fountaine Pajot Saba 50. This vessel is equipped with 5 private cabins each with private and 5 heads.

Trip costs are approximately $2500 per person, double occupancy, plus optional excursions, meals ashore, airfare and other miscellaneous personal expenditures such as souvenirs or shopping. Reserve your cabin with a $500 per person, non-refundable, deposit, due immediately.


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

Tentative Schedule:

Wednesday, November 1st – Arrive in Key West, provisioning, evening departure, night sail across the Gulf Stream

Thursday, November 2nd – Arrive at Hemingway Marina, Cuba

Thursday-Monday – Land-based activities in Cuba

Tuesday, November 7th – Early morning departure from Hemingway Marina, Cuba

Tuesday, November 7th – Arrive in Key West before sunset

Wednesday, November 8th – Disembark before noon, clear customs

Wednesday, November 8th – Optional overnight in Key West