Regardless of whether you fly direct to Cuba, or board MARCATO in Florida and transit the 85 nautical miles across the Gulf Stream through the Florida Straits, your starting point will be Havana. You can easily spend 2-3 days exploring this multi-faceted city and only scratch the surface. The choice is yours: explore the city, the coast? Or both?

The following itinerary will give you a taste of all that Havana and its surrounding areas have to offer.

Day 1

Fly into Key West. The crew will collect you at the airport and take you to MARCATO in Old Town, just off Duval Street. This is a great place to start your trip, because it is tropical, laid back and there is fun in the air. After you get settled in, you might walk around town, but don’t forget to tour the Ernest Hemingway Home & Museum, as this is where the adventure begins! Hemingway loved Cuba and his house is a great taste of things to come.

Day 2

Start the morning with a coffee on the top deck as daybreak illuminates the port of Key West on your way south to the Gulf Stream. The U.S. Coast Guard base is on your right and the U.S. Navy’s Truman Annex is on your left heading out the main channel, as your yacht departs the United States.

It’s only 85 nautical miles to Marina Hemingway, where you will clear customs into the Republic of Cuba. You can have lunch on-board, or take a ride into Havana and eat at a rooftop palador private restaurant overlooking Old Havana. You can walk through Old Havana and take in the architecture, meet artists in their studios, have a salsa lesson, visit a recording studio and stroll the Malecon We will map out your itinerary with you before you go but your captain and crew will remain flexible throughout your charter.

That evening you may want to relax on the yacht and let your chef serve dinner before you hit the Tropicana, jazz clubs, and perhaps the Cuban National Ballet. Or you may want to explore another palador in an exquisite private residence not far from the marina, and then see who wants to enjoy the night-life and who wants to get some sleep.

Day 3

The yacht can relocate to the Port of Havana with special permission from the Port Captain. This passage of 20 miles offers a different perspective of the hills of Havana’s best neighborhoods. After passing along the Malecon sea wall, the harbor entrance is dwarfed by the imposing fortress guarding the entrance to Havana Bay: Castillo de los Tres Reyes Magos del Morro, named after the three biblical Magi. The crew will drop you ashore by tender where a fleet of vintage fifties’ convertibles will whisk you away for a top-down tour of the city, including a stop at the Hemingway Museum Finca Vigia, where his beloved fishing boat, Pilar, is on display. Another interesting site is the University of Havana, which sits on a hill overlooking the city. Chat with law students to find out what they think about life in Cuba today and the future of their country.

Day 4

Cruise east to Varadero (85 miles). Take in the hilly coastline and do a loop through the Port of Matanzas. You will be surprised to discover the brand new, 1100-slip marina at Varadero, which benefits from outstanding facilities and is overlooked by a new Melia Hotel; so be ready to hit the gym!

Later in the day, sip cocktails on the rooftop bar of the Dupont Family Mansion, Xanadu, with stunning views on the pristine beach and the 18-hole course that golf enthusiasts can enjoy at their leisure.

Day 5

You can go diving on what are considered by many to be the most unspoilt reefs in the world; no industrial pollution and no fertilizer runoff. Your Cuban dive-master guide will introduce you to this hidden world. It is illegal to fish in Cuba, unless it is for your own consumption. So why not catch your dinner? Cuban fishing guides will take you to the right places and explain what makes their fishing the best in the Caribbean.

For those who have not had enough culture, there are art studios in Matanzas that must be visited. At the coops, you can meet the artists in their work studios and discuss symbolism, politics and, in some cases, the rage that appears in their sculptures.

Day 6

Cruise to local Cays and explore the coastal bays, or head inland to visit a tobacco farm and see Cuban cigars being made. Meet farmers and enjoy a meal at a countryside home. Alternatively, hit Havana again on your way back to Key West.

Day 7

Relax on the passage back to Key West, and start planning your next cruise to the south coast of Cuba, starting in Cienfuegos.

Please contact Ami G. Ira for further information on Cuban yacht charters and motor yacht MARCATO.