April 1st to April 14th – Marathon to Cuba


Our time at Harbour Cay Club in Marathon, FL is spent staging for our forthcoming voyage to Cuba, an event that will undoubtedly become the highlight of our winter cruise.  We first learned about this opportunity in January when we attended an organizational meeting for this event at the Sarasota Yacht Club.  The time has finally arrived for our departure.

Cutter Loose is one of fifteen yachts that will participate in a regatta to Marina Hemingway near Havana.  We have obtained a license from the U.S. Coast Guard to enter Cuban territorial waters on the basis of a “people to people” cultural exchange.  This requirement will be accomplished through a series of tours with Cuban guides that have been organized by the Sarasota Yacht Club in conjunction with TGC Travel of Boca Raton, FL.

Cruising friends Greg and Sharon of s/v Dream Catcher share our enthusiasm for a visit to Cuba.  Originally, the plan was to sail both Cutter Loose and Dream Catcher to Cuba.  When we learned of Sarasota Yacht Club’s crew requirements, we decided jointly to sail Cutter Loose to Cuba with Greg and Sharon on board as crew.

Sharon Greg together

Our time in Marathon is spent making final preparations for this voyage.  Securing yacht insurance, in particular, has been more difficult than anticipated.  Through our broker, Falvey Insurance issued a quote which we promptly accepted.  In the end, however, Falvey was unable to deliver a binder in time for our departure.  As a result, our only option for sailing to Cuba is to self-insure.

On Friday, April 1st, Greg and Sharon move their belongings aboard Cutter Loose.  At 9:45 AM, our spirits are soaring.  After months of planning, we are officially underway from Harbour Cay Club in Marathon on our two-week adventure to the land of Fidel.

The first leg of this journey takes us to Key West, our port of embarkation to Cuba.  Motor sailing under sunny skies and in light winds, Cutter Loose   covers the 51-mile run to Key West in record time.  By 3:45 PM, she is docked at Conch Harbor Marina.  The afternoon heat and humidity sends us scurrying to the pool, sipping on refreshing Painkillers while being entertained by the antics and attire of the younger crowd.

Key West pool

After dinner, a Friday evening stroll through the streets of Key West leads to Better Than Sex, an establishment that specializes in house-made gourmet desserts.


The weather forecast for the Straits of Florida predicts that winds will increase and shift north on Monday morning, retaining a northerly component for several days thereafter.  The narrow entrance to Marina Hemingway is exposed to the north.  In strong northerly winds, waves break in the entrance channel creating dangerous conditions.  The decision is reached to depart Conch Harbor Marina in Key West on Saturday afternoon in order to arrive at Marina Hemingway on Sunday morning in benign conditions before the wind shifts to the north.  Our early departure will place us in Cuba several days before other regatta participants arrive from Sarasota.  This will permit extra time for exploration on our own before the official Sarasota Yacht Club tours commence on Thursday.

At 5:30 PM on Saturday, Cutter Loose is underway from Conch Harbor Marina for the 120-mile, overnight run to Marina Hemingway near Havana.  With wind speeds of less than 10 knots for the entire passage, calm conditions prevail as we motor sail across the northeast set of the Florida Current which peaks at 4.5 knots.   Four seasoned sailors to share the watch schedule makes light work of tonight’s 16-hour voyage to Cuba.

Watch schedule

Cutter Loose is not alone in these waters.  The Straits of Florida are a popular route for commercial shipping from Europe and the east coast of the U.S. to the Gulf of Mexico and Central America.  Tonight, the 570’ cargo ship Tiberborg crosses our bow bound for Galveston, TX.  Next, the 653’ cargo ship Sarika Naree passes on a reciprocal course headed to New Orleans.  The 820’ tanker DHT Cathy overtakes Cutter Loose, bound for Delaware.

Ships passing in the night often stimulate one’s curiosity.  I frequently try to picture the scene on the bridge of those ships.  Who amongst the officers of the ship are standing watch?  Is the watch alert and engaged?  Are they listening to music in an effort to remain awake?  Do they see our AIS imprint and radar echo?  Do they even care about the presence of pleasure boats in this vast body of water?

Sea buoy 2

In the wee, small hours of the morning, a dim glow on the southern horizon confirms that Cutter Loose is approaching Havana.  At sunrise, the skyline of Havana is clearly visible.  Finally, the sea buoy marking the buoyed entrance to Marina Hemingway becomes visible at 9 AM. Our early departure strategy is paying dividends as the well-marked channel into the marina is perfectly flat upon our arrival.  An enthusiastic voice on the VHF radio welcomes us to Cuba and authorizes Cutter Loose to enter the marina basin.

Customs official near boat

The obligatory first stop this morning is at the Customs dock for clearance procedures.  Within seconds of our arrival, Cutter Loose is boarded by all manner of uniformed officials, each one smiling and welcoming us to Cuba.  Conducted mostly in Spanglish, the clearance procedure is straightforward, thorough and friendly.

Customs and Eric

Customs and Immigration personnel collect our passports and ship’s papers.  After a look around the cabin, they invite us into the Customs office for official photographs.  They ask if we wish to have our passports stamped.  We respond with an enthusiastic “por supuesto!” (of course!).

With Customs official

With tourist visas in hand, we are interviewed individually by a female doctor who records our body temperature with a digital thermometer.  She asks if we are experiencing any influenza symptoms. Meanwhile, representatives of the Ministry of Agriculture give a cursory glance into the ship’s freezer and refrigerator.  They inform us that it is forbidden to bring fresh fruits, vegetables or eggs into Cuba.

quarantine flag down

This flurry of activity culminates in the issuance of the coveted Certificado de Despacho by Harbormaster Miguel.  The Despacho authorizes Cutter Loose and her crew to depart Customs and proceed to Canal #1.  Once docked securely alongside a crumbling concrete dock wall, Miguel explains the marina’s rate structure and offers to exchange our U.S. dollars for Cuban CUCs, the local tourist currency.

CUC money

Marina Hemingway will serve as our base of exploration during the next eleven days.  Located nine miles west of Havana, construction of the marina began in the 1950s as part of a planned resort, including casinos.  Marina Hemingway is the closest marina to Havana.  As such, it is a very popular cruising destination as evidenced by yachts from around the world.

Eric and Pat Cuba flag

Development of the Marina Hemingway project was interrupted in 1958 by the Cuban Revolution, at which time casinos became outlawed.  Ultimately, the land and buildings at Marina Hemingway became the property of the new Cuban government led by Fidel Castro.  Since that time, the marina has remained almost completely devoid of repair and reinvestment.

Walking in ruins

There are two hotels and a few shops, snack bars and restaurants within the marina complex.  One hotel is vacant and partially demolished.

Canal Two

At the one remaining operational hotel, guests gather near the pool to avail themselves to Internet access which can be purchased for an hourly rate of $2.  This is one of the few WiFi hotspots that we encountered in Cuba.

Hotel pool

The marina grounds are cluttered with the remains of derelict boats.

boat through porthole

Personal possessions of several semi-permanent, live-aboard sailors have spilled over into the marina’s public areas with an assortment of grills, tables, outboard motors, used boat parts, motor scooters and lounge chairs.  Some of these salty sailors have lived at Marina Hemingway for over 20 years.

Campsite dockside

The centerpiece of our cultural experience in Cuba involves daily updates on rest room conditions. This is a popular topic of conversation amongst visitors from the U.S.  The collapse of Soviet financial support for Cuba in the 1990s resulted in significant hardships for the Cuban people. As a result, Cubans place little importance on rest room facilities and cleanliness.  Toilet seats and rest room paper products are rare in Cuba.  Furthermore, pressure in the public water distribution system has been reduced to a trickle.  Several hours are required between flushes to fill the toilet tank with water.  Some restrooms are equipped with plastic buckets to transport water from the sink to the toilet.

Armed in advance with information about the deplorable condition of Cuba’s restrooms, we arrive with a pre-assembled travel kit that includes the necessary accoutrements of the trade.

Cutter Loose potty pack

Our method of rest room analysis takes into account the relative presence of the following public restroom amenities:

  • toilet seat
  • TP
  • hand soap or sanitizer
  • paper towels
  • plastic bucket for  transporting water from external source to bowl

For the purpose of comparison, our rating system is as follows:

1 star – none of the above amenities

2 stars – one of the above amenities

3 stars – two of the above amenities

4 stars – three of the above amenities

5 stars – four or more of the above amenities

Sadly, most restroom experiences in Cuba fall into the 1 star or 2 star rating categories.  Only the more modern hotels and restaurants in Havana offer 3 and 4 star facilities.

Initially, our exploration is limited to the marina grounds.  Once we are familiar with our immediate surroundings, we branch out through the marina entrance gate to the tiny village of Jaimanitas which is located within a 15-minute walk from the marina.

Jaimanitas Sign

Jaimanitas is the home town of internationally acclaimed artist Jose Fuster.  Mr. Fuster has decorated public squares and private homes with ornate murals and colorful ceramic art.  This community art project is known locally as Fusterland. It is a popular tourist destination in Cuba.

Fuster man


As other Sarasota vessels begin to arrive on Wednesday, we hail a taxi for a self-guided walking tour of the Vedado neighborhood of Havana.  We begin at the Plaza de la Revolucion that features an enormous tower with a prominent sculpture of Jose Marti.

Jose Marti monument

From here, our self-directed walking tour passes through the hospital district where we pause for lunch.  A Cuban sandwich seems an appropriate menu selection for our first day in Havana.

Cuban sandwich

From here, it is on to the university district and the recently re-opened American Embassy.

US Embassy

A stroll along the waterfront walkway (Malecón) leads to a series of public plazas along the entrance channel to the industrial harbor of Havana.  Pleased with our progress for the day, a taxi whisks us back to Marina Hemingway for the reasonable fee of $20.

Bus Melacon

On Thursday morning, all of the participants in the regatta gather at the Marina Hemingway Hotel to board our tour bus.  Today’s narrated tour takes us to several plazas in Old Havana including Plaza Vieja and Plaza de Catedral.

Old square 3


Cigar woman

After a tour of a cigar factory, our bus heads back towards Marina Hemingway for a mid-afternoon lunch stop at paladar (privately owned restaurant) called El Laurel.

Lunch at El Laurel

This evening’s entertainment involves a high-energy stage show at the Tropicana night club in the Vedado section of Havana.  The talented singers and dancers here gyrate tirelessly for two hours.  Anxious for rest after an evening of jiggling, we return to Marina Hemingway by taxi well after midnight.


Earnest and Fidel

Friday is dubbed “Hemingway Day” by our tour guides.  The day begins with a visit to La Finca Vigía, Hemingway’s private villa a few miles south of Havana.  This setting inspired many of his novels, including The Old Man and the Sea. Hemingway’s 38 foot fishing boat, Pilar, is on display here.  It was purchased in 1934 from the Wheeler Shipbuilding Company for $7500.



Hemingway house outside

Next it is on to the nearby fishing village of Cojimar where Hemingway imbibed with local fisherman at the waterfront bar, La Terraza.

La Terrazza bar

Following lunch at the paladar La Fontana, we pause to visit a local arts and crafts warehouse and brewpub before stopping for daiquiris at another of Hemingway’s favorite hangouts, La Floridita.

La Floridita

At the request of the Commodore of the Club Nautico Internacional Hemingway de Cuba, all participants in the Sarasota Yacht Club regatta compete against local boats in a fun race from Marina Hemingway to Old Havana on Saturday.

Saturday Regatta

In the evening, we are invited to a reception at the Club at which time the Commodore makes an impassioned plea for expanded international yachting events between the United States and Cuba for the purpose of overcoming the cultural and political divide that exists between the two nations.

With Commodore

Sunday’s bus tour takes us to the landmark El Morro fortress which guards the entrance to Havana Harbor.

El Morro

Inside El Morro lies the remains of a wing section from a U-2 surveillance aircraft from the U.S. that was shot down by Cuban anti-aircraft batteries during the Cuban Missile Crisis.  This dramatic moment in history is recounted through the use of photographs, including a copy of President Kennedy’s written ultimatum to the Soviet Union.

USAF wing

El Morro provides an outstanding vantage point from which to view the impressive skyline of downtown Havana.  The City’s population of 2.2 million represents about 20 percent of Cuba’s total population of 11.3 million.

Havana Skyline

From here, we visit the original Sloppy Joe’s bar in Old Havana followed by lunch at paladar El Biky.

4 of us Sloppy Joes

In the afternoon, we are bused to the famous Hotel Nacionale where many U.S. entertainers performed at the casinos during the reign of Cuban President-turned dictator, Fulgencio Batista.

Hotel national full shot

The Hotel Nacionale is a fascinating museum of Cuban history.  Numerous heads-of-state have visited the hotel, as evidenced by an extensive photographic display in the hotel’s former gambling parlors.

Batista’s increasingly corrupt and repressive government negotiated lucrative relationships with the American mafia which controlled the drug, gambling and prostitution businesses in Havana during the 1940s and 50s.  To quell public discontent, Batista resorted to wide-scale violence, torture and public executions.  During this period, the Batista government received financial, military and logistical support from the United States.  This set the stage for a guerrilla uprising against the Batista government led by Fidel Castro.   The Batista government was defeated militarily by Che Guevara at the Battle of Santa Clara on New Year’s Day, 1959.  Batista was granted asylum in the Dominican Republic, then moved on to Portugal where he died of a heart attack in 1973.  Che remains a popular hero of the Cuban people.

Che Images from Market

We elect to remain in Old Havana on Sunday evening to explore the four major plazas of Vieja Habana and to take a leisurely stroll along the Malecón for some late evening entertainment.  Since dwellings are very small in Cuba, street musicians and people of all ages use the Malecón as an evening meeting place to chat and chill.

Young men on Melacon

On Monday morning, our tour bus is west-bound on the Carretera Central expressway for a day-long tour of the lush Vi­ñales Valley.  Vi­ñales is a rural town located in the Pinar del Río Province of Cuba, about 2 hours to the west of Marina Hemingway by bus.

Vinales town square

In sharp contrast to Havana, the countryside here is quite rural.

simple home

Some of the best tobacco in the world is grown in the fertile, red soil of this valley.

tobacco field

Here’s a view of the Vi­ñales Valley from the Hotel Los Jazmines overlook.

Vinales hills

Much of the region’s limestone has eroded away, leaving large outcroppings known as mogotes (haystacks) that point skyward with steep sides and rounded, jungly tops.

Vinales magotes

Several mogotes feature caves that invite exploration.

Cave Opening

Following lunch at paladar La Cabana, our final stop of the day is the prehistoric mural located a few miles west on the town of Vi­ñales.  In 1961, Fidel Castro visited the area and commissioned a painting on a steep cliff.  The painting depicts snails, dinosaurs and cave dwellers, all in garish colors.  The painted cliff is not particularly artistic, but it is unusual enough to attract the attention of tourists.

Prehistoric Mural

Alex tour guide

An important element of our “people to people” cultural exchange involves gaining insights into the Cuban way of life through conversations with our Cuban tour guides.  Our guides are young men in their thirties.  Their yellow shirts and microphones indicate that they are employees of the Cuban government.

In private conversation, our guides do not hesitate to express their hopes and aspirations for the future, even when their thoughts run contrary to the official party line of Cuban leaders.  Since their income is dependent on tourism, they are very welcoming to visitors, especially those from the U.S.  They feel strongly that the quality of life will improve dramatically for all Cubans as tourism grows, communication expands and as Cubans enjoy more face-to-face contact with U.S. citizens.

man sitting outside building

Our tour guides are proud to be Cuban.  They explain that their younger Cuban counterparts are less entrenched in socialistic dogma and are anxious for change.  They view the U.S. as an obvious mechanism for positive change in their homeland.  They acknowledge that the pace of change in Cuba is likely to be slower than they would prefer.   They are encouraged, however, by recent change that would have been unimaginable a decade earlier as Cuba moves continually in the direction of encouraging foreign investment and private enterprise.

Raul Obama sign

Cubans may apply to the Cuban government for travel visas.  Visas can easily be obtained for travel to Russia.  However, few visas are granted for travel to the United States. Obviously, the Cuban government views the potential for defection as a threat.

transporting pipes on bike

All employed and unemployed Cubans earn about $30 per month regardless of their educational background, skills or job responsibilities.  Doctors, lawyers and teachers earn the exact same salary as an unskilled worker.  Every household receives a rations book which entitles them to a monthly allotment of staples including rice, beans, sugar and flour.

street guitarist

By U.S. standards, meals at restaurants are quite reasonable in Cuba.  Most restaurants are owned and operated by the Cuban government.  However, the number of private restaurants (paladars) are increasing.  Here’s a shot of paradar La Cabana.

Lunch in Vinales

During our visit, the price for two complete meals including cocktails was in the $15 range.  Meals at restaurants are very expensive for Cubans earning $30 per month.

Street vendor

Many Cuban households depend on remittances from Cubans living abroad, mainly in the U.S.  It is estimated that Cuban-Americans send more than $1 billion in remittances to family members in Cuba every year.  On the surface, remittances appear to be a sensible humanitarian gesture.  However, our tour guides view remittances as inherently unfair.  For example, a Cuban doctor struggles to get by on $30 per month while teenagers whose family receives remittances from the U.S. spend money freely on gold jewelry, hip-hop clothing and nightlife.  There seems to be a considerable amount of resentment on the part of Cubans who do not receive remittances.

Couple hand in hand

Cubans pay no taxes and only a minimal amount for household utilities.  Rental housing provided by the government is quite spartan by U.S. standards but free of cost.  Many of the apartment buildings in Havana were constructed by the Russian government.   These featureless structures consist of individual concrete cubicles stacked ten or more stories high.  Our Cuban tour guides refer to them as “the absence of architecture”.

Apartment Building

Private dwellings are usually inherited from family members. With minor exceptions for farmers, all land is owned by the Cuban government. Public buses made in China are widely available…all filled to capacity with passengers.

street scene

Only about 30% of Cubans own an automobile.  Cars are economically out of reach for most residents.  Being on the streets in Havana is like stepping back in time to the 1940s and 1950s.

Wedding couple in car

Taxi drivers zip around town in their vintage Chevrolets and Buicks which were imported here prior to the Revolution.  An hour ride in one of these classic vehicles through the historic sites of Old Havana costs about $15.  Given the absence of parts for these older vehicles, it is a tribute to Cuban ingenuity that these classics are still on the road and looking quite spiffy.

Gold car

Antique cars on Melacon

Schooling through high school is compulsory and free in Cuba.  As a result, the literacy rate here is 97%…amongst the highest in the world.  Higher education is also free for those who pass entrance exams for a professional career.  Males are required to serve in the military for two years before entering university.  A trade school education is available at no cost for those who wish to become masons, electricians or plumbers.  Without question, there is a need for more plumbers in Cuba if for no other reason than to improve the functionality of the country’s rest rooms.

Chess children

Everyone is given a job upon graduation.  Certain professionals, such as medical doctors, are required to practice in rural areas for two years following graduation.

horseman closeup

The owners of paladars (private restaurants), particulares (private guest houses), taxi drivers and other Cubans working in the tourist industry have an opportunity to supplement their income with fares, fees and tips.

La Fontana tables

In order to increase revenues, the Cuban government now actively encourages private business development.

Buick red and white

There is no advertising in Cuba, nor is there much in the way of signage to denote business establishments. As a result, most buildings appear to be abandoned.

Street scene Eric

Political signs and billboards in Havana pay tribute to 58 continuous years of Revolution and other socialistic themes.  Images of Fidel, Che Guevara and Camilo Cienfuegos appear almost everywhere in Havana.

Vas bein Fidel

An interesting political billboard in Havana displays the message “Embargo (aka blockade)…the largest genocide in history.”  This slogan refers to the economic, commercial and financial embargo imposed on Cuba by the United States since 1960.  This embargo prohibits the sale of all products to Cuba with the exception of non-subsidized food and medicine.  Furthermore, foreign companies that do business in Cuba are prevented from doing business in the U.S.

Bloque Billboard

The embargo was triggered by Cuba’s nationalization of American-owned oil refineries without compensation. Cuba nationalized the oil refineries following President Eisenhower’s decision to cancel sugar imports to the United States.  The American embargo is the longest trade embargo in modern history. Critics of the embargo claim that free trade would be good for both the United States and Cuba.

Cuba USA flags

Privately, our tour guides acknowledge that the Cuban government habitually blames the U.S. for all of its economic difficulties.  They expressed hope that Cuban and American leaders will find a way to resolve some of their differences so that the embargo can be eliminated and so that the Cuban people and Cuban businesses will have full access to U.S. goods and services.  Our guides tell us that access to U.S. medication and food products will significantly improve the quality of life for all Cubans.  Clearly, there is a desperate need for basic infrastructure improvements and decent food in Cuba.  American companies and farmers could conceivably profit by selling their products and services to Cuban consumers.

Fidel quote

It appears that the Cuban people have adjusted reasonably well to their circumstance.  They seem content (perhaps resigned?) and positively engaged.  Panhandlers and street vendors are common in tourist areas, but there are very few beggars and no evidence of homelessness.  Crime is almost non-existent in Cuba.  The public infrastructure and quality of life here is much lower than that of the U.S. but at least equal to or perhaps somewhat better than that of many Caribbean islands.

After Monday’s tour of the Vi­ñales valley, Cutter Loose remains at Marina Hemingway on Tuesday and Wednesday awaiting favorable weather for the return to Key West.  Thursday’s forecast calls for lighter winds from the southeast.  This is just what the doctor ordered.  On Wednesday afternoon, we settle our account at Marina Hemingway and prepare for a Thursday morning departure.

On Thursday at 0630, we are underway from our dock on Canal #1.  There is barely enough daylight at this hour to maneuver Cutter Loose alongside the Customs dock for outbound clearance.  Customs officials perform a thorough inspection below decks to insure that there are no Cubans aboard.   At 0730, we bid a fond farewell to Cuba and enter the Straits of Florida bound for Key West.

Hasta luego Cuba

Our patience in waiting for favorable weather is rewarded with a moderate 15 knots of southeast winds on the beam with 3 to 5 foot seas.  Cutter Loose romps along at 8 knots for 80 miles before the wind begins to dissipate.  We had anticipated a boost from the northeast set in the Florida Current that worked against us during our trip from Key West to Havana.  To our dismay, the current is adverse again today, setting Cutter Loose to the southeast thus eliminating the possibility of a landfall at Key West before dark. There is always a price to be paid for re-entry.

At 9:45 PM, the sea buoy at Key West passes astern.  Carefully navigating the light patterns of the Key West ship’s channel in darkness, the anchor is down near Tank Island at 11 PM.  Today, 112 nautical miles have passed beneath the keel of Cutter Loose.  After 15 hours of travel today, we have re-entered the 21st century…worlds apart from our point of embarkation this morning at Marina Hemingway.

Today has been a contemplative kind of day, re-playing, absorbing and processing that which we have seen and heard during the past two weeks.  Factor in to the mix the powerful mental image of a makeshift Cuban chug that washed ashore during our visit to the Dry Tortugas a few weeks ago.  Nineteen desperate Cubans risked their lives to reach the United States in that decrepit vessel.

refugee boat inside

A visit to Cuba sticks in one’s gut…difficult to grasp and digest but a delight to the senses nonetheless.   Without a doubt, this has been a most enlightening and fascinating experience…one that we shall not soon forget.

One thing is certain.  Travel makes us ever mindful that we live in a country with extraordinary abundance, opportunity and freedom.  The freedom to come and go as we please, in particular, is a precious right that Americans should never take for granted.

Tomorrow, we will exercise our freedom of movement by sailing east to Marathon for a few days of rest and relaxation at Harbour Cay Club before commencing the long trip north to Annapolis.


“Travel is fatal to prejudice, bigotry and narrow minded-ness”

                                                            Mark Twain


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