Travel Destinations

Cuba - The Last Great Undiscovered Cruising Destination in the Caribbean

Bahamas / Caribbean
April 2017

The United States maintains an economic embargo against Cuba. Tourist travel to the country is not allowed by Americans as of this publication date. However, there are opportunities to travel to Cuba by personal boat, charter, cruise ship or airlines if you meet the criteria as set forth by the United States Office of Foreign Assets Control. Do your research and you will locate a company that can help you get there legally. Harmony Yacht Vacations and are good resources.

Why Cuba?

Because it's the last great undiscovered cruising destination in the Caribbean! Home to more than over 11 million people, Cuba has just about everything you could want in a destination -- friendly faces, stunning scenery, beautiful beaches and an amazing culture.

Change in Cuba is happening more quickly than at any time in the past 60 years. The political and cultural makeup will certainly shift with American influence and commercialism as more visitors from the U.S. make Cuba a destination. Cuban officials estimate that 1.5 million Americans would travel there annually if all restrictions were removed, unseating Canada as the main source of tourism.

The U.S. and Cuba have a long and somewhat complicated history. Now independent, at one time it was heavily under the control of the United States both politically and economically. Interestingly, the United States had an ongoing interest in annexing Cuba during the 19th century.

During the 20th century, Cuba was subjected to an ever-changing mix of freedom, authoritarian rule, democracy and increased corruption. At the same time, American economic influence became more entrenched, along with a corresponding rise in the activities of the American criminal element. Cuba was the place to go during Prohibition and plenty of rum made its way north. Gangsters frequented Varadero and had homes in Havana. They were active in nightclubs, casinos and prostitution. The notorious Havana Conference of 1946, a meeting of various American Mafia and Cosa Nostra families at the Hotel Nacional in Havana, featured none other than Frank Sinatra as entertainment. The story of this notorious meeting is a fascinating, if not frightening, look at a little-known part of America's and Cuba's shared history. Havana Nocturne, How the Mob Owned Cuba  and Then Lost it to the Revolution by T.J. English (Harper, 2007) is a great read on that era of Cuba's past.


When you look at Cuba on a chart, the first thing that strikes you is its size. Cuba is big! It is the largest island in the Greater Antilles group. A voyage along the North coast from Cabo Maisi in the east to Cabo San Antonio in the west is a journey of 760 nautical miles. With the extensive pocket bays, many not presently accessible under Cuban rules, Cuba's coastline expands to 3,102 nautical miles -- 1,732 on the north coast and 1,370 on the south.

If going by boat, you need to decide early in your planning just how much of this interesting country you have time to explore. The topography of Cuba is among the most varied you will find anywhere in one country. From the beautiful sandy beaches of Varadero to the mountains and tropical moist forests, Cuba offers something for every taste.

From a mariner's point of view, long sections of the north and south coasts of Cuba are a coastal cruising paradise. It is possible to meander from anchorage to anchorage and enjoy the truly pristine beauty of cays that are visited only by the wildlife on them, and perhaps the occasional fisherman or charter boat. You may see only one or two other pleasure boats along the entire coast outside of the marinas.

Havana -- Goin' Ashore

Havana is one of the most exciting cities in the western world -- an electric and eclectic mash up that has to be experienced to be appreciated. If your boat is tied up at Marina Hemingway you can rent a car, but this is probably the most problematic way to experience Havana, given the challenges you'll experience parking and driving. You're far better off getting a cab into town and then exploring Havana on foot, using the available pedicabs, horse-drawn carriages, buses and taxis to get around when walking isn't feasible.

Cuba has excellent taxi services, and you may as well opt for one of the old American autos that are used as cabs. The ride will cost you about $15 to San Francisco Square in Old Havana, which is a great jumping-off point for your walking tour. As always, negotiate the fare before you begin the ride. There are generally one or two of the old cabs floating around the marina. A third way is to take the local bus into Havana. The cost is low, but the bus gets incredibly crowded and uncomfortable and we can't recommend this. You may also find the bus from the resort next door to the marina as an option.

Once in Havana, there is so much to do and see that you will find yourself at a loss for what to do next. There are museums of every sort, from the Museum of Matrimony to the always-crowded Museum of Chocolate. Music throbs from the bars, restaurants and clubs throughout the city. Locals play dominos, chess or checkers at tables set up on the sidewalk, surrounded by spectators. Sculptures you would expect to see in museums sit in open courtyards. Street mimes entertain children and their parents. The tourist crowd outside of Hemingway's old hangouts shuffle in and out, hoping to get a mojito or Cuba libre and feel nostalgic about their literary hero. Kids play ball in the streets. Jiniteros encourage you to try a new restaurant, or show you a casa particulara, or buy their cigars - and it's all done with a smile and sense of élan not found elsewhere in the islands. The obvious places, like La Bodeguita del Medio, Floridita and Hotel Ambos Mundos are almost always crowded these days, so look for some new adventures. The restaurants are getting better and safety has never been a problem. Enjoy... you're in Havana.

Santiago de Cuba

At the other end of the island is Santiago de Cuba. You can either take a flight, rent a car or come ashore by clearing into the country on your boat into the well- protected harbor. Santiago de Cuba has a more Caribbean feel than Havana due to its weather and culture. Proximity to Haiti resulted in French and African ethnic influences brought on by migration during the Haitian Slave Revolt of 1791-1804. Santiago de Cuba is as vibrant and valued for its music and arts as is Havana. The music known as son, the foundation of salsa, originated in the region. The renowned Carnaval and Festival del Caribe bring the city to exuberance every year beginning in July. Casa de las Tradiciones in the city's Tivoli neighborhood is a pure delight. Musicians and dancers flock to the packed little club to gambol and mingle. Everyone is welcome.

San Juan Hill overlooks Santiago de Cuba and is where American Rough Riders and other volunteers turned the tide against the Spanish on July 1, 1898. An impressive park is perched on the hill with all manner of bronze and cannon plaques commemorating the battle. Sala Dolores is home to Orquesta Sinfonica de Oriente. Performances are held throughout the year and include music from around the world, featuring guest artists and stunning displays of talent by Cuban musicians of all ages. There are several hotels in Santiago de Cuba that cater to all but the most discriminating travelers. Advance reservations are recommended. Visit Parque Cespedes, the markets and walk the side streets. Depending on the time of year, it can be hot and humid during midday. In some parts of the city, the air can also be a bit dirty from exhaust fumes of motorbikes, diesel cars and trucks due to the topography. By nightfall, though, traffic slows and the streets go quiet except for music pealing from clubs, restaurants and street singers.

From Santiago de Cuba you are a short drive to Guantanamo province, where you may come across another music form known as Changui. A precursor of son and today's salsa, it's a style that originated in the early 19th century and stayed behind in the country while the more popular son moved to the cities. Ask around when you travel to Santiago de Cuba to find clubs, performances, restaurants and venues. You will seldom be disappointed. If you feel that you need a guide, visit one of the upscale hotels and ask the concierge for assistance. Cubans are congenial and accommodating to all reasonable budgets and personalities. And they are always interested in making a few dollars. Regardless of your destinations in Cuba, be prepared for a delightful experience and, above all remain patient and flexible. That's the Cuban way.

Ed Tillett is editor-in-chief, general manager of Waterway Guide Media. He began his travels to Cuba in 1998 with the University of Richmond. His work culminated in the production of a 75-minute documentary titled  Cuba: Rhythm in Motion (available on YouTube) in collaboration with Dr. Mike Davison. Ed's extensive travel to Cuba over the following 15 years resulted in Waterway Guide Media's release in February 2016 of Cuba Bound: The North Coast, a cruising guide for boaters. The next edition of Waterway Guide's Cuba will be released in February 2017 and will encompass the entire island. Co-authored by Addison Chan, the book will be an authoritative and comprehensive guide to Cuba for boaters, sailors and travelers. The new guide will also include bonus sections including the Florida Keys and The Bahamas, the two closest departure points for vessels leaving from American ports.

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