5 Reasons You Why Should (& 1 Why You Shouldn’t) Visit Cuba this Winter


Cuba_Domenic Scaturchio

You’ve probably been thinking about Cuba for a while. The music, architecture, food, and history make it unique. There is also something particularly alluring about a tiny nation largely cut off from the rest of the world. The United States resumed commercial flights to Cuba this summer with regular service for several airlines beginning in late November. The normalizing of relationships between Cuba and the US over the last few years resulted in the first regular US commercial flights to Cuba since 1961. Here are the reasons you should (or shouldn’t) fly, cruise, or sail a yacht to Cuba this winter.

Why Go to Cuba

1. Because You Can

For most Americans, this will be the first winter travel to Cuba is legally possible. After years of only learning about Cuba in movies or history books, now is a chance to witness it for yourself. That could be reason enough to make the trip. A trip to typical winter holiday locations might not give you much to post about other than the sun and sand. Cuba offers experiences that are distinctly different. You’ll probably also be the first person on your block to visit so you’ll have great stories to share.

2. You Need to Catch It Before It’s Gone

Sure, Cuba will still be there in a few years – and so will new resorts, more tourists, and what will probably be a more “Americanized” experience. With the renewal of diplomatic relations with the US, investors and developers are already making plans for development in Cuba. That could be a positive feature for travelers who prefer a luxurious all-inclusive resort-type experience. For those of us who want to capture a more authentic view of Cuba – peeling paint and all – this winter is your chance.

3. It Lives Up to Most of the Hype

Cuba isn’t perfect and, in terms of tourists’ offerings, the years it spent free from American tourists didn’t do the country any favors. Yes, you might spot a few buildings looking a little worse for wear. 

Cuba is the largest of the Caribbean islands and it is well worth a visit even if you only see the white sand beaches, palm trees, and tropical breezes. Fortunately, Cuba is much more than that. The architecture is distinctive with excellent Colonial Era buildings in a number of towns and cities. The country is home to rich history of amazing music. The cuisine is flavorful and robust and, yes, there really are plenty of classic old cars still on the road.

In addition to beautiful white sand beaches, Cuba has forests, caves to explore, world-class snorkeling sites, and pretty much anything you’re looking for in a tropical island. Unlike many Caribbean islands, Cuba has plenty of beaches and other beautiful sites that are not overly crowded with tourists.

4. It’s Not the Wasteland Americans Might Imagine

After more than fifty years of animosity between the US and Cuba, many Americans probably expect Cuba to be completely unprepared for tourists. In fact, Cuba has always had tourists. Travel from Canada, the UK, and other countries has continued over the years so hotels, restaurants, and other tourist facilities are already there.

There are many excellent resorts and plenty of opportunities for hiking through the forests, kayaking across beautiful blue inlets, and snorkeling over coral reefs teeming with fish. There is an excellent yacht club with yacht charters that allow visitors to sail around the island and explore even the uninhabited areas.

5. Who Knows?

After more than 50 years being at odds to Cuba, who knows what the next few years will bring. With a new US President taking office in January, there might be a new view on the thawing of relations. Nothing would be expected to change soon, but it might be a good idea to travel to Cuba this year, just in case.

The recent death of Cuba’s former leader, Fidel Castro, is not expected to significantly impact the country given his brother assumed control of the country several years ago. His death, however, and the aging of his brother does lead to questions about the long-term direction of the Cuba. This is another reason to enjoy Cuba now.    

Why Not Go

1. You Want Everything Just Right

Many of us love the idea of “discovering” Cuba before it become more commercialized. Not everyone feels that way. Sometimes it’s just nice to find everything well established and running smoothly. If you’d rather see more American-style offerings, you might prefer to travel to a different Caribbean location this year, and save Cuba for later.

For most of us, this is probably the best opportunity we’ll have to see Cuba as it really is. If you want to discover Cuba and experience it for yourself, this may be your only chance.

Photo Courtesy of Domenic Scaturchio

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