trip to Cuba

The iconic images you see on social media feeds from a trip to Cuba are enticing. All those salsa dancers, smiling kids playing baseball, and cigar-smoking men playing music or driving classic cars paint an exotic picture. You see visitors walking on deserted beaches, a fruity rum drink in hand. Don’t you want to beam right into that?

It can be an idyllic trip for sure if you can avoid the potential downsides. Your chances will improve greatly if you let an expert take care of the details on this vacation.

We have only covered mainland Latin America on this site unless you count dots right off the coast like Roatan Island and the Corn Islands. There are two main reasons for this. First, in the travel industry, Cuba, Puerto Rico, and the Dominican Republic are considered Caribbean destinations, islands in the sun for an easy beach getaway. Second, the islands are known as mass-market vacation destinations more than ones catering to luxury travelers. This has been especially true in Cuba since communism and luxury are seldom seen together in the same room.

So if you’re dreaming of traveling to Cuba when international trips get easier again, you’ll want to do it through a company that knows how to set up luxury Cuba tours. Even if you just want a long weekend with a couple of Havana tours, this is not a destination where you can pull everything up on Expedia and hit the “book it now” buttons. You need someone with experience, expertise, and connections. There are Cuba luxury private tours you can book, but you’ll need a specialized agency.

The Complications of a Trip to Cuba

luxury Cuba toursFirst of all, planning a trip to Cuba is unlike a trip for any other destination if you’re American. Traveling to Cuba from Canada is no big deal, but the USA’s complicated history with the island nation 90 miles from Florida has made vacationing there a complicated mess going back to when JFK was the president. Things started getting much easier finally during the Obama administration, then deteriorated again the past few years as diplomacy took a back seat.

You can still travel to Cuba from the USA legally if your visit is classified the right way, or you can incorporate some shades of gray by going through an indirect route. (Half the Americans I know who have been there are expats: they flew from Mexico, the Cayman Islands, or Jamaica to skirt the U.S. flight issues.) You need to do it correctly to stay out of trouble, so getting advice from a specialist agency is key.

Luxury Travel in Cuba Can Be an Oxymoron

If you’re picturing unforgettable experiences, in-depth tours, atmospheric hotels, and fine dining, you’re asking quite a lot out of a nation that’s been under one Castro’s rule or another since 1959. This is one of the most fascinating destinations in the Americas, the land of salsa, cigars, rum, and classic cars. Many visitors come back disappointed though because they got hustled and hassled at every turn trying to travel independently like they would in other Latin American countries. While finding a great meal in most countries can be as easy as asking around or pulling up Yelp, eating well in Cuba requires a lot of advance planning and local knowledge.

While governments around the world have encouraged private industry to build grand resorts and lovely boutique hotels, the Cuban government has actively stifled those kinds of private ownership developments. There’s been very little incentive—and a lot of risk—for foreign hospitality brands with ample capital to enter the fray here. You won’t have any problem finding a basic all-inclusive beach resort catering to Canadians and Europeans arriving on charter flights, but if you’re a discerning high-end traveler, it’s best to let an expert pick where you’re going to stay. Then you’ve got a better chance of ending up in a place like this:

luxury Havana hotel

There is also no shortage of guides willing to show you around and drivers willing to give you a lift in their ’57 Chevy in this country where salaried jobs earn a few dollars a month. If you want a real expert though with fluent English skills, you’ll want to use an agency that has the music, history, and culture experts on call. If you want good seats for the best performances, or want a private tour of some historic home that’s not normally open to the public, that’s not going to happen without connections who can navigate the rules and obstacles. The right Cuba travel specialist can mean the difference between frustrating and fabulous.

It’s Worth Paying for Cuba Travel Expertise and Connections

A trip to Cuba can be transformative, enlightening, and spectacular if done right. Judging by my conversations with dozens of experienced travelers who have been there, however, it’s even more likely to be none of the above if poorly planned. People who have traveled independently to dozens of countries before leave Cuba thinking, “What happened? I thought I was good at this!”

Once you’re set up right, you can enjoy what makes this island nation unique without being on guard all the time. You can enjoy the lack of billboards and commercialism, the roads that aren’t jammed with traffic, the slow pace of life in the countryside, and abundant wildlife. You can enjoy beaches that don’t have a wall of high-rise condos on them and talk with people who aren’t rushing off to a meeting.

deserted beach in Cuba

If you’re looking to visit this unique destination and want to have a vacation that’s surprising in a good way instead of bad, we recommend the Cuba Private Travel team. They’ve been doing this for 15 years and have built up a deep bench of local contacts. They have access to the very best in Cuban art, music, literature, dance, and architecture, as well as knowing which of Cuba’s beaches and resorts will be best for your visit. They’ll line up the best things to do in Cuba that meet your wish list and interests.

They can create tailor-made travel itineraries for your vacation that take you to the heart of Cuba’s culture, landscape, and people. You’ll have someone taking care of all the many rules to follow and their trips are fully U.S. Treasury Department compliant. You’ll have access to experienced personal guides, history experts, interpreters, and a 24-hour concierge, backed by a company that’s really based in Cuba.

See more details here: Cuba luxury private tours.