Cuba: Five to Know

I’ve had the privilege of visiting Cuba twice in the last few years – once before and then again after the most monumental news regarding US-Cuba relations in over half a century. The first time I visited, in 2014, there was already a distinct shifting and easing from years past. Some foreign brands were present and locals spoke more freely about their past and how the country is changing. My second trip, in 2015, followed Obama’s announcement about restoring relations and the arrival of the US Embassy. The changes between my visits, eighteen months apart, are noticeable. Here are five things to know before traveling to Cuba during this complex era.

Make plans for Cuba travel at least five months in advance. The opening up of Cuba to American visitors in effect opened up the flood gates. At the moment, operators are overwhelmed with business, and there are not enough beds in Cuba to accommodate all the requests. Despite its geographic proximity, Cuba is not a last-minute destination for travelers from the U.S. and trips should be planned at least five months ahead of time if you want to secure rooms in the most comfortable hotels.

If you are interested in visiting Cuba, go now. Crowds have multiplied, and there is no sign of the numbers letting up. Large group tours are being given preference in some hotels over individual travelers and smaller groups that book their trips on their own. Sites are distinctly busier and restaurants that cater to foreigners are overrun with large groups sitting at banquet-style tables. As more hotels are built and opened for business, the number of tourists will only increase.

Consider visiting other parts of Cuba in addition to Havana. Havana is home to the country's best infrastructure, but also to the crowds. Cuba's capital city is the architectural and cultural epicenter of the country and warrants at least three days to explore. But more adventurous, or repeat visitors, should consider traveling to other parts of the island. Hotels throughout the country are poor, but the vast geography and culture is exceptional.

Consider a boat charter to travel around the island. Though expensive, chartering a boat allows travelers more freedom to tour around the island, and depending on the boat, a quality of stay you may not find on land. Speak to Indagare about possible boat charters from the Florida Keys around Cuba.

Speak to Indagare about the reality of traveling to Cuba. A number of Indagare's Travel Specialists have traveled to Cuba, and we require all members considering traveling there to speak to staffer a who has on-the-ground knowledge of the country and its intricacies. We find that this conversation helps eradicate most concerns and allows the opportunity to frankly talk about expectations and quality of things like hotel rooms, transportation and cuisine.

The easing of the embargo against Cuba and shifting of the U.S.-Cuba relationship has set a new precedent for Americans traveling there. It’s important, however, to remember that Cuba is still a Socialist country and things – especially there – do not change overnight.

While Cuba does not yet have the infrastructure to accommodate the demand, it is doing its best to catch up, and numerous buildings are being reconstructed and outfitted as hotels. The utility network will need to be strengthened as well, as the new hotels will put a strain on the already precarious power grid where electricity failures and power outages are already common.

The easiest and quickest way to legally travel to Cuba as an American is still via the people-to-people cultural exchange visa, which is now part of a more general visa affidavit process. This limits certain activities such as spending time at a beach, as the cultural-based itinerary must be pre-approved by both governments before the visa is granted. Others may travel to Cuba under different means, however the people-to-people visa ensures that there are no questions about departing or reentering the U.S. We recommend our members continue to apply for this visa, so that we can work with local partners to ensure comfortable hotel rooms, dining reservations and tour guides.

There’s a reason that Cuba, its architecture and its people have inspired writers such as Hemingway and Pico Iyer; it tends to dig in and stay with you long after you’ve left. My hope is that on my next visit I will see positive change for Cubans from foreign investment and spending, but that international brands, large hotel chains and masses of tourists haven’t created a second South Beach. I urge everyone to visit Cuba in the near future to see a country simultaneously caught in time yet on the brink of momentous change.

Contact the Indagare Bookings Team to plan a trip now.