Everything You Need to Know About Booking Your Cuba Vacation

Photo credit: Getty Images
Photo credit: Getty Images

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We get it, it's confusing. You simply want to know: Can I travel to Cuba legally from the U.S.? It seemed like all was good there for a while, but then the new Trump administration tweaked the policy and it got all confusing again - not to mention the numerous reports of alleged bizarre sonic attacks affecting U.S. diplomats in Havana, which have prompted a U.S. Travel Advisory warning.

But for those still wanting to go to Cuba, the good news is that you can still travel to Cuba from the U.S., but there are some changes. We'll break it down for you, but first let's step back a bit to 2014 when President Obama rolled back many of the travel restrictions to Cuba after the U.S. re-established diplomatic relations. Travelers were, predictably, thrilled.

Airlines like Jet Blue and Delta started flying to the Caribbean island, and even AirBnB apartments sprang up, ready for the influx of individual travelers who seemed eager to visit. And while President Trump announced a new policy, which includes a tightening of the economic embargo against Cuba (meaning you're not allowed to spend money at any business that has ties to Cuba's military), many of the relaxed policies will remain in place, which is good news.

Photo credit: Getty Images
Photo credit: Getty Images

U.S. companies can still do business in Cuba, direct flights can continue to operate between the two countries, and cruises can still call into the island's ports. Additionally, the U.S. embassy in Havana will remain open, as will the Cuban embassy in Washington, D.C. But under the new policy, Americans won't be able to visit as private individuals on "people-to-people" trips, but will still be able to visit independently (if you don't opt for a tour company like Insight Cuba) by traveling under the "support for the Cuban people" within the 12 approved categories in which one can legally visit Cuba.

Keep in mind, if you do plan on visiting independently or through a cruise or tour operator, much of what you'll find on the island remains the same as before the new policy, such as paying for things in cash once you're there. Cuba's frozen-in-time atmosphere might not be for everyone (for example, service in hotels and restaurants may not be what you're used to from other destination places), but for some, that's the beauty of visiting a place like this. And who knows? The policy could change on a dime. For more information on the U.S.'s Cuba travel policy, click here and here.

Things to Know About Cuba

Currently, there are 12 approved categories for Americans to legally visit Cuba. Some of the ways that could pertain to Americans include things like family visits, educational activities, journalistic activity, religious activities, humanitarian projects, and support for the Cuban people; for a full list of the approved categories, click here. Keep in mind that all visitors will need both a passport and a tourist visa (your tour operator/cruise line or airline will provide this for you). Click here for more detailed visa information.

All-Inclusive Vacation Packages to Cuba

There are several tour operators offering trips to Cuba, which can range from a weekend in Havana to weeklong trips that take in the surrounding countryside and other cities and towns.

Photo credit: Getty Images
Photo credit: Getty Images

Insight Cuba and Tauck are reputable companies that have been running Cuba trips for years. They'll essentially take care of everything such as flights, visa, and the itinerary. Insight Cuba, for example, offers a four-day/three-night Weekend in Havana tour, which starts at $2,695. The itinerary includes interactions with locals, perhaps a visit to an artist's studio, a local food co-op, or a recording studio where the Buena Vista Social Club has recorded music. A walking tour of Old Havana is also included, as are group lunches and dinners in local paradores (privately owned restaurants) and hotel accommodations.

Cruises to Cuba

Cruising is quickly becoming a popular way to enjoy a Cuban vacation. Carnival is offering five-day cruises starting at $339 per person, with an overnight in Havana. Royal Caribbean offers four-night sailings to Havana from $419 per person, and coming this December, Oceania Cruises is offering nine-day sailings starting at $1,799 per person that call in at places like Havana, Cienfuegos, and Santiago de Cuba.

Photo credit: Royal Caribbean
Photo credit: Royal Caribbean

Flying to Cuba

Almost all of the major carriers now fly to Havana, including Jet Blue, Delta, American, Southwest, and United (New York, Miami, and Fort Lauderdale are the main departure cities). A recent search on Jet Blue from New York's JFK to Havana offered midweek roundtrip tickets in November 2018 for as low as $160.

Where to Stay in Cuba

The most upscale hotels are the Hotel Nacional, Iberostar Parque Central, and the Hotel Saratoga (where Beyoncé and Jay-Z have previously stayed). The larger hotels typically have comfortably appointed rooms (with air conditioning), efficient service, bilingual staff, an outdoor swimming pool, fitness center, and bars/restaurants. A Four Points by Sheraton Havana, the first U.S. hotel to open in 60 years, opened recently. Depending on the type of tour you're on and the company you've booked with, you could be staying in one of these hotels.

Photo credit: Hotel Saratoga
Photo credit: Hotel Saratoga

Many of Cuba's hotels are owned or managed by the military, which would put them off-limits to Americans under the new policy. While your tour operator will book hotels that are in compliance, as an individual traveler, you must make sure you don't book one of these hotels. The most current list can be found here.

To avoid this minefield, many independent travelers are opting to stay in an AirBnB. A recent search showed a one-bedroom apartment in Old Havana for an average of $50 per night. Using an AirBnB is a great way to avoid using a military-owned business and certainly fits with the "support for the Cuban people" category.

What to Do in Cuba

Most tour companies begin in Old Havana, with its cobblestone streets and Spanish colonial architecture. Top attractions include the Cathedral of Havana and Plaza de Armas, one of the city's central plazas. There's also El Morro fortress on the waterfront and El Malecon, the famous seaside boulevard, as well as museums like the Museum of the Revolution and the National Museum of Fine Arts.

Photo credit: Getty Images
Photo credit: Getty Images

In addition to Old Havana tours, there are Ernest Hemingway-themed tours, along with art-themed tours that take in galleries and studios where you can meet local artists. Beyond Havana is the countryside and smaller cities like Cienfuegos and Camaguey.

When to Visit Cuba

The best time to visit Cuba is November through May when the weather isn't too hot and there isn't much rain. The low season is typically June through October, with the weather being intensely hot, especially in summer. If you don't mind the heat, it might be a good time to visit because hotels and flights will likely be cheaper.

Money Matters

Your credit and debit cards won't work, so you'll need cash. The currency in Cuba is the Cuban convertible peso (CUC). When you're exchanging your money in Havana, you'll be charged a 10% penalty fee, so before you leave for Cuba, you might want to exchange your U.S. dollars to Euros at your local bank to avoid being charged the 10% penalty fee (you won't have to pay the fee to exchange from Euros to CUC once you're there).

Photo credit: Getty Images
Photo credit: Getty Images

Internet Matters

Don't expect your internet to work the way it does at home. Sometimes the only place to get online is in the big hotels or at a public park (tourists can buy prepaid cards at kiosks for a few dollars, which give them a few hours of Wi-Fi). Think of your visit as a digital detox!

Traveling Within Cuba

Havana is very walkable, but taxis are plentiful, too. Hail a taxi - usually an enormous vintage American car - fun!

Photo credit: Getty Images
Photo credit: Getty Images

Dining in Cuba

Paladares are privately owned restaurants and, as such, are not off-limits to Americans. There are numerous paladares in Havana, serving everything from chicken and rice to oxtail risotto. One of the best is San Cristobal Paladar, serving Cuban Creole fare (this is where President Obama dined during his visit). Other well-known spots to have a mojito, include La Bodeguita del Medio bar (once a favorite of Hemingway) and the Tropicana nightclub, known for its the over-the-top cabaret show.

Photo credit: Getty Images
Photo credit: Getty Images

Things to Buy

Cuban cigars, rum, and other trinkets are available. Americans are allowed to bring back $400 worth of goods - and that includes $100 worth of cigars.

Photo credit: Getty Images
Photo credit: Getty Images

Coming Home

Cuba no longer charges an exit fee at the airport, but keep in mind that the check-in lines at Jose Marti International Airport can be long, so make sure you leave plenty of time to make your flight back to the States.

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