Visiting Cuba is Easier Than You’d Think: A Travel Itinerary + Tips

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In the dead of winter, an island escape is a must {but really, any time of year is acceptable}. Palm trees, an ocean breeze, and the very idea of sipping a tropical drink seaside…need we say more. Only a few hours away by flight, Cuba is a great travel destination and has been frequented by many Americans ever since a former president lifted the restrictions, allowing Americans to travel to Cuba back in 2009.

In 2019, however, the current administration imposed new restrictions and banned Americans from traveling on “people to people” group trips, as well as entering the country via cruises, yachts, or fishing vessels. American Airlines was also banned from flying into any Cuban city other than Havana by the administration. All of that, however, doesn’t mean that traveling to Cuba is impossible. 

Although the U.S. has a tumultuous history with Cuba, visiting this Caribbean island is worth it for the rich culture, food, and all-around vibrancy. It might be a bit of a daunting task to get to Havana, but rest assured, it is possible. Read on for tips on how to travel to Havana, Cuba, and what to do in this remarkable city for an unforgettable long weekend getaway. 

havana cuba travel

Know Before You Go

cuba travel

Before booking a flight, travelers must first determine which authorized category they will be traveling under to get into the country. There are now 11 categories of authorized travel, some of which include journalism, government, or religious reasons, but for tourists, “Support For The Cuban People” is the way to go. 

As it suggests, under this category, travelers must support the locals. For example, rather than staying at government-owned hotels, staying in a casa particular, or Airbnb supports the local population. Other ways to support the people on the island include eating at local restaurants, visiting local museums, or taking salsa dancing or cooking classes, many of which can be booked through Airbnb experiences. Keep an itinerary just in case you get asked by customs and make sure to save all receipts as proof of supporting the Cuban people. 

Another very important tidbit is to bring enough cash for the entirety of the trip. American credit cards will not be accepted in Cuba, and debit cards will not work on ATMs. Many say the best currency to bring are Euros because American dollars are taxed heavier so travelers will get more bang for their buck if they exchange another currency such as Euros

It would also be helpful to do as much research as possible before arriving because cell phones will not work either. Unlike when traveling to Europe, data will not be readily available to purchase, and WiFi access is limited. Internet cards can be purchased for about $1 an hour and used at WiFi spots around the city at certain parks or hotels. It is helpful to keep a screenshot of a map just in case, too {#oldschool}. Otherwise, locals are friendly and eager to help, so they are the best source of information when seeking advice or asking for directions. 

Getting There

havana cuba

So you’ve done your research, brushed up on your Spanish, and now it’s time to book the flight, which is only about three hours from Newark to Havana. Several airlines fly directly out of Newark Liberty International Airport including Delta, JetBlue, American Airlines, and United Airlines. Travelers must obtain a Cuban Tourist Card as well, which can range from $50–$75 a person. Most tourist cards can be purchased at the airport on the day of travel, but be sure to check with the airline first, as rules may differ. 

As for when to book, the best time of year to explore the island would be anytime from December through May. June and July tend to be too hot and humid, while anytime from August through November is risky due to hurricane season. Get away from the brisk winters in New Jersey and enjoy the 80 degrees and sunshine of Havana in January. 

Read More: Weekend Getaway:  San Juan, Puerto Rico

Where To Stay

The best area for tourists to stay is in Old Havana. There are plenty of casa particulars { private accommodation or a stay at someone’s home} and Airbnbs in this area, and it is very easy, safe, and beautiful to walk around, day or night. Taxis are also easily accessible in the city center and are very reasonably priced. 

What To Do

Cuba has no shortage of fun activities for locals and tourists to enjoy. Here are a few musts:

Visit Callejon de Hamel

callejon de hamel

Callejon de Hamel is a must-see and will most likely be a stop along a tour of the city. It is an alley in Central Havana filled with Afro-Cuban art, vibrant murals, frescos, sculptures, and paintings. On Sundays, a live rumba band plays music on the street. 

Take a Salsa Dancing Class

Many dance classes can be booked in advance through Airbnb experiences for just $10-$20 per person, and are a fun and unique way to support the Cuban people. Learn salsa or rumba taught by professional dancers, and you will be sure to impress your friends and family upon your return. 

Go on a Convertible Tour of the City

convertible tour cuba

^ The view from the converitble tour!

The old classic cars are one of the most iconic aspects of Cuba. Take a tour around the city in a hot pink 1950s Chevrolet convertible while learning about Havana’s history from a local. Many of the convertible tours on Airbnb experiences include a photoshoot from a professional photographer, so your memories will forever be beautifully captured during this educational experience. Tours typically range from $30 to $60 depending on what is included. 

Take a Cuban Cooking Class

Another great way to support the Cuban people is getting taught how to make a traditional Cuban meal from a local. Enjoy some home-made pork, rice and beans, fried plantains, and a Mojito while getting to know a Cuban family. Classes are around $30, which typically include the class, as well as enjoying the meal that is prepared after the class.

Purchase Cuban Cigars

cuban cigars

See what all the hype is about and enjoy a real Cuban cigar. For the non-smoker, cigars also make excellent gifts to take home to family and friends. Cuban cigars should only be purchased in hotel shops to ensure that they are authentic, although many vendors may try to sell them to tourists on the streets, claiming they are the real deal. The hotel cigar shop clerk will know exactly how many cigars are legally allowed to be taken overseas {for Americans, the current legal limit is 50 cigars}. 

Take a Day Trip Tour to Vinales

Vinales is a gorgeous town three hours outside of Havana, filled with coffee and tobacco plantations. A guided tour can be booked in advance or at any of the hotels in Havana starting at about $60 per person including transportation to and from Vinales. Many tours include lunch, drinks, and a horseback riding excursion. 

A Day Trip to Santa Maria Beach

santa maria cuba

When in Havana, a trip to the beach is a must. Santa Maria is beautiful and very easy to get to from Centro Habana. A round-trip bus ticket to the beach is only 5 CUC {equivalent to about $5}. Grab a lounge chair for just 2 CUC and enjoy the warm breeze and soft sand while sipping a classic Cuban mojito.

Where To Eat + Drink

Food is the literal bread + butter of any trip, so be sure to take advantage of all the fabulous food Cuba has to offer.

For Breakfast

Although there are so many great restaurants around the city, the best way to experience breakfast in Cuba would be with your Airbnb host. Most casa particular and Airbnb hosts will offer their guests a home-cooked breakfast each morning for 5 CUC, or five dollars per person. It is also a great way to support the Cuban people and to get to know your host.

For Lunch + Dinner

Restaurante Antojos {Callejon Espada e/ Cuarteles y Chacon, Havana, Cuba}

antojos cuba

Antojos is a great option for lunch or dinner, serving classic Cuban cuisine and delicious cocktails, both frozen and on the rocks. They offer outdoor seating, so it is a perfect lunch spot for a warm, sunny day. 

La Bien Paga {Aguacate 259/Obispo y Obrapia, Havana, Cuba}

La Bien Paga, located in Old Havana, is perfect for a quick bite at lunchtime, or while on the go. They sell Cuban sandwiches, hamburgers, paninis, and more, all of which quite literally melt in your mouth.  

5 Sentidos {San Juan de Dios 67, esq. a Compostela, La Habana, Cuba}

This restaurant is another trendy spot in the heart of Havana, offering a mix of seafood and meat dishes. This place is likely to fill up quickly, so be sure to make a reservation in advance for dinner. The ceviche comes highly recommended as a starter, as well as the chicken curry or pork for a main dish. 

Habana 61 {Calle Habana No. 61 entre las calles Cuarteles y Peña Pobre, Havana, Cuba}

habana 61

For the seafood lover, Habana 61 is a great place to check out. It is a small space and is usually booked, so be sure to stop by and make a reservation at least a few hours ahead of time. They are highly rated by the locals, as well as on TripAdvisor. The vibe is modern and hip, with an upscale edge. Visitors recommend the fish croquettes or ceviche for starters, and the lobster for the main course.  

See More: An Itinerary for an Island Getaway to Anguilla

For Drinks

Floridita {Obispo 557 Esquina a Monserrate, Havana, Cuba}

flordita cuba

This historic bar and restaurant became famous due to author, Ernest Hemingway, who frequented this spot during his lifetime. Although it may be a tourist attraction, the cocktails are quite delicious, especially the daiquiri, so it is definitely worth stopping by while in the area. 

Chanchullero {Teniente Rey, 457A bajos Plaza El Cristo Habana Vieja, Havana Cuba}

Chanchullero is a three-story restaurant and bar with a great atmosphere, friendly staff, and good music. The third level of the bar is their rooftop, and worth the wait if given the chance. The mojito here is delicious and refreshing, and all items on their menu are very reasonably priced.  

Fábrica de Arte Cubano {Calle 26, La Habana, Cuba}

fabrica cuba

Fabrica de Arte Cubano is an art gallery and premier night club in the Vedado neighborhood of Havana. It used to be an old oil factory before it was transformed by Cuban musician, X-Alfonso. Now, it is a huge artistic hub with numerous rooms, each offering a different, unique experience for visitors with live music, DJs, performances, and more. There is a reason that it was chosen to be on Time’s Greatest Places of 2019 list. It is a must-see, and cover to get in is only 2 CUC a person. 

Casa de la Musica de Centro {Calle Galiano e/ Neptuno y Concordia, Centro Habana, La Habana, Cuba}

After taking a salsa dancing class, head on over to Casa de la Musica to show off some moves if you’re feeling brave. This club has live music, good mojitos, and a dance floor for when those mojitos hit. 

These are just a few of the numerous restaurants, bars, and activities that can be done in Havana, Cuba. It is a city that has so much to offer, and so much culture to absorb. Although the restrictions may seem to make it a tricky place to visit, once the research is done, and all the necessary documentation is gathered, it is truly worth the few extra steps. Supporting the Cuban people will encourage visitors to try new and cool experiences that will make for unforgettable memories.  

Have you visited Cuba yet, or do you plan to after reading this article? Tell us in the comments!EMAIL BUTTONS


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Alexis moved to Hoboken after she graduated college in 2015 and fell in love with the area right away. She currently lives in Jersey City with her boyfriend, Ewan, and works in New York City as a fashion buyer by day and an aspiring entrepreneur by night. In her spare time, when she is not exploring the new, trendy spots around town, you will find her working out at one of her favorite local classes, singing along to the soundtrack of Wicked, or creating macrame wall art and home decor that she sells on Etsy.


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