In June of 2016, we escaped Brooklyn to a place that felt much more like time travel than jetsetting. We “escaped” our familiar American culture and all that comes with it: the internet, our credit cards, cell phones, and readily available anything. We went to Cuba. Armed with a government approved itinerary, a Spanish-English dictionary, a couple backpacks and a healthy sense of adventure, our seven day journey took us from the bustling city of Havana to the incredibly scenic countryside towns of Viñales and Las Terrazas.

What we found in Cuba simultaneously baffled, frustrated, inspired, and delighted us. Its cities are a striking contrast of meticulous preservation and dilapidation; its countryside is pristine and nostalgic for simpler times. To the outside world, life in Cuba has changed very little since the 1960’s. But locals and tourists alike agree that Cuba will soon undergo dramatic change, thanks to the thaw in U.S. relations. Once government regulations open up, the influx of tourism and money are quite likely to spur rapid development on the island. Though it hasn’t quite happened yet, in this time of economic and cultural shift, the time to visit Cuba is now.

Visiting Cuba: Past and Present


In the early 20th century, American travel to Cuba was quite common. Havana was by far the most popular destination, and numerous luxury hotels, casinos and nightclubs were constructed during the 1930s to serve the flourishing tourist industry there. In 1958 alone, over 300,000 American tourists visited what was then considered the “Paris of the Caribbean.” But of course, that all changed in 1959, when relations between the United States and Cuba quickly deteriorated. In a political stalemate that’s outlasted 50 years, ten U.S. presidents, a failed invasion, and ultimately, a nuclear war crisis–Cuba has been forbidden for American tourists for half a century. But that’s slowly changing.

After renewing diplomatic relations with Cuba in December of 2014, the Obama administration announced significant changes to the regulations governing travel to the island. Although tourism is still prohibited, the revisions have made it much easier for individuals to travel to Cuba under one of twelve approved categories: family visits; official government business; journalistic activity; professional research and professional meetings; educational activities; religious activities; public performances and exhibitions; support for the Cuban people; humanitarian projects; activities of private foundations or research or educational institutes; exportation, importation, or transmission of information or information materials; and certain authorized export transactions.

How To Visit Cuba Now: Take An Educational Tour With Bridges Cuba


Under the umbrella of educational travel, U.S. citizens are allowed to travel to Cuba under the “people-to-people” educational license as long as they engage in a full-time schedule of educational activities that promote meaningful interaction between trip participants and Cubans. We traveled under this educational exemption, and were able to do so by booking our entire trip with the experts at Bridges Cuba. The Brooklyn-based startup’s itineraries are designed not only to fit the educational requirements, but also allowed us to experience Cuba in a way that wouldn’t have been possible without the knowledge of their local guides and specialists.

Bridges Cuba’s consulting and planning packages put an emphasis on experience, knowledge, and social responsibility–while still ensuring a fun, safe visit within U.S. government compliance. Before creating your itinerary, the team at Bridges Cuba will arrange a phonecall or meeting to match up your interests with activities during your trip that fall within government regulations. Though other Cuba travel companies promise the same thing, their trips cost much more, and rarely make an effort to get visitors to the island away from the already heavily-trod “cultural tourism” scene on the island. Bridges Cuba doesn’t do either. By working directly with local private guides who know all the islands nooks and crannies, trips can be made to fit all sorts of budgets and interests, for just the right amount of adventure, exploration and education. Bridges Cuba’s trips which include lodging, breakfast, guides, and all activities, average around $250 per day, depending on a group’s size and interests.

Another bonus in traveling with Bridges Cuba is access to their fleet of smartphones. While this sounds strange, consider how much we Americans take GPS, wifi, and texting for granted. And unfortunately, even if you’re prepared to pay for data roaming, your American phone wont work here. But Bridges Cuba provides travelers with iPhones that do work in Cuba that are loaded with apps, making communication and navigation much easier. The best feature? Having an English speaking, Cuban tour guide at your fingertips, to text or call anytime. After two days of checking out the city’s historic spots with our guide and new BFF Cesar, we ventured out on our own, and whether were totally lost, or just needed a restaurant recommendation, we were able to call him up and get cheerful answers to any questions we had. The phone proved to be an essential tool for travel within Cuba. It’s available for anyone going to Cuba to rent by the day, and is also included with all Bridges Cuba group trips.

While the U.S. regulations on travel to Cuba may sound off-putting (or intriguing), you can be absolutely sure that you’re in good hands with Bridges Cuba. Founder Brian Rogers has over a decade of experience living in and traveling across the island, and has a team on the ground in Cuba ranging from guides to hosts. He formed these relationships beginning in 2003-2004, when Brian lived in Havana studying Spanish Language and Literature at the University of Havana. In 2015, he began helping a group of Cuban friends who operate privately owned B&Bs by booking U.S. clients and providing consulting to travelers. As diplomatic relations improved, Brian began providing full-trip planning for Americans, including flights, accommodations, and custom-made educational itineraries. Using his expanding network and his knowledge of contemporary Cuba built on years of firsthand experience, Bridges Cuba was officially launched in the fall of 2015. All in all, Brian is super legit, experienced, and knowledgeable… he also happens to be really cool.

First Stop: The Crazy, Colorful City of Havana


Lodging, Dining, Drinking, and Exploring the City–What Not to Miss in Havana

LODGING IN HAVANA—Though there are some hotels in Havana, the best places to stay are in “casa particulars,” which basically means that they’re private family establishments that rent rooms. Staying at casa particulars are not only way more affordable than hotels, but they’re also the most rewarding; the cultural exchange is priceless. We learned this on day one at the first casa particular we stayed at, the “Casa de Gloria y Jesus” that was booked through Bridges Cuba. The hosts are two of the sweetest people in the world, who welcome travelers from all over Europe, Canada, and the USA. (Your dinner conversation is sure to be interesting!) Another perk is that many casas serve authentic Cuban meals to their guests. As soon as we arrived, Gloria whipped  up a tasty vegetarian dinner for us, while Jesus disappeared to make us a suprise beer run. Breakfast each morning was outstanding–a mix of fruits, eggs, vegetables, and bread served with coffee and/or a guava smoothie. Our room was simple and comfortable, right in the heart of Old Havana, and had an endlessly entertaining view out of the terrace into the alley. Day or night, it’s easy to pass time just watching the busy street below.


DINING AND DRINKING IN HAVANA—Though rice and beans are staples to any Cuban’s diet, the food in Havana is definitely the most diverse and innovative. Our most elaborate meal was at La Guarida, where delicious meals, strong mojitos and lively atmosphere are served in a three-story, spectacularly dilapidated Havana tenement. A close second was El Cocinero, whose location next to factory turned nightclub/art gallery La Fabrica make a one-two punch for a great night out. Other memorable meals included O’Reilly 304, where the cocktails are enormous and the food is great–and El Chanchullero, personally recommended by our guide Cesar from Bridges Cuba. It’s menu is more affordable than most touristy restaurants, allowing locals and tourists to mingle and dine together. For a meal with a fantastic view, check out the paladar (private house with a restaurant) El Penthouse de 17 y K, which had good food, great drinks, and a fabulous view from its 7th floor rooftop.

For drinks only, be adventurous and let the busy streets be your guide. Beer is generally $1-2, while cocktails are generally $2-4. If you’re in the Vedado area, check out the bar on top of the FOSCA building, which is the tallest building in Cuba. There’s a restaurant there too, but we preferred the bar side, where you can grab a seat that’s perfectly situated to watch the sunset.


VISITING THE CULTURAL & HISTORIC SITES IN HAVANA–Havana is rich with history and architecture dating back to the 1500’s, when the city was a key transshipment point between the Old World and the New World. As a result, colonial Spanish buildings are in abundance; while some are spectacularly restored, others are beautifully dilapidated. Through Bridges Cuba, we arranged for a tour guide to walk us around the city, who spoke to the history and culture of Cuba, pointing out significant buildings, structure and monuments. Having a guide our first day was essential–not only because we were on an educational tour, but also to help us navigate Havana’s hectic streets, and communicate with other Cubans for things like buying internet cards. (Yes, that’s a thing.)

One of the first stops on our tour of Havana was the Catedral de la Virgen María de la Concepción Inmaculada, located in one of the 15 major plazas in Havana. Built in 1748, the structure is mainly constructed from blocks of coral cut from the ocean floor; if you look closely, you can make out preserved marine fossils! It’s open to the public, so duck into the church for a self-guided tour, then head out the side door where you can climb to the bell tower. (Admission is something like $1/person.) Other highlights included the beautiful Necropólis Cristóbal Colón, which is regarded as the most historically and architecturally important cemetery in Latin Americas; and the Malecón, the iconic seaside roadway that stretches 5 miles on the coast.

Another fascinating aspect of visiting Cuba is seeing all of the Revolution-era landmarks and art. In 1959, Fidel Castro overthrew dictator Fulgencio Batista with the help of a revolutionary group, his brother Raúl Castro, and Che Guevara. The Revolución was widely celebrated in Cuba, as evidenced by the murals, monuments, and other imagery in Cuba. Probably the most important historically relevant place to visit is the Plaza de Revolución, which played host to many political rallies, and is where Fidel Castro and other political figures address the Cuban people. The square is dominated by the José Martí Memorial, with a 350 foot tower and 50 foot statue of the Cuban hero, who was an important figure in Latin American literature. The Museo de la Revolución is another must-visit, residing in the former Presidential Palace. Inside, the museum’s displays of the somber events leading to the revolution are a sharp contrast of the interior itself, which was decorated by Tiffany’s of New York.

Despite its tumultuous past–or perhaps resulting from it–Havana has been a haven for artists of all kinds for hundreds of years. This tradition is celebrated at the Museo Nacional de Ballas Artes, where works are displayed in chronological order starting on the 3rd floor and are surprisingly varied. On the more contemporary side of things, make sure to check out the Taller Experimental de Grafica, a collective space where printmakers and other artists share their work, ideas, and inspiration.


OTHER UNEXPECTED ATTRACTIONS IN HAVANA—Havana is a treasure trove that you could easily spend a few weeks in without repeating anything. One totally unexpected gem we found (thanks to our guide, Cesar!) was the forest whose foliage looks straight out of a science fiction movie. Nearby, the wealthiest neighborhood in Havana is Miramar, which is comprised of mansions and luxurious estates. Prior to the Revolution, Havana’s most affluent citizens lived here; it’s now mostly embassies, office buildings, and international banks. Right along the waterfront you’ll find the beaches where Cubans come to beat the heat. Other worthy pursuits include an “urban hike” from Old Havana to Vedado, or visiting Havana’s Chinatown, just beyond the Capitol building.

Second Stop: The Beautiful Rural Town of Viñales

The tiny town of Viñales is comprised of everything rural Cuba has to offer: tobacco fields, thatch huts, massive steep-sided hills (called mogotes), century-old palm trees,  roadside farms, colorful one-story houses, farm-t0-table dining, and some of Cuba’s most incredible vistas. Though the traffic is less car-heavy here, it maintains its own Cuban craziness in that packs of dogs and stray chickens are common roadblocks. The main street here, Salvador Cisneros, is quite touristy, but most of the attractions in Viñales take you outside town and into nature–whether it be hiking, swimming, horseback riding, touring the massive cave systems, biking, or otherwise exploring.

Once you’re in town, you can arrange most of your activities can be booked at the tourism offices located in the center of town. Don’t miss the $5 bus that takes you to the many tourist destinations around town, or hire a driver for $50 a day for a private tour. You can also arrange a ride-share for excursions to some of Cuba’s best attractions, including some of its most pristine beaches.

Lodging, Dining, Drinking, and Exploring the Rural Cuba–What Not to Miss in Viñales


LODGING IN VINALES—Nearly every home in Viñales is a casa particular, so there’s no shortage of places to stay. The small town is definitely a tourist favorite though, so rooms fill up fast. (Again, lodging is included and taken care of when booking with Bridges Cuba, so best to let Brian and his team figure it out.) In Viñales, expect simple but comfortable accommodations; casas that serve food are less frequent here, but no matter, because there’s so many places to eat and drink in town.


DINING AND DRINKING IN VINALES—Viñales’ main street, Salvador Cisneros, is lined with restaurants, casa particulars and boutiques. All of the restaurants we tried were on par with each other–though a few stood out with great views, great service, or just the fact that they had pizza. First, if you’re looking for breakfast, lunch, dinner, or a drink at 4 a.m., check out 3J Bar de Tapas. Virtually everyone there is a tourist, speaks english, and is armed with a Lonely Planet book–but we welcomed the change, and seized the opportunity to chat with other travelers. (Another plus is that they play cheesy/generic American music in the evenings!) Right across the street, El Barrio is another great spot–partially because of its terrace, mostly because it serves pizza. After a week of rice and beans, sometimes the comfort of home is nice. Not quite on the main strip, Casa de Don Tomas is also an absolute gem, with patios that overlook the mountains and the buildings below it. Outside of town, a worthy pursuit is Finca Agrocologica El Paraiso, an organic farm-t0-table restaurant where the food is grown just steps from the table. Meals are served buffet-style, and can accommodate any diet. The highlight is getting a tour of the beautiful gardens and farm, where workers explain the work that goes into the operation.


EXPLORING THE CUBAN COUNTRYSIDE—There’s a tour bus that makes an hour long circuit throughout Viñales, dropping tourists and travelers at the town’s most popular destinations. A ticket for $5 lasts all day, and you can hop on and off the double-decker busses as you please. For the best view of the region, make sure to get off the bus at Hotel los Jazmines, where a short stroll will take you up a hill and to a stunning overlook. (If you wish to visit the hotel, admission to the pool at the hotel is $7 and includes a drink.) Other drop-off points include the Cueva del Indio, where you can ride a boat through a massive cave system; or Palenque de los Cimerrones, a restaurant and disco inside a cave. The most popular tourist activity here by far are the horseback excursions though the countryside, where you’ll visit tobacco fields, meet farmers, take a dip in a swimming hole, and eat at a farm-to-table restaurant. (Unfortunately we visited during a tropical storm, and the tours weren’t available.) Finally, right in town, make some time at the beginning or end of the day at the Jardin Botanico de Viñales for a short guided tour with some fun surprises–including tiny pineapples, cocoa seeds, and a Hutia–Cuba’s native giant rodent that nests in the treetops.

Third Stop: The Eco-Village of Las Terrazas

Located just 45 minutes from Havana, Las Terrazas is a beautiful eco-village in one of Cuba’s many nature reserves. This mountain community of artists and organic farmers is easily accessed through public transportation, with bus tickets running about $20 per person to get there. It’s about halfway between Havana and Viñales. The region is home to the earliest surviving coffee plantations in Cuba–many of which you can visit in all their crumbling glory. The real draw here is the scenery though, which you can take in from Cuba’s only canopy tour, hiking, swimming, or just walking around town. Speaking of town, the apartments and buildings here are all white-washed, creating a unique and beautiful landscape from any vantage point.

Lodging, Dining, Drinking, and Exploring an Eco-Village–What Not to Miss in Las Terrazas


LODGING IN LAS TERRAZAS—Again, casa particulars are by far the most popular lodging experience in Las Terrazas. The bus will drop you off outside of town, so be prepared for a $2 cab ride though the hills to your casa. A unique alternative to staying in a casa is the Hotel Moka, which is Cuba’s only eco-hotel, and the only hotel we stayed in during our weeklong adventure. Located at the top of town, it’s surrounded by lush greens and palm trees, giving visitors the sensation that the entire place is a treehouse. (The trees growing though the lobby and though the hallways add to that!) It’s much pricier than a casa–expect to pay about 4x what you’re used to for a room in Cuba–but we indulged for a night. Breakfast and unparalleled views are included. If you’re really up for adventure, check out Moka’s creek-side rustic cabins at the Baños del San Juan.


DINING AND DRINKING IN LAS TERRAZAS—It’s a tiny town, so there aren’t too many dining and drinking options in Las Terrazas. Luckily, the options are almost all fantastic, so you can’t really go wrong! If you take the bus, it’s hard to miss Rancho Curujey, right at the bus stop. The ranchón-style restaurant overlooks a lake, and serves snacks and drinks. In town, a dinner at El Romiro is a must, and was the best meal of our trip. Its progressive vegetarian and vegan menu is absolutely incredible; the eco-restaurant is powered with solar energy, and uses organic vegetables and herbs for its plates. Another memorable experience is at the Patio de Maria, a cute coffee bar serving up some of Cuba’s best brews, with a view to die for. Last, whether you’re staying at the hotel or a casa particular, have a drink at the bar at Hotel Moka in the evening, where there’s likely to be a band or some kind of entertainment.


WHAT TO DO IN LAS TERRAZAS—There’s no shortage of stuff to do this this tiny town, much of it eco-based. Virtually any walk feels like a hike through Las Terrazas’ hilly, winding roads. Take some time to walk around town, stopping into the many artist studios, shops, and its eco-museum. Or, take it in from the air–Las Terrazas is home to Cuba’s only canopy tour, which you can book through Hotel Moka. The most popular activity in the ares is probably a visit to the idyllic natural swimming pools at the Baños del San Juan, though it doesn’t feel overcrowded at all! Make an afternoon of it, using the handful of picnic tables and grills, or have lunch at the riverside restaurant. Last, a visit to the ruins of the many historic French-Haitian coffee plantations are a must. We visited two: the Hacienda Union, which has a spectacular trail and garden around its ruins; and the Cafetal Buenavista, spectacularly located on the crest of a mountain. The ruins at the latter include a partially restored tajona–the massive grindstones that extract coffee beans from their shells–and the foundations of the platforms that were used to dry the beans, as well as crumbling slave quarters. Both plantations are beautiful, and have restaurants for a quick snack or meal.

In Closing… The Time to Visit Cuba is Now


As relations continue to thaw between the United States and Cuba, American tourism will become easier and easier to facilitate–for better or worse. Though we can’t really be certain when it will happen, or what happens when it does, the consensus is that Cuba is likely to change, quickly. The iconic, classic cars will slowly be replaced with new ones; its crumbling buildings will be purchased by American developers hoping to cash in on the influx of tourism. Not that these are all bad things–we certainly want the quality of life to improve for our Cuban friends! But there’s something magical and nostalgic about the current state of Cuba, and like many good things, that will probably soon change. So if you’ve been considering it, the time to visit Cuba is now–and we hope we’ve inspired you to do so!

This post was created in Collaboration with Bridges Cuba. All views and recommendations are our own.