Cuba Libre: Travel Tips for Outdoor Adventurers in the Land of Classic Cars, Cigars and Rock Climbing

Last updated June 6, 2019

To answer that burning question-- Yes, yes, YES you can still travel to Cuba as an American. President Trump's recent announcement in June about banning travel to Cuba is affecting those who are traveling under the people-to-people educational travel. This in turn affects both tour operators and cruise ships. The way in which we traveled, '“support for the Cuban people”, is not affected.

Based on the latest Treasury update here's the big changes:

  • Group people-to-people educational travel is no longer allowed. If you have already purchased your flight or booked your accommodation in Cuba prior to June 5, 2019, you are grandfathered in. This means President Trump does not want you to book your own accommodations via hotels, AirBnB, or a similar service, and wander about the country or lie on the beach all day. See our 'Tour Operators' section below for recommendations on approved Cuban tour operators that are doing their best at giving you an authentic experience.

  • Limited flights. Several airlines- Alaska Airlines, Southwest, American, Jet Blue and Delta still continue to operate, however they have limited both the number of flights and cities served. See our 'Getting There' section below for more info and links to all carriers flying to Cuba.

  • The time you can spend 'recreating' in Cuba may be limited. I'm not even going to address this ridiculousness.

  • Do your homework. It's hard to predict what President Trump and his advisors have planned. Do your homework by reading the links in our 'Resources' section. We've included the latest updates from the U.S Embassy and the Department of Treasury.

So, if you're still intrigued by this beautiful Caribbean country, read on to learn how we had the adventure of a lifetime! 

grab your adventure-loving friends

Cruising down the freeway with my fedora gently perched on top of my head. The Orishas, a Cuban hip-hop group, filling the air with music. Surrounded by my adventure-loving friends.

However, instead of sitting in a 1952 Ford Fairlane on the streets of Old Havana, I'm straddling my backpack, crammed in the backseat of a Dodge Charger, and flying across the Everglades towards Fort Lauderdale. Rule number one: Arrive early for international flights. Especially flights to Cuba. 

Somewhere over the state of Texas, 30,000 feet up, I decided a blog post about our journey was in order. No, is was not due to the frantic race to the airport this afternoon. Not because of a flight change and a missed connection that left us separated from the rest of our fellow travelers.

It was because I knew that these moments are precious. With jobs, kids and all the other things that keep us busy, it's not very often that we can rally our best outdoor adventure buddies for the trip of a lifetime. These travels also yield some of the greatest memories, and fill our late nights with tales of well-laid plans gone awry.

A 1950's Chevy Bel Air is your typical taxi in Havana.

A 1950's Chevy Bel Air is your typical taxi in Havana.

romanticizing cuba

With warm Caribbean breezes, charming, brightly-colored casitas, salsa dancing and classic cars from the 1940s rumbling through cobblestoned colonial plazas, I was eager to visit this exotic paradise.

Throw in the chance to wander through old hotels built by mobster Meyer Lansky, or pull up a bar stool at a swanky locale where Hemingway wrote his Noble Prize-winning works, and I was more than ready to hop a flight to Cuba.

What made me finally click 'add to cart' was when I discovered Cuba also has a thriving rock climbing community. In fact, just two hours west of Havana lies a lush, tropical rainforest with some of the best limestone cliffs and overhanging crags in all of the Caribbean.

I began emailing with Armando Menocal, co-author of the Cuba Climbing guidebook, and the man that helped put Cuba on the map for rock climbing.

Hiking through Raul's Farm to Mogote del Valle, one of several rock climbing areas in Cuba.

Hiking through Raul's Farm to Mogote del Valle, one of several rock climbing areas in Cuba.

A few months after booking our tickets, on our way to the airport, disaster stuck. A sequence of events unfolded leaving me in the back of this Dodge Charger, halfway between Tampa and Fort Lauderdale, Florida. 

In order to make your trip to Cuba less, um, eventful, here are some tips:

Getting there

  • Air travel. Southwest Airlines, Alaska Airlines, American Airlines, Jet Blue and Delta are all offering flights to Cuba. Most fly through Tampa or Fort Lauderdale, and then onto José Martí International Airport in Havana. There are also smaller airports in Cuba, such as Varadero and Santa Clara, however, most airlines from the U.S. fly into Havana.

  • Booking your tickets. We booked with Southwest Airlines, and we were able to use points! We did however have to book round-trip tickets to Florida, then separate round-trip tickets to Havana.

  • Fly non-stop. There’s direct flights to Havana from LAX with Alaska, from New York (JFK) to Havana on Delta or Jet Blue. If you are flying from the West Coast, I recommend Alaska Airlines. From the New York area? Go with Delta or Jet Blue. Especially after the ordeal we had connecting in Florida. Alaska Airlines is also the only carrier with daily non-stop flights from LAX to Havana.

My fearless travel companion and I finally en route to Havana.

My fearless travel companion and I finally en route to Havana.

Tips for Check-in and Packing

  • Ensure you arrive at least 2 hours before your departure time. It doesn't matter if you are an A-list member or a Platinum Superstar team member. Also, do not expect to use the kiosks to check-in, and forget about checking in online. You will most likely need to go to a special counter for Cuba flights once you arrive at the airport. In our case, this counter closed 60 minutes prior to departure. Again, just get there early.

  • Be prepared to pay $50-$85 per person for your visa. Your visa, along with all travel documents needed for Cuba, can be acquired at the airport counter or in advance through your airline. Have your passport ready, and be prepared to provide your reason for travel to Cuba. As we were donating rock climbing gear, we selected #8, support for the Cuban people.

  • Pack light. This is the Caribbean after all. You will not need more than a light sweater or rain jacket, even if you plan to head to the mountains in winter. There's also no need for dressy clothes. Even in the fancy hotels, like Hotel Inglaterra, or popular restaurants, like Floridita, shorts and flip-flops are the norm.

  • Do not bring a drone. Do not bring walkie-talkies. Yes, my outdoor adventure-loving friends were traveling with both. There's actually a lot of items that are prohibited or considered weapons, like that large statue of Jesus you have in your carry-on bag. Best to leave the fancy equipment and religious saints at home anyways.

Pack light and use the wi-fi parks to connect to the internet in Cuba.

Pack light and use the wi-fi parks to connect to the internet in Cuba.

WI-FI and phone service

  • International service. One of our travelers was excited to have CubaCel service when we landed, but two days into our trip, he received a call from AT&T that his roaming charges were nearing $700! Even if you have an international plan for your mobile phone, you will still incur roaming charges, as the U.S. carriers do not cover Cuba. If you really need to make phone calls and have data access, there are better options. The best bet is to leave your phone in airplane mode, or turn off cellular data to restrict all data to wi-fi, including email, iMessages, web browsing and push notifications.

  • Wi-Fi parks. As your taxi brings you into town, you will notice lots of local Cubans sitting in parks on their cell phones. This is because there is no internet access at home. Cuba's national telcom company, ETECSA, instead provides internet access in most major hotels and in wi-fi hotspots across the country. To log on, first purchase a wi-fi card, basically a piece of paper with a username and password on it, from a local bodega. The cost is $2 CUC per hour. In most parks, the wi-fi name will be 'ETECSA'. Click on it to access the login screen where you will enter your username and password. Keep in mind, most of your apps will not work the way they do in the U.S. Do not expect to be booking an Uber ride anytime soon.


  • No rental car needed. We were able to arrange transportation into Havana easily with one of the many taxis parked outside of José Martí International Airport. We were also able to book transportation through our hosts at our accommodations, as well as from a transportation center in the small town of Viñales. Even with five people and large backpacks filled with rock climbing gear, we always found it easy to coordinate a ride to the next town.

  • Sweatin' to the oldies. Do not expect air-conditioning in your 1952 Buick Roadmaster or your 1958 Chevy Bel-Air. Open the windows and enjoy the sea breeze. However, if air-conditioning is a must, Cuba does have many newer cars and shuttle vans with AC available upon request.

Leticia, our hostess with the mostess, and I at Casa Baralt in the Vedado district, Havana.

Leticia, our hostess with the mostess, and I at Casa Baralt in the Vedado district, Havana.


  • Casa Particulares. Cubans are becoming more entrepreneurial and are using their homes to host visitors. These are known as casa particulares and we booked in advance through AirBnB. You can book exactly like you would when traveling anywhere else. Features like Instant Booking and Superhosts are available, and we poured through reviews before selecting our homes in three different cities. Ensure you have met all the requirements for traveling to Cuba before finalizing your accommodations on your own.

  • Eat at home. Most hosts can arrange for you to have meals at the house. I highly recommend organizing this in advance. Who doesn't want a personal chef preparing your breakfast, lunch and dinner? This is also important as there are no large grocery stores in Cuba. Cubans still have the Libreta, a socialist food ration system, in place. The markets will have dry goods, and some may sell chicken or pork when available, however, it was hard to find dairy products, fresh fruits or vegetables. As a bonus, the food served at your casa particulares far exceeds what you will find at a government-run restaurant. In addition, you will get to practice your Spanish, and you can often have your host arrange transportation or book activities for you during each meal.

  • Make reservations before leaving the U.S. You may not be able to book using the AirBnB app while in Cuba. We had trouble with this, and had to message a friend in the U.S. to book our last two nights for us. Most of your phone apps will not work as they do in the U.S., even when connected to wifi. With the recent change in travel restrictions, you may need to book through a tour operator, who will take care of this for you.

  • Reserve a hotel online, pay cash upon arrival. In addition to casa particulares, there are plenty of hotels in Havana, Varadero or Trinidad, and many of these can be reserved in advance as well. However, just like in the U.S., you reserve a hotel online, and pay when you arrive. Bring extra cash if you plan to do this, or check with your tour operator before making any reservations.

Lunch at Raul's Farm in Viñales, Cuba.

Lunch at Raul's Farm in Viñales, Cuba.

Rock climbing in Cuba

The rock climbing in Cuba is on beautiful, yet jagged formations of limestone, found mostly around agricultural farms in the Viñales Valley. The Valley is a UNESCO World Heritage site, and the geology in this part of the country, known as a karst landscape, is fascinating. You will find everything from hidden caverns with stalactites, to giant tufas and jungle-covered mogotes. The routes are well-bolted, and therefore a 60-meter rope, slings and a dozen quickdraws will do. A trad rack is definitely not necessary. Helmet, headlamps, sunscreen and mosquito repellant are essential.

Plan on a 2-3 hour taxi ride to reach the town of Viñales, located in the Western part of Cuba. We had arranged accommodations beforehand, and I highly recommend reading though Armando Menocal's suggestions on finding casa particulares in the area.

Once settled into your accommodation, you can strap on your packs and enjoy a nice stroll through town. We picked up water for our Camelbaks at the grocery store before heading out to Raul's Farm. Plan on a 20-40 minute easy walk along dirt roads, depending on where your accommodations are in town, to reach the farm. Taxi's can always be arranged as well.

The Cuba Climbing Guidebook gives you all the climbing beta for the area, along with plenty of maps to make your way around. Raul and his staff that run the farm were incredibly accommodating, offering us snacks on the way to out to climb, and cervezas on the way back! Bring small bills to ensure you can buy your crew piña coladas to celebrate the day, then lie back in one of Raul's hammocks to catch sunset over the Valley.

Sport climbing in Cueva Larga, in Mogote del Valle area of Cuba.

Sport climbing in Cueva Larga, in Mogote del Valle area of Cuba.


  • Cash is king. American credit cards and debit cards will not work in Cuba. Even if you did have a credit card set up in Mexico or Canada, good luck trying to find some place to use it. Plan in advance how much money you will need for each day, based on your activities. We budgeted $100 per person per day, which was much more than we needed. Prices are much lower in Cuba than in the U.S., especially if you eat most of your meals at your accommodations, or outside of the major tourist areas.

  • The Convertible Cuban Peso (CUC) is 1:1 with the American dollar, however, the service charge for exchanging American dollars is almost 13%. We changed our cash at the airport in Havana when we incurred this service charge. Since Cuban pesos are not traded internationally, you cannot buy them outside of Cuba. You can also exchange money at your hotel, a CADECA or Casa de Cambio in major cities. We had recently returned from Baja, so we also had several hundred dollars in Mexican pesos with us. These were exchanged at a much lower rate. Keep in mind, you are prohibited from bringing Cuba pesos outside of Cuba. Definitely buy your last souvenirs and exchange your pesos for dollars before you fly out.

Dinner at Juany and Daniels, our  casa particulares  in Viñales, Cuba.

Dinner at Juany and Daniels, our casa particulares in Viñales, Cuba.

  • Meals are inexpensive. We spent $5 CUC per person on breakfast at our accommodations, and this included fresh bread, coffee, eggs, ham, cheese and a freshly squeezed juice or smoothie. Better than I would get at home! Dinner was $10-15 CUC and often included chicken or fish, vegetables, rice and dessert!

  • Dine out at a paladares. Privately-run restaurants are becoming more popular in Cuba, and will serve you much more than the meat, rice and beans you may find at a government-run establishment. Once again, the entrepreneurial spirit shines through. We had some of the best meals at local, family-owned paladares throughout Cuba. The pollo frito or fried chicken at one spot was the best I've ever eaten. In addition, $15 CUC often bought a lobster tail dinner, which rivaled the Puerto Nuevo-style lobster we are used to on the West Coast!

  • Have a piña colada...and a daiquiri! There is nothing better on a hot day than to return from your hike and have an ice cold piña colada waiting for you. After a day of rock climbing, we often enjoyed one or two Cristals or Bucaneros, the local cervezas, at Raul's farm. He also whipped up some of the tastiest piña coladas we've ever had. I'm not sure what type of blender Cubans use, but the blended cocktails and juices are fantasticó! Cuba is also home of the Daiquiri, and rumors are that Hemmingway helped perfect this concoction at his favorite watering hole, La Floridita.

  • Bring home a Cuban cigar. We saved the best for last, and we can report that yes, you can bring that Cohiba back from Cuba! Cuban cigars are inexpensive and easily found throughout Cuba. Raul, the local farmer who provided meals as well as access to the best climbing in Cuba, hand-rolled his own and sold them, 2 for $1 CUC. Quite the bargain. As of now, you can bring home up to 100 cigars and several bottles of rum on your trip back to the U.S. A quick tip: Cuban cigars help keep the mosquitos at bay in the warm, rainy season. We would light several at our climbing base camp, or while hiking through the jungle!

Cuba is the home of the Daiquiri, and la Floridita is one of the best places to enjoy it!

Cuba is the home of the Daiquiri, and la Floridita is one of the best places to enjoy it!

 I could keep going on about all the amazing sites, tastes, sounds and farm animals we met along the way. We felt very welcome wherever we went, and even while snorkeling at the local Cuban beaches outside of Havana, Playas del Este, we were impressed.

Below are more resources to help you make your decision:



Tour Operators

We hope President Trump's plans to roll back Obama era policies do not keep our fellow outdoor adventurers from adding Cuba to their bucket list. The people, their culture, the rock climbing, scuba diving and those thirst-quenching piña coladas definitely make Cuba our favorite place in the Caribbean.

For more photos and fun facts about our outdoor adventures, check out Top Rope Media's Facebook and Instagram pages. Or drop a comment and we'll be happy to answer any questions! 

¡Hasta luego!

Meredith McConvill