Make Your Next Trip Extraordinary
Seeing Cuba Legally and Privately: An Insider’s Guide
Use the tips below to make the most of your time in Cuba's capital of Havana, and beyond. Photo: Terraversed
The insider advice on this page is from Wendy’s Trusted Travel Expert for Cuba: Rob Fielding of Inbound Cuba.
Rob and his wife Ana, who grew up in Cuba, have connections there that translate into the ultimate experience of the island, from chefs and muralists to former journalists and museum curators, all of whom share their perspectives on Cuba’s past, present, and future. Legally speaking, such interactions qualify Rob’s itineraries under the “Support for the Cuban People” category of authorized travel. Rob favors privately owned casas particulares (B&B-style accommodations, often in renovated colonial homes) and paladares (family-run restaurants) whenever possible—thus putting travel dollars directly into locals’ pockets.
What to See and Do
The Viñales Valley is a UNESCO World Heritage site. Photo: Terraversed
Don’t miss
A behind-the-scenes visit to the Habana Compas dance troupe. You’ll be invited into their rehearsal space, where dancers and percussionists will both perform for you and explain the ideas behind their steps and rhythms, which mix together traditions from Africa and Latin America. Travelers have literally been brought to tears by the raw emotion that the artists exude.
Rob can get you this close to the Habana Compas dance troupe. Photo: Terraversed
Most Underrated Place
The Topes de Collantes nature reserve, near Trinidad, makes for an ideal day trip to see rural life in Cuba and experience a near-pristine natural environment. (It also has its own microclimate that usually makes it a refreshing 15 degrees cooler than Trinidad.) The coffee grown here is some of the most expensive in the world, but it’s not imported to the U.S. Rob can plan meetings with coffee growers, hikes with local nature experts, and visits to hidden artists’ alcoves.
Spend a day in the cooler mountain air of Topes de Collantes. Photo: Terraversed
Most Overrated Place
Varadero Beach may be Cuba’s most famous beach, but it’s actually very narrow and no more impressive than, say, Clearwater Beach in Florida.
Hidden Gem
Going to a ballet performance on a Saturday or Sunday afternoon. The Cuban National Ballet is world-renowned, but it’s particularly fun to attend a weekend show by a smaller company alongside lots of local families; many of them struggle to put food on the table but will spend a few pesos to expose their kids to this part of Cuba’s culture. It’s indicative of the importance of art and music in Cuban society, and the joy people there derive from it.
Cuba produces some of the world’s best ballet dancers. Photo: Terraversed
Don’t bother
The Tropicana club and cabaret is very touristy. If you want a high-production, Las Vegas-style show, this is the place. But if you’re looking for something more authentic, Rob can show you where the locals go for live music, like Casa de la Música in Trinidad (see “Cheap thrill,” below).
Cheap Thrill
An evening at Trinidad’s outdoor Casa de la Música, where you can hear multiple bands, watch dancers perform, and mingle with locals. The entrance fee is $10. Drinks are additional, but it’s just $5 for a delicious mojito.
Music is an integral part of Cuba’s culture. Photo: Terraversed
Bragging rights
Rob includes time with local luminaries on every itinerary. Depending on your interests, he can take you to the home of acclaimed guitarist Luis Molina, who will play for you while his wife sings. Or you can meet artist Máisel López, whose murals are all over Havana (and beyond). Perhaps you want to have dinner with a Cuban journalist, or meet a chef or farmer to learn about Cuba’s food traditions. Rob can make all of this happen, and more.
Farmers working on a tobacco field. Photo: Terraversed
Where to Stay and Eat
Best bang-for-your-buck hotels
La Reserva. Two former mansions have been converted into 11 guest rooms at this boutique B&B in Havana’s Vedado neighborhood, where much of the city’s best restaurants and entertainment venues are located, and a short drive from Old Havana. The onsite restaurant puts out some of the city’s most delicious meals, and the suites go for less than $300 per night.
A deluxe suite at La Reserva. Photo: La Reserva Vedado
In Trinidad, La Casona is a small property with casitas, an organic garden, horse stables, and wonderful views of the Valle de los Ingenios. It feels like an eco-lodge, but you’re just a five-minute walk from the city center. The suites and junior suites have huge, walk-in showers.
Best-value splurge hotel
Of the properties available to U.S. travelers, Rob has found that the INNSiDE Catedral, in Old Havana, delivers the highest quality experience. Their Town House Suite is a tremendous value for its size, and for the views out to Morro Castle.
Restaurant the locals love
5 Sentidos, in the heart of Old Havana, puts out consistently excellent Cuban dishes with European refinement that would earn praise anywhere in the world. (And since it’s got really good air-conditioning, Rob likes to send people here to cool off over lunch, ideally with one of their to-die-for piña coladas.)
5 Sentidos is one of the best restaurants in Old Havana. Photo: Terraversed
Dish to try
Ropa vieja de cordero is a slow-cooked lamb dish that is out of this world. Think of the best beef stew you’ve ever tasted, with a twist of Cuban seasoning: usually cumin, oregano, garlic, onion, bay leaf, but no hot peppers. Rob likes to order this at 5 Sentidos.
Preparing ajiaco, a Cuban stew. Photo: Terraversed
Meal worth the splurge
La Guarida is a Havana icon for good reason. The setting may outshine the sometimes overly ambitious food, but no one regrets an evening spent at one of their rooftop tables in the middle of Centro Habana, taking in the sights of classic cars driving by alongside a soundtrack of live jazz.
Enjoy a rooftop perch for your meal at La Guarida. Photo: Terraversed
Prime Picnic Spot
About an hour outside Havana is a UNESCO World Biosphere known as Las Terrazas, where Cubans love to go for weekend picnics and a swim in a beautiful river. To comply with U.S. requirements, make a day of it interacting with locals in the small village, which has a bohemian feel: You can meet an artist who paints on the bark of trees, and taste locally grown coffee in someone’s home.
Get a Personalized Trip Recommendation
For a travel solution tailored to your trip goals and preferences, click this green box.
Best Times to Go
Weather-wise, it’s most pleasant to visit Cuba from November through May; February and March bring the best weather but are also the busiest months.
Worst Time to Go
Mid-July through September are too hot, many places are closed, and it’s the peak of hurricane season.
Biggest Rookie Mistake
Not preparing for the amount of touring required of U.S. travelers visiting Cuba legally. Every day of your itinerary must include interactions with locals, and so you can’t spend part of your trip simply lazing at the beach.
Can't-Miss Photo Op
You and your travel companions with a classic car in front of Havana’s Morro Castle. Rob can arrange for a professional photographer to capture this quintessential shot.
Scam to Avoid
Most of the paintings for sale at Almacenes San José, Cuba’s largest art market, are not originals. You can get reproductions here quite affordably, but if you want an original, have Rob connect you directly with an artist. (Many already have mechanisms in place so that they can export their work to the U.S.)
Must-have App
It’s very expensive to use a U.S. cell phone in Cuba. Download WhatsApp before you go, and use it only when on WiFi.
Tipping Tip
Cuba is very much a tipping society; keep small U.S. bills on hand to tip those who do a good job. 10% is appropriate for services, restaurants, and bars.
Don’t Forget to Pack
Any medication you may need. Getting even a simple painkiller like Tylenol is impossible.
Our Latest Newsletters
