Consider your ideal Cuban itinerary. What are your primary interests? Would you prefer to go off-the-beaten-track? What kind of budget do you have? How adventurous are you and, conversely, how much of an educational component do you want? U.S. travelers should remember that for group travel, they are required by U.S. law to participate in a “people-to-people” program, which by necessity focuses on the educational aspect, even if it’s an active adventure. Your answers to these types of questions will help shape the perfect itinerary.
Touring Cuba by Region and Interests
If you’re an independent-minded traveler you can explore Cuba freely. But the island nation is enigmatic, with a complex history and culture—political, economic, and social—so traveling with a guide can help unravel much of the mystery and add to your understanding and satisfaction.
If you’re interested in art, architecture, and museums, virtually any city in the country has something to offer, but Havana is a treasure trove of possibility—give yourself a few days to explore the capital city. This article contains more details on what to see and do in Havana.
If music and dance is your thing, you’ll want to focus on either Havana, where the range of options runs the gamut from sizzling salsa clubs to jazz cafés, or Santiago de Cuba, ground zero for traditional trova and son. You'll also find musical forms reflecting a vibrant Haitian heritage. Trinidad is also a rich musical center, but almost anywhere in the country, you'll find traditional music and dance forms aplenty.
If you’re fascinated by revolutionary history and Che Guevara, your list of must-visit places should include Santa Clara and Santiago de Cuba. If you have an adventurous spirit and more time, then hiking to Fidel’s guerrilla HQ at La Comandancia de la Plata, in the Sierra Maestra Mountains of eastern Cuba, is a great add-on, as is the former Castro family estate at Birán, near Holguín.
Nature lovers are spoiled for choice, from horseback rides in rural Cuba to hikes at Las Terrazas, or in the Sierra Escambray, Pinares de Mayarí or the Sierra Maestra mountain ranges as top choices. For birding and wildlife consider visits to Parque Nacional de Guanahacabibes (in Pinar del Río province), Parque Nacional Zapata (Matanzas province), or any of the mountain zones and the coastal reserves of Ciego de Ávila and Camagüey provinces. You’d be wise to hire a local guide, especially since hawk-eyed naturalist guides increase your chances of seeing wildlife and can educate you about the ecology.
All these sights can be reached by car, but you can also join a guided tour. English is the de facto language of most tours.
Where and When to Go
Cuba’s Holy Trinity—Havana, Viñales and, Trinidad—are extremely popular destinations and can get crowded in winter months. Further afield the number of visitors thins, and it’s easy to find attractive off-the-beaten-track venues. Bear in mind that the further east you go, the higher the temperatures will be and that the summer months—the off-season—can be extremely hot and humid. Summer is also the rainy season.
Baseball fans should plan on visiting between August and April—Cuba’s baseball season: Consider joining a group tour that caters specifically to beísbol aficionados. And travelers for whom arts and musical culture are priorities should consider the timing of key events, most of which concentrate in November-January in Havana. For carnival, the best option is Santiago de Cuba in July. Here’s an article about the best times to visit Cuba.
Traveling on Your Own
If you have the budget, one of the most popular means of navigating the country on your own is by rented car. However, renting a car in Cuba is expensive, and in Havana demand often exceeds supply; advance reservations are essential. The state-run agencies are represented in every town, and in high season it may be easier to locate an available vehicle outside Havana than within it.
Roads in many places are deteriorated and there’s no shortage of hazards, such as deep potholes, ox-carts, and bicyclists on the road. But Cubans are cautious drivers, not speedsters, and the traffic police are highly efficient—it’s wise to obey all traffic regulations, especially regarding speeding. And although traffic signage has improved dramatically in recent years, many roads and junctions lack signs, so do your route research beforehand and plan your stops in advance.
Bicycling is a great way of exploring Cuba. You’ll need to bring your own sturdy mountain bike, plus all the spare parts and supplies you'll need.
Traveling between cities by public transport can be complicated. Víazul has a fleet of air-conditioned buses, for which reservations are needed. But visitors are barred from using public intra-city buses, and the rudimentary rail system serves only the provincial capitals on an infrequent basis. The alternatives are camiones (old trucks) or hitch-hiking. This article has additional information about travel options.
Almost everywhere you go you’ll find casas particulares (private B&Bs) and even in high season a room can be found; owners of B&Bs will call around on your behalf if needed.
Hiring Local Guides and Chauffeurs
The Cuban government has recently relaxed its monopolistic control of tour services and it’s now possible to find all manner of private local guides. Many of the best are English-speaking graduates of the state’s tourism schools and have learned the ropes as guides for the efficient state tour companies. Others are untrained freelancers of variable quality and trustworthiness; fluency in English is a positive indicator.
If you have a particular interest in, say in architecture, photography, or music, it pays dividends to hire a local with relevant expertise. They can take you to little-known gems, such as nightspots, known only to locals. Almost every town also has licensed horse-drawn carriages whose drivers can share an intimate knowledge of local sights.
Most national parks and reserves require that you be accompanied by an accredited guide. Elsewhere, if hiking off-the-beaten-path, it’s advisable to seek a local guide who comes recommended or one that you sense is knowledgeable about the area.
Taxi drivers can be hired for long rides, but the yellow state-owned vehicles are expensive. Far cheaper is to hire a classic American car with chofer (driver)—often they’re very knowledgeable.
Joining a Guided Tour
If you want to gain a broad (or special-interest) understanding of Cuba, then you’ll probably need to join an organized guided tour. Cuba’s state-run tour agencies offer day-long and multi-day excursions, with trained English-speaking guides to impart knowledge. Popular excursions from Havana visit tobacco country, Matanzas, Cienfuegos, and Trinidad.
Many U.S. companies also offer educational programs of every stripe. These include bicycling, kayaking and even motorcycling trips, to in-depth cultural excursions, plus those that cater to specific interests. Titled “people-to-people” trips, they all involve relevant cultural interactions with Cubans and may even include a non-Cuban expert about the island nation to help broaden your understanding. See this article for more information about legal travel for U.S. travelers.
There are more specialized tours as well. These include culinary study tours, LGBT tours, Jewish heritage tours, and more. You can cruise around the island on a luxury yacht or take photography tours with National Geographic photographers that visit more remote parts of Cuba. Plus you can go bone-fishing or scuba diving in the little-visited Jardines de la Reina, boasting one of the world’s most pristine coral reef systems.
These tours can be a great way to meet like-minded people, and there’s something for every budget, from penny-pinchers to luxury travelers.