Cuba

Cuba's accommodation landscape is unlike anywhere else in the Caribbean. The most authentic and affordable option is the casa particular, a licensed private homestay where Cuban families rent out rooms in their homes. In Havana, a clean, well-located casa in Centro Habana or Habana Vieja runs $25 to $60 a night for a private room with air conditioning and breakfast, and your host becomes your personal concierge, arranging taxis, restaurant reservations, and local tips.

For luxury, Havana has improved considerably: the Gran Hotel Manzana Kempinski on Parque Central was Cuba's first true five-star property, with rooftop pool views over the Capitol Building and rates from $300 to $600. The Hotel Nacional de Cuba, perched on a bluff above the Malecón, offers faded glamour and history - Winston Churchill, Frank Sinatra, and Nat King Cole all stayed here - at $150 to $250 a night.

In Trinidad, casas particulares are plentiful and excellent, often in restored colonial houses with rooftop terraces overlooking the Escambray Mountains for $30 to $50. Viñales has its own style of casa, often on the edge of the valley with views of the mogotes, from $20 to $40. In Varadero, all-inclusive resorts line the peninsula with rates from $100 to $300 for international-standard properties run by Meliá and Iberostar. Budget travelers can manage on $40 a day using casas, eating at private restaurants, and traveling by Viazul bus. Mid-range travelers spending $100 to $150 a day will eat well at top paladares and stay in the best casas or modest hotels.

Cuban food has undergone a quiet revolution. The old joke about bad Cuban restaurants no longer holds, especially in Havana and Trinidad where privately owned paladares have transformed the dining scene. In Havana, La Guarida remains the most famous paladar - set in a crumbling Centro Habana tenement that appeared in the film Fresa y Chocolate, with a rooftop bar and creative Cuban cuisine running $15 to $30 per main course. For something less touristy, Donya Eutimia on Plaza de la Catedral serves what many consider the best ropa vieja in Havana - slow-braised shredded beef in tomato sofrito - for under $10. San Cristóbal, the paladar where Obama famously dined in 2016, packs every inch with vintage memorabilia and serves generous portions of grilled lobster and lamb.

Street food is where Cuba shines on a budget: peso pizza (a thin, cheesy flatbread sold from walk-up windows for the equivalent of a few cents), croquetas, and pan con lechon are everywhere. In Trinidad, the best meal might be at Sol Ananda, where a young chef serves inventive plates on a rooftop overlooking the colonial center, or at the open-air tables along Plaza Mayor where grilled lobster tails cost $8 to $12.

Cuban coffee is strong, sweet, and served in thimble-sized cups - order a cafecito at any street window. Rum is the national drink: Havana Club 7 Años for sipping, Havana Club 3 Años for mojitos. Do not leave without trying a proper daiquiri at El Floridita, Hemingway's old haunt, though be warned the prices there are aimed at tourists.

Cuba's dry season from December through May offers the most comfortable travel conditions, with temperatures in the mid-70s to low 80s Fahrenheit and low humidity. January and February are the coolest months and coincide with peak tourist season, meaning higher casa particular prices and crowded attractions in Havana and Trinidad.

The sweet spot is March and April, when weather remains excellent but crowds thin. Hurricane season runs June through November, with September and October carrying the highest storm risk.

Summer months bring intense heat and humidity, particularly in Havana and Santiago, but also bring cultural festivals including Carnival in Santiago de Cuba in July, one of the Caribbean's most electric celebrations. Budget travelers will find the best deals from May through early June and again in November, when prices drop but the weather remains manageable.

Classic car taxis and Coco-taxis are available in Havana. Viazul buses connect major cities. Rental cars are limited and expensive. Domestic flights link Havana to Santiago and Varadero.