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🇨🇺From Havana's vintage cars to the cobblestone streets of Trinidad - the essential sights, and how to keep your own record of them.
Travel guide - last updated September 2026
Cuba runs on its own logic - decades of trade restrictions preserved a streetscape of 1950s American cars and crumbling colonial architecture that feels genuinely frozen in time, not staged for visitors. Havana anchors most trips, with Trinidad's even better-preserved colonial center and Varadero's beaches as the two most common additions. Here are 8 places worth building a trip around.
The sights most first-time visitors build an itinerary around.
Old Havana's colonial architecture is a UNESCO World Heritage site, and the city's fleet of pre-1960s American cars, kept running for decades out of necessity, is now as much a photographed attraction as any building.
📍 Havana
🚉 Havana has no metro: Viazul coaches link the cities for visitors, city buses run for pesos, and the classic American cars work as shared taxis on fixed routes along the main avenues.
Plaza Vieja is one of Havana's four main colonial squares, restored with cafes and galleries; the Malecón is the 8km seafront promenade where much of the city gathers at sunset.
📍 Havana
🚉 Both are in Habana Vieja, walkable from each other - the hop-on bus T1 runs along the Malecon, and coco-taxis and almendron shared cars cover longer stretches of the seafront.
A UNESCO-listed colonial town with cobblestone streets and pastel houses, largely unchanged since the 18th-19th century sugar trade that built it - widely considered Cuba's best-preserved colonial center.
📍 Trinidad
🚉 Viazul coaches from Havana take about six hours, and from Cienfuegos an hour and a half; the cobbled centre is walking-only, and horse carts run out to the Valle de los Ingenios.
Cuba's main beach resort area, on a narrow peninsula with some of the clearest water in the Caribbean - a common add-on for travelers wanting beach time alongside Havana's city sightseeing.
📍 Varadero
🚉 Viazul coaches run from Havana in three hours, and Juan Gualberto Gomez airport is 20 minutes from the resort strip - the peninsula's single road is served by a hop-on bus.
Cuba's music culture runs through casas de la trova (music houses) in nearly every town - Santiago de Cuba, in the east, is often considered the birthplace of son, the genre that later evolved into salsa.
📍 Santiago de Cuba
🚉 The Havana venues cluster in Vedado and Centro Habana - the Casa de la Musica, the Fabrica de Arte and the Buena Vista clubs are all short shared-taxi rides from the Malecon.
A tobacco-growing valley in western Cuba, with distinctive limestone hills (mogotes) and working farms where cigars are still hand-rolled using traditional methods.
📍 Viñales, Pinar del Río
🚉 Viazul coaches from Havana take three and a half hours to Vinales village; horses, bicycles and shared cars then cover the tobacco farms and the mogote trails.
Cuba's second city, in the east, with a strong Afro-Cuban cultural influence, the Moncada Barracks (a key site in the Cuban Revolution), and the hilltop Castillo del Morro fortress.
📍 Santiago de Cuba
🚉 The overnight train from Havana takes about 15 hours when it runs; the Viazul coach takes the same and is more reliable, and flights take 90 minutes.
A chain of small keys off Cuba's northern coast, connected to the mainland by a causeway, with quieter, more remote beaches than Varadero.
📍 Cayo Coco & Cayo Guillermo, Ciego de Ávila
🚉 The cays are reached by a 17km causeway from Moron, with Jardines del Rey airport on Cayo Coco itself - there is no public transport across, so transfers or hire cars are required.
In MyPassportStory, every country you mark - visited, lived in, or still on the list - becomes a stamp like these in your own travel passport. Add the cities you stopped in, draw the route between them, and turn the whole trip into a shareable passport-style image.
Open MyPassportStoryA week suits Havana plus Trinidad or Viñales well. Ten days lets you add Varadero or Santiago de Cuba without rushing.
November-April is the dry season and the most popular time to visit. Hurricane season runs roughly June-November, peaking August-October.
It's manageable with some preparation - internet access is limited and often requires purchased wifi cards used at public hotspots, and US citizens specifically need to travel under one of several permitted categories rather than as a standard tourist.
Most visitors need a Cuban tourist card (visa) arranged before travel, often through the airline or a travel agency rather than an embassy directly; requirements and the exact process vary by nationality and, for US citizens, by the specific authorized travel category used. Check the official visa information for your nationality: minrex.gob.cu.
Walking Old Havana's plazas and the Malecón costs nothing, paladares (private, home-run restaurants) are often cheaper and better than state-run alternatives, and staying in casas particulares (private homestays) is typically less expensive than hotels.
You can, but plan it carefully. Rental cars are state-run, limited in number and must usually be booked well in advance - turning up hoping to hire one rarely works, especially in high season. A foreign licence is accepted for visitors, and an International Driving Permit is recommended alongside it. Minimum age is 21 with a substantial cash or card deposit. Fuel shortages are common and queues can be long, road signage is poor, and driving at night is genuinely hazardous because of unlit carts and cyclists. Viazul coaches and shared taxis are what most visitors use instead. Official visitor information is published by the Ministry of Tourism at cuba.travel.