Like any intrepid traveler, you're probably keen to experience everything that Cuba is famous for: colonial history, a musical culture, tropical scenery, plus all those cigars and classic cars. Here are four sample itineraries that take the headache out of planning an unbeatable 10-day excursion, whatever your tastes. 

Overview

Stretching east-west for some 800 miles, Cuba is as long as California or Britain—and just as varied and beautiful. Whether you plan to take in the classic Havana sites, explore tobacco country, or dive the Caribbean coast, you can fit a lot into one trip if you have 10 days to spend.

#1: Hit the Hot Spots: Havana, Viñales, Bay of Pigs, Trinidad and Santa Clara

Classic car outside Gran Teatro, Habana
Classic car outside Gran Teatro, Havana

Spend your first day spent wandering Habana Vieja (Old Havana), the lived-in colonial heart of the Havana. Its cobbled plazas and narrow streets are teeming with museums, art galleries, and colorful street life. Savor a mojito or daiquiri at one of Ernest Hemingway’s favorite bars, like Bodeguita del Medio, and sample Cuban dishes at a cozy paladar (private restaurant) in the nearby area of Cinco Esquinas. On day two explore Parque Central and the Prado (formerly the Paseo de Martí), where you’ll find the Capitolio (Capital Building), Museo de la Revolución (Museum of the Revolution), Gran Teatro (Great Theater), and Museo de Bellas Artes (Fine Arts Museum).

At sunset head to the 18th-century fortress Fortaleza de San Carlos de la Cabaña for the 9 pm cañonazo (cannon-firing ceremony). On your third day rent a classic American convertible and explore the Vedado neighborhood and beyond, being sure to visit the Plaza de la Revolución, the Necropolis Cristóbal Colón cemetery, and Fusterlandia, an arts complex located in the seaside neighborhood of Jaimanitas and created by local artist José Fuster. At night, dance at one of Havana’s jazz or salsa clubs, or splurge on the ultimate cabaret—the Tropicana.

On the fourth day drive about an hour west to the mountain eco-resort Las Terrazas. Spend the day birding and hiking before continuing to the town of Viñales for two days. In the surrounding valley, you can visit a tobacco farm, ride horses, and explore some of the many famous caverns, such as the Cueva del Indio. Next is a four-hour trip southeast on the Autopista Nacional (freeway) to the Bay of Pigs (Bahía de Cochinos), site of the failed CIA-sponsored invasion by Cuban-American exiles in April 1961. There’s a superb museum here, the Museo Giron, plus gorgeous beaches, fantastic scuba diving/snorkeling, and great B&Bs and paladares.

On day eight continue east via the city of Cienfuegos (well worth a stopover) to Trinidad, the crown jewel of Cuba’s colonial cities. Spending two days here allows for excursions to the white sands of Playa Ancón, and into the Sierra Escambray Mountains for a nature trek. A full-day guided excursion by ex-Soviet army truck immerses you in the natural beauty of mist-shrouded pine forests as you hike to waterfalls, such as El Nicho. A delicious lunch of roast suckling pig is a real highlight. Back in town dance to the Afro-Cuban rhythms at the famed live-music venue Casa de la Trova. For more on travel in and around Trinidad, see this article. 

Complete the itinerary with a visit to Santa Clara, the city Che Guevara captured in December 1958, sealing the fate of the dictator Fulgencio BatistaThere's a large monument to Che here, plus a museum and his mausoleum. Wrap up your Cuban adventure by flying out of Santa Clara or returning to Havana along the Autopista Nacional.

#2: Mix City Life and Natural Wonders

Cuban crocodiles, Parque Nacional Zapata
Cuban crocodiles, Parque Nacional Zapata

Once you’ve enjoyed the capital, it’s time to head out of town. Begin by traveling about four hours to María La Gorda, situated on a lovely white-sand beach at the western tip of the island. This is a great base for snorkeling, scuba diving, and guided nature hikes into the dry forests of Parque Nacional Guanahacabibes. Two nights should suffice before doubling back about two and a half hours to Viñales, an adventure hub set amid stunning mountain and valley scenery. The village has lots of casas particulares (B&Bs), good restaurants, and a lively nightlife to enjoy.

On day seven head four hours east along the Autopista to Playa Larga, a small beach community at the head of the Bay of Pigs. Playa Larga is the gateway to Parque Nacional de Zapata. 18 of Cuba’s 25 endemic bird species are found here, including the zunzuncito, the world’s smallest bird. Local expert guides will help deepen your appreciation of local ecology, including the endemic Cuban crocodile, which is in abundance at the nearby crocodile farm. You can also spend time snorkeling, scuba diving, and even fly-fishing. Before leaving, enjoy a hearty Cuban meal while staying in a family home. It's the closest you can get to living like a local. Finish your itinerary by driving two and a half hours east to Trinidad. For more on planning your trip to Cuba, see this article.

#3: Coastal Calliope: Varadero, Cayos de Villa Clara, Playa Ancón, and Bay of Pigs

Playa Ancón, on the Caribbean coast
Playa Ancón, on the Caribbean coast

In Cuba, stunning sugar-white sands dissolve into turquoise warm waters off both the Atlantic and Caribbean coasts. First-time visitors will be richly rewarded flying into Havana and exploring the capital city before heading off to the beaches. Use the Havana portion of Itinerary #1 as your guide. Most beach destinations listed in this itinerary are linked by Víazul bus service, but for greater freedom have one of our specialists arrange a car reservation.

Whether arriving from North America or Europe, you can skip Havana if you prefer and fly into Varadero, a two-hour drive east of the capital. It's Cuba’s main coastal resort, with more than 50 hotels along the sprawling 8-mile-long, beach-fringed peninsula. Catamaran and snorkeling excursions are a nice alternative to sunbathing and swimming;  however, save your scuba diving for the south coast, which has far superior sites. On day two, depart Varadero, traveling four hours east to the city of Santa Clara, stopping to admire the Che Guevara monument, museum, and mausoleum. Then journey a half hour east to Remedios, another well preserved colonial city. Beyond this, it's a thrilling ride over a 30-mile-long pedraplén (causeway), which carries you over tropical lagoons to the coastal paradise of Cayos de Villa Clara. Allow yourself a day for bonefishing and scuba-diving, and enjoying the gorgeous beaches of this island chain.

When you’re ready to leave the sands behind, travel four hours south to Trinidad via Santa Clara and the Sierra Escambray Mountains (maybe stopping to enjoy a brief hike in the cloud forest). Spend the next day exploring this superbly-preserved colonial city and UNESCO World Heritage Site, with a second day for lazing at nearby Playa Ancón. You can rent snorkeling equipment here, and dive excursions are offered to a nearby coral reef. On your final day, head just over an hour west to Cienfuegos, pausing to admire the Palacio del Valle and lovely main square. Continue 90 minutes to Girón, known to the world as Bay of Pigs, with its superb museum dedicated to the CIA-sponsored invasion of 1961. Outside of town you'll find Playa Larga, where you can enjoy the sands and local hospitality in this charming fishing village at the edge of the Parque Nacional de Zapata.

U.S. travelers should note that U.S. law prohibits tourism per se, and especially beach vacations. In all cases, U.S. travelers are required to follow a regimen consistent with the license category under which they’re traveling, such as ‘people-to-people’ or ‘support for the Cuban people.’

#4: Oriental Delight: Santiago de Cuba, Sierra Maestra, Guantánamo, and Baracoa

Baracoa, with El Yunque behind
Baracoa, with El Yunque behind

The city of Santiago de Cuba and much of the mountainous Oriente (Eastern Cuba) region are quite distinct from Havana and Western Cuba and will entice travelers who’ve already explored the latter. 10 days spent here is 10 days spent off the main tourist trail, offering unique cultural and immersive experiences. Santiago and the city of Holguín—a four-hour drive from Santiago—are served by international flights.

Spend your first two days in Santiago de Cuba and get a feel for the vibrant street life as you wander its hilly and historic downtown. The city is crammed with sights of interest. Don’t miss Parque Céspedes, notable for the colonial cathedral and home of conquistador Diego Velásquez. There's also Cuartel Moncada, where Fidel launched the Revolution in 1953 by attacking this army barracks. San Juan Hill is a famous battle site of the Spanish-American War; plus there's Cementerio Santa Ifigenia, the sensational cemetery where Fidel and a pantheon of national heroes are buried. Further out lies the castle of El Morro, with a not-to-be-missed sunset cannon-firing ceremony nightly. Hire a local guide at each venue to provide a deeper understanding of the history. Santiago also has a rich cultural life, so don’t leave before visiting the Casa de la Trova and Tumba Francesa for an immersion in traditional music and dance.

Now you’re ready to explore into the mountains. Start by journeying an hour to Mayarí Arriba—at the end of the road in the rugged Sierra del Cristal Mountains—to visit the mausoleum and monument to the Rebel Army’s Second Front during the war to oust Batista. Enjoy lush countryside views as you travel east 90 minutes past fields of sugarcane en route to Guantánamo city, where an excursion to the Zoológico Piedra (Stone Zoo), which displays life-size animals carved of limestone, will enthrall. Guantánamo has a lovingly restored colonial center and lively cultural venues infused with Haitian and Jamaican heritage. Enjoy it to the full by staying overnight at a casa particular (private B&B).

Next day ascend the Sierra Cristal via the La Farola switchback road to arrive in Baracoa. Although lacking grandiose buildings, this ancient city—founded in 1511, it’s Cuba’s oldest—has an impressive setting. Atlantic waves crash against the seafront while rainforest-clad mountains rise on three sides. Allow yourself to slow down and go with the local rhythm. Be sure to arrange a guided excursion into Parque Nacional Alejandro Humboldt, a tremendous venue for birding. And a visit to a local cacao plantation is de rigueur—Baracoa is famous for its chocolate. Its distinct and delicious cuisine is also served at several excellent paladares (private restaurants). While many travelers stay at the hilltop El Castillo Hotel for its dramatic views, a local casa particular is a fun, family-friendly alternative.

Before heading back to Santiago, head east along the new coast road to arrive at Punta Maisí. Famous for its lighthouse, this is the eastern tip of Cuba, a 45-minute journey east of Baracoa. You can now overnight here, at a recently opened hotel, and enjoy the sunrise 40 minutes before it occurs in Havana. For options in where to stay in Havana, check out this article.