Havana is only a 45-minute flight from Miami, which makes a weekend visit easy. If you only have three days to spare, focus on quality rather than quantity with these itineraries, discovering landmark historical sites, great cuisine, and sultry nightlife in Cuba's capital.

There’s no end of possibilities for how to enjoy a 72-hour sojourn in Havana. Whether your prime interests are history, art, and architecture, or dining, cigars, and classic cars, it’s easy to combine your passions with sightseeing. In the capital, you'll find experiences that offer a vivid sense of what makes Cuba unique. Read on for five distinct itineraries that promise a great weekend in Havana.

#1 Havana Highlights

Plaza Vieja is a venue for art exhibitions

This itinerary gives you a good taste of Havana’s variety, focusing on the sightseeing, culinary, and cultural highlights while allowing enough time to let your hair down at night.

Upon arrival, head to El Aljibe for a classic Cuban lunch and, after checking into your lodging, start with a sightseeing overview by HabanaBusTour, which circles the entire city, stopping at all the highlights, such as Plaza de la Revolución, the Castillo Los Tres del Morro, and the community art project called Fusterlandia. Alternately, hire a classic convertible car and chofer (driver) to follow the same itinerary; then continue to Museo Ernest Hemingway—the former estate of the Nobel Prize-winning author. Enjoy dinner at the incomparable La Guarida.

Spend your second day walking Habana Vieja (Old Havana), the colonial quarter. Make an early start to see as much of this UNESCO World Heritage Site as possible, concentrating your time around Plaza de Armas, the Plaza de la Catedral, and Plaza Vieja, which has several good paladares (private restaurants) plus refreshing fresh-brewed suds at Fáctoria de la Plaza Vieja. In the afternoon, explore Parque Central, where the top draw is the Capitolio, the recently restored former Congress building. Now walk the sloping, tree-lined Prado (main boulevard) and take a guided tour of either the Museo de la Revolución (Museum of the Revolution) or Museo de Bellas Artes (Fine Arts Museum)—two of Cuba’s top museums. At night head to the Jazz Café to enjoy live jazz, or to the world-famous Tropicana cabaret.

In the morning, stroll the seafront Malecón boulevard and end at the 1930s-era Hotel Nacional, with time for a cigar and cocktail at the patio bar before you head back to José Martí International Airport for your departure flight.

#2 Say You Want a Revolution!

Mural of Che Guevara in Plaza de la Revolución 

Contemporary Cuba has been inextricably shaped by the Revolution. This doesn’t simply mean the 1959 toppling of dictator-president Fulgencio Batista, but the ongoing building of a new society. Whatever your politics, a pilgrimage of the revolutionary trail in Havana makes for a fascinating historical journey.

Fidel Castro claimed that the Revolution was inspired by Cuba’s National Hero, José Martí, leader of the 19th-century independence movement. So start your tour in Habana Vieja at his birthplace: Museo Casa-Natal José Martí. Then head to the nearby Museo de la Revolución, in Batista’s former Palacio Presidencial, for a complete profile on revolutionary history. Don't miss the Granma—the vessel that brought Fidel, Che Guevara & Co. from Mexico to launch the revolution.

Day two is for the Vedado district, including the Universidad de la Habana, where Fidel Castro studied. Next visit Museo Abel Santamaría, in an apartment that was secret headquarters for Fidel’s revolutionary movement. There's also the Hotel Habana Libre (the former Havana Hilton), where he set up his headquarters after Batista fled. In the afternoon head to Plaza de la Revolución—the seat of government—to photograph the mural of Che Guevara, then visit the Centro de Estudios Che Guevara, opposite Che’s former home. End your day exploring Necropolis Cristóbal Colón, the sensational cemetery containing many graves of revolutionaries.

On your last day explore Fortaleza de San Carlos de la Cabaña. The forecourt outside this 18th-century fortress has displays from the 1962 Cuban Missile Crisis, and nearby is Casa-Museo del Che, the comandante’s former headquarters. 

#3 Cars, Cigars, and Cabarets

Showgirl at Tropicana cabaret. Copyright Christopher P. Baker (all rights reserved)

To kick off this itinerary, you'll be met on arrival at Havana’s José Martí International Airport by a pre-arranged classic convertible car with chofer, which you’ll use throughout your visit. Head to a lunch of roast chicken in orange-garlic sauce, with rice, black beans and all the trimmings at El Aljibe, then follow the highlights tour in Itinerary #1, including the Museo Ernest Hemingway. In the evening savor a cigar and fine añejo (aged) rum on the patio bar at the Hotel Nacional.

Start your second day with a guided visit to a cigar factory—Fábrica de Tabaco H. Upmann is the best. Stock up on your favorite smokes here. Then spend time around Parque Central, chatting with the owners of dozens of restored classic cars that they rent out to visitors. If you want to know how locals travel, hop into a colectivo taxi at the corner of Neptuno and Prado. In the afternoon, visit the Museo de Ron, and savor mojitos next door at Bar Dos Hermanos—Hemingway’s favorite dockside bar. After dinner at La Guarida, head to Tropicana for a sensational ‘50s-style cabaret alfresco.

Before heading back to the airport, visit the Nostalgicar workshop to learn how this private business restores old clunkers.

#4 Architecture Appreciation

Gran Teatro on Parque Central

The buildings in Havana come in a spectacular amalgam of styles—from classical colonial mansions to Art Deco, Art Nouveau, and Modernist stunners in various states of repair. This itinerary focuses on the best examples in every genre.

Upon arrival head to Habana Vieja. The colonial quarter is chock-full of astonishing heritage sites, concentrated around the four main plazas. Don’t miss the Hotel Raquel, its jaw-dropping façade dripping with Art Nouveau adornment. It’s hard to tear yourself away from the old quarter, but spend the afternoon walking the Prado—a true journey back in time—and end by exploring around Parque Central, taking in the Edificio Bacardi (Cuba’s finest Art Deco exemplar) and the baroque Gran Teatro. At night savor cocktails, and perhaps a cigar, atop the Gran Hotel Manzana Kempinski, with its astounding view of the park and its floodlit architectural stunners.

Dedicate day two to Vedado, developed in the 20th century as an upscale neighborhood boasting grandiose mansions. Any stroll here is an architectural adventure in serendipity, but Calle 17 unfurls west past one astounding building after another. Turn right at Paseo for the Hotel Riviera—a superb example of mid-century Modernism courtesy the Mob. Cool off in the late afternoon with ice cream at Coppelia, built in 1966 with flying-saucer inspired architecture. Dine at La Casa, a paladar in a superb Modernist home in Nuevo Vedado, then end with cocktails and a cigar at the Hotel Nacional, with its Moorish interior.

On day three, head back to José Martí International Airport for your departure flight via 5ta Avenida through the tony Miramar and Cubanacán districts, which display lavish mansions. Don’t miss the outlandish Russian Embassy.

#5 Culinary Cuba

Grilled lobster anyone?

 “New Cuba” is experiencing a gastronomic revolution led by owner-chefs of the city's paladar private restaurants. In the morning, head to Habana Vieja, where the area between Cinco Esquinas and Calle O’Reilly—between Parque Central and Plaza de Armas—is an epicenter for these exciting new paladares. Lunch at El del Frente on superb ceviche or tuna tataki, washed down with rooftop cocktails. After feeding your soul on the sights, break for a pick-me-up cappuccino at Azúcar, on the Plaza Vieja; it serves delicious lobster in criolla sauce and has live music at night. Or head to nearby Mama Inés, where Fidel’s former private chef conjures up a divine octopus with garlic and pepper appetizer, and the best ropa vieja (marinated braised beef prepared with garlic, onions, and sweet peppers) in town.

The next day experience food like a local. Visit a bodega (ration store), head to a produce market such as Agropecuario Egido, then learn to cook a lo cubano with Niurys Higueras at her paladar Atelier, in Vedado. Mix up your day with some sightseeing. Then, having been sure to make reservations well ahead, take a sunset tour in a classic convertible car that will drop you at restaurant La Guarida—truly a stand-out dining experience!

On day three, head to the nearby community of Alamar for a fascinating guided tour of Organipónico Alamar—Cuba’s preeminent private organic farm—before heading to the airport for your departure flight.