Havana is mysterious and compelling: it feels like it's been magically frozen in time. Beyond its eccentricity and enigmatic allure, the city teems with attractions and experiences for every interest and taste, from the restored plazas of the colonial quarter and iconic revolutionary sites to fantastic nightlife. There are sensational museums and galleries to roam and excellent new paladares (private restaurants) to try. To top it all off, music and the performing arts are off the hook in Havana, from world-class ballet to jazz and reggaeton. Plan on spending at least three or four days in and around Havana to truly appreciate the place.
Cruise Around the City on a Double-decker Bus
First things first, and that means taking in an overview of the entire city. Hop aboard one of HabanaBusTour's open-air double-deckers. From 9 am to 9 pm, they run a circuit around Havana. A fixed price all-day ticket lets you hop on or off at any of 44 stops at key points of interest, then hop onto the next bus, and so on. Buses begin their routes from the west side of Parque Central, but you can begin anywhere along the circuit.
Take a Walking Tour of Habana Vieja's Plazas
Since Havana evolved westward from the bay, it makes sense to first explore the oldest part of the city: Habana Vieja (Old Havana.) The colonial city was once enclosed by a fortified wall that's long since been demolished. Today, it's walkable and lively; many of the colorful buildings are dilapidated, and the historic center is all the more fascinating for it. But the oldest section of the city, centering around four main plazas, has been completely restored.
Begin in Plaza de Armas, where the city was founded. Be sure to visit the 16th-century fort Castillo de la Real Fuerza, and the Palacio de los Capitanes-Generales, once the official governor's residence. Then head to Plaza de la Catedral, with its magnificent baroque cathedral. Next, follow Calle Mercaderes (or funky Calle San Ignacio) south to Plaza Vieja, the largest of the squares, lined with great bars and paladares, plus a planetarium, a museum, and more. Exit along Calle Brasil and turn left onto Oficios to enter pretty Plaza San Francisco.
Visit Parque Histórico Militar Morro-Cabaña
This massive twin-fortress complex occupies a ridge on the north side of Havana's harbor channel. It offers sensational views over Habana Vieja and the city beyond. Towering over the headland itself is the first fort, Castillo de los Tres Reyes del Morro, built in 1589. Today it houses an interesting little museum about Christopher Columbus, piracy, and Cuba's castles. Climb the lighthouse for panoramic views.
Further east, and stretching for half a mile (2/3 km) along the ridgetop, is Fortaleza de San Carlos de la Cabaña, erected after the British successfully seized Havana in 1762. Completed in 1774, it's the largest fortress in the Americas. Highlights include long batteries of 18th-century cannons and a museum displaying armaments through the ages.
The complex is part of a military zone and is partially staffed by real soldiers wearing 18th-century Spanish military costume. Visit after sunset to witness the nightly cañonazo (cannon shot.) Soldiers prime a cannon with black powder, and at 9 pm on the dot, they light it.
Survey Cuban Art at Museo de Bellas Artes
Havana's Museo de Bellas Artes (Museum of Fine Arts) is housed in two buildings that are located four blocks apart. The international section, in a Renaissance-style 1927 edifice on the east side of Parque Central, includes works from throughout the world (except Cuba).
More appealing is the Cuban section, in a well-lit Modernist structure to the north. Two floors are arranged chronologically, from the religious works of the early colonial period through the Cuban masters of Impressionism and Surrealism. Perhaps most interesting are the stunning works inspired by the Cuban revolution.
Relax in Parque Central
On the western fringe of Habana Vieja, tree-shaded Parque Central (Central Park) is a must-visit. Most visually striking are the several dozen 1950s classic cars parked all around. Most are available to tourists for chauffeured city tours. At the heart of the spacious plaza is a monument to José Martí, Cuba's national hero.
The most striking building is the exquisitely flamboyant Gran Teatro de la Habana Alicia Alonso. Opposite, art lovers may appreciate the international section of the Museo de Bellas Artes (see above). The park opens up to the southwest to the Capitolio, Cuba's former Congress and a copy of Washington's own Capitol Building. It's currently undergoing a multi-year restoration and is scheduled to reopen as the Asemblea Nacional (National Assembly).
Stroll or Ride Along the Malecón
Stretching for almost 4 miles (7 km) along the Atlantic shoreline, the Malecón is a boulevard that's populated 24/7 with Cubans of every stripe, from fishermen launching off the shore in giant inner tubes and old folks walking their dogs to lovers kissing and musicians practicing with guitars, trombones, and trumpets. There's no better place to strike up impromptu friendships — but beware of jiniteros (hustlers, or con men).
On weekend evenings the most popular section, between Calle O (in Vedado) and Calle Principe (Centro Habana), is busy with young Cubans swigging rum and partying.
Explore Cementerio Colón
The massive necropolis of Cementerio Colón is astounding. Laid out between 1871 and 1886 in rectangular blocks, and spanning 140 acres (57 ha), it's filled with fanciful Carrara marble tombs. The most flamboyant tombs are located along Avenida Cristobal Colón, the broad main boulevard that stretches from the triple-arch Romanesque main gate to the chapel. Allow at least one hour (two or three is preferable) to explore the main sites.
Don't miss La Milagrosa, the grave of Amelia Goyri de Hoz. Superstitious Cubans believe that she grants miracles, and a steady stream of people come bearing flowers to ask for one (or to thank her for granting one.)
Catch a Show at Tropicana
Cabarets are to Cuba as Dixieland is to New Orleans: they're a quintessential part of local culture. These flamboyant 50s-redux Las Vegas-style revues are still part and parcel of Cuba's night scene, regardless of where you are in the country. Havana has several, but the best is Tropicana, an open-air extravaganza held on a stage beneath the stars. It's not cheap, and there's barely a Cuban in the audience. But it's a fun experience that's worth the splurge: tickets include a bottle of rum with coke, not to mention a non-stop kaleidoscope of dancing showgirls in outrageous costumes.
Ride in a Classic Car
Riding through town in a 1950s classic convertible is the only-in-Havana experience par excellence. You'll find drivers waiting outside all major tourist hotels and around Parque Central. Rates are negotiable. The standard experience is a one-hour tour including the car and chauffeur.
Dine at La Guarida
La Guarida is the most famous and popular paladar in Cuba. ("La Guarida" means "The Hideaway," and it was featured in the Cuban Oscar-nominated movie Fresa y Chocolate, which was filmed here in 1993.) You'll understand its popularity the second you approach the entrance of this grand but faded three-story tenement building. As you pass from the lobby to the second-floor foyer, you'll spot laundry hanging out to dry between the crumbling columns.
The antique-filled restaurant upstairs is filled with photos of VIP patrons, from Jack Nicholson and Naomi Campbell to Beyoncé and Madonna. The modern Cuban dishes are sublime. When you're done with dinner, check out the open-air rooftop lounge-bar. Note that reservations are essential.
Take in the Landmarks at Plaza de la Revolución
This vast plaza occupies the highest point in Cuba and is the center of the Cuban government. Laid out as the Plaza Cívica between 1954 and 1957, before the revolution, it often hosts music concerts and political rallies. The plaza is surrounded by important buildings, including the Biblioteca Nacional (National Library), Teatro Nacional (National Theater), and Ministerio de Comunicaciones (Communications Ministry.)
On the south side, find the Ministerio del Interior (State Security), with its striking five-story metal mural of Che Guevara. On the north side, look for the Monumento á José Martí, a massive marble statue of Cuba's national hero. (Behind it, there's a soaring tower that looks like something from a sci-fi movie.) At its base is the Museo á José Martí. Virtually hidden from sight behind the monument is the Palacio de la Revolución, housing government offices and the headquarters of the Communist party.
Hit the Nightlife Scene at Fábrica de Arte
The hot nightlife spot Fábrica de Arte (Art Factory) is a multi-dimensional cultural space, with art galleries and multiple bars and venues for everything from fashion shows and experimental theater to live bands and DJ-spun house music. It occupies a former cooking oil factory, lending a New York Meatpacking District-style industrial vibe to the place. Get there early, as the line to enter usually stretches around the block.
Discover Ernest Hemingway's Cuban Home
Ernest Hemingway fell in love with Cuba and called it home for 21 years after buying Finca Vigía (Lookout Farm) on the outskirts of Havana in 1939. Here, he wrote many of his novels, including his Nobel Prize-winning The Old Man and the Sea. After his death, the house was seized by the Cuban government.
Today, it's maintained just as it was in 1961, with all of Hemingway's possessions in their original places — heads of animals he killed on safari look down from the walls. You can't enter, but you can peer in through the open windows and doors. His sport-fishing vessel, Pilar, occupies the former tennis court.
Indulge in Ice Cream at Coppelia
Cubans are crazy about ice cream, so it's appropriate that Havana claims the largest ice-cream store in the world. Coppelia takes up half a block in the heart of the neighborhood of Vedado. It was built in 1966, when Fidel boasted that it would outdo Baskin-Robbins in terms of the number of flavors. These days you're lucky to get two (vanilla and strawberry, and on rare days, chocolate).
Coppelia has various outdoor seating areas, plus additional tables inside a fantastical two-story Modernist structure. Each section has a separate line (on hot days expect long lines). Foreigners often get directed to a separate area with immediate service and higher prices. But eating at Coppelia is all about standing in line and eating at communal tables with the Cubans for one peso per scoop.
Gaze at the Avant-garde Artwork at Fusterlandia
Way out at the far west end of Havana, the once-sleepy fishing community of Jaimanitas was until recently as far off the beaten path as you can imagine. Today, it's awash with tourists who come to gaze at the phenomenal avant-garde artwork that adorns more than 50 buildings in Fusterlandia. It's the masterpiece of eccentric artist José Fuster, whose own home is a surreal dreamscape that's reminiscent of Gaudi and Picasso. As long as big tour groups aren't visiting, you can step into Fuster's studio-gallery.