4 Days in Havana, Cuba

Time stops in Havana, Cuba, yet you've never felt a city more alive. Picture it, just for a second: antique American cars from the 1950's flood the main esplanade, the Malecon, with windows open and tops down, while the surrounding streets, nestled between candy-coated colonial buildings, act as the stage for an open-air party everyone is invited to. Do you hear that? That's Cubans sharing a conversation over the sounds of salsa music. Do you feel that? That's the vibrancy of Havana, baby. Here's how to take it all in over a long weekend. For "How to Travel to Cuba as an American / from the US," check out my article here.

DAY 1

CHECK OUT EL CAPITOLO

You’re really here to start your day with the fried, jam-filled pastries called “cangrejitos” that are served from a cart across the street, but the National Capitol Building is also the perfect starting point to bop around Old Havana.

VISIT HOTEL INGLATERRA, THE OLDEST HOTEL IN HAVANA

The retro signage at this hotel makes for a great photo opp. Across the street is an easy stop for the Habana Bus Tour that takes you all around the city, if that’s your speed. Otherwise, take my advice and splurge on a private tour in an old American car. There are tons of options between Inglaterra and Central Park.

SEE THE SIGHTS IN AN OLD AMERICAN CAR & DRIVE ALONG THE MALECON

Your driver will take you to see all of Havana’s key sites, including the Plaza de Armas, Plaza de la Catedral, Plaza de San Francisco, Plaza Vieja, Cathedral de San Cristobal and Castillo de la Real Fuerza in Old Havana, the Plaza de la Revolucion where the famous Che Guevara mural is located, the Parque John Lennon where the Lennon statue resides and the Cementerio de Cristóbal Colón. On your way back, you’ll cruise along the Malecon, the famous waterfront esplanade that runs along the coast in Havana. On the other side of Havana Bay, you’ll see the Castillo del Morro and the Fortaleza de San Carlos de la Cabaña where they perform a cannon ceremony every evening at 9pm.

LUNCH AT EL DANDY, A HEMINGWAY-INSPIRED BAR

This little hole-in-the-wall is actually a fantastic spot for pulled chicken or carnitas tacos and a minty-fresh mojito. Sit at the bar to avoid the wait and enjoy the décor and ambiance.

STROLL ALONG OBISPO STREET

This main strip in Old Havana is flooded with colors, architecture and people. Catch the live music being played in the streets, enjoy some churros or fruit from a cart and take lots of photos in front of doors and other things. ;)

STOP IN TO HOTEL FLORIDA’S SECRET CIGAR SHOP

Okay, it’s really not a secret and you can pretty much see it as soon as you walk in, but they do have to open it especially for you and it is kind of cozy and cute. Get a pack of short Cohibas, the brand of authentic Cuban cigars.

ROOFTOP DRINKS WITH A SIDE OF VIEWS FROM HOTEL AMBOS MUNDOS

Just before sunset, make a visit to Hotel Ambos Mundos for expansive views of the city. You’ll arrive to an old-school, screen-cage elevator in the lobby where the operator will take you to the top of the building. During my trip, they were only serving beer (sigh) but allegedly they have one of the best mojitos in the city. Regardless, the views alone are worthy of the trip.

DINNER AT DONA EUTIMIA

This incredibly charming Cuban spot is a favorite among tourists and locals because of their generous price tag and portions, so make a reservation and come hungry. The menu reads as a list of the owner’s favorite recipes by her late mother, with items like ropa vieja, pork, rice and beans, and tamal, which encompass traditional flavors done right.

LISTEN TO LA ZORRA Y EL CUERVO JAZZ CLUB

La Zorra y el Cuervo Jazz Club is unlike any other in the city. Located underground in an intimate basement venue, top and emerging jazz players from Cuba and beyond perform here on a nightly basis. The run-of-show is – Arrive before doors open at 10pm. Pay 10 CUC entry, which includes two drinks. Sit as close to the stage as you can get. Drink said drinks and listen to these smooth beats until your heart is content.

DAY 2

COFFEE O’CLOCK AT CUBA LIBRO

Good morning, it’s time for a coffee. If you’re staying in Vedado (which you should) make this coffee shop and bookstore your first stop. It has a very chill, laid-back vibe and a solid selection of English books and magazines for you to peruse over a strong cup o’ joe.

PEEP THE MOSAICS AT FUSTERLANDIA

This neighborhood is about a 20-minute car journey from Vedado, but it’s completely worth the trek. Artist Jose Fuster transformed his suburban fishing town of Jaimanitas into a complete work of art, taking inspiration from Gaudi and Brancusi to create a whimsical, childlike paradise. Here, you’ll see everything from fountains and offices to homes and bus stops covered in his work, an impressive spectacle of color and texture. This display of Cuban modern art is one of the most visited sites in Cuba, and with good reason. There’s also a nice place to grab a bite right on the docks called Restaurante Santy Pescador. Get the ceviche and grilled fish.

DINNER AT EL COCINERO

El Cocinero is one of the best meals you’ll have in Havana, hands down. Make sure you make a reservation ahead out time – you can do this online & then call when you’re local to confirm. Sit on the rooftop – terrace —bar level and you’ll dine under the stars with good music and even better vibes. Order here: octopus, fish tacos, ropa vieja (signature Cuban dish).

SOCIALIZE AT THE FABRICA DE ARTE

If there is ONE thing you MUST do in Havana, it’s this. Fabrica de Arte is a three-story art gallery, bar and dance club housed in a former oil factory that’s completely interactive and acts as the cultural center for the city. It’s open Thursday through Sunday from 8pm onward, so get there early, wait in line, and get ready for an experience. 

DAY 3

BEACH MORNING AT PLAYA DEL ESTE

Havana is an incredible cityscape, but sometimes you just need a little break from urban life. About 20 minutes from the city lies Playa del Este, a beach with turquoise waters and plenty of local flare. You can negotiate with a taxi driver to take you here (main beach is called Santa Maria), wait for you and then drive you back within your agreed upon timeframe. There are plenty of cabs if you don’t want to commit to a time, but this is a semi-cheap option (about $40) if you’d like to have a plan. You can rent beach chairs here for $2, and there’s beachside food and drink service, so keep those pina coladas coming.

LATE LUNCH AT CAFÉ LAURENT

Perched on the top floor of a Vedado mansion, this bohemian chic restaurant has all of the charm of your typical mom-and-pop but with restaurant-quality, home-cooked food. The menu feels distinctly European and slightly Spanish with dishes like jamon serrano, meatballs, tuna carpaccio, red snapper with clams and shrimp and slow-cooked lamb. A note to not be deterred by a "doorman." As you’ll see in my initial Cuba post, sadly foreigners are subjected to hustlers even in the most mundane of circumstances, so in this case they’re looking for a kick-back to let you in the door. If you surpass them, you should be able to go up the stairs and speak to someone about a table being available.

EXPLORE CALLEJON DE HAMMEL

This narrow alleyway is home to funky street art, colorful murals and sculptures made of objects like bathtubs and pinwheels. Designed by a Cuban artist, you'll be captivated by the energy here.

MOJITO BREAK AT NAO BAR PALADAR

It’s time for a mojito, right? Right. This spot is set in a cute little alleyway close enough to the Malecon to get an ocean breeze. Have two or a few. Or if you're sick of mojitos (and this will happen), the daiquiris and pinas are also right on the money.

DINNER AT MEDITERREANEO HAVANA

Food lovers take note – you are about to be in-the-know about one of the best restaurants in Cuba. While there’s nothing traditionally Cuban about this place, it is housed in a former Vedado mansion, so there's some architectural cred right off the bat. As for the atmosphere, you’re immediately transported to Sardinia in the Mediterranean Sea with breezy white-blue interiors and attentive service to boot. The menu skews Italian and feels classic yet modern, featuring dishes like warm focaccia with ricotta spread and pizzas that rival anything from Naples. Also not to be missed is pasta dishes like lasagna, and the whole roasted fish.

THE PARISIEN CABARET AT HOTEL NACIONAL

The Parisien Cabaret show is a cultural fusion of American, Indoamerican, Hispanic and African cultures, and showcases the best of Cuban music in an over-the-top production with elaborate costumes and interesting characters. It’s entertaining, hilarious, impressive and cheesy at all once, and I promise it will be memorable. The show begins at 10pm, so buckle up.

DAY 4

HAVE A GIANT, LEISURELY CUBAN BREAKFAST

Most Casa Particulares will offer this for a very low price, and today is the day you must take advantage of it. Have a sleep in and wake up to a complete spread of ham, eggs, cheese, tomatoes, toast with butter, fruit, fresh juice, milk and coffee.

VISIT THE ALMACENES SAN JOSE ARTISANS’ MARKET

Before you’re homeward bound, explore this two-story warehouse for handmade, unique souvenirs to bring back for your squad (or for yourself… no one’s judging).