9 Streets You Need To Know In Old Havana

The Malecon

My dear friend Katie, who visited Cuba a few weeks before us, perfectly put it: The Malecon, a 8km-long ocean drive from the modern neighborhood of El Vedado, where the iconic Hotel National is situated, to the Havana harbor in old town, is basically the city’s more soulful PCH. Walk to The Malecon esplanade if you ever feel lonely. Mingle with locals over ice-cold beers and watch the sun go down over the sea while blasting the catchy tunes of local reggaeton superstar, Jacob Forever.



This charming street is named after Alejandro O’Reilly, an Irish mercenary who led the Spanish in occupying the city in the late 1700’s. On our first night in town, we tried to get a table to 304 O’Reilly, a popular mixology bar & paladare – the word to refer to a family-run restaurant – with stellar TripAdvisor reviews. Call ahead of time for a reservation: it’s meant to be some of the most innovative spot for Caribbean cuisine in Havana.

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Calle Concordia

Our Airbnb had a double balcony overlooking the daily hustle and bustle of Calle Concordia. On the wall of my baby blue bedroom hung a laminate poster of Cuba’s Oscar-winning gay comedy, Fresas and Chocolate, which was filmed at La Guarida across the street. With its haunting staircase, cinematic dining room and a rooftop bar that overlooks the whole city, the restaurant has become an emblem of Havana. Don’t miss out on the photo opp at the entrance (cue: Khloe Kardashian Instagram scandal), and be sure to order the three tenderloin dish – it’s out of this world!

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At Casa Miglis a Swedish fine restaurant and bar located on Lealtad, we found our happy place. Monica, a gorgeous rockabilly bartender who proudly sports a Gil Elvgren pinup tattoo on her forearm, served us strawberry daiquiris and spoke eloquently of her experience growing up as a woman in a place like Cuba. “I hate salsa music,” she growled. Definitely fascinating to get her unique perspective on life while catching a rum buzz.


Calle Galiano

Calle Galiano – also called Avenida de Italia – is one of the most important shopping arteries of Havana, where old prestigious department stores were transformed in eclectic bazaars. You’ll find the iconic The America apartment building, two movie theaters, and the Fin de Siglo and Epoca stores; where you can shop for glassware and knick knacks. Also on the avenue are coffee shops, ice cream parlors, and banks. If you want to listen and dance to some of the best salsa and reggaeton and don’t mind mixing with some other tourists, head over to Casa de la Musica.



If you’ve watched the Cruise 2016-17 CHANEL show set at Havana’s Paseo del Prado, chances are you’ve been dreaming about walking the alluring tree-lined street that divides Centro Habana and Old Havana. Chilling on marble benches, locals like they have all the time in the world, not giving a flying f*ck about selfies and Snapchat. Hustlers trying to lure you into dark rum bars and kids are dancing tango. If you walk far enough on Prado toward the Malecon, you’ll bump into a famous local skate spot, where we met with Miles Jackson, the founder of Cuba Skate, a Washington, D.C.-based nonprofit initiative created by two University of Michigan graduates who formed strong ties to the Cuban skate community while participating in a study abroad program in Havana.



El Floridita is where Havana meets Key West, but it’s worth a stop. Get a selfie with a life-size bronze Hemingway at the bar and enjoy beautiful drinks, music and AC in this historical room.


Calle 26

This is where one of the coolest cultural hub in Cuba is located. According to its founder, La Fabrica del Arte ‘attempts to give Cubans a meeting-place where the best of the island’s avant-garde arts can be enjoyed, with all the artistic manifestations under the same roof and with prices making it accessible to the majority of Cubans…[Fabrica del Arte] is a place where everyone is an artist. A musician is just as valuable as a person making a living fixing coffee makers… We Cubans carry art around inside of us.’ My kinda place.

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L’Agent Goodies…