• 90 mi off the coast of Florida, this small island is chock full of culture & history and seemingly trapped in time. (*lifted restrictions between US & Cuba relations will soon give way to fully legal American travel. Now is the time to visit!)
  • Cash is king! Convert money to CUC (Convertible Cuban Peso) at the airport cadeca (money exchange). Many advise exchanging in Havana center for better rates, but the lines are ridiculously long. There is also a CUP (Cuban Peso) that locals use and tourists can use for taxis or street food, but most transactions require CUC. Beware of scams involving paying in CUC’s and receiving CUP’s!
  • Particulars‘ refer to services that are private and once illegal. Casa Particulars come highly recommended as opposed to the overpriced government-run hotels and taxi particulars are perfectly safe and cheap.
  • Chat with the locals! Cubans are some of the most friendly people and it’s fascinating to hear their viewpoints considering many have never left.
“My mojito in the Bodeguita del Medio and my daiquiri in the Floridita.” - Ernest Hemingway


  1. Ride in an almendron (classic car) on the Malecón
  2. Sip on a mojito at one of Hemingway’s favorite haunts
  3. Live music at Casa de la Amistad
  4. Taste the street food pan con lechon (roast pork sandwich) or frituras de malanga (deep fried taro mixed with egg and crushed garlic)
  5. Dinner at a paladar, in-home restaurants that were illegal in the 90’s
  6. Sunset drinks at Ambos Mundos Hotel
  7. Visit to Ernest Hemingway’s House, Finca Vigía
  8. Day trip to Viñales to see the cigar farms
  9. Wander Old Habana Vieja
  10. Sample the cigars at one of the Casa del Habano’s


Casa Particular chic
Contact home owners for a stay



  • Hop on/Hop Off Bus | Normally, I would never recommend something so generic and touristy, but sitting high provides a wonderful vantage point for Havana. The locals are friendly, but you will be bombarded with offers for taxis, classic car rides and pedicabs (especially if you look lost). Grab the double decker in Parque Central and orient yourself with the city while grabbing snapshots of the beautiful architecture.
  • Cafe Laurent | Lunch at this paladar begins with an antique elevator ride to what feels like an old Miami penthouse. The billowing white curtains frame views of the Vedado neighborhood on the 5th floor terrace and interior walls are covered in 1950’s newspapers. You can’t go wrong with a seafood entrée from the Spanish-influenced menu.
  • Hotel Nacional de Cuba | Just around the corner is the historical hotel built on the site of the Santa Clara Battery dating back to 1797. During the Cuban Missile Crisis, it served as the defense headquarters set up by Che & Castro. In addition, the hotel has hosted numerous celebrities from Churchill to Sinatra to John Wayne. Wander the grounds and relax with a mojito on the terrace overlooking the Malecón.
  • Museo de la Farmacia Habanera | Just off Teniente Rey, you’ll find a beautiful building founded in 1886 that functions as a museum and working Cuban pharmacy. The elegant interiors are highly photogenic.
  • El Chanchullero | This hole-in-the-wall bar is very unexpected given its slightly off the beaten path location. Head upstairs for a seat at one of the rustic tables to order tapas & a Cuba Libre. The walls are covered in Cuban cinema posters, hip hop music blaring and trendy clientele.
  • El Capitolio | The National Capitol building was the seat of government until the Revolution in 1959. Now it’s home to the Academy of Sciences and a great spot for catching photos of the classic 1950’s cars driving by.
  • La Guarida | One of the most unique architectural spaces for dining, a meal here is a must! Housed inside a dilapidated mansion, climb the sweeping ornate staircases that look like they belong in Paris. (interesting fact: Beyonce & Jay Z were photographed walking down these while thousands of Cuban fans awaited them on the street!) While the main courses were nothing to write home about, the marlin tacos & papaya lasagna starters were great and the ambiance is unparalleled.


  • Café El Escorial | It’s never too early to add a little rum to your coffee in Havana. Grab a sweet treat and a caffeinated drink to enjoy on the umbrella-ed patio overlooking Plaza Vieja.
  • Museo Nacional de Bellas Artes | The National Museum of Fine Arts has an extensive collection of Cuban art and the building itself is impressive. One wing is dedicated to solely Cuban artists and the other house international works.
  • Santy | Drive along the Malecón until you reach the unassuming fishermen’s shack serving excellent sushi and fresh seafood courses. It can be difficult to find so ask a local if you miss the alley entrance.  There are no menus as you’ll be served whatever’s freshly caught that day.
  • El Gran Palenque | Every Saturday, Vedado neighborhood hosts a ‘Sábado de la Rumba‘ (Rumba Saturday) starting at 3 pm and lasting for roughly 3 hours. Everyone is welcome to join the party and with the rhythmic congas, you’ll be hard pressed not to join in. Members of the Afro-Cuban dance company make the rounds and help instruct dance moves.
  • Ambos del Mundo Hotel | The place for a sunset cocktail overlooking Habana Vieja. It’s touristy, but what hotel bar isn’t in Old Havana.
  • El Cocinero | Enjoy the chic and trendy setting of what was once an olive oil factory with an 80 ft chimney stack. Climb 3 flights of stairs until you reach the rooftop terrace with attractive waiters and a scene you’d find in NYC or LA. Can’t go wrong with any grilled item on the menu paired with a fresh fruit daquiri. Some of the best food Havana has to offer.
  • Fábrica del Arte | Head next door to the multi-use space including an art exhibit, bar, café and club. Grab a drink and wander through the exhibits. Later in the night, the space functions more as a live music venue or club.
  • Casa de la Amistad | What better way to experience the music Cuba is famous for than at one of Buena Vista Social Club’s members regular hangouts. The Italianate mansion including a Renaissance-style garden is a beautiful setting for listening to the melodic Latin music. Visit the cigar shop before settling in for the show.




  • Bacardi Building | One of the best 360 panorama views of the city is surprisingly in the old rum company’s HQ. The 193o’s art deco building is beautiful in its own right. After the Cuban revolution, Bacardi left the country and the building was converted into offices. Just tell the doorman you want to see the city views (“la vista”) and he’ll direct you to the elevator’s top floor.
  • St. Francis Church | Now used for concerts, the baroque style monastery dates back to 1730. Wander down Oficios until you hit Plaza Armas. Keep an eye out for the old movie posters being sold. They are handprinted and make excellent souvenirs.
  • Hemingway’s Haunts | By now it’s apparent that Hemingway had a very large presence in Cuba. He loved the country & it’s people and the Cubans loved him. La Floridita was his favorite daquiri and you could see why the Paris-loving author enjoyed the bar. La Bodeguita del Medio definitely has more of a hole-in-the-wall aesthetic, but unfortunately both spots are completely overrun with tourists. Still, a trip to Havana is not complete without paying a visit, so order your mojito and daquiri in honor of the celebrated author.
  • Bar Monserrate | Just down the street from La Floridita is a true local’s bar. Open shutters face the busy street as cars and people walk by going about their daily business. A guitarist, bassist and vocalist trio serenade you during a relaxed service.
  • Casa Miglis | You’d never expect to find Swedish-Cuban fusion, but this place delivers. The funky, hip interiors are dimly lit with candles and the bar is packed with an artsy crowd. Don’t miss the Seafood Casserole or the Toast Skagen.


  • Optional Day Trips: 
  • 1) Finca La Vigía | A 20 min taxi ride to Ernest Hemingway’s “lookout farm” is well worth a visit. Hemingway wrote three of his most famous novels, “For Whom the Bell Tolls”, “The Old Man and the Sea” and “A Movable Feast” here. Purchased for $12,500, he spent over 20 years in the house until his death in 1961. The house is almost exactly how he left it and while visitors are not allowed in the interior, windows and doors are opened to reveal his collection of LIFE magazines, taxidermy and typewriter. The house is beautifully preserved and it’s one of the most unique historical sites commemorating the life of the beloved author.
  • 2) Beach | If the weather is nice, do as the locals and head to the nearest beach. Veradero is where the resort goers flock, but the beaches in Playa del Este are idyllic and less touristy. Tell a Havana taxi driver “Guanabo” and they’ll know exactly where to take you. There are also casa particulars and restaurants if you’re looking to spend some time there, however, you could easily spend a week in Havana and it’s a short car ride away.
  • 3) Viñales Day Trip | The 2.5 hour car ride to the beautiful region of Pinar del Río is definitely worth the trip. It’s lush and tropical with valleys, caves, and tobacco farms with fresh rolled cigars. Hire a driver for the day round trip from Havana and be sure to stop by Cueva del Indio for a boat tour through the cave. If you’re feeling adventurous, ride horseback through the valley stopping to see how cigars are made and sugar cane juice is extracted from the plant. (**contact for assistance in booking your trip to Cuba)
  • Café Madrigal | Located in the trendy Vedado neighborhood, this bar feels more like a place you’d stumble upon in a cosmopolitan city than the middle of Havana. A Cuban filmmaker opened this tapas bar attracting the hipster crowd. Often accompanied by live music, grab a drink and enjoy the chill atmosphere.
  • Doña Eutimia | This small restaurant serving traditional Cuban food is tucked away just off the Plaza Catedral.  Be sure to sample the classic ropa vieja (pulled beef in a tomato sauce) accompanied with piles of rice and beans. It’s welcoming, affordable and one of the best places in town for classic Cuban food.



Includes every location mentioned above
Lauren Greenberg
Itinerary By

Founder of The Weekender

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