When T and I spotted a JetBlue winter sale last year, we did what any travel-loving couple would do—we booked two tickets to Cuba on a whim. A few weeks later, we found ourselves boarding a plane for what turned into 18 unforgettable days exploring this Caribbean island, just 330 miles from Miami and a short four-hour flight from New York.
We kicked off the trip with four nights in Havana, joined by friends flying in from Atlanta. From there, we continued on our own to discover other corners of the island. While Havana wasn’t the city that ultimately stole my heart, it was the perfect place to begin—vibrant, high-energy, and bursting with music at every corner.
Staying Local: Casa Particulars
Rather than booking hotels, we decided to rent Casa Particulars throughout our trip. These are private homes opened up by locals—essentially Cuba’s version of a bed-and-breakfast—and they’re an amazing way to experience the country authentically while supporting residents directly.
In Havana, we stayed in Miramar, a leafy neighborhood home to several embassies and just a short taxi ride from the action downtown. Our particular Casa was a stunning four-bedroom mansion complete with outdoor space, a private chef, and even a bartender. All of this came to about $75 per person—a steal considering the experience.
We arrived on a rainy afternoon and were welcomed with complimentary Cuba Libres, followed by a home-cooked spread of roasted chicken, rice and beans, and piles of fresh fruit. With bellies full, we surrendered to post-travel naps before gearing up for our first night in the city.
Havana Nights: Rooftops, Rumba, and Rum
The nightlife in Havana is legendary, and for good reason. Our first evening began with cocktails at El Del Frente, a chic spot in Old Havana with a rooftop terrace overlooking the city. Afterward, we headed to Otramanera, a serene Spanish-inspired restaurant tucked away in Playa, known for its inventive dishes and impeccable service. The pork meloso was unforgettable.
One of the things that surprised me most about Havana was just how safe it felt to explore after dark. We strolled through the city, hopping between bars, asking locals where to buy ETESCA Wi-Fi cards (1 CUC for an hour of use), and riding around in vintage cars that felt straight out of a movie. Nights often ended late—sometimes at 3 a.m.—with music, dancing, and more Cuba Libres.
Four Days in Havana: What to Do
If you’re planning your own Havana adventure, here’s a breakdown of our four-day itinerary, blending food, culture, and plenty of music.
Day 1
- Dinner: Otramanera – Refined Spanish-inspired dining in a calm, modern space.
- Night Out: Sábado de la Rumba – A Saturday afternoon block party full of drumming, dancing, and neighborhood vibes.
Day 2
- Brunch: Callejón de Hamel – Arrive before 10:30 a.m. to avoid tourist crowds and inflated prices.
- Sightseeing: Museo Hemingway Finca Vigía – Hemingway’s home, preserved just as he left it.
- Cocktails: La Bodeguita del Medio – Famous for its mojitos and Hemingway connection.
- Dinner: 304 O’Reilly – Trendy, bustling, and perfect for foodies.
- Late Night: Fábrica de Arte – A unique fusion of art gallery, performance space, and nightclub. (Closed Mondays.)
Day 3
- Breakfast: Café Bohemia in Plaza Vieja for strong Cuban coffee.
- Sweet Stop: Helad’oro – Ice cream worth lining up for.
- Sightseeing: Fusterlandia – A mosaic wonderland created by artist José Fuster that transformed an entire neighborhood.
- Lunch & Drinks: San Cristobal Paladar – A lively spot with a reputation for strong cocktails.
- Dinner: Paladar Vistamar – A seafood restaurant in Miramar with ocean views.
- Drinks & Dancing: La Flauta Mágica – A sleek club with oceanfront views and top-notch live music.
Day 4
- Lunch: El Cocinero – Stylish dining beneath an old factory chimney.
- Pool Day: Hotel Nacional – Pay the day rate (about 20 CUC, credited toward food and drinks) to swim, lounge, and sip cocktails at this iconic hotel.
Final Thoughts
Havana may not have been my favorite city in Cuba, but it was undoubtedly one of the most fun. Between late-night salsa dancing, long walks along the Malecón, vintage car rides, and endless mojitos, it offered a whirlwind of energy and culture that’s impossible to replicate anywhere else.
If you’re planning a trip, give yourself at least four days here to soak it all in. Stay local, eat well, dance often, and let the music of Havana sweep you away—you’ll return home with stories worth telling and rhythms you won’t soon forget.
