Weekend Guide to Havana

Contributed By Justyna Della Valle

If you’re looking for an under-the-radar getaway to the Caribbean, then a private Havana, Cuba city tour is guaranteed to be filled with a unique array of sights, sounds, and tastes.

Cuba is often associated with its rich history and distinct hold on the past; but it’s so much more than what once was – the country is forging a new way forward with its unique flair. Between the flavorful gastronomy and history of blending American jazz with salsa, this destination is rich with opportunities for discovery. And while many believe Cuba to be a time capsule, working with a SmartFlyer travel advisor and our partners at Cultural Cuba ensures that your Havana, Cuba city tour will reveal the country’s unique interpretation of modern arts and culture.

Every itinerary we work on is customized, but as a starting point, we’ve tailored a guide that will walk you through the ins and outs of Old Havana. Journey through the storied capital’s streets, taking in the historic buildings dating all the way back to colonial times. Then, dine on authentic Cuban cuisine including the freshest seafood or the daiquiri in its birthplace. You’ll also be invited to enjoy live music and enjoy nightlife in various venues across the city. So pack your favorite pair of dancing shoes, and let’s dive into what to expect on this cultural adventure through Cuba.


Gran Hotel Manzana Kempinski is a 246-room hotel situated at the heart of Old Havana and surrounded by the country’s UNESCO World Heritage buildings. All of their accommodations feature sweeping views of the city. Additionally, guests can enjoy delicious gastronomic experiences at Lobby Bar El Arsenal and their San Cristobal Panoramic Restaurant. We recommend taking advantage of this hotel’s rooftop scene at sunset following an appointment at their European-inspired spa.

La Reserva Boutique Hotel is a historical boutique hotel that perfectly reflects the soul of the Cuban community. Originally designed as an expansive home, their rooms are filled with charming local Havana art pieces. Guests can also dine on authentic Cuban dishes at La Bodega de La Reserva before heading out to explore the neighborhood.

Bienvenidas a Havana

Your journey to Cuba begins with an afternoon touchdown at the José Martí International Airport. There, your VIP escort service will guide you through security and your hotel of choice via private ground transfer. On the drive into Havana, your driver will also give you a tour of Revolution Square. Be sure to also capture pictures of the Che Guevara “Hasta la Victoria Siempre” mural opposite the famous José Martí Memorial while on this Havana, Cuba city tour.

After freshening up in your room, meet your guide at the bar before heading over to Ivan & Justo for dinner. Locals know this restaurant – opposite the Museum of the Revolution – for being led by Chef Ivan, Fidel Castro’s former personal chef. Following dinner, your guide will treat you to a private rum tasting and cigar pairing with the head sommelier of Havana Club Rum. Here, you can learn the process behind Cuban rum production while sampling the brand’s Maestro collection alongside curated cigars. Finally, close out your first night with a nightcap at the world-famous El Floridita. This iconic music bar is known for being Hemingway’s favorite and the birthplace of the daiquiri.

Your guided walking tour of La Habana Vieja

Following breakfast at your hotel, you’ll begin your guided Havana, Cuba city tour on foot with Professor Luis Eduardo González Diaz. This architecture expert will highlight the history of the city’s design and give insight on Cuba’s various restoration projects. On the way, you’ll also stop for a visit of El Taller Experimental de Grafica, a community-based graphic design studio.

In the spirit of continued education,  your next stop will be at the Old Havana Preschool. This beautifully restored colonial building is an excellent place to learn first-hand about the local Cuban community. Afterwards, your guide will lead you to one of the city’s cigar factories to observe the traditional hand-rolling process. You can even purchase some of these cigars from brands like Cohiba, Romeo y Julieta, Partagas, and Montecristo.

This iconic music bar is known for being Hemingway’s favorite and the birthplace of the daiquiri.

Take some time to refuel at 5 Sentidos, one of Havana’s top family-run restaurants. Their kitchen is known for its unique interpretations of classic Cuban cuisine and high-touch service. After lunch, you’ll also be guided to Ecopapel and Dador. The former is a small recycling workshop that transforms Embassy documents and other local sources into handcrafted artisan paper goods. For example, the handbound journals here are perfect gifts to bring home for friends. Dador is a female-led designer shop. Here, Founder Lauren Fajardo will walk you through her interpretation with Cuban fashion or walk visitors through the creation of custom-made pieces.

This evening, get ready to move in your private salsa dance class at Casa del Son. First established in 1715, this fully restored dance school invites guests to learn various genres of Cuban dance. Whether you choose son, cha cha cha, rumba, salsa, casino rueda, or folklore, your guide will transfer you back to your hotel to freshen up before dinner. We recommend trying out at Antojos tonight, set just a few steps away from Yarini’s Bar where you can also test out your new moves with help from their live band. To keep the party going, explore the city’s nightlife with your private guide and duck into some of Havana’s “paladars” – secret bars and clubs that the growing middle class of Havana’s entrepreneurs, artists, musicians, and restaurateurs often frequent.

Courtesy of Cultural Cuba

A glimpse into Arte Cubano

Following breakfast, your guide will meet you in the lobby and transfer you to Nelson Ramirez de Arellano Conde’s photography studio. This cityscape photographer serves as the director of Cuba’s National Museum and Gallery of Photography. While there, Conde will guide you through his collection and share insights on the evolution of Cuba’s arts community. You can also take a brief tour of the Fucina de Artistas, a private studio where you can observe emerging artists at work.

…this dance company is sure to deliver an awe-inspiring show.

Afterwards, take a twenty-minute private transfer to meet the members of Habana Compás Dance. There, the dance company will treat you to a one-of-a-kind performance that blends dance and percussion (think: Stomp!’s flamenco cousin). Whether it’s the beating of the drums or the fusion of ballet and folklore dance, this dance company is sure to deliver an awe-inspiring show.

Following lunch back at the hotel, it’s time to prep for a photography-worthy evening. First, your guide will bring you to your transfer into town via one of Cuba’s iconic 1960s convertibles. Your driver will take you through the scenic route along the Malecon as the sun lowers below the sea. After your dreamy drive, your driver will drop you off at Hotel Nacional de Cuba. While there, your guide will walk you through this hotel’s historic landmarks such as the Santa Clara Battery.

Enjoy a refreshment and a cigar on the hotel Terrace before heading to dinner at La Guarida. Arguably the country’s most famous restaurant, guests can dine on inventive dishes like smoked marlin tacos and whole roast pig. Your final night in Havana will close out with a special rooftop performance by Robelejo Jazz Trio. For a nightcap, we also recommend heading to the restaurant’s VIP Cigar Lounge or Casa del Musica or Café Miramar for more live music.


Revolution Square
José Martí Memorial, Plaza de la Revolución
Ivan & Justo, 4JRV+CH3, La Esquina, Aguacate, La Habana, Cuba
El Floridita, 4JPV+X36, Obispo, La Habana, Cuba
5 Sentidos, 4JQW+P42, y, Compostela, La Habana, Cuba
Ecopapel, 4JPV+MVG, Lamparilla, La Habana, Cuba
Dador, 253 Amargura, La Habana, Cuba
Casa del Son, Empedrado #411 entre Compostela y Aguacate, La Havane 10100, Cuba
Yarini’s Bar, San Isidro # 214 between Picota, Compostela, La Habana 10100, Cuba
The Malecon
La Guarida, 418 Concordia, La Habana, Cuba

Craving this vibrant tasting menu of the Cuban capital? Get in touch with your SmartFlyer travel advisor to craft your own trip through Havana.

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