The Perfect Long Weekend in Havana Itinerary

If you caught last week’s post, you know that having a written itinerary of activities that support the Cuban people is a condition of travel for Americans. Today I’m sharing the perfect long weekend in Havana itinerary that will ensure you see all the highlights. Feel free to use it as a base for your visit, adding or subtracting sights based on your stamina and timeframe.

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From what I’ve read, it’s not common for anyone to actually check your itinerary, but (just our luck) we did have border patrol agents in Havana request ours when we landed in Havana. I had our rough outline in a OneNote file. They took a few quick snaps of it with their cell phones and it was deemed sufficient. Feel free to use this document as a base for your planning.

NOTE: Be sure to verify dates and hours based on your actual itinerary. For instance, cigar factories and the Hemingway home are closed on Sundays. Fabrica de Arte Cubano is open Thursday – Sunday evenings. Etc.

The Perfect Long Weekend in Havana

Day 1

Today you’ll be making your way from home to Havana. As a quick reminder, we used Sun Transfers to get from the hotel to our lodging, Residencia Santa Clara.

Get settled, freshen up, and then enjoy an early dinner at Los Mercaderes Paladar, a privately owned place in Havana Vieja. After that, head out to the nightly canon show at Fortaleza San Carlos. Have the restaurant call you a cab that will wait while you enjoy the show. For the best viewing position, try to get there by 8:00-8:30. If it’s already crowded, follow the Cubans up to the balcony for a great overview.

Day 2

Start today off with the architectural wonder that is Havana Vieja! We took a walking tour that took us to all the major plazas/sights and gave context to the complex history of the country. In Havana Vieja, you’ll want to visit Plaza Vieja, San Francisco Square, Plaza de Armas, Cathedral Square, and Calle Obispo. Keep an eye out for the Camera Obscura in Plaza Vieja, the history mural on Calle Obispo, and the Museum of the Revolucion, located in the former presidential palace, in use through the Batista years.

We used Free Walking Tours Havana for our tour and our guide Nek was fantastic! Strawberry Tours Havana is another highly recommended agency. Plan to spend 3+ hours enjoying this tour. After your tour, stop for a quick lunch break at one of the many quaint venues in this area. TIP: The app AlaMesa gives a nice overview of dining options in Cuba with menus included where available.

After lunch, take advantage of your location in Havana Vieja to either tour a cigar factory, the Museum of Rum (both state-run) or do some shopping and wander around these incredibly interesting streets. Photo ops abound and many Cuban citizens have private shops set up selling their artwork and handcrafts. Support the Cuban people!

Take some time to rest and freshen up before dinner then check out San Cristobal Paladar for tonight’s meal. It’s famous as the location where the Obamas ate when they visited Cuba. You could peruse the many photos and old clocks on the walls for days!

After dinner, head to the Fabrica de Arte Cubano. This incredible art gallery, music venue, and bar was named one of Time’s 100 Greatest Places in the World. We concur! Located in a converted oil factory in Vedado, it contains progressive art displays, several live music/DJ rooms, and a smattering of specialty bars. You’ll see LOTS of Cubans here enjoying a night out. NOTE: Open Thursdays – Sundays, no need for a cab to wait, plenty outside although expect to pay more for late night returns.

Day 3

Tour Central Havana with one of the same walking tour providers listed yesterday. Central has a much different vibe and you’ll get a greater feel for authentic day-to-day life in this area. Major sights include the newly restored Capitol, the Paseo del Prado/walking street, the Grand Theatre, the Art Museum, Revolution Plaza, Chinatown, and more.

TIP: The Cuban Ballet is one of the top-ranked in the world. If performances are showing while you are in town, be sure to book one. It’s also a much more authentic feeling night out than one of the tourist-centered shows.

Our Central Havana guide was Beatriz, also with Free Walking Tours Havana and we both absolutely fell in love with her. She is extremely knowledgeable and shared so much about the realities of daily life for Cubans in 2022. Today’s tour has a LOT of walking. Be prepared. If your tour concludes at the Hotel Nacional (state-run) take the opportunity to stop for a quick drink in its lovely garden.

Enjoy a bit of lunch and rest your feet then arrange for a cab to take you to Fusterlandia, about 20 minutes outside of Central Havana. Have the driver wait here as cabs aren’t always plentiful in this area. The small neighborhood has been transformed by the artist Jose Fuster. Take about 30 minutes to an hour to explore the streets, the small 3-story house/museum, and then return to your casa.

Cool down, rest up then get ready for dinner at La Guarida, arguably the most famous paladar in all of Havana! Be sure to snap some pics on the staircase and enjoy the views from the rooftop patio. After dinner, catch some live music at one of the many little bars in town or enjoy an evening at either the Tropicana, Legendarios del Guajirito, or the Cabaret Parisien at the Hotel Nacional. NOTE: These show venues are all state-run entities.

Day 4

Today, catch up on anything you’d hoped to see but didn’t get to earlier. A few of my recommendations include:

• A 1 hour+ vintage American car tour. You’ll see some of the sights from Central as well as the Cristobal Colon Cemetery, John Lennon Park, the Bosque/forest of Havana, etc. Explore more of the Vedado area after your tour.

• Take a taxi to the Hemingway House/Finca Vigia (state-run) and have your cab wait for you. This is the home where Hemingway wrote Old Man & The Sea and For Whom the Bell Tolls. While you can’t enter the house, the rooms are visible through open windows.
• Spend more time exploring the forts on the other side of Havana Harbor. Stop and see the Christo statue while you’re there.
• If it is Sunday between noon and 3 PM, make a quick stop at the weekly rumba event at Callejon de Hamel, another unique artist community in Vedado, much smaller than Fusterlandia.

• Explore the town of Cojimar, a small fishing village 15 minutes outside of Havana. A fisherman from Cojimar was the inspiration for Hemingway’s Old Man & The Sea. Have your cab wait or pre-arrange for a pick-up as cabs are scarce here. If you’re there at mealtime, Ajiaco Cafe comes highly recommended.

• Arrange for a cab to take you to the beaches of Playa del Este and Santa Maria del Mar.
• Take a food tour and experience all the neat little stalls/windows run out of people’s homes as well as more established dining venues.

Day 5

Our flight left early in the morning so we just had time for a quick cup of coffee before our Sun Transfers ride to the airport showed up. If you don’t depart until later in the afternoon, enjoy a new sight or revisit one that you especially liked.

If you are anything like us, you’ll already be daydreaming about a return trip and the chance to explore more of this one-of-kind country!

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