Cuba Weekend Itinerary: 3 Days in Havana

The vibrant streets filled with a kaleidoscope of colors adorning colonial architecture and tantalizing aromas— Cuba beckons with an irresistible allure. The anticipation of exploring this enchanting Caribbean island, steeped in history, culture, and unbridled energy, ignites a fervor in the soul. From the bustling streets of Havana to the serene countryside and the sun-kissed beaches, the promise of uncovering Cuba’s myriad treasures fills the heart with an exhilarating sense of wanderlust and adventure. 

Read This First: Everything You Need to Know About Visiting Cuba as an American

No lazy beach days here! In order to satisfy the “people to people” travel requirement, you must commit to exploring locally – staying only at “Casa particulars,” individual vacation rentals like Airbnbs, not government-run hotels, eating only at family-owned restaurants called “paladares,” and booking tours run by independent operators like Civitatis, which means your days will be jam-packed immersing yourself in the island culture.

Get ready to explore because here’s everything to do with 3 days in Havana to hit all the best attractions in Cuba.

Day 1: Arrive in Havana

Havana-oh-na-na. Spend the day exploring the old city, getting your bearings, and taking in the sights and sounds of Cuba’s capital. Immerse yourself in the living history that whispers tales of revolutions and resilience. Wander through the maze of narrow alleys adorned with colorful facades, each corner revealing a piece of Cuba’s storied past. Places to Visit:

• Plaza de la Catedral – A gorgeous church that’s one of the four central squares in Old Havana
• Plaza de Armas – Havana’s oldest and most architecturally diverse square, it was used for former military exercises and is elegantly lined with royal palms.
• Plaza Vieja – initially called Plaza Nueva (New Square), the Old Square has some of the best examples of colonial architecture. 
• Plaza de San Francisco – A harbor stop for Spanish explorers and a former covenant, a market was historically held in this square, which was eventually moved to the Plaza Vieja after the monks complained about the noise. 
• Museo de la Ciudad – the City Museum. This former palace was once the residence of regal Spanish captains.
• Castillo de la Real Fuerza – A military fortification and UNESCO World Heritage Site, the castle is the oldest standing fortress in all of the Americas.

Enjoy lunch at a paladare like Teniente Rey, which was the most authentic meal we had on the trip. Be sure to try the ropa vieja, a local delicacy of shredded beef, which translates to “old clothes” and comes in an adorable heart-shaped dish.

When you’re ready, head back out to explore the area around Parque Central outside Hotel Iberostar.

Sites to check out include: 

• El Capitolio – the National Capitol Building 
• Museo Nacional de las Bellas Artes – This museum houses the most extensive collection of fine art in the country. 
• Museo de la Revolución – A comprehensive look at Cuba’s revolutionary history, exhibiting collections of photographs, flags, documents, and weapons, including Fidel Castro’s yacht

If you don’t book a day trip to Vinales, you can also make a reservation to tour the Partagás cigar factory.

There are a number of FREE local Havana tours available through Civitatis.com that satisfy the “people to people” travel requirement – day tours, night tours, bike tours, and neighborhood tours that visit many of these Havana hotspots.

Enjoy dinner at a paladare like O’Reilly 304, which boasts tapas and good cocktails.

After-hours: Cuba’s a late-night destination, and things heat up after dark. Head to the iconic Tropicana cabaret show that hasn’t changed since the 1930s to see sexy men and women swing, dance, and sing under the stars. The headdresses and glittery costumes are as fabulous and extravagant as you imagine. Doors open at 8.30, and the show starts at 10 pm and runs until midnight. There are three price levels for tickets. We did the middle tier but didn’t need to, as there’s no bad seat in the house. All tickets include rum and coke, with dinner optional, but I highly recommend eating beforehand because the food is a bit airplane-esque. 

Overnight: Casa Particular

Our Airbnb was absolutely amazing – one of the best I’ve stayed at anywhere. Right next to the capital, we had the whole floor of a pastel apartment building to ourselves, with three huge bedrooms and three en suite private bathrooms for just about $130/night, which included free WIFI, US power plugs, hot water, and air conditioning …all a bit of a rarity in Cuba.

Day 2: Day trip to Vinales Valley 

Most casa particulars (Airbnbs) have the option to include a daily home-cooked breakfast for a small fee, so be sure to pre-arrange this so you have energy for the day.

Today, you’re off to Viñales Valley for a whole day guided tour. A three-hour drive, this UNESCO World Heritage Site looks like a lush, ancient jungle world. It’s an immaculate landscape where you’ll spend the day exploring every corner of this captivating landscape, from its peaks to its valleys.

Our first stop is the overlook at Hotel Los Jazmines for the best view of the valley. Grab a coffee and a snack from the bar (ham and cheese sandwiches are common) and snap photos of the beautiful panorama. Pro Tip: Don’t be scared when the sculpture moves; he’s one of those weird street performers who loves messing with tourists. 

From there, it’s off to the tobacco plantations to learn how the famous Cuban cigars are made from the fertile valley. The one we went to was La Esmeralda. You’ll be taken into a straw hut to see where the leaves are dried and rolled and hear about the years-long process straight from the farmers. They’ll let you puff a few to taste the difference in the variations the traditional way, the tip dipped in honey for sweetness, paired with a native mojito or fresh sugarcane or fruit juice.

Can you bring Cuban cigars back to the US? I never got a straight answer on this – so do it if you dare. Read my full experience here. 

From there, it’s off to the caves. There are two in Vinales, but the one we visited was Cave India, which has a river running through it. You’ll get a taste of the indigenous culture and can actually take a short boat cruise under the stalagmites and stalactites.

Before heading back to Havana, you’ll make one final stop at Mural of Prehistory. Depicting prehistoric dinosaur life and the evolution of life in Cuba, it’s one of the largest open-air paintings in the world. If you have time, jump on a horse as a beautiful way to tour the valley.

When you make it back, enjoy dinner at a paladare. San Cristobal is a celebrity magnet, with every inch of wall covered in quirky antiques and photographs. They’ve served everyone from Beyonce and were put on the map by Obama’s iconic visit. Reservations are highly recommended.

Overnight: Casa Particular

Day 3: Beach, Please 

Enjoy breakfast at your casa particular.

What would an island be without a little beachin’? Instead of sunning and sanding, we satisfied the “people-to-people” requirement with an active Airbnb snorkel tour of Playa de Estes, the closest beach to Havana. You’ll swim out 200 meters in search of one of two nearby shipwrecks. Depending on the conditions, it’s not the most relaxing activity, but it is a way to get wet and wild “legally” with a great couple of locals for a morning dip.

Once you’ve worked up an appetite, enjoy lunch at a paladare like Mojito-Mojito.

This afternoon, book a classic car with a local guide to tour the island for the photo shoot of your dreams. We requested a Barbie pink convertible, and it did not disappoint. Drive the Malecon, the 5-mile beach boardwalk, wind blowing in your hair en route to Fusterlandia, which was inspired by Gaudi’s mosaic city in Barcelona. After you’ve lived your best cover girl life, drive through Almendares Park, where the rainbow classic cars congregate. You could spend hours wandering the “fairy forest”– it’s beautiful, romantic, and a natural oasis hidden right in the heart of Havana.

Have the car drop you off at El Floridita, Hemingway’s famous hangout for happy hour. The iconic daiquiri spot is always hopping with people grooving to live music.

For your last night, if you can get a dinner reservation, head to the most romantic rooftop in town: La Guarida Paladare, which consistently tops the list of best restaurants in Cuba. 

For a nightcap, it’s off to the Cuban Art Factory (Fabrica de Arte Cubano), which is part gallery, part pop-up, part nightclub, and ever-changing space. It’s a vibe that really embodies the creative energy of the island.

Overnight: Casa Particular

Have More Time? Looking for More Ideas?

• Take a day trip to Trinidad, another UNESCO World Heritage Site that’s a cross between white sand beaches and colonial Caribbean charm.
• See the art and murals at Callejon de Hamel – a colorful alley full of street art and sculptures. 
• Take the ferry to Morro Castle – one of the oldest Cuban castles and fortresses. 
• Sign up for a Cuban cooking class or salsa lesson.
• Shop at Almacenes San José – an indoor vendor market of artisan crafts and the best place for handmade souvenirs 
• Tour the Havana Club Rum Distillery – Drink up and sip the local beverage.
• Visit the Hemingway Museum – learn about the acclaimed writer and follow in the footsteps of his inspiration.