Cuba in five days, Havana to the Viñales Valley and back: colonial plazas and a cigar factory, a two-hour convertible tour and a night at the Tropicana, then tobacco farms and a cave river out west. Real hotels, real drive times, and 2026 prices for every stop.
Day 1Arrive in Havana
A short transfer into Old Havana, a sunset walk on the seawall, and a first dinner with live music before settling into a landmark hotel.
🚕 Airport Transfer — José Martí International Airport (HAV) to Old Havana
~50 minutes · $44 USD, fixed rate for up to 3 people
A flat-rate taxi covers the drive from Havana’s international airport into the colonial core — book ahead or arrange through your hotel to skip the negotiation line at arrivals.
Havana Airport Taxi · thehavanaairport.com
🌆 Malecón Sunset Walk
~1 hour, self-guided · Free
Havana’s five-mile seawall promenade is the city’s evening living room, with waves breaking over the wall, fishermen casting lines, and a skyline of crumbling pastel facades turning gold at dusk.
🍽️ Dinner — Café Taberna
~1.5 hours · Est. $25–$40 USD / person
A Buena Vista Social Club-themed restaurant on Plaza Vieja, dedicated to the singer Compay Segundo, with live son cubano most nights over classic Cuban dishes like ropa vieja.
Café Taberna
🛎️ Overnight — Hotel Nacional de Cuba
From $150–$220 USD / night, for 2 people
A 1930s landmark on a bluff above the Malecón, once host to Frank Sinatra and Winston Churchill, with palm-shaded gardens, a cannon-lined terrace, and a lobby bar that’s a Havana institution in its own right.
Hotel Nacional de Cuba · hotelnacionaldecuba.com
Day 2Old Havana
A walking day through the colonial core’s four grand plazas, a cigar factory tour, and dinner at Havana’s most famous paladar.
🏛️ Old Havana Walking Tour
~2.5 hours, self-guided · Free
A loop through Habana Vieja’s UNESCO-listed core connects Plaza de Armas, Plaza Vieja, Plaza de la Catedral, and Plaza San Francisco, past baroque churches, colonial mansions, and street musicians playing for tips.
🚬 Real Fábrica de Tabacos Partagás Tour
~30 minutes · Est. $10 USD / person
One of Cuba’s oldest working cigar factories, rolling hand-made habanos since 1845 — a short guided walk through the torcedores’ floor ends, as always, at the gift shop.
Real Fábrica de Tabacos Partagás
🏛️ El Capitolio
~1 hour, self-guided · Free to view the grounds and exterior
Modeled on Washington’s Capitol and completed in 1929, this was the seat of Cuba’s government before the revolution — the restored dome and grand front steps are the city’s most photographed backdrop.
🍽️ Dinner — Paladar La Guarida
~2 hours · Est. $35–$55 USD / person
Havana’s best-known private restaurant, set in a crumbling colonial mansion made famous by the film “Fresa y Chocolate” and visited by Barack Obama and Beyoncé — book a table on the rooftop terrace well in advance.
Paladar La Guarida · laguarida.com
Day 3Classic Cars & Tropicana
A vintage convertible tour of the city, an afternoon at a mosaic-tiled artist’s village, and a legendary cabaret to close out Havana.
🚗 Classic Convertible Car Tour
~2 hours · From $80 USD per car (up to 4 people)
A 1950s American convertible — a Chevy Bel Air or Buick Roadmaster, top down — with a driver-guide loops past the Capitolio, the Plaza de la Revolución, and the Malecón, radio playing and horn-honking encouraged.
🎨 Fusterlandia
~1.5 hours, self-guided · Free (donations welcome)
Artist José Fuster spent three decades covering his home neighborhood of Jaimanitas in a Gaudí-inspired sea of mosaic tile — rooftops, benches, and entire building facades now form Cuba’s most colorful outdoor art installation.
💃 Tropicana Cabaret
~2.5 hours · From $158 USD / person
An open-air cabaret running since 1939, with dozens of feather-and-sequin dancers moving through the palm trees under a canopy of lights — a welcome cocktail and rum are included with every ticket tier.
Tropicana Cabaret · tropicanacabaret.com
🛎️ Overnight — Hotel Nacional de Cuba
From $150–$220 USD / night, for 2 people
A third and final night at the Nacional before tomorrow’s drive west to the Viñales Valley.
Hotel Nacional de Cuba · hotelnacionaldecuba.com
Day 4Havana to Viñales
A scenic drive west into Cuba’s tobacco country, ending with a horseback ride through the farms below the valley’s limestone hills.
🚗 Private Transfer — Havana to Viñales
~2 hours 45 minutes · From $100 USD, private car for up to 3
The drive west leaves Havana’s suburbs behind for the red earth and royal palms of Pinar del Río province, arriving at the mogotes — steep-sided limestone hills — that ring the Viñales Valley.
🐴 Tobacco Farm & Horseback Ride
~3 hours · $35 USD / person
A horseback loop through a working tobacco vega stops at a farmer’s drying barn for a hand-rolled cigar demonstration and a taste of the valley’s coffee and honey rum, with the mogotes rising on every side.
🛎️ Overnight — Hotel Los Jazmines
From $70–$90 USD / night, for 2 people, breakfast included
A hilltop hotel with the valley’s best view, looking straight down over the tobacco fields and mogotes from every balcony — arrive in time for the terrace at sunset.
Hotel Los Jazmines
Day 5Viñales & Departure
A last look at the valley and an underground river before the drive back to Havana to close the loop.
⛰️ Viñales Valley Sunrise Viewpoint
~30 minutes, self-guided · Free
The Los Jazmines terrace itself is the valley’s classic sunrise view — morning mist usually still sitting in the fields below the mogotes.
🚣 Cueva del Indio
~45 minutes · $5 USD / person
A walking trail through a limestone cave leads to an underground river, crossed by a short boat ride to the cave’s far exit — one of the valley’s most popular stops, best visited before the midday tour buses arrive.
🚗 Private Transfer — Viñales to Havana Airport
~3 hours · From $100 USD, private car for up to 3
The return drive retraces the route back through Pinar del Río province to José Martí International Airport, with buffer time built in for Cuba’s often-slow check-in lines.
✈️ Departure — José Martí International Airport (HAV)
Self-guided
Closes a five-day loop that ran from Old Havana’s colonial plazas and a Tropicana cabaret night to the tobacco farms and cave rivers of the Viñales Valley — check international carriers’ recommended arrival times, typically 3 hours before departure.
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