Trip highlights
- 1Havana Vieja — UNESCO Baroque colonial city
- 2Classic car tour of Malecón at sunset
- 3Valle de Viñales tobacco farm
- 4Trinidad cobblestone colonial streets
- 5Live Buena Vista Social Club-era son cubano
Daily spend
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Day-by-day plan
Arrive Havana
Sunday, January 10
Est. spend
$120
per person
🌅 Morning
Arrive José Martí International Airport
José Martí International Airport, Rancho Boyeros
HAV airport is 25km from Havana Vieja. Official taxis (registered yellow cabs) cost CUP 2,500–3,000 ($25–30). Private taxi (almendrones) from the unofficial rank are cheaper but agree price firmly. Staying in a casa particular (private home B&B) is the authentic Cuba accommodation choice.
CRITICAL: Cuba operates a dual currency system. CUP (Cuban Peso) is the local currency. All tourist transactions are now in CUP. US cards DO NOT work in Cuba (no Visa, Mastercard, or Amex). Bring all cash you need for the trip in EUR or CAD (not USD due to 10% surcharge). Exchange at CADECA exchanges, not hotels.
☀️ Afternoon
Havana Vieja UNESCO walking tour
Havana Vieja, Havana, Cuba
The historic core of Havana — Plaza de la Catedral (18th-century Baroque cathedral), Plaza de Armas (the oldest square, bookstalls), Plaza Vieja (the most photogenic square), and the Obispo pedestrian street. The buildings are crumbling and magnificent simultaneously.
The official Havana guide app (available offline) gives excellent self-guided walking tour information. A licensed guide adds context unavailable elsewhere — ask your casa particular host to recommend one.
🍽️ Meals
La Guarida, Havana Centro
Cuban · $35 · The most famous restaurant in Cuba — in a crumbling Havana tenement building, used as a location in the film Fresa y Chocolate (1993). The ropa vieja (shredded beef) and the lobster are both excellent. Book ahead.
Havana — Malecón and Classic Cars
Monday, January 11
Est. spend
$160
per person
🌅 Morning
Hemingway sites — La Bodeguita and La Floridita
Empedrado 207 (La Bodeguita) / Obispo 557 (La Floridita), Havana
Ernest Hemingway's two favourite Havana bars — La Bodeguita del Medio (the original mojito bar, crowded and tourist-heavy but historically significant) and La Floridita (the birthplace of the daiquiri, bronze Hemingway statue at the bar). Both on Obispo street in Havana Vieja.
A mojito at La Bodeguita costs $5 (the most expensive drink in Cuba). The bar is genuinely historic — Graham Greene, Gabriel García Márquez, and Nat King Cole all sat here.
☀️ Afternoon
Classic car Malecón tour at sunset
Malecón, Havana
The 8km Malecón sea wall is Havana's open-air living room — in a 1956 Chevrolet Bel Air convertible (hire from $35/hour), driving the Malecón at sunset with the sea spray and crumbling buildings is the definitive Havana experience.
Classic car hire is everywhere near the Parque Central. Negotiate the hourly rate (CUP 2,500–3,500/$25–35) for an open-top American car of your choice — the 1958 Impala convertibles are the best.
🌙 Evening
Casa de la Música — live Cuban music
Casa de la Música, Calle 20 #3308, Miramar, Havana
The best live Cuban son, rumba, and salsa performance in Havana at the Casa de la Música Miramar — professional musicians and dancers performing the music made famous by the Buena Vista Social Club. Cover $15–20.
The Fabrica de Arte Cubano (FAC) on Friday–Sunday nights is the most creative contemporary Cuban art and music venue — visual art, performance, and live music in a former oil factory. Entry CUP 200 ($2).
🍽️ Meals
Paladar La Fontana, Miramar
Cuban · $30 · Excellent paladar (private restaurant) in the Miramar district. The lobster (when available) is extraordinary value at $20.
Havana Museums & Forts
Tuesday, January 12
Est. spend
$80
per person
🌅 Morning
Museo de la Revolución
Refugio 1 e/Zulueta y Monserrate, Havana
The former Presidential Palace houses the history of the Cuban Revolution — the actual Granma yacht (the boat that brought Castro and 81 rebels from Mexico in 1956) in its own memorial pavilion behind the museum. Entry $8.
The museum is presented from the revolutionary perspective — the 'Wall of Shame' displaying Reagan, Bush, and Batista satirically is one of the most unusual museum exhibits in the world.
☀️ Afternoon
Fortaleza de San Carlos de la Cabaña
La Cabaña, East Havana
The massive 18th-century fortification on the hill across the bay — the largest Spanish colonial fortress in the Americas. The nightly cañonazo (9pm cannon firing ceremony) has been performed every night since 1674. Entry $8.
Cross to La Cabaña by ferry from the Old Havana waterfront (5 CUP / $0.05) — one of the best deals in Cuba. The evening cannon ceremony at 9pm is spectacular and free once inside.
🍽️ Meals
Café El Escorial, Plaza Vieja
Cuban café · $10 · The best coffee in Cuba (proper espresso, not the bitter Cuban sludge) and good food. The Cuban coffee experience is worth understanding.
Valle de Viñales
Wednesday, January 13
Est. spend
$130
per person
🌅 Morning
Drive to Valle de Viñales — tobacco country
Valle de Viñales, Pinar del Río Province
The UNESCO landscape 3 hours west of Havana — dramatic limestone mogotes (steep-sided hills) rising from the flat tobacco valley, subsistence farms, and the world's finest tobacco grown in red-soil fields. The best Cuban cigars come from this valley.
Private taxi from Havana: CUP 3,500/$35 one way (shared taxi from Viazul Bus Terminal is cheaper). Stay overnight in Viñales — the casas particulares are excellent.
☀️ Afternoon
Tobacco farm visit and cigar rolling
Tobacco farms, Valle de Viñales
The working tobacco farms welcome visitors — farmers explain the cultivation, drying, and fermentation process, then demonstrate hand-rolling a Habano cigar. Buy directly from the farmer (much cheaper than official cigar shops).
The best tobacco farms are accessible on foot or by hired horse from the Viñales town centre. Your casa host will direct you to a specific farmer they trust.
🌙 Evening
Sunset at the mogotes viewpoint
Hotel Los Jazmines, Carretera a Pinar del Río, Viñales
The Gran Hotel Los Jazmines pool terrace gives the classic Viñales view — the entire valley visible with the limestone mogotes glowing at sunset.
You don't need to be a hotel guest to use the terrace — buy a drink at the bar (CUP 500/$5) and watch the sunset.
🍽️ Meals
Casa del Vegano, Viñales
Cuban · $15 · The most reliably good restaurant in Viñales. The ropa vieja and the corn tamales are excellent.
Viñales Hike & Drive to Trinidad
Thursday, January 14
Est. spend
$150
per person
🌅 Morning
Mogotes hike — Los Aquáticos and caves
Valle de Viñales, Cuba
The day hike circuit from Viñales town through the tobacco fields and up the mogotes walls — 4 hours, moderate difficulty, guide required for the cave sections. The Cueva del Indio (indigenous cave with underground river) is accessible by motor boat.
☀️ Afternoon
Drive to Trinidad
Trinidad, Sancti Spíritus Province, Cuba
Trinidad is 5.5 hours east of Viñales — the most perfectly preserved colonial town in Cuba (UNESCO). The drive passes through Santa Clara (Che Guevara's mausoleum).
Stop at the Che Guevara Mausoleum in Santa Clara — a complex of memorials and museum to Che, whose remains were repatriated from Bolivia in 1997. Free entry.
🍽️ Meals
Casa del Campesino, Santa Clara
Cuban · $10 · Good roadside lunch near Santa Clara.
Trinidad Colonial Town
Friday, January 15
Est. spend
$115
per person
🌅 Morning
Trinidad UNESCO city walk
Trinidad, Sancti Spíritus Province
The most intact colonial city in the Caribbean — cobblestone streets that actually are 18th-century cobblestones (carriage ruts and all), the Plaza Mayor with its elegant mansions converted to museums, and the Iglesia de la Santísima Trinidad. Entry to most museums: $2–5.
The Museo Romántico in the Palacio Brunet (Plaza Mayor) has the finest colonial interior in Cuba — French crystal chandeliers, Chinese porcelain, and Wedgwood in a 19th-century Cuban mansion. Entry $2.
☀️ Afternoon
Playa Ancón — Trinidad's beach
Playa Ancón, Trinidad, Cuba
Playa Ancón is 12km from Trinidad — one of the best beaches in Cuba. White sand, calm turquoise water, and completely uncrowded on weekdays. Taxi there and back: CUP 600 ($6).
🌙 Evening
Casa de la Música Trinidad — steps concert
Callejón de Galdós, Trinidad, Cuba
The Trinidad Casa de la Música is a unique venue — an outdoor staircase concert hall where live Cuban music (son, guaracha, bolero) fills the plaza every evening from 9pm. One of Cuba's most atmospheric cultural experiences. Entry CUP 200 ($2).
🍽️ Meals
Restaurant Sol Ananda, Trinidad
Cuban · $20 · Excellent paladar in a colonial house courtyard. The lobster ranchera is outstanding.
Return to Havana & Departure
Saturday, January 16
Est. spend
$100
per person
🌅 Morning
Trinidad to Havana — Viazul bus or taxi
Trinidad Bus Terminal → Havana Airport
Viazul tourist bus Trinidad to Havana: 6 hours, $22. Private taxi: CUP 4,000/$40, 4.5 hours and much more comfortable. Allow 4 hours before international departure from HAV.
Book Viazul bus seats at viazul.com 3+ days ahead in high season — they sell out. Private taxi is more flexible but agree price before departure.
🍽️ Meals
Final mojito at Hotel Nacional bar, Havana
Cuban bar · $15 · The Hotel Nacional terrace bar overlooking the Malecón and the sea. Churchill, Sinatra, and Meyer Lansky all sat here. Mohito and a cigar for the farewell.
Before you go
📅 Best time to visit
November–April: dry season, temperatures 25–30°C. January–February is the coolest and most comfortable. The Havana Carnival (July–August) is extraordinary. The hurricane season (June–October) is unpredictable.
🛂 Visas
Tourist card (Tarjeta del Turista) required — $75–85 depending on where purchased. Buy at the check-in desk when purchasing your flight. US citizens: travel must fall under a legal category (people-to-people, support for Cuban people, etc.) — the regulations change; check the latest OFAC guidelines. Most nationalities have no restrictions.
💱 Currency
CRITICAL: No US credit or debit cards work in Cuba. No Visa, Mastercard, Amex. Bring EUR or CAD cash for the entire trip. Exchange at CADECA offices (better rates than hotels). Budget $80–120/day per person for comfortable travel. CUP is the only currency since the 2021 unification — do not exchange to the old CUC.
🆘 Emergency numbers
police: 106
ambulance: 104
tourist emergency: (7) 863-0121
💬 Things you won't find in a guidebook
- Internet access is limited and expensive in Cuba — WiFi cards purchased at ETECSA offices ($1.50/hour) are the only option, and connectivity is slow. Plan for a largely offline trip.
- The black market (el mercado negro) offers better exchange rates but is technically illegal. Most tourists who use it report no problems — but understand the legal risk.
- Paladares (private restaurants) have dramatically better food than state restaurants. Your casa host will recommend the best local ones — always better than tourist restaurants.
One thing worth not skipping
A 7-day trip to Cuba without insurance is a gamble. Medical emergencies, cancelled flights, lost luggage — cover yourself before you leave.
Comprehensive cover for 150+ adventure activities, medical evacuation, trip cancellation, and baggage. Recommended for most travellers.
Subscription-based travel medical insurance. Best for longer trips, digital nomads, or frequent travellers. Renews weekly or monthly.
Tripzeeker earns a small commission when you purchase — at no extra cost to you.
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