Havana in 4 Days: Classic Cars, Rum & the Streets of Old Cuba
1950s Chevrolets, Hemingway's bar stool, Habana Vieja's UNESCO palaces, a Trinidad day trip, and the best live son music in the Caribbean. The complete 4-day guide.
Delhi · Visited: Kedarnath, Gangotri, Manali, Shimla, Rishikesh & more · April 2026 · 14 min read
Havana is unlike any other city — a perfectly preserved time capsule where 1950s American Chevrolets cruise past crumbling colonial palaces, where Hemingway's bar stool is still warm, and where the rhythm of son and salsa pours out of every doorway after dark.
⚡ What Havana Actually Is
Havana is the capital of the only country in the Western Hemisphere that remained outside the American economic orbit for 60 years — and it shows. The city was flash-frozen in 1959 when the Revolution cut off American investment and imports. The result is a city that looks, sounds, and feels utterly unlike anywhere else on earth: 18th-century Spanish colonial architecture slowly returning to the ground, 1950s American cars still running on improvised parts, and a population of 2.1 million who have developed their own sophisticated, resilient, deeply musical culture in the space between the ideology and the reality.
Habana Vieja — Old Havana — was declared a UNESCO World Heritage Site in 1982. It contains over 3,000 colonial-era buildings across four major plazas: Plaza de la Catedral, Plaza de Armas, Plaza Vieja, and Plaza de San Francisco de Asís. The Baroque cathedral, the 16th-century castles guarding the harbour entrance, the covered arcades and covered stone arcades of the old port district — all of it survived because Cuba simply couldn't afford to knock it down and replace it.
Four days lets you absorb Old Havana's UNESCO streets, drive the Malecón at sunset in a convertible, take the essential day trip to Trinidad, understand the rum and cigar culture from the inside, and find the live music that makes Havana the best city in the Caribbean after dark. The cash economy, the dual-currency hangover, and the infrastructure quirks are real — but navigable with the right preparation.
HAV (José Martí)
Airport
Nov–Apr
Best Season
UNESCO 1982
Old Havana
$60/day
Budget From
🌡️ Best Time to Visit Havana
Nov–Apr — Dry Season — Best Time
Recommended
22–28°C, low humidity, virtually no rain. This is when Havana is at its best — the light is golden, the streets are comfortable to walk all day, and the Malecón is alive with Habaneros every evening. December and January are peak tourist months; November and March offer the best balance of weather and crowd levels.
May–Jun — Shoulder Season — Viable
Good value
28–32°C with increasing humidity and afternoon showers. The city is less crowded and prices are lower. Morning exploration is very comfortable; afternoons can be oppressively hot and humid. The occasional heavy downpour transforms the colonial streets — atmospheric but inconvenient. Good budget option.
Jul–Oct — Hurricane Season — Caution
Check forecasts
Cuba sits in the hurricane belt. July–October brings heavy rainfall, high humidity (85%+), and the genuine possibility of tropical storms or hurricanes. September and October are the riskiest months. Some infrastructure — including the Trinidad road and coastal areas — can flood. Travel insurance covering weather cancellations is essential.
Dec–Jan — Peak Season — Book Ahead
Book in advance
The most popular period. Christmas and New Year in Havana are genuinely festive — street parties, live music everywhere, Cubans and tourists mixing freely. Casas particulares fill up 3–4 weeks in advance for this period. Book accommodation early and expect 20–30% higher prices. Worth it for the atmosphere.
✈️ Getting to Havana
Key detail: Havana José Martí International Airport (HAV) is 25km south-west of Old Havana. The official taxi from the airport to the city centre costs $25 USD (agree the price before getting in) and takes 30 minutes. State taxis are metered; private colectivo taxis are cheaper but require negotiation.
Fly into HAV — José Martí International Airport
Main entry pointDirect flights from London (Air France via Paris, Iberia via Madrid), Toronto, Mexico City (Aeromexico), and Panama City (Copa). No direct flights from the USA except from select US cities under authorized travel categories. From London: 10–11 hrs via European hub. From Toronto: 4.5 hrs direct (Air Transat, Sunwing, Air Canada). From Mexico City: 2.5 hrs direct.
Airport to City — Taxi ($25, 30 min)
Standard transferOfficial airport taxis (yellow cabs) charge a fixed $25 to central Havana and Old Havana. Agree the fare at the taxi stand before departure — don't accept approaches inside the terminal. The journey takes 30 minutes in normal traffic. The highway approach into Havana gives you your first views of the Malecón and the city skyline.
Airport to City — Colectivo Taxi (CUP 200, shared)
Budget optionShared colectivo taxis (CUP 20–50 per person depending on direction) run between the airport and central Havana. Ask at the colectivo stand outside the domestic arrivals hall. These are classic American cars stuffed with 4–5 passengers heading in the same direction. Cheaper, slower, and a genuine introduction to how Habaneros get around.
Tourist Card — Required Before Boarding
Essential documentAll visitors need a Cuban Tourist Card ($25–30 USD). Most airlines sell it at check-in or the departure gate. It's a paper card you keep with your passport throughout your stay — not a visa sticker. Cuba also legally requires proof of health insurance for all visitors; most airlines include basic coverage in the ticket. Verify before departure.
📅 4-Day Havana Itinerary
Each day card is expandable. The itinerary runs from Old Havana outward — covering the UNESCO core, the Malecón and Vedado, Trinidad day trip, and the arts, rum and music scene on Day 4.
- ●Arrive and check into a casa particular — a private homestay with a Cuban family, $25–50/night, marked by a blue anchor sign outside the door. Staying in a casa is categorically better than a state hotel: you get home-cooked breakfast (fresh mango, black beans, eggs, strong Cuban coffee), a local host who knows the city, and money that goes directly to a family rather than the state.
- ●Old Havana morning — Plaza de la Catedral: the Baroque cathedral (free entry) and the surrounding 18th-century colonial palaces are among the finest architecture in the Americas. Arrive at 9am before the heat and the crowds. The square fills with artists, musicians, and cigar sellers by mid-morning — the photography is excellent in the early light.
- ●Plaza Vieja — the most photogenic square in Havana, surrounded by restored colonial buildings in yellow, blue, and terracotta. The Camera Obscura on the corner ($2, top-floor panoramic view of Old Havana) is genuinely underrated. The Belgian-style craft beer brewery at the corner of the square is the only one in Cuba.
- ●El Capitolio — Cuba's 1929 Capitol building, modelled on Washington DC but actually taller. Entry to the main hall costs $6; the exterior is free and architecturally stunning. Parque Central directly opposite is where the best collection of vintage American cars congregates for taxi fares.
- ●Evening — book a vintage car ride for sunset ($20–30/hour in an open-top 1950s Chevrolet, Buick, or Ford). Drive the Malecón at golden hour with the sea crashing against the seawall — this is one of the great city experiences in the Caribbean. Agree the price and route beforehand.
- ●Morning — walk the Malecón seawall (8km from Old Havana to Vedado district, completely flat, free). Havana's great promenade is where everyone comes: fishermen casting lines at dawn, couples at dusk, musicians at night. The crumbling pastel buildings behind the seawall and the blue-green sea ahead frame one of the most cinematic urban walks in the world.
- ●Revolution Square (Plaza de la Revolución) — the vast concrete plaza where Fidel Castro addressed crowds of over a million. The Che Guevara steel silhouette on the Interior Ministry building is the most-photographed image in Cuba. The square is free. José Martí Memorial: take the elevator to the top ($5) for a 360° panoramic view over the city from 142 metres.
- ●Vedado neighbourhood lunch at a paladar — La Guarida (Concordia 418, between Gervasio and Escobar) is Cuba's most famous private restaurant, set in a crumbling Havana mansion used in the film Fresa y Chocolate. The peeling frescoed walls and the dark staircase are part of the experience. Lunch $15–25, dinner $25–40. Book ahead.
- ●Hemingway pilgrimage — La Bodeguita del Medio (Calle Empedrado 207): Hemingway's mojito bar, walls covered in 70 years of scrawled signatures. Touristy, yes — the mojitos are excellent ($6–8). Then: El Floridita (Obispo 557), the bar that invented the frozen daiquiri. Hemingway's regular stool is marked by a bronze statue. Daiquiris $8–12. Live band plays from 11am.
- ●Evening — Fábrica de Arte Cubano (FAC, Calle 26 and 11, Vedado, CUP 200, ~$8) opens Thursday through Sunday from 8pm. The converted vegetable oil factory is Havana's premier arts complex: multiple gallery spaces, live music stages, film screenings, and bars all running simultaneously. The most exciting cultural venue in Cuba.
- ●Early morning bus to Trinidad (5 hours, $10–15 with Viazul) or shared colectivo taxi ($25–35 for faster, more comfortable 2.5-hour journey). Trinidad is the best-preserved colonial city in Cuba — founded in 1514, it barely changed between 1850 and 1990. The cobblestone streets, pastel houses, and horse-drawn carriages create an atmosphere unlike anywhere else in the Caribbean.
- ●Plaza Mayor — Trinidad's central square surrounded by the Museo de Arte Colonial (a perfectly restored 18th-century mansion with original furniture, $2), the Iglesia Parroquial Mayor church (free), and the Palacio Brunet. The square is paved with the same grey cobblestones that have been here since colonial times.
- ●Valley of the Sugar Mills (Valle de los Ingenios, UNESCO) — the 78 ruined sugar mills that made Trinidad the wealthiest city in Cuba in the 19th century. Taxi tour $20–25. Climb the Iznaga Tower (45m, $1) for views over the valley — the plantation bell that called enslaved workers to the fields still hangs at the top.
- ●Afternoon — Casa de la Música in Trinidad for afternoon salsa. The steps of the Iglesia become an outdoor music venue. CUP 50 entry ($2). Local Cuban couples dance here as naturally as they walk — this is not a performance for tourists but real Trinidad social life. Go at 3pm when it starts.
- ●Return to Havana on the evening Viazul bus or stay overnight in Trinidad at a casa particular ($25–35/night — the old colonial houses are excellent value and the city at night, after the day-trip buses have left, belongs to the Trinidadeños).
- ●Morning — Museo del Ron Havana Club (Avenida del Puerto 262, between Sol and Muralla). The 30-minute guided tour ($7, includes a mojito at the end) walks through the sugar-to-rum process using original 19th-century distillery equipment. Havana Club 7 Años Añejo is the benchmark Cuban rum — buy a bottle at the museum shop for less than anywhere else in the city.
- ●Museum of the Revolution (Museo de la Revolución, CUP 100, ~$4) — housed in the former Presidential Palace with original bullet holes still visible in the walls from the 1957 attack on Batista. The yacht Granma (in which Castro and 82 revolutionaries sailed from Mexico in 1956) is preserved in a glass pavilion outside. Unapologetically one-sided and genuinely fascinating.
- ●Coppelia ice cream parlour (Calle 23 and L, Vedado) — Havana's legendary 1960s state ice cream palace, subsidized to CUP 10–20 per portion (less than $1). There are two queues: a tourist fast-track ($1 entry) and the Cuban queue (20–40 minute wait, free). Wait in the Cuban queue. It's one of the great slow-travel experiences — watching Cuban families eat ice cream under a concrete Space Age pavilion on a hot afternoon.
- ●Afternoon — Street art in Havana Centro: Callejón de Hamel, a narrow alley of murals and Afro-Cuban religious art created by artist Salvador González Escalona over 30 years. Weekend rumba performances (free, 11am Sundays). The alley is also a living Santería shrine — the artistic and the religious are inseparable here.
- ●Farewell — final live son or salsa at Casa de la Música (Galiano 267, Vedado, $5–10 cover). The real son — pre-Buena Vista, pre-tourist-show — is played in small bars and terraces throughout Havana most evenings. Ask your casa particular host which bar has the best músicos playing on your last night. They will know.
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🏛️ Havana Landmark Guide
The essential sites in order of priority. All Old Havana plazas are free to enter; museum fees noted individually. CUP prices at the approximate 2026 rate of $1 ≈ CUP 25.
Habana Vieja (Old Havana)
The UNESCO World Heritage core: four major plazas (Catedral, Armas, Vieja, San Francisco), the old harbour, and over 3,000 colonial buildings from the 16th to 19th century. You can walk the entire historic centre in 3–4 hours; allow more for exploring individual plazas and buildings.
Malecón Seawall Promenade
The 8km seafront promenade running from Old Havana to Vedado. The social spine of the city — everyone from fishermen to lovers to musicians congregates here. Best at sunset and after dark, when the crumbling buildings glow and the sea spray catches the last light.
Revolution Square — José Martí Memorial
The vast plaza of the Cuban Revolution, dominated by the José Martí monument. Take the elevator 142 metres to the top for the best 360° panoramic view in Havana. The Che Guevara and Camilo Cienfuegos steel outlines on facing ministry buildings are the most iconic images in Cuba.
Fábrica de Arte Cubano (FAC)
Havana's leading contemporary arts complex in a converted vegetable oil factory. Open Thursday–Sunday from 8pm, closing around 3am. Multiple gallery spaces, live music stages running simultaneously, film screenings, and bars. The most exciting cultural venue in Cuba — miss it and you've missed modern Havana.
El Floridita — Hemingway's Daiquiri Bar
The bar that invented the frozen daiquiri and Hemingway's regular haunt from 1932–1960. His bronze statue occupies his favourite stool at the end of the bar. The drinks are excellent, the live band plays from 11am, and it earns its tourist reputation. Obispo 557.
La Bodeguita del Medio
Hemingway's mojito bar on Calle Empedrado 207 since 1942. The walls are so covered in decades of visitor signatures that new ones are written over old ones. Touristy and proud of it — the mojitos are genuinely good and the bar is genuinely historic.
Ron Santiago / Museo del Ron Havana Club
The Havana Club rum museum on Avenida del Puerto. A 30-minute guided tour through original 19th-century distillery equipment, ending with a mojito. Buy Havana Club 7 Años Añejo at the shop — cheaper here than anywhere in the city. Recommended for anyone with any interest in rum.
Tropicana Cabaret
Cuba's legendary open-air cabaret show, running since 1939 in the same Miramar venue. Sequined dancers, live orchestra, aerial acts under the palm trees. Touristy and expensive by Cuban standards — but the production is spectacular and the setting unique. Book through your casa or a tour agency.
Havana — Classic Cars, Colonial Streets & the Malecón
The Caribbean's most cinematic city, frozen in a beautiful contradiction.
📸
Classic 1950s Cars on the Malecón
Classic 1950s Cars on the Malecón
The image that defines Havana — a 1955 Chevrolet Bel Air convertible cruising the Malecón with the sea and crumbling colonial skyline behind.
💰 Havana Budget Breakdown
Cuba operates a complex currency system. In 2026 the Cuban Peso (CUP) is the official currency at ~$1 = CUP 25 official rate. Tourist prices are often quoted in USD or CUC-equivalent. The most practical approach: bring euros or Canadian dollars (better rates than USD), exchange at a CADECA office, and use CUP for street food, colectivos, and local bars.
| Category | 💰 Budget | ✨ Mid-Range | 💎 Luxury |
|---|---|---|---|
| 🏨 Accommodation | $25–50/night | $80–180/night | $300–800/night |
| 🍽️ Food | $15–25/day | $35–60/day | $70–150/day |
| 🚗 Transport | $5–15/day | $20–40/day | $50–150/day |
| 🎭 Activities | $10–20/day | $30–60/day | $80–200/day |
| TOTAL per day | $60–110/day | $165–340/day | $500–1,300/day |
💚 Budget ($60–110/day)
Casa particular ($25–50), eat at paladares and street food, use colectivo taxis (CUP 20–50), buy a ETECSA WiFi card (CUP 30/hr). Completely comfortable in Havana — the backpacker and budget infrastructure is genuinely good.
🌟 Mid-Range ($165–340/day)
Premium casa particular or boutique hotel ($80–150), dine at La Guarida and Café Madrigal, hire a vintage car for sunset ($30/hr), take a private guide for Old Havana. This is the sweet spot for Havana.
💎 Luxury ($500–1,300/day)
Gran Hotel Manzana Kempinski ($400–800/night), private guides and boat charters, Tropicana cabaret, private rum masterclasses, and exclusive Partagás cigar factory access arranged through the concierge.
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🏨 Where to Stay in Havana
The single most important accommodation decision in Cuba: stay in a casa particular, not a state hotel. Casas are private homes licensed to rent rooms — marked by blue anchor signs. The food, the local knowledge, and the human connection they provide are irreplaceable. State hotels charge similar prices for a worse experience.
Casa 1932
Boutique casa particular · Old Havana
One of Havana's most celebrated casas — an Art Deco mansion from 1932 on Campanario street, perfectly preserved with period furniture, stained glass, and antique fittings. Three rooms, personal service, and breakfast served in a dining room that looks like a film set. Book weeks in advance in high season.
La Casa Blanca Habana
Premium casa particular · Vedado
A restored colonial house in Vedado with a rooftop terrace overlooking the neighbourhood. Six rooms, private bathrooms, strong WiFi (rare in Havana casas), and a host family with excellent English. The Vedado location is quieter than Old Havana and better positioned for the Malecón and Revolution Square.
Gran Hotel Manzana Kempinski
5-star luxury · Parque Central
Cuba's only internationally managed 5-star hotel, in the restored 1910 Manzana building (Havana's first shopping arcade). Rooftop pool overlooking the city, the best breakfast in Havana, and a concierge who can arrange the experiences that money can open in Cuba. The benchmark for luxury accommodation on the island.
Budget Casas Particulares — Old Havana
Budget casa · Habana Vieja
Dozens of licensed casas operate in Old Havana offering clean, simple rooms with breakfast for $25–50/night. Look for the blue anchor sign. The best cluster around Obispo, Obrapía, and the area between Plaza Vieja and Plaza de la Catedral. Ask the host for the latest guidance on currency and local tips — this information is not in any guidebook.
🍽️ Where to Eat in Havana
Always eat at a paladar — a private restaurant — rather than a state-run restaurant. The quality difference is enormous. Paladares are legal, licensed, and provide far better food and service. The word entered Cuban Spanish from a TV soap opera and stuck.
La Guarida
Iconic paladar · Concordia 418, Centro Habana
Cuba's most famous private restaurant, set in a crumbling colonial mansion used in the 1993 film Fresa y Chocolate. The peeling frescoed staircase and the rooftop terrace with Old Havana views are as much the experience as the food. Ropa vieja, lobster, and a wine list. Lunch $15–25, dinner $25–40 per person. Book 2–3 days ahead.
El del Frente
Rooftop paladar · O'Reilly 303, Old Havana
Four floors above O'Reilly street with a rooftop terrace overlooking Old Havana rooftops. Cuban cocktails, grilled fish, and a menu that updates with the seasons — unusual for Havana. The rooftop at golden hour is genuinely spectacular. $12–20 per person. More relaxed vibe than La Guarida.
Café Madrigal
Wine bar paladar · Calle 2, Vedado
An intimate paladar in a Vedado house with mismatched antique furniture, imported wine (rare in Havana), and a creative menu of Cuban dishes with European influences. Popular with the Havana arts and intellectual crowd — the most European-feeling restaurant in Cuba. $15–25/person. Reservations recommended.
Street Food — Mercado Agropecuario
Local market · Various locations
Havana's produce markets (agropecuarios) sell food at CUP prices for Cubans — ripe fruit, fried snacks, sandwiches, and fresh juice at CUP 20–100 ($0.80–4). The market at Tulipán and the 19 y B market in Vedado are the most accessible. This is how most Habaneros eat — and the empanadas and tamales are excellent.
El Floridita & La Bodeguita del Medio
Historic bars · Old Havana
El Floridita (Obispo 557) for a frozen daiquiri at Hemingway's bar — $8–12, worth every cent for the setting. La Bodeguita del Medio (Empedrado 207) for a mojito — $6–8. Both are unavoidably touristy and both are genuinely good. Do both, back to back, on Day 2.
Where to Stay in Havana Cuba
Verified prices · Instant booking
Gran Hotel Manzana Kempinski
5-star luxury · Parque Central
Iberostar Parque Central
4-star hotel · Old Havana
Hotel Saratoga
Boutique hotel · El Capitolio
Casa Particular Old Havana
Private homestay · Habana Vieja
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Things to Do in Havana Cuba
Tours & experiences · Instant confirmation
Old Havana Walking Tour
Best introClassic Car Tour — Malecón at Sunset
Iconic HavanaTrinidad Day Trip from Havana
Must doRum & Cigar Tasting Experience
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❌ Mistakes to Avoid in Havana
Staying Only in Havana and Missing Trinidad
Nearly every first-time visitor to Cuba makes this mistake — staying in Havana for all 4 days and skipping Trinidad. Trinidad is one of the best-preserved colonial cities in the Americas: cobblestone streets, pastel mansions, and a working Cuban community that has been living inside a UNESCO World Heritage Site since 1514. The Viazul bus is $10–15 and takes 5 hours. A shared colectivo taxi is $25–35 and takes 2.5 hours. There is no excuse. Trinidad is unmissable.
Staying in State Hotels Instead of Casas Particulares
Cuba's state-owned hotels charge similar prices to casas particulares but deliver significantly worse service, worse food, and no genuine Cuban experience. A casa particular gives you a Cuban family as hosts, home-cooked breakfast (ripe mangoes, fresh juice, eggs, black beans — the best breakfast in the Caribbean), local knowledge unavailable in any guidebook, and money that goes directly to a family rather than the state. Always choose casas particulares.
Relying on Cards — Cuba is a Cash Economy
Non-US bank cards work at some Havana ATMs and larger hotels — but Cuba's banking infrastructure is unreliable and machines run out of cash. US bank cards do not work anywhere in Cuba. Always carry enough cash (euros or Canadian dollars convert best) for 2–3 days. Split your cash: bulk in your hotel safe, daily float in a front pocket, and an emergency backup stash in your bag. Petty theft is real in tourist areas — don't carry everything in one place.
Eating at State Restaurants
The distinction between state-run (gobierno) and private (paladar) restaurants is everything in Havana. State restaurants are cheaper but deliver food of noticeably lower quality with indifferent service. Paladares — private family restaurants — invest in their reputation because their livelihood depends on it. The price difference is small ($5–10/person) and the quality difference is enormous. La Guarida, El del Frente, and Café Madrigal are all paladares.
💡 Pro Tips for Havana
Vintage Car at Golden Hour — the Malecón Photograph
The iconic Havana image — a 1955 Chevrolet Bel Air convertible cruising the Malecón at sunset — requires timing. Book your vintage car tour to start 90 minutes before sunset ($20–30/hour, agree price and route beforehand). The late afternoon light turns everything amber. This is the single best hour you will spend in Havana.
Trinidad's Casa de la Música — Most Authentic Salsa in Cuba
The tourist salsa shows in Havana are professionally performed but feel staged. Trinidad's Casa de la Música — the steps of the Iglesia at the top of the cobblestone square — is where Cubans actually dance: couples who've danced together for 20 years, children learning from grandparents. CUP 50 entry ($2). Go at 9pm. Stand at the edge for 5 minutes and someone will ask you to dance.
Coppelia — Wait in the Cuban Queue
There are two queues at Coppelia: a fast tourist queue ($1 entry, no wait) and the Cuban queue (free, 20–40 minute wait). Wait in the Cuban queue. The wait is how you meet Habaneros — families, couples, elderly men in guayabera shirts who have been coming every Sunday for decades. The ice cream is CUP 10–20 ($0.40–0.80). The experience of eating it in a concrete 1960s Space Age pavilion with Cuban families is extraordinary.
Internet — Buy ETECSA Cards Before You Need Them
Cuba's internet is state-controlled and limited. Buy ETECSA WiFi cards (CUP 20–30/hour) from ETECSA offices or from street vendors at a small markup — don't wait until you desperately need internet. The cards work at any ETECSA hotspot (look for people on phones in plazas). Download offline maps, translation apps, and guidebook content before arrival.
Find the Real Son Cubano — Ask Your Casa Host
The Buena Vista Social Club shows at tourist venues ($15–30 entry) are polished and enjoyable. But real son cubano is played in small neighbourhood bars, terraces, and casas de la cultura every evening for CUP 50–100. Your casa particular host knows exactly which bar has the best musicians on which night. Ask them the evening before and they will give you better advice than any travel app.
Currency — Exchange at CADECA, Not at Hotels
CADECA exchange houses (blue signs, found near major tourist areas) give significantly better rates than hotel lobbies for exchanging euros and Canadian dollars into CUP. Bring euros or Canadian dollars — the USD exchange incurs a 10% surcharge due to US sanctions. Exchange a moderate amount at a time since CUP is not easily convertible outside Cuba.
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