Chrome and Cobblestones — A Central Cuba Road Trip
A driver-guided vintage-car journey through central Cuba: Havana's boulevards, central Santa Clara, French-built Cienfuegos, cobblestoned Trinidad, and time-frozen Remedios.
For: Couples and small groups, photography fans
1 · Budget first
A transparent, itemised estimate for 2 travellers · 9 nights · comfort tier. Every line is a planner range in USD — an estimate to budget with, not a quote.
| International airfare | $600 – $1,900 |
| Entry documents (tourist card) | $60 – $150 |
| Travel insurance | $80 – $300 |
| Accommodation | $630 – $1,350 |
| Local transportation | $770 – $1,505 |
| Food | $720 – $1,404 |
| Guides & activities | $720 – $1,620 |
| Connectivity | $30 – $110 |
| Tips | $45 – $180 |
| Water, laundry & sundries | $27 – $108 |
| Emergency reserve | $308 – $1,009 |
| Total (2 travellers) | $3,990 – $9,636 |
- Per traveller
- $1,995 – $4,818
- Per day
- $443 – $1,071
- Ground only (no airfare)
- $3,082 – $6,727
- Airfare est. / traveller
- $300 – $950
Basis: standard hotel · comfortable food · private driver · 9 guided days.
Adjust every number in the planner →Estimates in USD to help you budget — not observed prices, quotes or guaranteed availability. Most US cards don’t work in Cuba; carry cash and keep the reserve.
2 · Fly in
Newark / New Jersey (EWR) → Havana (HAV) — José Martí International
Cuba's principal international gateway — the only truly diversified one, with links across the Americas, Europe, Asia and Africa.
Example dates 2026-09-15 → 2026-09-24 (adjust on the live search). CubaAtlas books nothing — these open live results:
3 · Day by day
Where to sleep and dine each day is a real listing from the CubaAtlas provider dataset, nearest your base.
Morning
Arrive and meet your driver and his polished 1950s convertible.Afternoon
An open-top cruise of the Malecón, Vedado and Miramar's mansions.Evening
Dinner in Old Havana and a rum on a rooftop.
StayHotel Blau Arenal Habana Beach4★ · Grupo Cubanacán · La Habana(53 7) 77991200/ 77991274Website ↗Map →Source: Cuba Travel (MINTUR official portal)DinnerCantabria, Restaurante Hotel Armadores de SantanderCimex · Internacional · La Habana(537)8628000Map →Source: Cuba Travel (MINTUR official portal)Open Havana on the map →Nearby: Viñales, Varadero, MatanzasMorning
Walk the four plazas and the Capitolio with your guide.Afternoon
The fort across the harbour and a stop at a cigar factory.Evening
Live jazz in a cellar club, the car waiting at the door.StayHotel Blau Arenal Habana Beach4★ · Grupo Cubanacán · La Habana(53 7) 77991200/ 77991274Website ↗Map →Source: Cuba Travel (MINTUR official portal)DinnerCantabria, Restaurante Hotel Armadores de SantanderCimex · Internacional · La Habana(537)8628000Map →Source: Cuba Travel (MINTUR official portal)Open Havana on the map →Nearby: Viñales, Varadero, MatanzasMorning
Drive the central highway to Santa Clara, top down through the countryside.Afternoon
Parque Vidal, the Teatro La Caridad and the colonial centre.Evening
The city's bohemian nightlife and a late dinner.Morning
Short hop to little-visited Remedios, twin churches on a sleepy square.Afternoon
The parrandas fireworks museum and colonial lanes; a coastal detour to Caibarién.Evening
Village paladar dinner on the plaza.DinnerLa CriollitarestaurantMap →Source: OpenStreetMap (ODbL)Morning
Drive south to Cienfuegos, laid out in neoclassical grace.Afternoon
A convertible spin down the Prado to Punta Gorda and the bay palace.Evening
Seafood on the water and a stroll past the grand theatre.DinnerPaladar Achérestaurant · Cuenta PropiaMap →Source: OpenStreetMap (ODbL)Morning
The historic botanical garden outside the city.Afternoon
Boat across the bay to the Jagua castle at the harbour mouth.Evening
Sunset drinks at Punta Gorda, dinner by the water.DinnerPaladar Achérestaurant · Cuenta PropiaMap →Source: OpenStreetMap (ODbL)Morning
Coastal drive to Trinidad past the sugar valley.Afternoon
Plaza Mayor, pastel streets and a bell-tower panorama.Evening
The open-air music steps and dancing under the stars.Morning
Drive out to the Manaca Iznaga tower and the sugar-mill ruins.Afternoon
Beach hours at Playa Ancón, the convertible parked on the sand.Evening
Grilled fish by the harbour and a horse-cart night ride.Morning
Scenic drive back to Havana with countryside photo stops.Afternoon
Last shopping in the old city and a final open-top loop.Evening
Farewell dinner and a toast to the road before the flight.StayHotel Blau Arenal Habana Beach4★ · Grupo Cubanacán · La Habana(53 7) 77991200/ 77991274Website ↗Map →Source: Cuba Travel (MINTUR official portal)DinnerCantabria, Restaurante Hotel Armadores de SantanderCimex · Internacional · La Habana(537)8628000Map →Source: Cuba Travel (MINTUR official portal)Open Havana on the map →Nearby: Viñales, Varadero, Matanzas
4 · Visa, entry & customs
Every visitor needs a Cuban tourist card (tarjeta del turista) plus a passport valid for the stay and proof of onward travel and medical insurance. Buy the tourist card before you fly — the price and colour depend on your departure country and airline.
Travelling under US jurisdiction: there is no general tourism licence. US persons travel under one of OFAC’s authorised categories — most commonly Support for the Cuban People or family visits — which carry record-keeping duties and a full-time-schedule requirement. The tourist card for US departures is the pink one. Confirm your category before you book.
5 · Book direct, or compare an agency
This plan is costed to book direct — the $6,062 (expected) above is what the trip actually costs, itemised, with no package margin. A travel agency bundles flights, hotel and transfers into one price and adds a service fee for the convenience. We don’t quote agencies (we’d never invent a price) — so take a package quote and compare it line-for-line against the breakdown above.
Operating United States agencies serving Cuba, if you prefer a package:
- Cuba Travel Services (CTS) ↗
Long-running US seller of scheduled and charter air to Cuba plus packages.
Sells: flights, charters, packages, hotels
- ABC Charters ↗
Miami charter operator to Havana and other Cuban cities.
Sells: flights, charters · +1-305-263-6555
- Marazul Charters ↗
One of the oldest US–Cuba travel providers.
Sells: flights, charters, packages
- Xael Charter ↗
Direct flights Miami/Orlando/Tampa to Havana, Cienfuegos, Santa Clara, Camagüey, Holguín; since 1988.
Sells: flights, charters, hotels, cars, tours · (305) 643-2200
- insightCuba ↗
Non-profit people-to-people and custom group tours; since 2000.
Sells: tours, packages
- Cubamax Travel ↗
Flights, packages, shipping and remittances; 13 Florida branches.
Sells: flights, packages, hotels, cars · +1-305-512-0303
CubaAtlas is non-commercial and takes no commission. Agency links go straight to the operator; we don’t book, broker or earn from them.
Every Cuba agency, compiled — with the free equivalent for each →Questions
- How much does the "Chrome and Cobblestones — A Central Cuba Road Trip" trip cost?
- An estimated $3,990–$9,636 all-in for 2 traveller(s) over 9 nights ($3,031 per traveller expected), including airfare, lodging, food, transport and a reserve. It is a planner estimate, not a quote — you book each part direct, with no agency margin.
- Do I need a visa to travel to Cuba?
- Every visitor needs a Cuban tourist card. Travellers under US jurisdiction have no general tourism licence and travel under an OFAC category such as Support for the Cuban People or family visits. See the CubaAtlas visa & entry guide.
- When is the best time for this trip?
- Best months: November–April (open-top weather).
- Can I book this trip on CubaAtlas?
- No — CubaAtlas is a free, non-commercial planner. It gives you the itinerary, the budget, live flight-search links and real hotel and restaurant listings, and you arrange each part directly at the source. We book nothing and take no commission.