A self-drive trip designed for a traveling couple: Miami and the road down the Keys, a short flight to Havana, then Viñales, Cayo Levisa, and Trinidad, all arranged end to end, lived behind the wheel.
The itinerary
The idea behind this itinerary: four days of Florida behind the wheel (Miami, the Everglades, the Overseas Highway down to Key West), then a flight of barely an hour to Havana, where a second car is waiting. On the Cuban side: colonial casas, the Viñales valley, the beach at Cayo Levisa, and Trinidad, before returning through Santa Clara and a final night in Miami.
The budget shown is an estimate, flights included: each itinerary is then tailored to your wishes and the season, at a fair price.
01Day 1
America begins on Ocean Drive: car picked up at the airport, then check-in at an Art Deco hotel across from the beach, pastel 1930s facades included. A first swim in the Atlantic, dinner on a terrace with Latin-Caribbean flavors, a rooftop cocktail to take the measure of the glittering city. Jet lag will do the rest. Tomorrow, the Everglades.
02Day 2
An hour from Miami, the airboat glides deep into the “river of grass”: motionless alligators, wading birds, a local guide who reads the marsh like no one else. In the afternoon, head south to Key Largo, first of the Keys, for snorkeling above the coral at John Pennekamp State Park. The night is spent at a hotel with retro charm, private beach and seafood at dinner.
03Days 3 to 4
The road skips from island to island along the Overseas Highway, its bridges laid over turquoise water: a swim at Bahia Honda, lunch with your feet in the sand at Little Torch Key. In Key West, Hemingway's house, the Southernmost Point buoy, and the sunset celebrated at Mallory Square. Back to Miami Beach the next day, with dinner at Versace's former villa.
04Day 5
Car returned at the Miami airport, an early-morning boarding, and less than an hour later Cuba pulls you in. A near-obligatory first stop: a mojito at La Bodeguita del Medio, its walls covered in signatures. You stay in a colonial house on Plaza Vieja, balconies over the square; the afternoon drifts through cobbled lanes, vintage American cars, and colorful facades, until dinner at a paladar.
05Days 6 to 7
The Carretera Central crosses a countryside of horse carts and tended fields to Viñales, where a family-run villa looks out on the mogotes. On horseback among the tobacco plantations, a guide shows how cigars are rolled, with a tasting of local rum to finish. The next day, thirty minutes by boat from Palma Rubia: a wooden bungalow right on the beach at Cayo Levisa, snorkeling over the coral, and a seafood dinner.
06Days 8 to 9
The boat returns to Palma Rubia, the road to Havana: a daiquiri at El Floridita, dear to Hemingway, then sunset on the Malecón among the regulars. The next day, the road skirts the Escambray mountains to Trinidad. Cobblestone lanes, pastel houses, a night in an eighteenth-century mansion, and salsa under the stars on the steps of the Casa de la Música.
07Days 10 to 11
The Cuban countryside rolls past one last time to Santa Clara, where the car is returned at the airport before the 6 p.m. flight to Miami. The evening belongs to Brickell, at a modern hotel facing Biscayne Bay, rooftop and infinity pool included. One last morning: a stroll through Bayfront Park, a speedboat run across the bay with Thriller Miami, then a private shuttle to the airport and the evening flight home to Geneva.
The budget, line by line
Geneva to Miami round trip via Lisbon, plus the Miami-Havana and Santa Clara-Miami flights.
One vehicle in Florida, another in Cuba, basic insurance included on both sides.
An Art Deco hotel in Miami Beach, colonial casas in Cuba, breakfast included at most addresses.
Airboat in the Everglades, snorkeling at John Pennekamp, horseback riding in Viñales, park entrances included.
Boat crossings to Cayo Levisa and a private shuttle to the Miami airport on the way home.
A day-by-day itinerary sheet, trusted addresses, and practical tips for both countries.
Estimated budget: $3,500 for two, flights included, then fine-tuned to the season and your wishes.
This trip has its own film: the footage we brought back from scouting it on location.
Watch the film of this trip
