This is a suggestion for a road trip from Havana, for three to five days, by car. If you go by bus, you'll need more time.
Cuba is full of interesting cities and unique experiences. There is enough to do there to keep travellers entertained for well over a month. Here is my recommended itinerary for this short trip, to get a taste of the colonial times of the sugar barons and the revolutionary times of the communist barons, spiced up with visits to two beaches.
You can hire a car with a driver; your landlord or hotel can arrange that. It will cost you about 170USD per day, which includes petrol and the driver's costs including his accommodation. Or you can hire a car, across the road from Hotel Nacional in Havana, for about 120USD/day, excluding petrol. It is safe to drive across the country.
First go to Varadero beach for an afternoon (or even overnight). It takes about two hours to drive there from Havana. It is Cuba's biggest resort with a hotel zone but there are also public beaches, with some restaurants just across the road. No vendors on those pretty beaches and very few tourists. Bliss! For more info, click on the link in the title.
2. Santa Clara
This city is known as Che Guevara's town because his Mausoleum and Museum are here (a true socialist enormous monument). We found a great music scene here, at the restaurant Santa Rosalía, at the bar La Marquesina (with Septeto Los Gimez, the local Buena Vista band of guaracha music). You can try El Mejunje, the country’s only official gay club with a drag show. Or just sit in the main plaza, in beautiful Parque Vidal, for people-watching. The drive from Varadero takes about 3.5 hours.
In an hour and a half from Santa Clara you can find yourself in the Valley of the Sugar Mills, surrounded by Escambray Mountains National Park. There are a few haciendas here that tell the story of the sugar barons and the slaves. Manaca Iznaga's icon is a tall bell tower. The bell was used to announce the beginning and end of work and the tower was for observing the slaves working (and not escaping). The hacienda belonged to Pedro José Iznaga and his family. They became rich and built palaces in the nearby town of Trinidad.
The city of sugar barons is only a 20-minute drive from the hacienda. It is like a fairy-tale full of colonial palaces of sugar barons, frozen in time. Very well restored, the best city for strolling around. Don't miss the Convent of St Francis, with great views of the city from its bell tower.
5. Playa Ancón
Only about 12 km outside Trinidad. Unspoilt, long public beaches with fine sand. Go to Grill Caribe restaurant, where you can hire beach lounge chairs and use the bathrooms. If you are after diving, go to Punta María Aguilar. This coast used to be attacked by pirates in the colonial past so you can dive to see galleons and boats shipwrecked here or see the coral line, only about 20m from the coast.
The Pearl of the South can be reached in an hour and a half. This is another city of sugar barons. Do three things here: walk about the central plaza, Parque José Martí, then the main artery of the city, Paseo del Prado and the malecón (waterfront promenade). In all those places you will see the amazing elegant colonial palaces of the local sugar barons. Visit one of them, Palacio del Valle, at the end of the promenade called Punta Gorda. Have a mojito on its roof while you listen to a live band and enjoy the view of Jagua, the narrow channel which connects Ciefuegos Bay with the ocean. The journey home takes four hours non-stop. Refresh at petrol stations as the rare road restaurants don't serve food anyway (only juice).