This province in western Cuba is one of the most beautiful in the country: Stunning mogotes (limestone mountains) tower over the Vinales valley, where lush fields of tobacco are grown to make the legendary Cuban cigars. The city of Pinar del Rio, which is 100 mi/160 km southwest of Havana, is a sleepy backwater famous for its pushy jinteros. These touts offer everything from home-stays to cut-price cigars. As a result most visitors bypass the city, heading instead for the bucolic charms of nearby Vinales.
Tour buses leave for daylong trips from Havana and typically stop at a cigar factory in the city of Pinar del Rio along the way. We recommend renting a car to make the trip, though: That will allow you to stop when you want to take photos and to linger as long as the magic holds you.
For the most magnificent scenery, take the main highway from Pinar del Rio city to the exit for Vinales. Although the road is potholed in some parts, the scenery becomes more dramatic as you approach Vinales. The valley is studded with tall limestone outcroppings laced by caverns and interspersed between fertile valleys. Vaqueros (cowboys) and vequeros (tobacco farmers) till their tobacco fields in age-old fashion using ox-drawn plows. You can stop along the way for refreshments (or a dance) at Cueva de Vinales, a cave that has been converted into a disco bar, or enjoy a boat ride through subterranean caverns at Cueva del Indio.
Good country-style tourist meals are found at the Valley of Prehistory (where restaurant patrons have an excellent view of a gaudy 590-ft/180-m mural that adorns the cliff face of Mogote Dos Hermanos); at the Cueva del Indio; and at Restaurante Casa Tomas, in the peaceful time-warp village of Vinales, which also has several quality paladares (private restaurants). Stick with the northern coastal road on the way back to Havana (the water is on your left, beautiful hills and valleys to your right).
Although the entire drive can be made as a day trip from Havana, we recommend taking things at a slower pace, overnighting along the way, which allows you to enjoy one of the magical sunsets and sunrises that turn the valley into the kind of fairy-tale territory dreamed up by Chinese watercolor artists—and all the daytrippers will be gone by then. A side trip to Cayo Levisa is well worth adding one or two days to your itinerary; it's a great place to relax on sensational white sand beaches and it has excellent accommodations.
West of Pinar del Rio, lying on the southwestern tip of Cuba itself, is Maria La Gorda. It's definitely off the beaten track, but divers rave about untouched reefs teeming with marine life lying only minutes from the shore. At least 5 mi/8 km of splendid white-sand beaches front the warm, crystal-clear water. Guanahacabibes National Park has plenty of endemic wildlife, plus trails—guided hikes are offered. It's a very long drive to get there, so be sure that driving or nature hikes are on your agenda, as there is nothing else to see or do, and there is just one (quite acceptable) hotel.
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