Pinar del Río sits about 200 kilometres west of Havana, and most visitors treat it as a base rather than a destination in itself. The city is pleasant enough — colonial architecture lines the main boulevard, and it has a low-key charm — but it can't compete with swinging Havana for atmosphere. What it does offer is access to some of Cuba's most spectacular countryside.
A short drive north brings you to Viñales, a small valley of extraordinary beauty. Mogotes — steep-sided limestone hills draped in forest — rise dramatically above tobacco fields and red-earth paths. You can hike between farms, visit tobacco drying houses, and buy cigars directly from the growers. Be aware that buying cigars outside official government stores means you won't get the purchase receipt required by customs to take them out of the country legally.
To the southwest lies San Juan y Martínez, the heart of Cuba's finest tobacco-growing land. Farmers here will happily show you around their fields and explain the process from leaf to finished cigar — it's one of the more genuine encounters you'll have on the island.