Begin at a centennial tavern set on the ground floor of the building where Spain's most celebrated novelist once lived. Over a glass of vermouth and a plate of Manchego cheese, your guide explains the ritual behind Madrid's favorite aperitif, along with the history embedded in the walls around you, a fitting start to an evening built entirely around the city's past.

Next, walk to a family-run tavern serving garlic shrimp, a dish invented as a way to stretch a poor family's ingredients and now one of Spain's most-loved plates. Alongside it, taste a house wine made at the family's own vineyard and served here for generations. The sizzle of the pan reaches your table before the plate does.

Before the evening's final stop opens its doors to the public, your group heads inside a restaurant recognized as the world's oldest, starting on the lower floor and into a wine cellar once nearly lost to flooding and normally off-limits to outside visitors. Upstairs, look into the wood-fired oven that's cooked without interruption for more than 300 years, through war, famine, and even a pandemic, kept alive by generations of the same family.

The evening ends at the table, with a full dinner inside the same historic dining room, past centuries of tiled walls and artwork, closing out a night that traced the city's history one stop at a time.