Explore Castile’s wine roads on a private three-day loop from Madrid: medieval Chinchón, Segovia’s Roman aqueduct and Alcázar vistas, and the castle-crowned vineyards of Peñafiel. Expect cellar tours, curated tastings, and included lunches across three days of easy walking and scenic drives.
More ways to explore the area's outdoor wonders
Stone heat rises from Chinchón’s Plaza Mayor as morning light slides between arcades; market stalls fold and the town exhales into quiet as the tour group disperses into narrow lanes. The first day is a study in human scale—plazas, carved balconies, and a winery cellar where oak barrels hum with time.
Difficulty
easy
Duration
3 days
Fitness Level
Suitable for travelers in average health who can walk short distances on uneven surfaces; no strenuous hiking required.
Wildlife
History
Segovia’s aqueduct dates to the Roman Empire and anchors a medieval urban core; Peñafiel’s castle has long been a strategic stronghold and now interprets the region’s wine heritage.
Conservation
Many wineries in the region practice sustainable viticulture and water-conscious farming; visitors are encouraged to respect private vineyards and follow marked paths to minimize impact.
Reserve your spot on the 3Days Exclusive Wineries in Chinchon and Segovia and Peñafiel today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Comfortable footwear
Cobblestones and gravel at wineries mean low-cut hiking shoes or sturdy sneakers are best for all-day comfort.
Hydrate between tastings
Drink water between wine samples and use palate-cleansing snacks provided at lunches to keep energy steady.
Timing matters
Visit Segovia early or late in the day to avoid peak crowds at the aqueduct and Alcázar viewpoints.
Tasting etiquette
Spitting is acceptable and common in professional tastings—don’t feel obliged to finish every glass.
Sturdy walking shoes
Support and traction for cobbles, gravel cellar floors and short walks between sites.
Light wind jacket
Evenings on the high plateau can be cool and windy, especially outside summer.
fall
Reusable water bottle
Stays hydrated during tastings and drives; many wineries will refill bottles.
summer
Small daypack
Carries maps, purchases, and layers without getting in the way during tastings.