San Sebastian & the Basque Country: An Overnight Journey from Madrid

It's our answer to the rushed day trip. Overnights take some of our favorite journeys and extend them — adding an overnight stay, an evening to explore on your own, and the time to actually experience a place instead of just seeing it. Think of it as the depth and magic that only happens when you slow down.

Yes, and it's a highlight. Your first evening includes our award-winning Ultimate San Sebastian Pintxos & Wine Tour, the same experience that's earned thousands of five-star reviews. You'll eat, drink, and learn your way through the Old Town's best bars with a local guide. It's included in the price of the Overnight.

You'll experience two very different Spanish wine regions in the Basque Country. In Rioja Alavesa, you'll taste several wines during a guided winery visit — from young, fruit-forward reds to aged reservas. On the Basque coast, you'll try Txakoli, a crisp, lightly sparkling white that's the signature pour of the region. Both tastings include food.

If you're already planning to get from Madrid to San Sebastian, this is a far better way to do it. Instead of five hours on a train, you'll stop in Rioja Alavesa wine country for a winery visit and lunch, arrive in San Sebastian with a pintxos tour waiting for you, and continue to the Basque coast and Burgos the next day. Same journey, completely different experience.

A maximum of 8. That means real seating at every stop, actual conversation, and the kind of access you don't get in a bigger group.

A carefully selected boutique 4-star hotel inside Toledo's historic center. It's comfortable, charming, and ideally located for evening wandering. We wouldn't put you somewhere we wouldn't want to stay ourselves.

15+ tastings at 8 spots—more than enough for a full meal. Come hungry! Water will be served at some spots, but we recommend bringing a water bottle if you get thirsty.

Yes, especially in Toledo, where the evening is entirely yours. Guided visits throughout the trip are balanced with independent time to explore, shop, eat, or just sit on a terrace and soak it in.

We’ll do our best. There are usually vegetarian options, but vegan, gluten-free, or allergy-specific substitutions may be limited due to the traditional nature of the tapas. Let us know in advance and we’ll do what we can.

You'll be walking on cobblestone streets with some hills, especially in Toledo and Segovia, but the pace is relaxed and there's plenty of downtime between stops. Comfortable shoes are strongly recommended. (Leave the cute-but-painful ones at the hotel.)

All food and drinks across 4 stops, plus an expert Devour guide who brings the evening together. You'll taste petiscos, oysters, artisan cheeses, a refined main course, dessert, and 5 paired drinks including regional wines and a cocktail.

Consider what you're getting: two full days of private guided travel across northern Spain, two winery experiences, our best-selling pintxos tour, a night in a 4-star hotel in San Sebastian, and all the food, wine, and logistics handled for you. Planning this independently would cost a comparable amount in train tickets, hotels, winery fees, and food tour bookings — and you'd spend hours coordinating it all. This is the same trip, minus the spreadsheet.

This tour is not recommended for children under 15 years of age due to busy, crowded bars. We love hosting families and we recommend you look at our other daytime offerings for more family-friendly experiences.