Insider notes
Things to know before you book
Pintxos are not tapas
In most of Spain a tapa arrives with your drink, or you order a few to share at a table. Here you stand at the counter, point at what you want or order from the board, and settle up on the way out, on a system that many bars still run on trust. The thing to understand is that you are not settling in. One or two pintxos and a small glass, then you leave and do it again. A proper night is four or five bars. My first evening I found a place I liked, ordered a full round, sat down and had a very nice dinner, and completely missed the point of the city.
Every tour here rates 4.9 or 5.0, and that is useless
Nearly all the San Sebastián pintxos tours I checked display 5.0 or 4.9. One has more than 1,300 reviews. Another has eight. Those are not remotely the same claim and the booking sites present them identically, which means sorting by rating teaches you nothing at all. The number doing the real work is the review count in smaller type beside the stars. I now look at that first and the stars second, and it has changed what I book everywhere, not just here.
Check the cancellation policy on wine days
Almost everything in the city is free cancellation up to 24 hours, which is the norm and what you should expect. Two of the expensive Rioja day trips are not. They are non-refundable, and one only confirms your booking within 48 hours, subject to availability. I nearly recommended one of them before I noticed, which is exactly why I am flagging it: the policy sits in a small gray box under the price and your eye slides straight past it. Committing €500 a head with no refund path to a tour with a single review is a bad trade however good the photos are.
The bilingual option is a different tour
One of the well-priced Rioja day trips sells a cheaper "bilingual group" option. Tucked into the itinerary text, in brackets, are the three things that option quietly removes: the second winery, the lunch, and the hotel pickup. A tour sold on two wineries and a meal becomes one winery and no meal. It is not a scam and it is not hidden exactly, it is just disclosed in the one place nobody reads. Check which option you are in before you pay, and if the price looks too good next to the others, that is usually why.
When to go out
The Parte Vieja gets genuinely hard work between roughly 8:30 and 10:30pm in summer and on any weekend. Bars three deep, no view of the counter, and the kitchen orders that make the good places worth visiting taking twenty minutes to land. Go at seven instead. You get counters you can reach, bartenders who will talk to you, and the same food. The city does not empty out, it just becomes possible. Every guided tour here runs in the evening, so this is for the nights you are on your own.
When to book
The Rioja days book furthest ahead by a wide margin. The €110 tour averages around 45 days of lead time and one of the private options around 50, which for a single day out is a lot and tells you something about demand. Pintxos tours are easier, though the Devour Old Town tour goes in peak weeks. So if your dates are fixed, book the wine day first and arrange the pintxos around it. Doing it the other way round is how people end up not getting to Rioja at all.
For related reading: how pintxos work if it is your first time at a pintxos bar, what to eat in San Sebastián, dish by dish, the best pintxos bars, bar by bar, in the old town and Gros, what makes a good Basque cheesecake and where to eat one, Barcelona vs San Sebastián if you are choosing between them, how tapas actually work in Spain for the rules pintxos bend, and how to order tapas in Spanish.