Basque Country Itinerary for 4 - 5 days

I really liked Bilbao. It has been cleaned up and I didn't see anything I'd call "rough" in 2016. San Sebastian is more in-your-face touristy with a very lively/crowded tapas district (the old quarter). Bilbao's Casco Viejo is not particularly near the Guggenheim (you can take a tram, I think), so it is less touristy, which I preferred. Bilbao has a second good art museum (Bellas Artes), and I really enjoyed walking through what I call the "business district" with its very nice late-19th / early-20th century architecture. Yes, I am a Bilbao fan. If you're a foodie and/or a bar person, I think you might prefer the vibe in San Sebastian, which has more of a party atmosphere, though Bilbao certainly has plenty of restaurants and bars itself. As a solo traveler I didn't much enjoy trying to get served during the lunchtime crush in SS.

If you stay in SS and have some extra time, Hondarribia (border town to the east) is a worthy side trip. There are frequent buses. It has a fishermen's district full of restaurants and a hilly medieval district, so more to see than you typical coastal town. There are a bunch of fun, smaller towns along the coast between SS and Bilbao, but you'd need a longer trip to squeeze them in.

There's frequent and good bus service between Bilbao and San Sebastian, perfectly usable if you don't have a car for that part of your trip. There's train service, but it's an historic rail line, extremely pretty but also extremely s-l-o-w. You won't have time for that.

Train service to Vitoria-Gasteiz exists but is fairly infrequent. It's about 30 minutes faster from SS than from Bilbao. The bus is quicker from both origins. If taking the bus, the trip will be faster from Bilbao than from SS. (Isn't this fun?)

If you expect to use a bus to go to or from San Sebastian, post again and I will explain about the location of the new bus station.

Between Vitoria-Gasteiz and Logrono is the small hill town of LaGuardia, which I think is on the edge of/just outside the La Rioja area. Extremely atmospheric. I saw a number of wine bars. Although easiest by car, it is on the bus line that runs between V-G and Logrono. Rome2Rio.com doesn't know about that bus, but Google will find it for you. Logrono has connections to Pamplona.

There is nothing wrong with Pamplona. It has an attractive-enough historic district, and there's a nice life-size sculpture of a running-of-the-bulls scene. But I agree with the guide books, which mostly give it a sort of lukewarm recommendation. I much preferred Vitoria-Gasteiz (and it was pouring rain on my V-G day). Of all the places you mentioned, Pamplona would be the one I would omit. Expect Pamplona to be hotter on average than the other places under discussion.

Burgos is very pretty. The architecture in the historic district is very nice, but expect that area to be full of other visitors because it is a major stop on the pilgrimage route. Away from the immediate area of the cathedral, you may be the only American around. The cathedral is lovely, and there are a couple of convents on the edge of town (different areas) that are worth visiting. Rick and I disagree on which one is the top priority. The convents are more easily reached by car. I walked, but that would be too time-consuming for you. There are some buses, at least on weekdays. Burgos is set on a very pretty little river. Perhaps that's why it is so unbelievably windy (as mentioned by Rick, I think). Hold on to your hat or don't wear one.

Thank you for your thorough insight. In Bilbao, can you recommend a hotel. We're more into historical charm and local lifestyle rather than the bar / night scene. We do prefer fairly nice hotels. Old Town, near Guggenheim or elsewhere?

I'm a low-end budget traveler, so the place I stayed would not meet your expectations. I hope someone else can assist.

In general, I found the biggest risk with Spanish hotels was that (in my price range) the rooms could be very small. The basic infrastructure was generally fine--there were elevators, and they worked; the bathrooms were functional and, though some showers were quite small, they were not as tiny as the worst I saw in Italy; the promised air conditioning functioned; and the Wi-Fi was usually sound.

I did have a lot of rooms with windows opening onto airshafts, which I think is particularly an issue in small, low-end hotels. I hope that is not something to worry about in the upper price brackets, but definitely read a bunch of reviews before committing. If you opt for a classic hotel in an older building, also watch for comments about there still being some steps to deal with even though an elevator is present. I did have that situation in two of my Spanish hotels.

You can check reviews on booking.com even if you choose to go elsewhere to make a reservation.

Edited to add: For the location, I think I might look for a place that's between the Guggenheim and the Casco Viejo (old town). That's what I (inaccurately, no doubt) think of as the "downtown" area. Use Google Maps to plot restaurants to be sure you don't choose a hotel that's in a food desert.

Sorry not to be of more help.

On my last visit to Bilbao I stayed at the Hotel Conde Duque. It is a clean, comfortable hotel with spacious rooms and an excellent breakfast buffet. The hotel also has a very good restaurant if you prefer to eat in. It is located across the river from the Guggenheim Museum right at the modernistic pedestrian bridge.
I like Bilbao a lot and feel its Old Town area is too often overlooked by visitors who focus only on the museum. This old section of the city, less than a 10 minute walk from the river, Is tailor made for exploring. There is a great enclosed plaza (Plaza Nueva) and many small streets teeming with interesting architecture. I am sure you will enjoy a visit there.

I forgot to mention the free tour of the Guggenheim in Bilbao that Rick describes in his book. The English tour is sometime around mid-day. You present yourself at the information desk, which will give you a sticker (quantity limited), then you can wander around until time to show up for the tour. My tour was on the ground floor and did a pretty good job of covering that area. I don't know that that is consistently true. I'd suggest asking the info-desk staff if they know where the tour goes so you spend your free time pre-tour elsewhere in the museum.

Thanks to both of you. Have been moving things around, but not exactly as you suggested. So here's my latest plan:

Tuesday 7/25 fly into Bilbao from Barcelona early morning. 1 night.
Wednesday 7/26 afternoon Bus to Pamplona (I know, you suggested this might be skippable). 2 nights. On second day, bus to San Sebastian for the day, return to Pamplona.

Friday 7/28 bus or train in the a.m. to Vitoria for 1 night.
Saturday 7/29 bus or train back to Madrid for flight next day.
Any further comments / suggestions would be appreciated. I wish I had more time, but I'm kind of squeezing in this particular vacation.

I think it's workable, and Pamplona might turn out to be your favorite. I trust you'll come back and tell us if that turns out to be the case, so I can temper my lukewarm non-recommendation in the future!

I do note that you don't have an evening in San Sebastian to allow for a fancy meal there.

If you didn't take the tour of the cathedral-under-reconstruction on your earlier visit, that's something you might enjoy in Vitoria-Gasteiz.