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Trip planning advice - Paris and Northern Spain?

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Newbie traveler here!

I'm currently planning my first trip to Europe, and hoping to get some advice on the itinerary, must-see places, transportation, etc. I've done quite a bit of research on the areas, but would love to hear some first-person advice.

The Timing:
Late September/Early October. I know we'll probably see some rain in Spain, but this is the best time it fits into our work and family schedules.

The People: I'll be traveling with a friend. Both single, in our mid-twenties, and come from pretty similar backgrounds. The big difference is that she's traveled internationally with her family many times while I've never used my passport.
She's letting me take a lead on the planning and is seems pretty content with my food/art focus. I'm a former art student, so for me, this trip won't be complete without at least one Gothic cathedral, some really famous artwork, and some really old buildings. We're also both pretty excited to enjoy pastries in Paris, and tapas in Spain.

The General Plan:
Fly into Paris and get a hotel or apartment for several days. See the sights, eat the food.
Overnight train to Hendaye, then over to San Sebastian. Use San Sebastian as home base for several more days. Daytrips to Pamplona, Bilbao, maybe a wine tour and/or tapas tour...
I'd love to figure out a way to fit a trip to see the cave paintings in Puente Viesgo, but it seems difficult to get there without a rental car, and is a pretty log day trip from any cities we might want to say in.
I'm undecided where we'll fly home from. We can spend all of our Spain time in the Basque region and fly out of Bilbao, or take a couple days in Madrid or Toledo and fly out of Madrid.

Some Questions:
- Nothing is booked yet, so our time in each location is TBD. How would you split the 2 weeks?

- We've decided not to do a completely planned tour, but are thinking about some general day tours in Paris and San Sebastian to help us get a feel for each place. Any suggestions on good city tours? I've been considering at the Intrepid Travel Urban Adventures.

- Any tips on Packing, Public transit, Hotels vs. Apartments?

- I've been focused on food and art activities, but totally willing to branch out. Am I missing something big?

TLDR; 2 weeks, Paris, France and Northern Spain. Help!

Thanks in advance!

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