You should take a serious look at Belle Epoque San Sebastián close to the French border. The culinary capital of Spain and a great local culture that people take great pride in. Beautiful landscapes both in the immediate surroundings, along the coast towards vibrant Bilbao or inland up in the mountains.

I have lived here (the best seven months so far) and visited almost every year since the late 80's: http://marshlands.blogstream.com/

Here you'll find excellent apartments for short-time rent in San Sebastián: http://www.friendlyrentals.com/en/ap...modation-5.htm

Some other great and less expensive options:

http://www.rentalia.com/houses/file.php/ref/26665.htm
This is ideally located on Calle San Martín in the city center, just by the La Concha beach and five minutes from the Parte vieja/Old town. Could be some traffic noise in the morning.

http://www.rentalia.com/houses/file.php/ref/63452.htm
Just by the nice Plaza Easo, close to the center of town and 10-15 mins walk to La Concha beach and the Old town/Parte vieja.

http://www.rentalia.com/houses/file.php/ref/80152.htm
Two blocks away from the Zurriola beach on the other side of the river in the Gros district, five minutes walk to the Old town and city center. Some of the city's most popular pintxos/tapas bars on your doorstep (Ramuntxo, Bodega Donostiarra and Garbola).

http://www.rentalia.com/houses/file.php/ref/69355.htm
This is also in the Gros district, but on the far end of the Zurriola beach. Would be a 10-15 mins walk into the center and Old town.

We have spent considerably time in Spain including a month each in Madrid and Barcelona and we thoroughly enjoy Italy.

Although Madrid is not our favorite city, it is the perfect location for visiting other cities and town in Spain. Besides the nearby towns that create spokes like Toledo, Salamanca and Cuenca with the advent of the AVE Barcelone and Sevilla and now Valencia are not that far away. And it has incomprable museums.

San Sebastian has the best food in Spain and the town and the area is beautiful and there many day trips.

Barcelona has a sense of style that is found in few places.

I would not spend a month in Florence. It is tourist epicenter and not that relaxing, even though the city offers many charms. There are so many regions of Italy that a month would be wonderful, but my choice would be Sicily, especially if you enjoy antiquities.

Kimhe - San Sebastian was where I was originally trying to get us in Spain, so your reply is so helpful. My dh is leaning towards wanting to stay in Positano or SS. If we had our druthers, we would prefer non-smoking, no pets & wifi. Unfortunately, if you Google that combo and not much turns up . DH & DS1 have allergies. I know it is cool there, but we have found that apartments with A/C can help filter the air, but probably moreso with central air instead of the machines on the ceilings. There is one place that fits, I am going to cross reference it with your recommendations above on location.

For a month, I would go for a big city. Rome is my favorite city in Europe so far, after Istanbul of course!
For a shorter stay in Spain I would go for Madrid, for a longer stay probably Barcelona because of the contact with the Mediterranean. Cadiz could also be an option. I have never been bored in any Spanish city apart from Badajoz which was very easy to leave. I found a bus to Lisbon (which is yet another lovely city). If Rome is my favorite city, Spain is my favorite country.

Venice. a) So much to see and experience there, after 6 weeks so far (spread across 5 holidays) we feel we have only half seen it. b) If you did want a change, good train connections to many nearby interesting cities. c) You don't need a car, just walk (mainly) or get the boat everywhere. And no Italian traffic to get sick of ! ) Great markets so a wonderful place to stay in an apartment for a longer period.

I really like some of the smaller towns suggested, especially Arrezzo, but I wouldn't want to stay there for as long as a month (unless I could actually move there to live...).

I'm sure Friendlyrentals.com will find you places that fit. Just ask me about location.

I can recommend the hike along the coast over Monte Ulia in the eastern end of town towards pictoresque Donibane/San Juan. Includes a three minutes boat-ride, the boat leaves all the time. Several excellent seafood restaurants at the waterfront. Very good value lunch menus (Menu del Día): http://www.euroresidentes.com/eurore...s/san-juan.htm

Once, I walked further on, and reached beautiful Hondarribia on the French border. Some 4-5 hours walking from San Sebastián. http://www.google.no/search?q=Hondar...w=1379&bih=751

Had the meal of my life in one of the restaurants in the harbour in Getaria back in 1996, some 15 miles along the coast towards Bilbao. All of the restaurants are plain fantastic and expensive. It was something like this: http://www.thepauperedchef.com/node/255

Continue along the scenic coast-drive towards small and charming Lekeitio: http://www.pbase.com/cyracuse/lekeitio

Go a little inland to the Aralar mountain range. A cradle of Spanish skiing! http://www.turismo.navarra.es/eng/or...so.aspx?o=3064
Aralar pictures: http://www.google.no/search?q=Sierra...w=1379&bih=751

And you are only a couple of hours away from the spectacular Picos de Europa National Park. http://www.spain.info/en/disfruta/en...de_europa.html
Pictures of Picos de Europa:
http://www.google.no/search?q=Picos+...w=1379&bih=802

Not to forget San Sebastián itself, one of the most beautiful cities in Europe: http://www.youtube.com/watch?v=RTOyyfd5dO8