My wife and I are planning to spend 1 month in a rented condo or house (we’re both in our mid 70s) preferably in either Italy or Portugal. We are looking at either April/May or Sept/Oct to avoid the high tourism months. Highly regarded food and beverage options, charming neighborhoods, walkability, food markets, interesting and varied surrounding areas to explore (will have car rental) , better than average cultural options with decent health care facilities if needed. Looking for city/town on a smaller scale towns even thought there might not be a major airport. Any recommendations would be appreciated !! Thanks in advance.
Posted by
San Diego, California
5604 posts
April 20, 2025 is Easter. You may want to avoid the week before and after in either country. Have a wonderful adventure!
Posted by
Salem, Oregon, USA
2723 posts
Also 2025 is Jubilee year, so things may be busier in Italy. https://www.iubilaeum2025.va/en.html
Posted by
Gettysburg PA
7162 posts
Welcome!
Have you been to either country before?
April/May and Sept/Oct are still going to be crowded
Italy also has 2 holidays April 25 and May 1 which will mean increased crowds
There really isn’t much “shoulder” season anymore
Because of Easter and Jubilee I’d go as late as possible -month of October
Tuscany/Florence with a base in or near Siena would give you lots of options
You could spend a month in Rome and never run out of things to see
Other locations would be Padova or Vicenza or Bologna
Portugal-I’m not as familiar with but I think I’d stay in Lisbon or Cascais
Make sure you do your homework on driving in either country
All drivers will definitely need an IDP in Italy, I’d recommend for Portugal as well
Posted by
8242 posts
Tuscany is my favorite area of Italy and Siena and Lucca are smaller cities that you might like.
Also, in Umbria, Spoleto, Spello, Assisi or Perugia would be great.
Posted by
San Diego, California, USA
1094 posts
Hello twverhey, and welcome to the fourm!
I just got back from a trip that included a month in Lucca and it was an interesting experience. My criteria was basically small Tuscan town life without some of the drawbacks of real small Tuscan town life - flat, train access, larger city around etc. - and Lucca was a great choice for what I was looking for.
My advice is to check the festival, convention and celebration day calendar wherever you are looking. Lucca has a comic-con that swells the population of the town a ridiculous 8x and we specifically shifted our time to avoid it due to the renting difficulty since that weekend people can charge huge rates. The same issue exists with lake and beach towns in summer.
Having just stayed in one place for a month one of my concerns would be getting into a situation where you're renting something sight unseen and it turns out not meet your expectations. AirBnB has erased the longer vacation market for real estate agents in Italy so you probably won't find anyone willing to work with you for such a short term rental. So you're likely stuck with AirBnB, VRBO or Booking.com as your only real choices. I reached out to a realtor based on an article he wrote on Italian rental terms and issues and he referred me to the rentals specialist who just sent me AirBnB links. All the sites I found that advertised longer term rentals received no reply or "We don't do that anymore but if you want to rent for 1 year+ or buy let us know."
I would also recommend learning some Italian or whatever the local language is. It is not required to generally get around but sometimes it really helps when you really need something. It also really helps if you are trying to live somewhere and experience being part of the community. Italians love to talk more than anything and if you can't talk with at all it really leaves you outside the main social function.
I would try and articulate the experience you want and then develop a criteria for the place you think you could best find that and then start from there in terms of a town search. If your time is set than that might very well narrow the list and budget might figure in as well. If you want more details on my stay hit my on a private message. I may do a trip report in the future since people seem to have the same kind of idea about longer stays.
I'm not necessarily saying Lucca will work for you but I wanted to share my thoughts just having done this kind of thing.
Hope that helps, have a great stay!
=Tod