1 month in Europe in spring 2019 with 3-year-old

Take a look at Lucca, Italy. Right on the train lines to Florence, Venice, Siena, one direction, and Pisa and beaches the other direction. Very walkable; very family friendly. Everybody and her sister seem to be on bicycles. There is a large walking/biking path all around the wall surrounding the city, and bikes to rent several places. Plenty of art/music/street life, yet the city is small enough to be very friendly, not need a car at all. When I was there a couple of years ago, I was struck by how many families with small children were out strolling in afternoons and evenings. Kiddos running around in the central piazzas together, kicking balls, punching balloons and blowing bubbles. And the train station is just outside the walled part of the city, very close for pedestrians.

February in most of mainland Europe is the coldest, wettest month, so I would try to travel later in the year.

Some places such as the Algarve in Portugal offer cheaper winter lets if you take a place for 28 nights until the end of March, so you can get some great deals. Airbnb isn’t the best value - consider Trip Advisor rentals, Booking.com or VRBO.

Some of your requirements are contradictory eg “not a huge city” but “amazing art” and “gorgeous scenery”, but “not wanting a hire car”. The best art tends to be in the bigger cities and rural Europe tends to have poor public transport.

Unless you are heading for major cities, most places January to March will not be overrun with tourists.

Malta has a good bus service, but isn’t a happening place in the winter. I don’t know what the WiFi is like, but it generally tends to be better in mainland Europe than on many of the islands.

A car is handy in southern France.

Somewhere such as Jerez in Spain may suit - sherry tasting, a good horse school and good value in the town. Cadiz, Seville and Granada are all possible day trips nearby.

Tavira in Portugal is also another possibility, where the weather should be milder. Good public transport and a great base to explore Portugal and southern Spain. Car hire in Portugal is cheap out of season.

Nice, France
Dijon, France
Strasbourg, France
Bologna, Italy
Vicenza, Italy
Sevilla, Spain

I suggest Nice or Barcelona.

To Suki's list, I'll add Nancy, France.

Does he actually hold an Irish passport?

From what I see, the best place is Basque country in Spain, Bilbao or San Sebastian. The weather will be mild there during that time of year. You will be close to beaches and not far from day trips to other parts of Spain and Northern France. The Basque country is also known for its culinary and architecture. I like Nice but it might be too pricey to do a rental there. Dijon could be an option in France.

Bilbao: https://www.bing.com/images/search?q=bilbao+spain&qpvt=bilbao+spain&FORM=IARRSM

San Sebastian: https://www.bing.com/images/search?q=San%20Sebastian%20spain&qs=n&form=QBIR&sp=-1&pq=san%20sebastian%20spain&sc=8-19&sk=&cvid=7D3F2C7A106243F29623D6F872DFA026

A bientot

I second the suggestion of Lucca and the later in April you can go the better the weather is likely to be. Almost any decent sized town with a normal population of young adults with children will have family friendly areas and lots of things for little ones to do.

I would not choose the Basque Country at that time of year. It is great in mid-summer when the rest of Spain is baking, but southern Spain would be much warmer Feb-Apr and a lot drier.

A month in Sicily would be heaven, but the concept of one base and only occasional car rental won't work very well there. The island is large, with key destinations all over the place. Public transportation exists but is not very fast, thus the need for a bunch of different bases. I'm not sure it's as strong in art-as-in-paintings as you might want, either. It certainly has a wealth of Baroque churches, though. I think you could get four rentals of 7-8 days each for a very reasonable total cost.

My first thought was southern France because of the art. Hotels in Nice are surprisingly affordable outside of June-September; I'd imagine the pattern holds for apartments as well, but I don't know that for a fact. I'd use booking.com for a quick check. You can specify apartments rather than hotels.

Nice has many art musuems, plus there's good train service along the coast to a lot of pretty towns, many of which have museums of their own. Buses go up into the hills. Nice is a large, bustling city, so it may not be the place for you--though I suspect there are more child-friendly activities in larger cities.

A smaller town within an easy train ride of Nice might be a decent compromise. Menton (38 minutes from Nice) is supposedly the warmest place on the Riviera in the winter, with a February lemon festival. It's practically on the Italian border. West of Nice you have Antibes (about 25 minutes). There are smaller places along the coast heading in both directions. I'm not a fan of extended stays in really small towns, especially without a car and out of season. But that might be just what you want, in which case you can consider any place on the rail line.

Take a look at Lecce in Puglia in southern Italy. We just spent 2 weeks in March in Puglia with our 3-year-old grandson and he loved it all.

You can take trains from Lecce to many other towns in Puglia, the food in Puglia is great (maybe my favorite in all of Italy), there's a cool train museum, the outsides of the churches have sculptures of animals on them, it's a very walkable town with lovely squares where a kid can run around, great gelato, a Roman amphitheater in the center of town, cooking classes and food tours, and not heavily touristed.

Thank you, all, for your insight and suggestions! After lots of discussion (and reevaluating of certain priorities!), for various reasons we're closing in on Italy. Current top spots are Siena, Livorno, Bologna, and Naples. I realize this is quite a range, and in some cases directly contradictory to some of our earlier criteria! If YOU had the opportunity to spend March in one of those four cities (with a three-year-old), does any one in particular stand out? Many thanks again. :) (I will also post in the Italy forum!)

OK Stephanie, I’ll cast my vote: of your 4, I’ll say Siena first, and Bologna second. Siena is a smaller town, very historic, beautiful architecture, excellent food, and close to many other interesting places in Tuscany, especially Florence, a 1-hour bus ride. Siena was the place I thought of first when I first read your original post. Bologna second, although to me it has the feel of a bigger city, and not as wide-open as Siena. It has fantastic food, and has a number of other interesting towns nearby, for visits, including Ravenna, a very beautiful and liveable town I found, but not in the center of many nearby spots. I like Naples, but it is a much bigger city, very congested, etc. Some people really likely Naples a lot, but others really dislike it a lot. I wouldn’t suggest going there for a month with a small child, unless you already know and like it very much. Livorno (Leghorn) I don’t know much about, except that there is a US Navy nearby.