For a warm winter climate, go to the Algarve region of Portugal. There is a train that goes there from the Oriente station in Lisbon.

Those passes are rarely a good deal.

In some countries you need to add on a booking fee. Even if you don't it's often much cheaper to just book in advance.

Thank you all for your helpful input. I should have mentioned that I speak French (very proficiently) and Spanish (good comprehension, speaking abilities are decent), and my husband speaks Spanish (almost fluently). I have been looking more into the documentation I may be expected to provide. Sounds like I'll want proof that my author business is based in the US and that my children are homeschooled or enrolled in online school (though this shouldn't be a problem until the end of our year, if the timeline shapes up to be what we hope). Aside from that, I intend to bring proof of international health insurance, some financial statements, and a few other things to ensure we are prepared to answer questions at the border.

As of now, I'm most concerned about where to spend the colder months—November through February. We spent a month and a half in Southern Spain (Seville and Malaga) and the Algarve last January/February, so we'd love to go somewhere new this time around if anyone has any suggestions.

How about Sicily for the colder months? I hear Siracusa is gorgeous, interesting Greek and Roman history, my daughter was supposed to study abroad there last year but the program was canceled due to Covid. It looked charming, big enough to keep one engaged and university students out and about.

We also love Barcelona! An easy, walkable city with amazing history, architecture and food. I’m not sure of the weather in the cold months though.

Florence also might be mild in the winter. Or perhaps a town on the shore that is more temperate like Sorrento or Santa Marguerita.

What do you consider cold? In a normal year Rome barely gets below freezing overnight. Florence is a little colder. I think so is Barcelona.

The advantage of Rome is it's big and well connected. Easy enough to hop around by train or plane.

Where to spend winter depends on what sort of experience you want. For us, who almost never experience snow, being somewhere truly wintry would be a real draw. But if I lived somewhere where snow was a regular visitor then maybe somewhere warmer. What about Crete? I've never visited in winter so don't know but I seem to recall a recent post about winter in Crete on the Tripadvisor forum. I agree that a city like Rome would be great, especially as there are places to easily retreat from the weather. And Sicily might also be great (but have yet to visit there).

I have been in Barcelona in November and in February, weather was nice both times, also check out Tarragona one hour south. It is a Roman city, on the sea. Or Valencia a bit farther. Not sure about December and January in those places.

Canary Islands or Morocco for the winter months. Just because Morocco is not in Europe it is a very friendly place. Marrakesh would be good.

Puglia, Southern Italy! It is an amazing plance.I'm going to attend a wedding by Sept.

I was married in Puglia in September. Lovely place May to September, a bit dull in the winter months

Definitely come to Switzerland for awhile. If you have a car, you’ll find cheaper rental flats/houses. Look at central Switzerland for a home base and then go on day trips from there.

For some reason the question of the Schengen visa has been skirted around. Without a long stay visa somewhere, you will be limited to 90 days (not three months) out of 180 days. It never resets. It is a look back situation. You look back 180 days from today and if you have been in the Schengen zone for 90 days you are done. Same for tomorrow and next week. All of the documents you mentioned above is only going to be useful applying for a visa and you do that before leaving the US. A question that could trip you would be your return flight plans. If suspicious about your long term intentions they could ask for your return plans.

And it is strictly enforced, there are reports here and on other travel sites when travelers have overstayed by a few days and were hit with stiff fines and being ban from returning a few years. Don't take it lightly.

the OP is aware, read the first post. I’m assuming the 90 days (not three months) thing is understood.

While the suggestions of where you might go that you are getting are good ones, the specifics about the Schengen rules are not exactly clear and some are contradicting each other. For example, I don't think you can spend 90 days in Schengen countries, leave for 3 months and then go back in again. I think you need to leave for 6 months. So I'd check this out very carefully, the advice being given here is a little vague. However, there are quite a few places besides the UK that you can go. Croatia and Ireland are good choices.

Also, the tourist schengen deal where you can stay up to 90 days visa free specifically says 'for pleasure'. I think you telling them you are an author and you have a business is going to get you in trouble. I don't see how they could ever find out if you you are doing some writing while you are there, but if you can't 'honestly' say you are on sabbatical or 'not working at present' (both of which would essentially be true) then I don't think it will work. And you haven't said yet what your husband does.

But as someone else mentioned, there are tons of people over there who are vlogging, working on podcasts, taking photos, writing articles, novels or whatever. I don't think most people consider those activities as 'cheating'.

Also, I think your biggest problem will be your return flight info. If you book a return flight and it's not for a year that will be a reg flag. If you do not book one at all, that might also be an issue. I have a friend who was going to the UK to visit her boyfriend. She definitely intended to only be there about a month or two (so nowhere close to the six month limit) but as she wasn't sure how long exactly she didn't buy a return ticket. She was not allowed entry at all. Once I was entering the UK to visit my daughter who was studying there for a year (she had a visa). I was only going for two weeks and had a return ticket. When they asked where I was staying and I said with my daughter they wanted the address. I didn't know it as we only communicated by phone and email which did not require my knowing her street address. She was meeting me in London and I was going back to the town she lived in with her so I didn't need the address for that (I knew the town name, just not the street address). They did let me in but gave me a really hard time about it. Just saying, the UK is especially strict.

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No the rules look back six months. If you haven't been in the area for more than ninety days in the last 180 you're okay.

Six months would have the beginning rolling off

a one-way ticket would be an absolute red flag for going into the UK while not having an address for contact just triggers the border people's antennas

Plus in both cases it was to visit family or a partner, which would also trigger them.

That's too much time in the UK, in my opinion, but there is an issue with the limited stays in the Schengen region. I would definitely choose some of the more eastern countries- as being cheaper and less touristy. I LOVED Estonia when I was there in 2019. Hotels around the country have basements with huge pools, fountains and water features that your kids would love. Prague is worth a visit, although you'd want to stay outside it, but the trains are cheap. Get to the Loire Valley and spend a day at the Puy du Fou, including the light show at night, although it will be past your kids' bedtimes. It's worth it. Italy is amazing- we rented a two bedroom place for a month for a very reasonable price and did day trips around the Tuscany area, to the charming small towns and to Florence. Don't stay in Florence- the trains are great, and you can get an apartment or house much cheaper than a hotel in Florence. All of Italy is amazing. But Spain is pretty fabulous, too! Try VRBO to find places to stay- you don't want to be stuck in hotel rooms So, for me, the Loire Valley in France, somewhere in Italy, Estonia, the Czech Republic, Estonia, and maybe Menton on the Med in France, which is less known and less expensive than nearby areas, but with easy access to Nice, Villefranche, Cap Ferrat and Monaco.

There's no problem with health care just about any place in Europe. I've been to doctors in France- they all speak English.