6-8 weeks base in Portugal, late-January to late March/early April 2021

I have no suggestions, just questions re your Sicily winter. Was the language a problem? How did you occupy your time? Did you have a car?

I have spent March in the Algarve for a couple of years, but now head to Fuerteventura in the Canary Islands where the weather is more reliable. January and February can be wet in Portugal, more so in Lisbon than the Algarve. March days can occasionally be beachable if it’s not too windy, but you will still need warm layers for the evenings.

Scenario 1 - I would opt for Lagos or Tavira. Smaller resorts such as Salema and Manta Rota are effectively closed for the winter. I don’t care for Albufeira, Vilamoura or Praia da Rocha.

Scenario 2 - I would opt for Tavira, Cabanas or the places east of Faro that have train stations if you don’t have a car. There are many Canadians these days wintering in Cabanas. Food and wine is fantastic value and there are plenty of walking options.

Many places offer winter deals for stays of a month or over - in normal times these are booked a year ahead, but the current situation may have freed up some accommodation.

I’d already done a lot of the touristy visits in Sicily in previous trips. I basically tried to go out & about everyday, but many days I’d stay in and read if I felt lazy or the weather was cold & damp. Nine weeks gives you the time to “farniente”. :)

Ortigia was an absolute treasure for walking & poking my nose in its ancient corners. Plus the very best daily market was less than a 5 min walk from my apartment. I got by with English and my very limited Italian, most times. Although I understand a fair bit of spoken Italian, I really struggled to make heads or tails of the local Sicilian. Most of the fresh fish at the market I could not recognize. One of the guys was really good at trying to explain (in Sicilian) how to cook it - if I caught the gist of it, I bought it. He also figured out that I had no clue if any given fish needed to be skinned / filleted / scaled, etc., and with flicks of his knife would make it pan-ready for me. Man, oh, man, the food!!! I have greatvphotos of the stuff that I cooked those weeks... shrimp, squid, and I never did find out what various fish I was eating for the most part. Every so often, I’d head to the supermarket with my wheeled cart on the bus, to pick up what I couldn’t in my immediate neighbourhood.

At least once a week, I’d hop an intercity / regional bus or take the train and go exploring for the day. I also hit a couple of local festivals, for which I’d overnight at a B&B (the Carnevale in Sciacca, the Festa di Sant'Agata in Catania.) I also overnighted a couple of times in other small towns, returned to Palermo for a couple of days, and did do the round-trip train over the Straits of Messina (just to do it, and watch the whole load/unload of the train onto the ferry - very cool!) I rented a car for only a few days, to get to some parks, wineries, and to circumvent Mt Etna. The time flew.

I would recommend Sicily for an extended off-season winter stay if you: are very open to new experiences; can go a bit without meeting someone with whom you can have an entire conversation in English; understand that things in Sicily move at their own pace and in their own way; and pick a “bigger” town place to stay in the off-season (like Siracusa), not a smaller tourist town that basically shuts down for the most part.

Thank you very much Jennifer!

Lagos has been mentioned to be as well, and appeals. I’ll look into Cabanas. What are your thoughts about Faro itself?

I’d really like to spend more time in Lisbon, so am seriously considering splitting my stay and spending all of March there.

I wouldn’t mind the Canary Islands, but find it too far/complicated to get too. Madeira may be an interesting choice as well...

Madeira is stunningly gorgeous. It has no natural sandy beaches, but there are wonderful walks along the levadas (irrigation canals). I would guess that it would be a bit more expensive than your other options, but I may be mistaken. I went there twice, but in the summer and decades ago.

As you have already received good information on the Algarve, I will add a bit about the Lisbon/Cascais area.

The biggest problem with winter is the rain. It never gets that cold, but there are rainy and foggy days. But, definitely not every day and rarely does it rain for an entire day. It’s usually brief showers periodically through the day. The sunny days are glorious. I eat outside at restaurants regularly during the winter, just planning around the sunny days.

There are few tourists, which in a normal year, is lovely. Visiting the Lisbon museums and attractions is much better due to smaller or no crowds. I know at least 2-3 couples from Canada and the US who winter here every year. English is widely spoken, and there are a number of expats, making it easy to actually have conversations without speaking Portuguese..

Both Lisbon and Cascais are very doable without a car. I’ve been here five years without one, with no plans to change that.

I think the Alentejo would also be nice, but you would need a car. I also can’t imagine being in the Algarve without one.

Thank you, Diane, for your description of your winter in Sicily.

Kathryn, thank you very much for the info about winter in Cascais.

My husband will be landing in Lisbon later than me, on the Friday Feb. 12th (Valentine’s week-end.) I’m thinking of spending a romantic week-end with him in Cascais, before we head to the Algarve for a 3-week apartment rental (with a car.)

Would you have a recommendation for a particularly romantic place to stay in/near Cascais that week-end? Do you know if the Grande Real Villa Itália would likely have a special Valentine-theme Sunday brunch, as the 14th falls on a Sunday?

Since Shrove Tuesday falls on Feb. 16 in 2021, should we plan on catching a Carnaval somewhere that week-end instead? Assuming that it wouldn’t be cancelled, would the Carnaval in Sesimbra be worth including in our planning - would it fall right on Feb 16? (I’d try to book cancellable accommodation for it ahead of time, with built-in flexibility.) Many thanks in advance for your insights!

It looks like we may include a couple of weeks of non-planned wandering from the Algarve, likely to the Alentejo (and maybe towards Merida) before returning the car in Lisbon and spending the end of March in the city, before going home. I love Portugal, and we’re looking forward to returning this winter.

The Grande Villa Italia would be quite romantic and I think it has a regular Sunday brunch. The Fortaleza, toward Guincho beach will have a Valentine’s Day special but I wouldn’t want to be out there without a car. If money isn’t an issue, my pick would be the Albatroz. It’s in a old villa and is recently remodeled, but leaving the old tiles, etc. It’s my favorite place for an afternoon drink as the views are wonderful. And, it’s right in town and close to the train station, so walking everywhere is actually preferred due to the challenge of parking in Cascais.

As Carnaval isn’t a big think in Portugal, I’m not familiar with the celebration in Sesimbra. And, it would be difficult without a car, IMO. You really need to go to Spain for the big Semana Santa (Carnaval) celebrations.

Let me know if you have other questions. I would be happy to help, if I can.

Others have greater expertise than I do with the Algarve, but we went there in February a few years ago for about a week and it was horrible. We were in Lagos and Tavira. Nothing was open, it was (honestly) ugly and the weather was terrible. Lots of tacky, touristy places geared toward the Dutch and Brits. I've been to just about every corner of Europe and I've never been to a worse place. We left early and stayed in Lisbon, which we liked. There are dozens of other locations I can think of that would be a much better experience. Madeira, already mentioned, definitely comes to mind as does anywhere in Andalucia.