Trying to pick a destination

Your focus seems to be on Iberia. Nothing wrong with that, Spain and Portugal are great.

You mentioned Sicily, which, is a viable option, but pales compared to Tuscany and Rome. Consider Florence or if you prefer a smaller city, then Siena or Orvieto. Italy is hard to beat for art, architecture and history. St. Peter's Basilica in Rome is special, especially with the Sistine Chapel in the Vatican.

Porto is nice, and the Douro River Valley is the most scenic in Europe. Still, it is not known for cathedrals. Salamanca, Spain is not too far and worth a day trip or short stay.

Near Madrid is AMAZING Toledo, the gem of Iberia. 500 years ago it was the capital of Spain and is very well preserved. Segovia, just north of Madrid is a great day trip.

Other great places for cathedrals are, as follows:

England- Winchester, Salisbury, York Minster, Durham, Canterbury, and of course St. Paul's in London.
France- Notre Dame in Paris, Reims, Strassbourg, Chartes. Also, the Chateaux in the Loire Valley. Versailles is near Paris and special.
Barcelona- mainly just to see Sagrada Familia, which is one of a kind.

So, if you were to spend 20 days in one place, seeing all the
cathedrals, museums, palaces, historic sites, and just relaxing and
wandering around, which of those 4 places would you choose? Porto,
Valencia, Madrid, or somewhere in Sicily.

Okay, well, you listed four places I have never been to. But of the four the only one on my radar is Sicily. It sounds like it especially does well under the wandering around and history category; and it isn’t a hot bed of tourism. Now, since geovagriffith threw out some unsolicited ideas (laughing), for S&G's I will give you my two cents.

You speak as though you have done several trips to Europe and you speak as though you have concentrated on very conventional (nothing wrong with that) destinations. My history was pretty much the same. I went to Europe once and loved cathedrals, museums, palaces, historic sites and kept returning to what I loved. So I get that. Then on one trip I sort of unexpectedly ended up in a totally different environment and I discovered that I had missed a lot of other things that I also found that I enjoyed just as much; but it was like a new world. So for a few years I started doing the safe bet with the wild card. Now, only the wild cards.

So, my suggestion is to do both to test the water. Spend the 5 to 7 days some place totally new in concept and style, then 10 to 12 days in something you have greater confidence in, like Sicily. Do this on each trip and you might make some great discoveries. From Sicily you can reach 3 cities in Romania, 3 cities in Greece, Sofia, Budapest, Dubrovnik, Malta, Istanbul; all non-stop starting below $100 one way. Then go to the safe bet and lay back and talk about your adventure on the way to Sicily. These other places are so inexpensive compared to the West that the extra airfare cost is wiped out.

Or not. LOL

Being a city girl, and having been to 3 of your 4 choices I would narrow it down to Sicily or Madrid.

There is so much to see and do in Madrid, even without day trips, that you would have no trouble filling up your days. I have found that large museums, such as the Prado, need a few short visits. For us, 2-3 hours in any museum is our limit, so repeat visits would be welcome. Food, people, museums, activities galore in and around Madrid - cooking classes, dance class, bullfights, best soccer team in Europe, Flamenco shows. Much to choose from.

We went Sicily in April 2022 and were very pleasantly surprised at how much we enjoyed our visit. We were guests of in-laws who were taking an ancestral trip. We were invited along as a translator (husband, not me). Anyway, we loved Palermo and were surprised at how much. The people were friendly, plenty to see and do, cleaner than we expected, and great food. Sicily is not that large an island and you could easily see other cities.

We were just in Porto in September. We did enjoy our stay but for me, 3 weeks would be too long. We could have missed some areas though. Porto is not a city I would put on my ‘must visit again’ list.

If it were my choice, Madrid would win hands down! Nice choices to have though, good luck with choosing.

The only one of the four that I've been to is Porto and while we liked it, 2-3 weeks may be a long time for just it.

• Will you have a car or willing to rent one for a day or two at a time, or are you going to be reliant on public transportation to make day trips?
• Even though you're renting an apartment, are you open to booking a hotel overnight for extended daytrips?

There are plenty of worthy destinations in between Porto and Lisbon, and driving would be more convenient. A couple of my favourites are Obidos and Sintra which would make more sense as a 2-3 day trip.

I have been to all the places you list. I would stay in Ortigia, Sicily for your twenty days. Rent an apartment and a car when needed for day trips.
Every place you listed is worth a trip there!

I have recently returned from a Mediterranean cruise and one of my ports was Messina, I chose an excursion to Taormina which was beautiful and interesting. I did not spend any time in Messina but it seems like there is a lot that meets your criteria. But I was there late October and it was still very hot and crowded. All of Taormina was a museum.

In a previous cruise, I ported in Porto but took an excursion to Braga. I do not remember the exact number but Braga has more churches than people. I did go to the Cathedral and also visited a magnificent shrine to Mary. I also was there late October but remember the weather being more pleasant than this last cruise and Braga was not crowded.

Poland. It has all your interests. And certainly a change from Spain and the Med.
I understand the premise of one place but how does it work for you? Do you only do day trips from there? Because if you visit longer to anywhere else you are paying again for night stays which you already have at your home base. If you want to save on that then it inhibits places you may actually otherwise go. It is limiting.

My wife says she will go wherever I want as long as we have never been there before.

She's a keeper!

Valencia I would choose over Madrid, personally, as there is so much to do there and the coast is beautiful. Lots to do in Madrid, too, but it's a huge city and I found it to be a bit too hustle-bustle for my tastes. Food scene in Valencia is terrific.

Sicily is just an entirely different kind of place. I'd be very happy to spend 2 or 3 weeks there. There's not any urban center there, though, with the resources you'll find in Valencia or Madrid.

I'll also echo the suggestion to consider Poland. Great food, tremendous art, culture and history. We loved our 11 days there, and I'd welcome a return. Not sure my wife agrees, though.

Have a great trip!

Treemoss2, you ask, how does it work for me? We love it. We might take a day trip or two, but mostly, it's just seeing the sights in that city, wandering around, eating the food, sitting on a park bench watching the locals walking their dogs. It's a relaxed way to travel. There's nothing wrong with hopping from one place to another, 1 day here, 2 days there, but that's not the way we do it. I'm always seeing people saying things like "You don't need more than 3 days in [great European city]." I don't know how people can say that. To each their own, I guess.

Appreciate everyone's response so far, but just to clarify, we've already been to London, Paris, Rome, Florence, Venice, Zurich, Vienna, and Barcelona. So I have to rule those out, because my wife will not go back to any place we've already been.

Nick mentioned Malta.

I was going to mention Malta in my first post but it is not Sicily or any of the other places that you mentioned.

On my last cruise, I visited Valletta and took an excursion titled "Malta's Scenic Beauty". I was really struck visiting Valletta. It was awesome. It grabbed me and still has not let go. I sort of feel haunted by it.

I would encourage you to research Malta. I think that you and your wife might easily be able to spend 20 days there.

Easily Sicily, but as mentioned above, it's too big to see all of from one location. So you could consider Eastern Sicily or Western Sicily and easily fill 20 days whichever "side" you pick.

To my mind, the food anywhere in Italy is superior to the food in Spain. That would also influence my choice. It may not be important to you (you don't mention it in what you're looking for, so it probably isn't).

I would wait a few years on Valencia due to the awful infrastructure problems they are likely to have there for a while.

You guys have convinced me I should give up the idea of staying in one place for all 20 days.

Three weeks is a great length of time to spend in Sicily. You do need multiple bases to cover the highlights of the island. Two of them definitely should be Ortygia (the medieval section of Siracusa) and Palermo. Others would depend on what you want to see and how you prioritize staying in one place vs. not spending a lot of time making out-and-back day trips. Keep in mind that Sicily doesn't have express trains. The trains are rather slow, and sometimes you need to take buses.

If you really, really want to spend 3 weeks in one city, I think it needs to be Madrid from among those you initially listed. Madrid has an unusually long list of fabulous day-trip options. They include Toledo, Segovia, Cuenca and Alcala de Henares. Salamanca and Cordoba are farther away. The thing is, you could spend 2 or more nights in every one of those places on my list, and I wouldn't like to have to take two or three trips out of Madrid to the same place.

What I discovered over the years is that some places didnt live up to my perceptions, and was glad on more than one ocassion that the trip had more than one destination. Holidays were rare things and not to be wasted on a less than expected trip. Then there was the ocassional low expectation that turned into .... oh wow! why did it take me 10 years to get here! And the diversity of destinations helped me to understand what I really enjoyed the most and plan better trips overall.

Marty, I appreciate your reply about what do you do in settling on one place for 20 days. I see you are reconsidering such a jaunt this time around.

I have friends who do such things and it seems OK on the face of it. Getting to know one place in situ. I do not think it is for me. Note Mr E reply above. Ostensibly to remain in one place is often equated with saving money. But traveling is not always about that. Diversity of place and is primary. Experiencing the different. Relaxing and wandering around the same place for 20 days seems limiting.

Over the last few years we have taken to trying two different vacations rolled into one. Whereby we go to one place and top it off at the end with another, often much different place. In the same trip. In fact almost like two vacations in one trip.
That is why I mentioned Poland. Since your heart seems to be liking the Mediterranean area and you may be depriving yourself when returning there again and again. Albeit to different cities but all in the same genre.
We have rolled Malta/Paris. Crete/Vienna. Greece/ Bulgaria.

Your wife seems to be onboard for new things. Lucky you. Keep her.

Not one of your four, but Vienna and the rest of Austria fits the bill.

Well, that depends on the extent of the topics. Vienna history that you can still see and touch is pretty much limited to a few hundred years. The art tends to be of the Habsburg dynasty period. Sicily has ruins and museum pieces and art going back to the 11th century BC and facinating history that you can see and touch extending up through the Habsburg golden age. Architecture? From Greek till today. Cathedrials? Only a half dozen really impressiv ones. And I mean really impressive if you understand the architecture.

No yes or no or right and wrong ... all about what interests you.

You have barely 3 full weeks to spend. My choice would not be included among the 4 listed.

Yes, weather is an important factor. It's one reason I don't do trips in the winter or even in the so-called shoulder season.

For seeing and visiting those items important to your itinerary, museums, cathedrals, etc. , I would choose France, and don't limit yourself to those regions of France normally inundated with tourists, lots of areas and towns are intriguing to visit , along with their chateaux and museums.