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Deciding between Naples, Brussels, or Lisbon

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I need some help deciding where to go on my next trip in November 2012. I have 2-3 possible destinations in mind, and for the life of me I can't decide which one to choose. I need to do some thinking out loud, and would really love to hear people's thoughts, impressions, etc.

For background, this trip will be approx. 2 weeks long, divided into two parts. The second part will be spent with family in England, and they'll actually be flying back with me to Canada, so England has to make up the second half of the trip.

The first part of the trip is where I need some help. I will be flying Air Transat, which means extremely limited flight destinations to choose from. I will probably be traveling alone (maybe not, but doubtful bf can get away in Nov). I will not have a car and will therefore be taking public transportation. I'll be packing light.

Most importantly, I will have 5-6 nights to spend.

I've narrowed down my options to Naples, Brussels, or Lisbon, and I'd love to hear your subjective opinion on one or all of these cities. Did you love it, hate it, don't care? Where would you go and why?

There are other cities I've considered, like Madrid, Berlin, and Istanbul, but the logistics of getting there (given my limited parameters) are too difficult for this trip. I've been to both London and Paris a few times and want to go somewhere new, so that's why I've omitted them from the list of possibilities.

I'm also open to any new suggestions ((d))

But here are my own quick, preliminary, rambling thoughts.

My heart says Naples. It's been on my wishlist forever. The history and character are what interest me. I've been to Italy twice before (Florence and Rome) and loved both trips. In fact a part of me is thinking of returning to either Florence or Rome instead, but another part of me really wants to go somewhere new, i.e. Naples.

Want: explore/wander the city, churches, architecture, opera, Archeology Museum, Pompeii, food, stay in the city centre (looking at the Hotel Pinto Storey).

Logistics: I would be flying into LGW from YYZ, arriving LGW at 10:10am.

To get to Naples, there is a BA flight departing LGW at 2:20pm. That is only a 4 hour window, and it worries me. The other option would be to spend the night (in London or at Gatwick) and take the 7:30am BA flight the next morning. I don't like the idea of wasting a night like that. No option to fly direct to Naples from YYZ (and I'm pretty much stuck with Air Transat). Getting to Naples is the problem. Coming back is not an issue, I'd fly back to Gatwick, train to St Pancras, and go from there.

I would definitely stay put in Naples the entire time.

My head says Belgium. Brussels, Bruges, Ghent, and Antwerp have also been on my wish list forever. I LOVE the Flemish Primitives, and I want to learn more about Magritte and Art Nouveau.

Want: museums, architecture, food, churches, museums, and more museums.

Logistics: Easy. Fly into Gatwick, train to St Pancras, Eurostar to Brussels. There are plenty of Eurostar trains to choose from throughout the afternoon and early evening, so there is less chance of me missing the train. If, due to some massive delay with the plane, I did miss it, there are others that day I could take (cost not withstanding). Coming back is simple, I'd just take the Eurostar back to St Pancras.

Not sure how I would divide my nights in Belgium- stay in Brussels the whole time and take day trips? Or move around a bit in order to experience one or two smaller cities at night/early morning?

I really think I am going to feel rushed in Belgium with only 5-6 nights.

Wildcard. It's a distant 3rd right now, but I could probably be convinced otherwise. Many years ago I was dying to go to Portugal and started planning a trip with an old bf that fell through. Then I sort of forgot about it, although it's never been completely off my radar as a destination. The character and atmosphere is certainly appealing to me.

Want: explore/wander, churches, architecture, food, history, ??? would need to do more research for specific places.

Logistics: Easy. I could fly directly to Lisbon (stopover in Faro but on one airline ticket). This is actually what made me consider Lisbon for this trip in the first place. I haven't looked at flights from Lisbon to London but I'm not picky about the airport.

I would probably stay put in Lisbon and take a daytrips.

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