October city trip: Madrid or Florence/North Italy?

I've been to them all many times, and you have nothing but winners to choose from.

If you've not been to Venice, I would suggest you go there and then catch a train down to Florence. Or vice versa.
It's hard to beat the food in Italy. We were in Venice last June.

We also really enjoyed Madrid, Granada and Barcelona on another trip. Spain is substantially less expensive to travel in.

How many nights are you going to be in Europe?

Or a Florence/Milan/Bologna. This option is the most "complex" as we'd have to book multiple hotels, so only if it has a significant upside.

Why would you have to book multiple hotels? If you fly in and out of Milan you could sleep in Milan and take a day trip to Florence by direct train (no transfers) that takes 2h. Bologna is even closer (1h 15m): https://www.trenitalia.com/en.html.
If you get an early start, you can take a direct train from Milano Centrale to Venezia S Lucia (end of line) in 2h 30m. There’s a direct train departing at 8a and returning at 7:18p.

Mainly, we aim for a (authentic and luxury hotel&food) city trip with plenty of walking around the city and doing cultural activities and taking in the sights. (Short) day trips are also possible

Madrid works perfectly here with a day trip to Toledo.

I would spend all 6 days in Florence, with a day trip to Siena. Madrid has more of a big city feel. Florence is my favorite walking city in Europe.

You can't go wrong with either like saying do you prefer the apples or the bananas. Probably the biggest difference will be that Madrid feels larger and more urban, but as well will have more things to do and sights to see than Florence, as a capital city.

Consider as well Sevilla, I think is the best of both worlds, and might be exactly what you're looking for, plus October is a great time to visit.

I’m leaning towards Carlos’ idea to include Sevilla - perfect for October. Fly into Madrid and take the train directly to Sevilla for half of your time and finish in Madrid.

You probably won’t need day trips, but there’s Cordoba from either location, or if you wanted to stop on the way back. Cadiz from Sevilla and Toledo from Madrid.

Thanks for the replies.

All of what you describe appeals ! In any case, if I don't do one now it is certainly next on the list.

If you decide to take a day trip to Cordoba, you should do it from Seville (45 min. away) rather than from Madrid (1 hr. 45 min. away). You could also see Cordoba in transit between the two (though the city is worthy of an overnight or two, or three). You'd need to find a place to store your luggage. There are lockers at the Cordoba bus station very near the train station, but you should definitely have a back-up plan, because they might all be full when you arrive.

Note that it can still get very hot in Seville in October, especially in early October.