I habitually travel for Thanksgiving holidays. As a kiddo, it was to see family and eat lots of pies (yes plural). In my 20s it evolved into long weekends in Europe because it was cheaper to fly to Europe than to fly home.
Sometimes, I convinced friends to join me. Sometimes I traveled solo. Europe in late November is generally cool and rainy and cheap. It’s the off season and deals are available for airfare, hotels and tours. Because it’s the off season crowds are fewer.
I discovered I liked 3-4 days in a city. It’s enough to see the main sights and not enough to get bored. It definitely helps if you can train yourself to sleep or doze on a plane both going and coming back. The standard tricks, earplugs, eyemask, pillow, all help. A business class lay-flat bed is a fabulous use of mileage points, if you have them.
I think one of the great advantages of city-break long weekends is the focus it gives you. You generally won’t have time for day trips out of the city and you won’t need to worry about transportation, most European city centers are walkable or have great, cheap transit options. You get to settle into one hotel and not pack/unpack every day or two. Which can be exhausting.
While you focus on one city, don’t overschedule yourself. It’s your holiday. I try not to have more than 3 things planned for any given day. That said, it’s very often worth getting up before sunrise to get photos without crowds of people. Or to get that amazing sunrise view. It’s your vacation, you can take a nap after lunch or not.
For a long time I would do my research ahead of time, or on the flight, and head out to explore as soon as I dropped my luggage at the hotel. (Did you know hotels will almost always hold your luggage even before you can check in? I’ve never been denied.) It’s easier now with mobile navigation apps, but I have fond memories of free tourist maps and an adventurous spirit wandering the streets of Rome.
I avoided the Hop On Hop Off style bus tours because I prefer wandering and walking, but they can be helpful and give an overview of the city and take the worry out of getting lost trying to find something. And there are times when you don’t want to face another day of 30,000+ steps.
Some will say flights are long and expensive and you should maximize your flight value by staying longer and seeing more than one place. It’s all about what works for you. For me it’s now 3-10 nights in one place so I can actually sit in a cafe in Paris with a coffee (or wine) and just relax watching the world go by.