Rome, Florence, and Capri OR Venice?

I suggest early May for somewhat fewer crowds.

I suggest Venice-Florence-Rome in that order. You don’t want to fly out of Venice, airport is not easy to get to and flights tend to leave really early (think catching an expensive water taxi at 5 a.m).

Capri is fine but an advanced topic. Also check travel times. I made it to Capri only on my third visit to Italy, and then as a day trip from Sorrento.

Nothing could be easier that Venice-Florence-Rome on the train.

What do you mean by touristy? If you mean crowded by tourists it’s a tough call, the time you are going all these places will be crowded. You would be likelier to find a quiet spot in Capri, I guess, than Venice.

Capri is a rocky island. It does not have a lot of sandy beaches. Yes, it's a water resort, but it's not like Florida or the Carribean or Hawaii. I like the previous response's term "advanced topic." It's also remote and hard to get home from promptly. I am astounded how many flights to and from the East Coast USA there are for Venice.

Venice is a much more important monument of world culture, possibly higher than Florence - but that's debatable! Venice will only get wetter and harder to visit, so you should go now. It is magical place, and much less work to visit than Capri.

It is hard to explain in a nutshell why Capri is an advanced topic, but if you had allowed us to see you home city (in your public profile (look under my name, for example)), I might be able to compare it to someplace you know. One of the problems with Capri is that, like Positano, it's infested with the same global luxury boutiques that are displacing local businesses in all the major cities of the world. It's still unique, but you have to work hard to keep that feeling. I can say accurately that going to Capri is more stressful than going to Venice. (referring to your OP.)

We put off Naples, Sorrento, Positano, Ravello, and Capri until our fifth or sixth visit to Italy. If you want to visit wineries, Tuscany goes way ahead of Capri. Even the Veneto goes ahead of Capri on wine.

Hi Caroline and welcome to the RS forum gang -

My vote would be for Venice as it just makes the most linear sense (I'd recommend flying into Venice and out of Rome if coming from the U.S.). Save Capri for a future trip that you can combine with Naples and the Amalfi Coast. Capri, BTW, is not known for its beaches so if sand and sun is the goal, I'd pick a different location. for that. We enjoyed hiking around the island during our 2 nights there but didn't choose it for beach lounging or water activities. Yes, Capri is considered by many to be "touristy" and it's very crowded during high season but you can escape most of the mob if willing to expend some shoe leather. Otherwise, it's at its best in the early morning the day trippers arrive, and in the evenings after they leave.

Editing to add: we found Positano more "touristy" than Capri but did it as a day trip without time for much hiking away from the masses (it's pretty small) so....

The "Holy Trinity" (Venice, Florence + Rome) is the classic first-timers trip and a very nice one indeed as all three cities are very different and all are well used to hosting visitors from all over the world. Trains between them are easy to figure out, run rapidly and frequently, and drop you off in (or nearly in) the middle of the action. All three cities are also wonderful to walk: while you will probably use some water transport now & again in Venice, we didn't need any public transit in Florence, and used it very little in Rome over several trips there

All three cities will be VERY busy in late May/early June (high season) but as with Capri, you'll find breathing room if you limit the amount of over-visited attractions to just one or two a day, and spend the rest of your time enjoying other attractions or just doing some people watching.

3 nights Venice, 4 nights Florence and 4 nights Rome is great, IMHO. Can't help you with wineries as we skipped those in favor of stuff we can't do/see at home. Still, exploring the local grape can be a daily adventure with lunch and/or dinner! 🍷🍷

Even if it weren’t your first time in Italy, I would say that 4 nights on Capri is too much. It’s a small island. Also, getting to it from Rome and from it to Florence would be quite time-consuming. Each of those journeys would eat up the better part of a day.
I often wonder what people mean when they ask if a destination is “touristy.” Both Capri and Venice attract hordes of tourists. Capri is very beautiful, but has limited number of attractions other than its venues of natural beauty. Tons of shops and restaurants.

Venice is stunning, in a different way. I still remember our first visit in 1984, approaching, by boat, down the Grand Canal. Magical! True, there are many, many shops and restaurants; but there is also much world class art. It is hard to exaggerate the important role Venice played in European history. Capri doesn’t come close as a choice for a 3rd destination.

I agree with the others- leave Capri for another visit that centers around Naples and the Amalfi Coast. If you need a beach day, go to the Lido in Venice. If you just need a relaxing day, do a small group Tuscan winery tour while you're in Florence. Venice, Florence and Rome are good combinations for first time visitors,- very different from each other, filled with things to see and do, and very accustomed to dealing with international visitors. Train travel between them couldn't be easier.

All of the places you've mentioned are touristy; and crowded, since your dates are in high season.

Thank you everyone for your replies! Looks like Venice is the favorite so far! We unfortunately have to wait until late May to travel due to work obligations.

We will look into flying into Venice and out of Rome.

Tim - I live in Los Angeles currently, but lived in Chicago for the past 6 years, and Wisconsin before that.

Thanks!

YES do Venice! Capri is nice but it's far from Rome or Florence. If you are flying into Venice then start there, do Florence (day trip to Lucca and Siena) and end up in Rome. The tourists shouldn't be too bad while you're there - school isn't out yet. My favorite part? Planning next year's visit while I'm on the plane going home!

Compared to Venice, there’s practically nothing to do or see in Capri.