Doable? 14 Day Trip?

What is missing here is your transportation plans from spot to spot. Every location (with the exception of the vague "Tuscany") is easily accessed by train. Do you have a spot in Tuscany that you have in mind?

My other question is , "what are your favorite types of activities to do on vacation? Are you focused on museums, restaurants, cultural experiences, outside activities?"

Suggest that you treat yourself to a day room or lounge access at Chicago during that long layover.

Hi!

We will stay with family in Chicago on the way back and will get lounge access on the way to Italy.

We are looking for cultural experiences, restaurants/food/wine I would say are the top of the list. We will obviously do tours but would prefer a leisurely agenda over a strict itinerary if at all possible.

Sounds like we need a driver if we need want to go to Tuscany.

Rome - Hotel Eden or Hotel Manfredi
Tuscany - Castello di Casole
Florence - TBD
Venice - Hotel Bauer Palazzo
Lake Como - Grand Hotel Tremezzo or Mandarin Oriental, Lago di Como or Grand Hotel Villa Serbelloni

If you have other hotel options you’ve experienced that would be super helpful.

I looked up the location of the hotel you listed for Tuscany. You could get within an hour by train and then rent a car or hire a driver from there.

You might consider reversing the order
Start in Milan or Lake Como-a better place to recover from jet lag

As it is you have only 3 nights in Rome, really just 2 full days as I imagine your arrival day will be a bit blurry

As Christine wisely says, Rome is not a good place to start. It's a big city with noise and traffic and impressive sights. Start somewhere slow (Como or Venice). End in Rome when you're acclimated to Italian ways and can enjoy the experience. I'd recommend staying in Florence for all 4 nights. Day trip by bus or train to other Tuscan towns. Siena for day by bus, you can combine Pisa and Lucca by train in one day. You can arrange a winery/tasting tour for a day or a half-day.

Thanks for the advice on flipping the trip! I went ahead and made the flight changes…..thinking we’ll start off in Como, Venice, Florence and Rome.

I like the thought of making day trips to Sienna, Pisa, etc…..

I like the thought of making day trips to Sienna, Pisa, etc…..

Just leave enough time for Florence itself! Lots to see there so limit your day trips so that you're not spending MOST of your time elsewhere. Also 'culture' is much more than food and wine; it's history, architecture and the arts as well so yes, do plan on taking in some of those things!

You definitely do not need tours for everything, assuming you're up to a fair amount of reading/research on your own. But you haven't mentioned what time of year you're planning on taking this trip? A 'leisurely agenda' is a challenge if wanting to visit certain attractions during high season, and doing so on a limited schedule. For instance, you've planned only two full days in Rome, and its two most-visited attractions, Colosseum/Palatine/Forum and Vatican Museums, require timed-entry reservations or tours, booked well in advance, to get anywhere near them. As well, both are going to eat up large chunks of your time and energy so something to consider if the usual highlights are on your list? I sure wish you were planning 3 full days/4 nights in Rome and at least two full days for Florence (not counting day trips).

You'll need advance, timed-entry tickets for the Uffizi as well, if planning to do that one. Do you HAVE to visit the premier art museums in Rome and Florence? Nope, not if art isn't your thing but it's part of the 'culture', and especially so in Florence so I'd try to work at least some of the Renaissance patrimony into your visit.

Since you have changed your itinerary to fly into Milan, you might think about going straight to Lake Como on arrival. Spend 3 nights there then on to Venice. That frees up that 1 night stay you had in Milan, you can give it to Rome.
(If you want to see Last Supper you could still do that on your way to Venice without having to stay the night in Milan- you’ll need to get tix as soon as they are available. It is closed on Monday. It is truly amazing and was the highlight of our stay in Milan, but on a busy/short trip such as yours I wouldn’t want to give a night to Milan for it. We finally did see it on our 4th trip to Italy)

I also agree with Chani- stay the 4 nights in Florence and day trip to Tuscany hill towns. (Either easily on your own or with a guided group)
Those two 2 night stays you have are just too short. 2 nights really just 1.5 days- you spend half your day getting to/getting settled, etc. You would need a car or driver in Tuscany if you stay there and getting a car for just 2 days is almost not worth the stress/expense.

Your trip would then be just 4 locations in 14 nights rather than the 6 you had planned. All with easy transportation by train.
Lake Como 3
Venice 3
Florence 4- this allows 2 full days for Florence and 2 days for day trips
Rome 4

In Rome I would stay in the historic center, close to Pantheon, P.Navonna area
The 2 hotels you’ve listed look wonderful but that’s the high end shopping area

We are arriving in Milan Tuesday, May 23rd (early afternoon) and leaving Rome Tuesday, June 6th (mid morning).

Nothing in between is booked just that we’re settled on the following itinerary from the great feedback you guys provided.

Como - 3 Nights (23rd, 24th and 25th)
Venice - 3 Nights (26th, 27th and 28th)
Florence - 4 Nights (29th, 30th, 31st and 1st)
Rome - 4 Nights (2nd, 3rd, 4th and 5th)

:)

Looks like you’ve landed on a good itinerary.

My thoughts are: don’t try to do day trips from Florence as your time there is short. Tempting, but you may miss out on Florence itself. (We were in Florence for 28 nights with 5 of those nights spent in other towns, did 3 day trips and still felt like we missed a couple of things we would have liked to do in Florence itself. As an aside- a wonderful experience and close by is an e-bike tour in Fiesole with Giovanni. I have stories to tell, but my husband loved it.)

Venice-walk your socks off. Study a map (over and over and over) so you can take all the side ways to get from place to place. You cannot totally get away from the crowds but can minimize the impact. (A truly delightful experience is rowvenice.org-worth every penny.)

I’m looking forward to a lake experience spring of 24 so like seeing what others say about any of the 3 northern lake destinations.

Enjoy!