We want to go to Europe for around 10 nights in June and spend 2-3 days in Rome, but are open to suggestions on the rest of the trip. 4 Adults and a 15-year-old. Right now, we are thinking:

Fly into Rome, spend 2-3 nights
Trains to Florence, Milan, Venice, spending 2 nights in each city

• Maybe stay longer in Florence and take a day trip somewhere

Fly out of Milan or Venice

If it makes sense financially, we could even fly into Paris, Barcelona, or some other city and then take a regional flight to Italy. Rome can be first, last, or somewhere in the middle on the itinerary. We've spent many days in Rome on previous trips and seen all the highlights, but we want to return during the Jubilee year.

We've been researching pricing on several travel sites, but it's pretty overwhelming and we may need some help. I know there are several travel agents on this board. Does anyone have experience with booking a multi-city European tour?

FYI - I am a newb on Europe, but do know Rome is going to be extraordinarily crowded. It is a jubilee year for Catholics, and they are anticipating 2025 to be Uber crowded with pilgrims to Rome.

Yes, that's why we are going, but also why I don't want to spend more than a couple days there.

skip milan or just do 1 night, see the plaza, eat supper and leave

Look at Costco Travel - they have multi city trips like you are looking for. You can do most of your research there and you do not need to be a member.

Spend more time in Florence. We spent 2 nights and could have spent 4 or 5. We did not love Rome; even when it was a little less busy in shoulder season it was still a zoo. Definitely wouldn't go within 50 miles during Jubilee but to each their own.
If you're set on Milan, I'd take an extra couple of nights and go up to Como. It is gorgeous. Also if you haven't bought your flights back Emirates has a daily A380 from Milan to JFK. It is fun to fly on a middle eastern luxury carrier when you don't have to fly through the UAE and their prices can be pretty competitive on that route.

Our favorite hilltop town was Montefalco. It is in Umbria (the state next to Tuscany and basically baby Tuscany without all the tourists). Look up "Agritourismo", they are very popular in the countryside and are basically B&Bs usually on working farms or vineyards.
If you want to do any cooking class/wine tasting/truffle hunts I would 100% recommend Antonelli San Marco. We did their truffle hunt + cooking class + wine tasting/tour and it was spectacular for the price. They are also building a new B&B and I believe they have an Agritourismo you can stay at as well. We would go back there in a heartbeat.

Have a great trip. We are going in a month

As a travel advisor that specialized in Italy I would first recommend more nights in each destination and to potentially cut out a location. As others have said Jubillee will be huge in Rome and all thru Italy and add to that peak summer travel. I spent 18 days in Italy this past summer as a family of 4, transportation time takes more time than expected and the last thing you want is to come home feeling exhausted from your vacation. If you need expertise in planning my contact info is in my Bio

Recently did Florence, Rome, Bologna (which was really day trips to Verona and San Marino, mostly) The high speed trains are great but it does take time to get there, get ticketed, board, etc. min 3,days per city or you'll spend too much time traveling, checking in, finding places to eat, and trying to book things and not get enough time actually at any place. Rome will be crazy next year so plan on some long wait times and book tours way way ahead. It is also going to be quite warm that time of year. We went in late October and it was just barely cool enough for jeans/pants by afternoon. It'll still be great, though, but don't try to do too much in too few days.

Im one of the few that doesnt love Italy other than the dolomites, however if you go to Milan you only need one night and go see The Last Supper at the Basillica di Santa Maria delle Grazie. You need advanced tix.

Thanks for mentioning Emirates from Milan! We hadn't looked at flights with them and they also were not showing up in any search engines we were using. After a bit of digging around, we found some great deals using points/miles and were able to book flights for all 5 of us for a total of about 250k miles/points plus $1,200 ($240 per person). Our previous searches were averaging 750k-800k miles/points or $8,500 ($1,700 pp), so this is saving us over $7k!

Now we need to book the hotels and plan the rest of the trip. We are on Emirates from JFK-Milan, landing about 12:15pm. After reading other's comments, we'll likely spend just that night in Milan and then take a train to Florence early the next day. Spend 4 nights in Florence, taking a day trip somewhere while we're there, and then 4 nights in Rome. We are coming back from Rome on KLM.

We've been to Rome, so we are very familiar with the city, but it was in the non-tourist season. Things will be crowded and hectic due to the Jubilee, but that is the main reason we want to go to Rome again in 2025 so it'll be worth it to us.

https://www.seat61.com
Also look here for good advice on train travel.

Great!! I'm glad you were able to take advantage of it!
We flew that same flight for our honeymoon earlier this year and were fortunate enough to get business class seats using points. The week of the trip we got lucky and were upgraded to first. All of their seats looked really comfortable and the economy definitely seemed a lot nicer than US carrier economy!

Not sure if you've still got a lot of points leftover but when we stayed in Florence we stayed at the Hyatt Il Tournabuoni. It was a fantastic location and we were able to easily walk to everything. I'm not sure what the cash price is but I think it was around 25k Hyatt points/night when we booked. (We transferred Chase points).
Make sure if you're going to do the Duomo to get tickets in advance.
We climbed Giotto's Bell tower instead of the dome itself. The views were amazing and you are able to get a great view of the dome from the top. You can get a ticket to do both but that's a heck of a lot of stairs and the bell tower was enough for me. It will really take it out of you!
This is the website for the tickets, I'd only get them from this one because there's a lot of fake tickets out there.

https://tickets.duomo.firenze.it/en/store#/en/buy?skugroup_id=3006

We got the 'Giotto pass' which gets you into everything except climbing to the top of the dome. (There's a separate museum across the square, and it gets you into the baptistery, cathedral, and the ancient ruins underneath it). I'd recommend getting the earliest ticket in the day that you can and to get there right before your time slot opens up. The line for the bell tower was the longest when we were there because it takes a while to do and only so many people can fit at once.


Edit to add: the line at the bottom of my picture is the line to get into the duomo itself. It moved pretty quickly for as long as it was and maybe took 20 minutes when we waited in it (it was that long when we got in it). The bell tower line got just as long but moved much slower.


Also, if you're interested in getting leather goods when you are in town, there's actually a leather school "Scuola del Cuoio S.R.L." Maybe 20 minutes away walking from the dome. It's not necessarily cheaper than any of the street market vendors but the leather is much higher quality and you can be sure it is real Italian stuff, not the fake imported stuff that you might see in a lot of the Bangladeshi markets that are around town.

Let me know if you need any other recommendations! I can give some good food ones from our trip.

That Hyatt in Florence looks amazing. It was the first hotel we looked at, but they don't have any points rooms available for the nights we are there. They'd also require us to get 2 rooms due to party of 5 and the regular price is about $1,000 per night per room. We stayed in a 3-bedroom apartment last time we were in Rome and it was great. We're looking to see if we can find something similar in Florence.

Rome was blah. Skip it and go to the Amalfi Coast.

Up north, skip Milan and go to Lake Como.

Como and Amalfi are the best places to go in Italy.

I would add that spending a few days in Siena can be really cool also.