Anniversary Trip Itinerary Feedback

Posted by Mabel on 10/31/25 11:22 PM

Hello everyone! My husband and are hoping to travel to Italy for our anniversary next year, and I am in the beginning stages of planning that trip. We visited Italy for the first time this past summer—my husband had a short work trip and I tagged along. We were based in Milan (which we enjoyed) and took day trips to Bergamo and Verona. Unfortunately, I began to fall ill during our trip to Verona, which put a damper our plans for the remainder of our visit. However, we both came home in agreement that another trip was in order!

We are looking at a 10-12 day trip in November 2026. Nothing has been booked yet, but flights in and out of Milan look to be cheapest and most convenient. (We’re fine with less than perfect weather and shorter daylight hours if the trade off is less expensive accommodation and hopefully fewer crowds.) Originally I was thinking Venice, Florence, and Rome. But I’d also like to go back to Verona, as we left it early due to my getting sick. We also missed out on a day trip to Bologna, which I had been excited about. I’m feeling a little on the fence about Rome due to the descriptions of “chaotic” that I sometimes hear—although I do feel excited about the ancient history sites of the city. I can’t decide if we should switch out Rome for some time in a quieter, smaller town, or just embrace the hustle and bustle! I’d love some advice from seasoned travelers to help me narrow down our itinerary. As you can see, I’m all over the place and know we can’t do it all!

If it’s helpful, here are some experiences we loved from our recent trip:
Exploring Bergamo’s medieval Citta Alta (and a touristy dinner in the piazza listening to a violinist); train travel; people watching; architecture; church art; caffe and cornetti at the local bar; all the gelato!; exploring the streets of Milan’s Brera neighborhood; Milan Duomo rooftop

We like museums but would probably burn out pretty quickly on all art, all the time (especially my husband). We enjoy a mix of planned activities and unplanned time for exploring, especially off the beaten path. We are also adventurous eaters!

Here are 2 itineraries I’ve been considering:

Itinerary 1
Fly round trip Milan. Train directly to Verona on arrival.
1-2 nights Verona;
3 nights Venice;
5 nights Florence (day trips?);
1 night Milan;

Itinerary 2
(Fly round trip Milan or into Milan/ out of Rome?)
1 night Verona;
3 nights Venice;
4 nights Florence;
3 nights Rome;

Would welcome your advice and feedback! Thank you!

Posted by Jean

Idaho, USA

11/01/25 12:19 AM

9002 posts

Hi Mabel,

There’s so many options, but I will just start with some basics. You should look at multi-city flights. It’s an arrival and a departure at two different cities, but they are on the same reservation #. So for instance, fly into Venice and fly home from Malpensa (Milan) or fly home from Rome. It may or may not be more expensive, but the train and time to get to a location should also be considered in that equation.

You were there in the summer. Going in November will be much different if you were enjoying those extra hours of sunlight doing activities outside, or sitting in a piazza. The Citta Alta portion of Bergamo might be dark & slippery on those beautiful lanes, by contrast. And if it’s raining, will you be happy doing indoor activities - museums, churches, cooking classes, etc. vs. walking & exploring outside? I am not trying to talk you out of November! Just want you to be aware, so we can help plan to realistic expectations.

Some ideas: Venice, Verona, Ferrara (day trip to Ravenna), Florence, and fly home from Milan. You mentioned Bologna, but Ferrara is less expensive and fantastic food, plus a castle in the center of the city.

Rome is more expensive, but there’s a lot more options for activities, especially when daylight will be short. Give Venice more than one day. It is fantastic! I would say 3 days is ideal, but 2 if you’re stretched for time.

You mentioned violin music. Cremona, near Milan, is the city of Stradivari, and there’s a wonderful violin museum there. Go on a weekend, so you can hear a short concert (buy tickets ahead). The church in Cremona is gorgeous with the beautiful frescoes, and if you enjoy climbing towers, the clock tower has a solid center core, so there no scary view as you climb.