Itinerary Help - Northern Italy with Teen Boys

Maybe cut a day from Venice and go to Alto Adige instead of Como. Gorgeous wine country, and you could spend a day up in the Dolomite Alps, hears the cow bells, ride a mountain coaster etc. Nice small cities up there too.

Also consider transiting to Venice on your first day. If you're going to be resting that day anyway a 3 hour train ride from the airport is fine. It feels good to have the initial travel completely out of the way.

Just to be clear, when you say 1 day in Milan, do you mean you are sleeping in Milan for 2 nights? Or are you counting your arrival day as 1 day in Milan, and you leave for Venice the next day?

As for keeping the teens interest: skip the winery tours. As a non-drinker, I would be bored! Limit the cathedrals and museums. After two cathedrals and museums, they all start looking the same to my teens. Do your “must see” first thing, when energy levels are high. Limit the day trips, unless there is something of interest for the kids. Focus more on making memories than ticking things off the list of sights.

I agree that two full days (3 nights) in Lake Como are plenty. I would add the extra day to Milan. Maybe the kids want to do some shopping? Or just relax.

I also agree with Hank regarding going straight to Venice on Day 1. From Venice, there are great day trips to Padua, Vicenza, Verona, Treviso.

Florence is my favorite place in all of Italy, so I'm admittedly biased, but I'd add an extra day onto Florence, since you barely have any time in the city itself (3 days, 2 of which are day trips). I think it's impossible to get bored in Florence, because there's something for everyone.

Some teen-specific recommendations...If they're ok with being in tight spaces, then I've heard the Duomo climb is excellent. (I can't do the narrow stairs, so I climb the belltower instead.) The Secret Passages Tour at the Palazzo Vecchio is fascinating, especially if they've seen (or read) the Inferno by Dan Brown. If they like leather accessories (belts, wallets, briefcases, bags, etc.), the Scuola del Cuoio is a historic leather school attached to Santa Croce (which you can access without paying admission to the church) that has high-quality leather items that make for excellent souvenirs. My husband still has his leather briefcase he purchased from there over 10 years ago.

Last year when we were there, we did a river rafting tour with Firenze Rafting and had a great time. My son (5 at the time) liked being on the water, and our guides gave us a great overview of the city. We only did the very calm ride down the Arno under the Ponte Vecchio, but they also offer actual river-rafting excursions further outside of the city.

I wouldn't add any additional overnight cities for just a one-night stay. It will eat up so much of your time. Even if you decide you don't want to spend your additional day in Florence, you could do Bologna as a day trip from Florence and it would save you having to pack/unpack for just one night.

Venice - 3 days

This needs clarification. Will you stay in Venice for 3 NIGHTs or 2 nights? a 3 night stay equals 2.5 days. You'd need to spend4 nights to get 3 days.

Lake Como - 2 days

Same here- how many NIGHTS is this? To get 2 days you need 3 nights. Every time you change locations you lose a half a day and Florence to Como (assuming Varenna?) will take at least 4 hours.

planned day trip to visit Siena & Pisa during this stay

This is difficult to do all in 1 day if that is what you mean- unless you are booking a guided bus tour?

If you travel right to Venice on arrival you eliminate that split stay/1 nighters in Milan. Put the 2 Milan nights together at end of trip.

You could simply add your extra night to Venice giving it 4. Arrival day is jet lag day and travel from MXP so that hardly counts. Then you have 3 full days in Venice- take vaporetto out to Burano/Torcello/Murano, consider doing Row Venice- always gets good reviews here.
https://rowvenice.org
In Venice they would probably enjoy the Secret Itineraries Tour of Doges BUT in July it will be wicked hot up there!

In Milan take the boys up on the Duomo Roof Terrace- that's a really cool way to visit yet another church.

Wow, so many great ideas, thank you all! We have some good things to discuss now.

Hank, I did think of the Dolomites at one point but then it seemed like it was too difficult to get there via train, so we scrapped that idea. If that is not the case, please advise.

Travel4fun, we were planning to sleep one night in Milan and leave the next morning for Venice. And yes, I definitely think we will need to be mindful of too many cathedrals. Thanks for the feedback!

Erin E. I do really like the idea of not having to pack/repack one more time. And thank you so much for the interesting suggestions! I am definitely going to have them read Dan Brown - great thought. My husband and I read his books years ago, but I hadn't thought of having the boys read it for the trip. I also think they may be very into the river tour idea. Thanks again!

O and I mean nights, not days, I guess. Each of the numbers in my OP refers to our plan to sleep there that night. So if we were to add on one more night in Venice, skipping the first in Milan, then we could use the extra day in Milan, or Como, or Florence possibly.

11 nights

4 Venice
4 Florence- you need 3 here just for Florence, add 1 night for each day trip
2 Lake Como
1 Milan- this is fine- you'll get here early enough from Como or wherever you are staying. Drop your bags at a hotel near Centrale and hit the streets

There is horseback riding on Haflinger horses up on Alpe di Siusi, but it takes a long time to get there from Venice. Maybe there are other possibilities near Castelrotto, but even that is far—-3.5 hours by train from Venice to Bolzano, where you transfer to a local bus for the ride to Castelrotto. Then you would need transport from your hotel to the actual stable.

I am going to make an alternative suggestion that offers a nice range of outdoor activities as well as scenic beauty and good food and wine: Lago di Garda, specifically the lakeside town of Malcescine. Go to Garda instead of Lake Como. You could put it after Venice before Florence, or after Florence on your way back to Milan. Either way, you head to Verona. From there you can either take a 15-minute train ride to Peschiera del Garda and a ferry from there up to Malcescine, or you can book a shuttle directly from the Verona train station to your hotel in Malcescine.

I am suggesting this town because of all the activities on offer. Monte Baldo rises thousands of feet behind the town and you can ascend by cablecar. There are hiking trails and mountain bike trails, with gorgeous views over the lake. The lake itself offers a couple of nice sandy beaches, plus windsurfing, kite surfing, SUP, kayaking. . . You name it. The area is Watersports Central. (Unlike Lago di Como. We found the water at Varenna very unappealing for swimming—too many birds fouling the water.)

https://www.visitmalcesine.com/en

Note that many Malcescine hotels will have a 3-night minimum in summer, so Hank’s suggestions for adjusting your time allocation are good. You do need to spend the night before your flight in Milan, but you do not need to stop there for the night on your way to Venice. It is a nice comfortable train ride and you can rest on the train. And save yourselves one hotel change.

Arrive at Malpensa. Take the train from Malpensa to Lake Como - 2 days.
Verona - 2 days (see the Roman Arena). I liked the city bike tour to see the sites, hear about the history and also a fun, easy ride. [I am using the extra day, plus the first day in Milan that I removed to give you two days here.]. Day trips from here are Vicenza or Padova, but my favorite would be Mantova, and it’s less than an hour by train.
Venice - 3 days
Florence - 3 days (train from Venice) - planned day trip to visit Siena & Pisa during this stay (not booked yet)
Milan - 1 day (last night - see what we can and rest up before early morning flight the next day)

And ideas for Florence. Here’s two my daughter & I did last September:

Two other activities that we definitely recommend were a city bike tour with “I Bike Florence – Original City Bike Tour” and a cooking class, “Pasta Class Florence, The Art of Pasta – Authentic Recipes”. I have been to Florence a couple of times. The bike tour took us to some of the places I hadn’t seen previously, and it was an overall fun experience for both of us. We saw so much during the three hours! Our guide, Martina, was excellent with lots of info, too. The pasta class was excellent! Our chef taught us how to make three different filled pastas and three widths of straight pasta. He offered me a job after seeing my rectangle of pasta dough & shapes. Hmmm! ; ) (Probably from my experience of making lots of croissants after a class in Paris.) His sauces were wonderful – some new excitement added to traditional recipes. We will definitely be making these recipes at home! Two places across the Ponte Vecchio bridge to recommend: I found my favorite Florence gelato shop again – Gelato Mancuso on Via Guicciardini

My children are in their twenties not teens but they loved Lake Como. We were there in August and we spent 5 nights. I would have been happy with 4 but we had an extra night snd that is where they wanted to spend it. There are lovely gardens which we all enjoyed. We also loved taking the ferry and exploring the towns. It was hot while we were there and our kids loved swimming. The beaches are rocky and we live in Florida so I wasn’t quite as crazy. But the views were beautiful. I also had numerous hikes planned but we didn’t do most of them because it was too hot.

We went to Verona and Venice also and they enjoyed those as well. Some of our group of 7 liked Lake Como best while the others favored Venice.

I would skip the winery tours with teens.

My $0.02

Go to Lake Como on arrival day. Great place to unwind and adjust to the time zone change.

Then Venice, Florence, and last night Milan for the flight back home. Add that 'extra night' to Florence to make a day trip somewhere else easier to do.

I would add a day to Florence. 2 days seeing Florence. 1 day visiting Lucca and Pisa. 1 day in Siena