3ish week trip with 3.5 year old and 10 month old

I have never traveled to Italy with small children so won’t comment on that. We did, however, go to northern Italy in August. I would pick a place with conditioning. If you can’t, then September would be better than August.

Commuting to Rome from Ostia with 2 small kids sounds ugly. If you want to see Rome, I would do it at the end of the trip and stay IN Rome.

As for rental car, I would suggest a larger location for pick up to have better odds of them having the 2 car seats you will need (or were you bringing yours?)

For me late Aug - early Sept without A/C could be uncomfortable to miserable. Check the historic temp averages and the 3 past years for the locations you plan to be.

Screens are not the norm for windows in Italy, so open windows in a non-a/c place has, at least the possibility of, bug issues.

I applaud your efforts to modify your trip to the needs of your children, but after all the modifications, are you really experiencing much that you can't do closer to where you live? There are great beaches in California, ( and Hawaii), farm experiences closer to home, etc.
You have airline flights with ear pressures issues , major jet lag, scheduling naps, and unpredictable events, maybe colds, and the Summer heat. You must have air conditioning, as most places in Italy don't have window screens, so you then have bugs, especially mosquitos. Your children may be up all night and then want to sleep all day, with the jet lag.

Have you traveled with the children across country, with maybe a three-hour time difference, to see how they adjust?
I say this based on the valiant attempts of my step- children, who swore that having kids wouldn't deter their travel lifestyle , and ended up exhausted and frustrated after their first international trip with young ones. They then had to admit they were too tired to experience much culture, and decided to wait until the children were older for international travel. As the kids got older, they also took grandparents along, to help out.
Obviously, this is your trip and I'm sure you need a change. Again, your efforts are admirable. Maybe others will have more encouraging stories. I wish you well!

I commend you for wanting to undertake such a trip and to try to take it easy, but I’m afraid I can only agree with the concerns expressed by other posters. Being in the Foreign Service for 20 years, I flew internationally with my kids from the age of 3 months to 11 years. It was NEVER easy—tolerable yes, and over the years it certainly got easier. But the thought of wrangling two kids the ages of yours along with strollers, car seats, toys, feeding equipment of whatever type, clothing, etc gives me the shakes. I did all of all of this, but I also had a cat in the cabin, and it wasn’t something I’d recommend to anyone, no matter how flexible you and your kids are. If you’re in western Canada, I’d reconsider and explore closer-to-home destinations (California maybe?) Italy is wonderful, no doubt, but a long flight, time zone adjustments of up to an hour per timezone, new routines, foods and your desire to see places and cities with kids who could not care less just doesn’t sound appealing. I understand that it may be a long time before you can undertake a trip like this, but I’d wait anyway. It would be shame to sink all that money and effort into a trip that may well be unpleasant for everyone.

We took our 15 mo old to Paris and Italy and had a great time, but it took 3 adults to carry all her stuff. She was a very adaptable child and this would not have been as easy with a child that was less go-with-the-flow.

My teenager had been globe-trotting with my husband and me every year since she was 20 months. You can definitely travel to Italy! My advice is to go in September when it’s a bit cooler weather, pick one (yes, one!) location with good public transportation (for example Rome or Florence) rent an apartment and just enjoy parenting somewhere that is not your own home for a few weeks. Keep your trip simple. One of my favorite memories of traveling with my daughter when she was very young was our daily visits to “our neighborhood” playground in Paris.

Thanks for the positive response Amy! And I appreciate everyone's concerns too. We are going to take Rome out of the equation and just plop ourselves in Tuscany! Airbnb has highchair and pack and play so we'll be set!

3 weeks anywhere on the west coast would cost us the same if not more so, just excited to just be in Italy. Thanks again!

Veronica, I believe you said the place in Tuscany does not have air conditioning. Myself, and other OP's, are strongly recommending air conditioning for summer months. It gets very hot and humid at the time, and there are bugs!
Have a great trip and we'd love to read your Trip Report afterwards, as I'm sure it will be valuable to other parents with young children. Safe travels!

That sounds perfect, Veronica! Enjoy your time in Italy with your family.

Are you still planning on flying into Rome or will your plopping in Tuscany change that?
Is the agriturismo just outside Arezzo in that Castiglion Florentino?

I ask because renting a car might really be ideal as you most likely will want to day trip a bit from the agriturismo. Therefore, choosing an easy location for pick up and drop off will play a part. Certainly there is somewhere between Rome and Arezzo to do so. Rome is further away as an entry point than say Florence, but Florence might mean a layover on the trip over . If Rome is non-stop=much more desirable with the two young ones.

September definitely! Even then, it can be incredibly warm in Italy. A/C would be nice, but possibly being in the countryside will allow a bit of cooling at night and ability to have open windows. IF anyone is a mosquito magnet be sure to take along the appropriate repellent. They can be vicious in Italy.

Enjoy. Hope you have a relaxing and recuperative time. It will be special.

Sounds like an awesome trip. My wife and I have been traveling to Europe with our two kids since they were just a bit older than yours. You got this.

It has been a while, but a few things that I recall that were extremely helpful.

Umbrella strollers for the win. Even for the older one, they crash while you stroll. This allowed us to keep going while they were passed out. Small, portable, and will also provide some shade. Maybe a front pack for the little one as well.

Backpack diaper bag for the necessities, but also a good place for general walk around stuff for you. I prefer my hands free when I travel, but especially true when my kids were young.

The kids gear stayed in the rental car at nearly all times when not in use. Let the car do the work whenever possible.

Locate the luggage carts in the airport.

Have a great time!

I recommend an agriturismo (farmhouse converted to vacation country villa) or even more than one at different locations.

Both in August and September air conditioning is a must, especially if you come from BC and are not used to the Mediterranean’s scorching temperatures of summer. With kids I would even consider one with a swimming pool. There are plenty such choices throughout Italy, especially Tuscany. August is peak time, but in September you might find better pricing after schools start. In Italy schools start in mid September (depending on regions), but Northern European schools (Northern Europeans are heavy users of agriturismo stays) start in the very beginning of September. The Italian website below gives a list of the best websites where to search for agriturismi (farmhouse) stays in Italy.
https://www.freeonline.org/dir/c-305/Agriturismo
If you’d like some time near the coast there are plenty of available accommodations on or near the coast of Tuscany or Latium. In southern Tuscany I like the Maremma area, which is not too far from Rome airport (about 2 hour drive north), especially the Argentario peninsula.

For rental cars I would use AutoEurope, a broker/consolidator, they have multiple websites. Check pricing in all.
www.autoeurope.com
www.autoeurope.eu
www.kemwel.com
You will need child seats, so not sure the car size you need. Car seats need to be EU approved, therefore I wouldn’t take one from Canada. I know they cost at least €30/day to rent from the rental car companies, but it is what it is.
Since you will likely arrive in the afternoon, rest at an airport hotel the first night, then rent from the airport the next day. Forget Ostia. It’s too crowded in August and not that great. Drive away the next morning.
Leave Rome for last before coming home.

We traveled to Italy last year with our then 10-month old and had a blast. We traveled around north Italy, mostly by train, staying 3-10 nights in each place. In hindsight would be better to do fewer places for longer since getting from place to place was such a hassle due to all our luggage! Renting a car should make that a lot easier. We ended up renting a carseat from the AirBNB host since the rental car rate was close to what it would cost to buy it new! Note that US car seats aren’t legal in Italy.

Like you, we spent our first 3 days where we flew in just to get over jet lag. We arrived in the evening which was nice since we could go straight to bed. Almost all restaurants had high chairs (“seggiolone”), but diaper changes were done on the floor, on park benches, and even in the stroller. Everyone was very friendly and our son enjoyed the attention (and watching the pigeons).

Ignore the naysayers, you will have a wonderful time and make a lot of great memories!!

is it possible to do a dry run ASAP? Take 4 days at least and try managing with the 2 kiddos lugging all the stuff you would take with you to Italy. I don't believe any of the posters had 2 kids which I think might change the scenario a little bit.

Grandparents--hear me out--is there any possibility they could care for the 3 yr old as I imagine it might be better for you to take the baby. Just a thought!