Help deciding 4 week itinerary with a young child

Milan is more than a day trip. Fly in or out of here and spend a night or 2, you'll need to adjust to the time change.
Lake Como - stay in Varenna.
I would not recommend Venice as a day trip. If you are choosing between Venice and Verona, definitely stay in Venice.

Anywhere you fancy in the Amalfi area will be great, but keep in mind it's hard to get around in that area, with no trains, and trecherous driving. You could stay in Naples and take day trips, or use a driver, or rent a car to see this area, easier than staying there.
I haven't been to Dolomites or Assisi.

In 4 weeks you can see it all.

I would fly to Milan (2 nights), train to Como (3 nights) train to Garda or Dolomites (3 nights), train to Venice (3 nights), train to Florence for Portofino, Cinque Terre, Pisa, Assisi (6 nights) train to Naples for Pompei, Amalfi Coast (6 nights), train to Rome (7 nights) and leave from Rome.

Hi!

I agree with Julie that in 4 weeks you can see all of the places you propose, and agree with her caveats.

I would further suggest, though, that traveling with a largely non-ambulatory child of under a year is VERY different than traveling with a toddler. You can carry/plop in a stroller your under-a-year-old kiddo.

Toddlers, however, sloooowwwww e v e r y t h i n g dooowwwnnn to close to their pace. They have short legs, their own idiosyncratic preferences, and Big Feelings, and can generally put a hitch in your giddyup. Even if you pack a sturdy, capacious buggy and bung them in it, they are going to want to get down, feed the seagulls, play in the fountain (and the mud), run around and grab at people’s dogs, etcetera.

All of which is to say that I might trim or adjust your schedule just a bit. You’ll be tired from keeping up with kiddo, as well.

You probably already know this… but I couldn’t help but put a point on it here. I hope you all have an absolute blast! :-)

Thank you both for the recommendations! This really helps me get a start in how many nights are best at each location and I can continue my research regarding what to see and what to begin filtering out.

And I know that right now my mind is imagining my son doing this trek with us at his current age. I still have NO idea what he will be like as an almost 4 year old! Haha, I can definitely see him doing all those things you mentioned and more.

I have been travelling with my daughters since they were two years old. Plan on being able to do 3 hours of stuff in the morning and another three in the later afternoon.

Your plan is too hectic for a younger kid. They do not do well with so much change. Slow down and let them have a few days in one location and they will start asking to go back to a certain playground or gelato shop. Then the compromise becomes easy for you both.

Without knowing what time of year here is what I would do for 4 weeks.

1. Sorrento for 4-5 days. Use it as a base for the Amalfi coast, Capri, Naples and Pompeii. Your kid will dig the ferries from town to town and the ride will be a chance for a quick nap. So similar to Cinque Terre that you can skip it.
2. Venice at least 3-4 nights. Remember, your kid will be limited by the need for a nap so longer day trips may be a challenge. However, Verona would be nice to see.
3. Ortisei in the Dolomites. 4-6 nights. A great base for day hikes where you can take a lift up, walk around for as ling as your kid tolerates, have luch at a high alpine hut and then take a lift down. Plus Ortisei has a community pool that is great.
   1. Lakes 4-5 nights. The kiddo may be bored by Como but, on Garda, Riva del Garda has a nice beach and adjacent playground that he will love. There is also Gardaland down at the south end if yall can stomach an amusement park.
4. Florence 3-5 nights. Day trips to Sienna to let kiddo chase pigeons around the square and Lucca to walk the city walls.
5. Rome 4-6 nights

Hi Michelle,
I wanted to comment on traveling with your son when he is 4 & the expectation as to what it will be like. We took my son to Italy last year at the age of 5 (we did Rome at 7mo then Covid happened). Like another poster mentioned, let him chase the pigeons. My son chased them in Piazza Pio while in Pienza and again in Assisi. It is such a fun memory. He had his moments of crankiness, like when we were in Gubbio & he demanded to be “at the front of the line”… we were walking downhill . Kids are resilient and will go with whatever you want, but remember to give breaks & lots of gelato or a special trip to McDonalds (Assisi has a nice one near the train station).

Our son has been asking to go back to Italy since we got back. We will return in October, we’re letting him think it’s because he kept asking :) we are visiting Venice for the first time, so I can give you insight as to what that looks like with a young child when we return.

Happy planning!

Note that there are no shoulder seasons in Italy anymore. Spring and fall are cooler, tho. Avoid the week before and the week after Easter. Also avoid the May 1 Labor Day holiday and surrounding weekend.

We love Lake Como, but it's just getting too crowded, and the transportation has become difficult. Think of standing on the train from Milan to Varenna with a four year old in your arms, for an hour, shoulder to shoulder. Also, Varenna and Bellagio are all steep steps . In many areas, there are no railings. So maybe Lake Garda is a better choice.
https://community.ricksteves.com/travel-forum/italy/is-lake-como-getting-crowded-like-the-ct-and-ac

For the Sorrento / AC Coast area, moving about takes time and patience, as the infrastructure has been sadly neglected. Traffic congestion is legendary, and the train from Naples to Sorrento is like a NYC subway, but without air conditioning. Perhaps Rome to Salerno would be a better option, then ferry to Naples or Sorrento. Pompeii is very difficult walking for everyone, because the stones are so irregular. If you visit The AC, I'd skip Cinque Terre, because both are coastal hill areas.

I love Venice , so maybe four nights here. There are small steps and bridges everywhere, but they are doable for a four year old. Venice is a great first stop for working thru jet lag.

Wishing you a great family trip. You do have lots of planning time.

I was just going to add to put your planning efforts into how you pack as well. With that many moves + a small child, think about what makes the most sense and will be easiest so that you don’t spend your first and last hours at each location scrambling to find things/repack things. Labels and packing cubes by location will help.

Thank you all! I’m glad I started inquiring about this trip early on because there are many things I had not thought of. After filtering some places out, this is what I have in mind:

Milan - 3 nights (and do day trip to Lake Como?)
Lake Garda- 3-4 nights
Dolomites (Ortisei)- 3-4 nights
Venice- 3 nights (I like the idea of starting here, and maybe working backwards up to Milan, then train from Milan to Florence)
Florence- 5 nights
Rome- 5 nights
Sorrento- 3-4 nights
Amalfi- 3 nights (and possibly fly back from Naples?)

I still have to work through deciding if staying in Amalfi is worth it in the end considering all I’ve been reading about traffic and difficulty navigating transport.

Once again, I appreciate the feedback and insight :)

I would check to see what you wanted to do in Verona and weigh it against what you wanted to do in Lake Garda.....I did 85% of interesting things to myself in Verona in a day and continued onto Peschiera del Garda for 2 nights which I LOVED. You could do it in a day trip, and then use the rest of the time using the ferries around the lake. I LOVED the tiny town of Peschiera and I want to go back.

If you're staying in Sorrento, there's not much need to stay in Amalfi TOO, unless you're not setting foot on the Amalfi Coast before you leave Sorrento. Transportation stinks on the AC and I ALWAYS lean towards the ferries which are more fun. If you MUST stay on the AC, I would say Amalfi would be your best bet as it has the best transport links, but unless you are solely using your Sorrento time to visit things besides the AC (like Capri, Napoli, Ercolano, and Pompeii) then you will be already covering that ground from Sorrento without having to move locations. If you wanted to visit Capri, Amalfi, Positano, Paestum, and Caserta, you could do those easily from Salerno which is at the end of the Amalfi Coast and is a bigger town. And getting to the towns on the coast from Salerno by ferry is WAY easier than taking buses. I really try not to set foot on a bus to a city that is on the water, it's not appealing to me for crowds and possible carsickness for other folks.

If you wanted to visit Napoli, and you wanted to fly out of Napoli (it's way better to be CLOSE to the airport the night before, not in a far off place), you could skip it as a day trip and get there early in the morning the day before you fly out and do what you want there and not have to stress the next morning. Either stay in Napoli that night, or Sorrento, as it's SLIGHTLY closer than Amalfi. That being said, if you're not ending in Amalfi, and putting it second to last, I vote you travel to Amalfi through Salerno, approaching it from the sea (which is the best view), with the ferry dock being probably a 5-8 min walk from the train station.

Katherine, Peschiera looks beautiful! I am definitely adding it to my list of must sees! :)

With regard to the Coast, places I really want to see are Amalfi, Ravello, Atrani, and of course Positano (even if it’s just for the post card photograph, haha). Is it possible to do all of these in a day trip? Or would it be suggested to visit the towns over a couple of days via ferries from either Sorrento or Salerno as opposed to staying overnight in Amalfi?

I also like the idea of leaving Napoli for last and staying there overnight to take a flight back home.

It depends if you're traveling the AC Coast by land or water . It's actually prettier from a boat ride.

I found Positano a big let- down, just a collection of high- end shops. And the steps are crazy steep, so what is your plan for moving your four- year old about? The Positano peer is small, and is often out of service due to the weather.

We did a car trip from Sorrento to/ from the three AC towns, and it took nine hours total. So half the day was spent in the car. I would not recommend that.

What are your plans for your son on day trips when he needs a nap? I know it's hard to predict two years in advance.

Keep on planning!

I traveled in Europe with kids, my son was 5 when we first did this.
Forget museum with a toddler.

Frankly, if you can find a grandparent or sitter, best to leave the child at home.

Well, Peschiera is delightful....if you need a town on the lake with good train connections.....I bet the towns on the north side are prettier. It was so nice though with how small it was and I had the BEST gelato in the north there. There are a lot of ferries though, so you just have to scheme with your preferred locations to plan the trips.

For the coast, Atrani is just a walk from Amalfi, I have never been there, but it can't take THAT much time? I only aim to do 2 locations in the time I have in a daytrip to the coast. Usually it's Amalfi and Ravello, or Amalfi and Positano, I think I would feel rushed if I tried to ferry/bus to more. If you had a private driver, that might make it faster. I WOULDN'T aim to do the AC solely from Sorrento. I would choose a ferry from Salerno every time over traveling from Sorrento. I think the decision to stay in Amalfi (it would be my TOP choice on the coast to stay because it has the best transport options, all the buses start and end there) would end up on what you want to experience. It is MUCH less busy when all the day trippers leave. If you wanted to do more than a day on the coast it might be good to BE there, as the earliest buses to Ravello will be WAY LESS CROWDED before the ferries and day trippers get there.

I like wandering about through the towns before and after dinner, and Amalfi would bore me after a while since it's so tiny. Salerno and Sorrento have way more lanes and streets to explore.

I feel like I am contradicting myself, but at least gives you something to think about!

I'm a supporter of taking children on European vacations, but only if the trip is largely planned with consideration of their needs, limits, interests, etc. Let's re-think what a 4-year old will find interesting and enjoyable. As examples, I could see him liking Venice because there will be rides on boats and lots of wandering. Climbing up and down bridges and looking down at the water will be a good activity. He might enjoy watching glass-blowing, walking through a few ancient churches, maybe looking at the Arsenale but no art museums, please. In comparison, I don't think Milan has much appeal for a little boy. Maybe the Castello Sforzesco but not the fashion district, art museums, or opera house. I imagine you could take him into the cathedral but I doubt young children would even be allowed on the popular roof-top tour. Think through what you would actually want to do in each destination---and how will those activities fit in with a young child.

I'd suggest a more limited itinerary so there are fewer changes of hotels/b&b's. This isn't the time to do the fast-paced, check off the box, type of travel. Please build into your planning the need for "down time" each day and an earlier bedtime for a pre-schooler. Meals also tend to go slower with little children. As a preschool teacher once commented to me, you can't dine with a young child; you just eat, and at their pace. Look for parks with playgrounds where he can run and yell without disturbing others. Consider skipping some of the cities in favor of a small town, or even an agriturismo stay. Finally, if you decide to continue with the fast-paced itinerary, maybe there's a family member who would be willing to have your son as a guest while you enjoy your anniversary vacation.

Your post is quite timely. I am also planning a family vacation in Italy for May 2026 with my son, daughter, son-in-law and two grandchildren, ages 5 and 3. We're celebrating our 40th wedding anniversary. Our plan is to go in May for 9 days. We know it's impossible to see the country in that time frame so we are focusing on Florence & Tuscany and a couple of nights in Rome. We consider this a "sampler" trip. I'll keep my eye on the suggestions and comments. We've heard Lucca is great and there is a park nearby called the Pinocchio Park. Sounds charming. Our idea is to rent a villa/house with a pool and use that (and gelato) as the reward for tagging along with us to all the sights.

Ooooo Anita's post makes me think more......you might not even want to be on a windy road bus for an hour with a tiny human along the AC! You might be stuck with ferries, and if you needed some playgrounds, or at least parks, I am a big supporter of Salerno :) Paestum, a big archeological park with the temples that YOU CAN WALK INTO might be super neat for the little one.

With regard to the Coast, places I really want to see are Amalfi,
Ravello, Atrani, and of course Positano (even if it’s just for the
post card photograph, haha). Is it possible to do all of these in a
day trip? Or would it be suggested to visit the towns over a couple of
days via ferries from either Sorrento or Salerno as opposed to staying
overnight in Amalfi?

I would not try to do them all in one go. Positano is vertical, so it's gonna be challenging with the little one. Ravello will require a bus or taxi up (fingers crossed no motion sickness!). I would take it very slow and easy -- you should see some of the complaints adults have about the transport in this area. Plan this part way more slowly than your constitution tells you to. Nap time is likely gonna dictate some things. It looks like you have about six days planned for the region overall, with one day allotted for Pompeii, so it is realistic to spread it out and that is really what this area is for, leisure! I think a 4yo will be more challenging to travel with versus an infant, as they can complain, and they can run (lol)--so good luck!

I'm guessing that your child is more like our two sons and less like our two grandchildren --- we've traveled to Italy (and other places) with kids and their personalities make a big difference. So far, I've only written one trip report about traveling with young children, but here it is because it has ideas for you about Venice and Rome: https://community.ricksteves.com/travel-forum/trip-reports/bologna-ferrara-venice-rome-in-december-with-kids

If I were you, I would pick a cooler, less crowded time of the year than September, if you possibly can --- you'll have an easier and more comfortable time. We are big fans of late October, November, December, March, and early April.

With a child along, a trip with just a few home bases plus day trips will give you flexibility and allow you to stay in apartments instead of in hotels. It can be a much more simple but still very rich trip. Also, I hope I sound realistic and not pessimistic, but we've spent 400+ nights in Italy (not counting travel days to and from) and on almost every trip at least one of us has been ill or injured (3 ER visits so far), and we were glad we weren't on a tight schedule of getting from place to place. Staying a little longer somewhere means you can take turns going to a museum or art gallery while the other parent goes to a playground or tourist-train-ride or park.

You list several very, very popular places in Italy we have never been to and do not ever want to go to, so take my recommendation with a grain of salt to skip a bunch of those (especially if you stick with September), but how about flying into Venice and staying a week or more, then Florence and Rome, but with one or two smaller and somewhat less heavily touristed towns/cities added in as bases in between the big three. Say, Ferrara or Lucca or Siena or Orvieto or a seaside place in Liguria like Camogli, or a town in the Dolomites.

We are planning 3.5 weeks in Italy starting October 20th with our 7, 4.5 and 2 year old. We're flying in and out of Rome and then want to head down south somewhere. We travelled a lot before kids but haven't since the oldest was 4 months old. We're going with 3 so it's different than one, but we're much less optimistic and planning to do just Rome and then find a coastal town in the south where the weather is hopefully warm enough to hang out on the beach (we're Canadian so 20 Celsius is great beach weather!). @nancys had some good thoughts and I'm curious to know her recommendations for travelling in the late fall in Italy. I'll let you know how our trip goes and tips we have after!

I think to make a trip like this best work, think of it not so much as, “we want to travel around and see Italy for a month with a three year old”, but rather, “we want to live in Italy for a month with a three year old.” Kids that age thrive on routine. Pick two places, or even just one, and rent an apartment there in a nice residential neighborhood for at least two weeks each place. Rome would be great, but lots of good choices. Big enough apartment so your son has his own room. You don’t want to have to have lights out for you at 8 pm because you’re in a hotel room and that’s his bed time. Nor do you want to have to eat every meal in a restaurant with a 3 year old for a month, no matter how well behaved he is. Not fun and very expensive. Better to go out to restaurants occasionally and enjoy getting to know how to food shop in Italy for the amazing local produce, get to know the local shopkeepers (at least to some extent) and cook him some nice pasta with a fancier version for you with wine. His routine would include the local park and playground, stopping with you at a favorite coffee bar in the morning, gelato place later, market, some day trips, nap time, etc. And as noted you can trade off child care while one of you goes to see a museum. When I was 5 my family lived in London for several months (for my dad’s work, not vacation) and the fond memories I have are of those kind of daily routine things there, rather than traveling around sightseeing, and I think my mom would say the same.

Hi Michelle,
We just got back from Italy so I can throw a few suggestions out there...

I have 6 kids, my youngest is now 9, so I've seen quite a few 3-4 year olds, lol. A stroller is not going to be your friend on this kind of fast paced travel that you want to do. Especially in the Amalfi Coast. I highly highly suggest getting a baby carrier, and putting him on your back, or your husband's back. Please don't get one of those crazy metal structured contraptions, lol.... there are so many good soft carriers around these days, and ones specifically for toddlers. I mostly used an Ergo carrier in my day, but there are more options now. Soft and lightweight is what you want, basically you'll just be giving him a piggy back ride. He can nap back there, too.

The Amalfi Coast has a TON of steps. Steps everywhere. So, a stroller will definitely be a hassle. We stayed in the town of Amalfi, in an AirBnB. We flew into Naples, and had a driver take us to the apartment. Most everyone got carsick on the way because of the windy roads. Do yourself a favor, and pack a few barf bags in your purse!! This is not the time to discover that your kid really does get motion sick. They make these little sea-band things, that are accupressure, for kids, they do help with the motion sickness. I had to give my older kids dramamine.

Staying in Amalfi, it was easy to walk down to the town, or take the local bus to and from our apartment. (it was a 5 min bus ride). Ravello required booking a driver, we actually did a combo tour with Mondo Tours, I HIGHLY recommend them - it is a Rick Steves recommended vendor, actually, and I can see why. We hired them to take our family of 8 to Pompeii, Amalfi, and Ravello for a day. They picked us up in a van, drove us 1hr to Pompeii, gave us a fantastic guided tour there, then drove us to Ravello and gave us a guided tour of Ravello, and Amalfi. It was an 830am pickup, and we were done around 3pm. If you've got the stamina you could tack Atrani on to that day, but I would just save Atrani for another afternoon. It's an easy hike from Amalfi, and is described in the Rick Steves guidebook.

To visit the other little towns on the Amalfi Coast, we opted for the ferries given everyone's propensity for motion sickness in the cars. The ferry from Amalfi to Sorrento took 1 hour - it stops at Positano first. We did not get off at Positano, it was an absolute ZOO. SOOOOO crowded. It is better seen and admired from the boat, lol. We spent the afternoon walking around Sorrento, then headed back on the ferry. It was very nice, and the down time on the boat was nice for the kids, several took little naps. We also booked a day trip to Capri through Mondo Tours, again highly recommend - but it was also a long day, and might be too much for your 4 year old. It was an 830 pickup in Amalfi, then a 1 hour ferry to Capri, where we transferred to a small little boat that then took us around the island. After that we went on the island and they took us to Capri (super insanely crowded, we only had time for gelato) and then over to Anacapri (less crowded and very picturesque, we ate lunch there). Then it was back on the ferry for 1 hour to Amalfi, back around 4pm.

We were in Amalfi for 4 full days, and felt it was plenty of time. On the morning of the 5th day, we had a driver take us to Naples, where we caught the train to Florence. The train was GREAT. Super comfortable, even in Economy class. Very straightforward to get there, board, etc.

Florence - we arrived in the afternoon on a Tuesday, and basically had 1 1/2 days in Florence itself (Tues. and Weds.). On Thursday we did a half day excursion to Siena (highly recommend), and on Friday we went to Assisi, spent the day there (recommend!!) and then continued on to Rome, arriving in Rome around 7-8pm. We hired a private driver for that.
Florence was a little rushed because we wanted to see ALL the things, but it was do-able.

oops. Ran out of room on my last reply.

We also spent a week in Rome. It felt like a good amount of time. I think anywhere from 4-6 days would be great for Rome, be mindful to avoid going during a very hot and crowded time of year if you can, if you can't, then manage expectations and pare back what you do because no 4 year old is going to be pleasant in scorching stifling heat.