Hello, hello! I truly didn’t mean to take so much time off from daily blogging but I suppose that’s the reality of traveling with two toddlers while pregnant — there really aren’t enough hours in the day! We are now back in Connecticut through my due date in September and I’m very excited to have some time in front of my computer to share our trip with all of you and prioritize getting our lives back in order (all the unpacking, laundry, nesting, etc.!) before baby #3 makes his debut. I appreciate you bearing with me during this hectic time!

Today’s post will be all about where we stayed in Italy, what worked well, and what we’d do differently next time. I hope it’s helpful for any of you planning on traveling with toddlers and/or while pregnant, but please let me know if I can answer any other questions in the comments!

P.S. You can see all our toddler travel gear in this post!


traveling to italy with toddlers vrbo house rental

The view from our VRBO in Massa Lubrense!

traveling to italy with toddlers | local beach in Massa Lubrense

A local beach in Massa Lubrense a quick (but very steep!) walk from the house.

Bougainvillea | traveling to italy with toddlers

Bougainvillea everywhere!

traveling to italy with toddlers massa lubrense local beach

toddler sunglasses  //  swim trunks (size down)  //  waterproof loafers

traveling to italy with toddlers vrbo in massa lubrense

The drive from the town Massa Lubrense to the house we rented.

matching raffia slippers | traveling to italy with toddlers

Enjoying the view with my mom in matching raffia slippers (natural/orange here and pink/tan here!).


We booked this house rental through VRBO in Massa Lubrense, a town about 15 minutes outside Sorrento on the Amalfi Coast. The rental was largely dictated by the number of bedrooms and bathrooms we needed to accommodate a large group with young children as opposed to ideal proximity to particular destinations, restaurants, etc. so I would keep that in mind if you’re looking into a similar trip! The property housed our large group very comfortably, showed off with the most extraordinary sunsets every evening, and was a short (albeit very steep) walk to the local beach at the bottom of the hill.

But if you’re looking for proximity to popular destinations on the Amalfi Coast, it might be worth looking into other options that aren’t a $50+ cab ride one way. Also worth noting: there were 73 steps from the garage to the main floor of the house, which were definitely a hurdle while pregnant and traveling with kids, so something to note if accessibility is a factor for your group! 

tips for traveling to italy with toddlers

traveling to italy with toddlers and grandparents

traveling to italy with toddlers capri boat day

traveling to italy with toddlers vrbo for large group

traveling to italy with toddlers | walk to massa lubrense beach

My parents, brothers, and one of their girlfriends were all so incredibly hands-on with our two boys and my cousin’s son as well! We literally couldn’t have done this trip without their energy, enthusiasm, and readiness to pitch in and hope we can repay the favor someday. 🙂


First and foremost

We couldn’t and wouldn’t have done this trip with kids while pregnant without the help of many family members pitching in throughout the day. Things like having my mom sit next to Teddy at dinner or my dad walk around with Peter on the plane were absolutely crucial to our survival and enjoyment of the whole experience!


My cousin’s husband is extremely organized and very generously took the lead on booking restaurant and beach club reservations throughout the trip. One request that I think worked out pretty well was to space out our outings with a couple more low-key days close to home in between. For instance, we gave ourselves a couple days to get settled and adjust to the time difference at home before doing a day trip to Positano. Then another couple days honoring normal nap schedules and just doing the local beach in the afternoons. Then a day trip to Capri followed by a couple more days close to home, etc.

I think this made it 100x more manageable with kids who are used to napping at home vs. on the go in strollers (particularly when it was so hot outside) and while pregnant (it made it easier to find the energy to be out and about all day knowing I’d have a couple “easier” days at home to rest up afterwards). Of course it wasn’t a perfect system once we factored in jet lag, people needing to work or take calls at various hours of the day and night. And just the general exhaustion of traveling internationally with kids while pregnant.

But the combination of having a ton of family members around to help with kids and giving ourselves real down time between bigger outings made the whole trip so much more enjoyable than if we’d been trying to cram a dozen things into every day like we were often inclined to do before having kids.

il cantuccio massa lubrense

If you find yourself in Massa Lubrense, definitely have dinner one night at Il Cantuccio! 

il cantuccio restaurant massa lubrense

So grateful to have found an outdoor restaurant close to our rental that was so accommodating of our large crew.

hotel corallo sorrento

My parents watched the boys one night so the “kids” could venture a little farther out to Hotel Corralo in Sorrento to celebrate my cousin’s birthday! I wore this dress, these sunglasses, and these espadrilles (my cousin’s jumpsuit is no longer available but this and this give me similar vibes!). 


We found a restaurant called Il Cantuccio in Massa Lubrense that was a five-minute drive from the house and that offered a courtesy shuttle to and from dinner. I think we wound up having dinner there at least five times throughout our trip because they made it so easy for us to get there and back and the atmosphere was welcoming of both our large group and three kids under the age of three. Before having kids, I would have mapped out a different lunch and dinner reservation for every day of our trip, but ease and familiarity for the kids definitely beat out novelty and wanting to try every cool place I’d saved on Instagram before the trip. 

traveling to italy with toddlers sorrento in july

traveling to italy with toddlers sorrento beach clubs

traveling to italy with toddlers on design darling


Being on or by a body of water was crucial for surviving the heat with kids. We tried to take a pleasant stroll through Sorrento the day after we arrived and it was brutally hot compared to the days we spent at a beach club in Positano, on a boat in Capri, and at the thermal spring pools in Ischia. 

Last but not least

A few much closer-to-home weekend trips with our boys in the spring helped me adapt a completely different mindset about traveling with kids that I think was imperative before taking on this longer and more involved trip. I really relinquished the idea that there is one perfect packing list or one comprehensive set of baby gear that would prevent any hiccups or missed naps or misbehavior during the flights.

I accepted that those moments were absolutely inevitable and those lowered expectations made it possible to be genuinely grateful for the great moments sprinkled throughout our trip vs. constantly disappointed by the more challenging ones. Travel with kids is an adventure and the whole nature of an adventure is that you can’t perfectly anticipate or be in control of every aspect of it!

massa lubrense beaches

traveling to italy with toddlers


I think if we did this again, we would probably prioritize finding a house with a pool for the kids — we are very much a beach-loving family, but the hike down to the very rocky local beach sometimes felt like a big undertaking just for a quick dip before dinner. 

Ideally, you’d also visit the Amalfi Coast in particular in either May/June or September/October when it’s not quite so hot, but my parents’ academic year schedule dictated the timing of the trip and I’m so, so glad we went during the hottest time of the year vs. not going at all! 

Also, I am the last person on earth to prioritize practical over pretty footwear, but I accept in hindsight that all the Amalfi Coast packing lists that include some kind of water shoes for the rocky beaches are admittedly onto something. I don’t think you have to break down and order a pair of Crocs for the occasion, but maybe a pair of these that you can tuck in your beach bag? 


I have lots of photos to share from our day trips to Positano, Capri, and Ischia that I’ll spread throughout this week and next, but let me know if there’s anything else you want to see!



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  1. This looks like such an incredible trip, so wonderful that your family was able to spend this time together (and in ITALY)! I can’t wait to read more.

  2. Great post! We are currently planning a trip to the south of France for next summer with my daughter who will be 2.5, and these tips will come in handy as we choose a rental house and plan activities! I am definitely on the team of traveling with kiddos, even if it is hectic.

  3. This is so timely! We are planning a trip to Italy in October, but we have just one very active 4-year old. My husband and I are arguing about whether or not to take stroller. He says absolutely not, and I think we should. I feel like if we want to visit museums or sites, and my son gets tired — carrying him will wear us out. (We’re planning on doing Rome, Florence, and the Amalfi coast)
    What do you think? Did you take a stroller and did you find it a hassle like my husband thinks it will be. Thanks! Great photos!

    1. I know you weren’t asking me who takes a fold up scooter and helmet to europe. Her kid has been everywhere, multiple times, in Europe, and it saves his legs while also getting some energy out. I think she puts it in a backpack when they go in places.

      …I’d also definitely bring a stroller 😉

  4. I love your attitude! And I applaud your family. We have not traveled with all our kids and grandchildren because even during the holidays at home it’s a goat rodeo. Everyone has a different schedule and a different agenda,Not the least bit enjoyable. So much easier to break up into smaller groups.
    I’m looking forward to ‘meeting’ your new little one in September. Stay cool and good luck!

  5. Glad you had a nice trip! I have a question that I truly do not mean to come across at judgmental, but given that you mostly swam in the water and wish that you got a house with a pool, what was different about being there rather than Nantucket where you can also swim, boat etc.? I mean yes obviously I realize you were in Italy and the scenery is different etc, but do you think it’s really worth the schlep?

    1. I wrote in another post that we booked the house and flights just before I found out I was pregnant so the timing certainly wasn’t ideal, but given it was a bucket list trip for my parents and I have no idea if/when we’ll ever be able to coordinate so many people’s schedules to all be there at the same time again, I’m so happy we made it happen! Totally understand why someone else would make a different call but for us the juice was worth the squeeze. 🙂