Italy with Two Strollers

After an exhausting trip crossing the Atlantic with two toddlers in tow, we awoke on day two in a better state.  We had chosen Sestri Levante as our base to tour the Cinque Terre and surrounding coast because it was easy to access with a vehicle and flat, which is a necessity when traveling with two strollers.  What I did not consider was 1) how steep the Cinque Terre and many of our other destinations during this trip were and 2) the fact that we were traveling with not one, but two, strollers! I really do not know what I was thinking would happen when we arrived at each steep destination. There are no elevators or even many ramps located in towns constructed during the middle ages. The first lesson of our trip was learned the hard way:  when traveling with young children, do not choose the destination based on your bucket list, but rather choose wherever is the easiest to maneuver with your small children and all the excess baggage that comes from traveling with them.  Hindsight is 20/20, so I was happy to learn this lesson early in my traveling with children endeavours. Any mistakes that I have made I can now share with others wanting to take their first steps of traveling with young children so that their experience is not necessarily better, but easier.  

In Sestri Levante, we stayed at a small family run hotel.  The rooms were small, but we had a nice sized balcony.  The balcony had no view, but it was such a nice reprieve after our busy days to enjoy a bottle of Italian wine while the boys fell asleep in their baby cots.  I knew to book rooms with balconies, but it was not until we were on the trip that I realized what a necessity it is to have a balcony when traveling with young children.  

The hotel could not have been better located, we walked to everything we could possibly need – parking, train, beach, shops, and restaurants.  Not that we really needed restaurants because our hotel had a fantastic restaurant that we could have happily eaten at every night. Normally, I would want to try as many restaurants at a destination as possible, but knowing that we would be especially weary from the boys adjusting to a new place and time zone, we opted to dine two nights at the hotel restaurant.  Breakfast was included every morning of our stay, and we received a half board rate for the two nights that we dined at the hotel.  The meals did not disappoint – antipasti followed by a primi plate and a secondi main finished with dolci, all prepared by a very entertaining chef who made the boys giggle, was more than we could have hoped for.  

All of the staff were so helpful throughout our stay. We would attempt to clean up the boys mess after each meal, but the staff would not let us insisting that we let them do it. When we worried about the boys crying the first night, they reassured us that it was okay.  They even went to the room next door and acted out a loud scene to prove that the rooms were soundproof. The effort was Italian gold!

Our agenda for Day 2 was simple enough.  Drive 1.5 hours from Sestri Levante to Portovenere, a charming seaside town often overlooked because of its proximity to the Cinque Terre.  The only hiccup we had here was that we were forced to park a short hike from the town, but it was a beautiful stroll along the water with playgrounds along the way to entertain the boys, so we really did not mind stretching our legs after sitting most of the previous 36 hours.  

We ate along the waterfront, but I think the restaurant fell into the category of tourist trap because the only thing I recall from that meal is the view.  One really cannot complain much about food when staring at the Mediterranean Sea on a sunny spring day while a gentle sea breeze cures your jet-lagged fatigue.  

Upon completing our mediocre meal, we walked around the corner and discovered the pedestrian thoroughfare that you would probably conjure up if you were asked to close your eyes and  envision a charming Italian pedestrian street.

We stopped for our daily gelato at a quaint little shop, then stumbled upon the La Cambusa stall at the entrance to the pedestrian area where we sampled the most amazing pesto.  

Until this fateful day, I did not even know that I really cared for pesto, but unbeknownst to us, we were in the region where pesto originated.  People take pesto seriously here. In fact, there is even a Pesto World Championship!

One taste of Pesto Genovese on a piece of fresh bread was all we needed to leave Portovenere with a fresh loaf of bread and way more pesto than we could possibly consume over our two remaining days at our hotel where we had a small refrigerator.

After carb loading on pasta and bread dipped in pesto the night before, we awoke on day three ready to take on the world … or at least the Cinque Terre!  We knew it would be the most ambitious day of our trip, but logistically it made the most sense to do it on this day because we had one day after to recoup before heading to our next hotel.  Logistics are very important to considerwhen de veloping an itinerary with young children.

We awoke to gloomier weather than the day before, but despite its threats, rain never hampered our day.  A short stroll to the train station in Sestri Levante and we are on our way to Monterosso al Mare where our plan was to catch the ferry to Riomaggiore, the furthest of the villages, then stop at Manarola and Vernazza during the return trip. 

Upon disembarking the train in Monterosso, we quickly made our way to the ferry, bypassing the village opting instead to visit it on the return. Time was of the essence, and the ferries would only get more crowded as the day progressed. We waited in line amongst many tourists and when the ferry arrived and we saw those in front of us walking the narrow ramp onto the boat, we wondered how we were safely going to get the boys and strollers on board.  We hastily took the boys out of their strollers and instead of folding the strollers up or pushing them up the ramp, Rob proceeded to lift the stroller above his head not thinking of what was stored underneath the seat of the stroller. I watched in horror as my newish DSLR camera tumbled into the sea below. It was as if it happened in slow motion. The ferry crew leapt into action and retrieved my camera from the waves below, but it was too late.  My camera was never to work again.  Of course, the time it took to recover my camera was more than what it would have taken to see if the stroller could have been pushed up the ramp or to collapse the stroller. 

At this point, I would like to bestow upon you another lesson about traveling with children, do not rush.  Most people have sympathy for the person traveling with small children and when you are traveling, many people around you are also tourists and not really in a hurry anyway.  

Nowhere did we rely on the kindness of strangers more than in the Cinque Terre. Things started out well as it was a fairly flat walk from the train station to the ferry in Monterosso.  However, things changed quickly as we disembarked the ferry at Riomaggiore.

Everywhere we looked, there were stairs.  How were we going to get up and down all those stairs with two strollers?  Especially since I was less than a year and a half from having had back surgery.  Do not get me wrong, we were not completely crazy and were far from the only tourists with a stroller.  But we were definitely the only tourists with two strollers and only one able body able to carry the stroller up the maze of stairs that led the way to the village’s main piazza.  Once we were in the main part of village, there were fewer stairs and the commercial areas were at an incline. I could push a stroller uphill with a few rests built in, but carrying a child and stroller up stairs was out of the question which made the route from the ferry to the village very intimidating.  This was our system:

Rob carried child #1 strapped into a stroller up a set of stairs while I waited with child #2.

Rob would quickly descend stairs while I quickly ascended same stairs so that neither child was left unattended for more than a couple of seconds.

I would wait with child #1 while Rob carried child #2 strapped into his stroller.

We both pushed strollers to the next set of stairs.


Luckily, the kindness of strangers was our saving grace.  An innumerable amount of thank yous and gratzis were uttered this day.  

We had no expectations of dining in the Cinque Terre.  One adjustment that needs to be made quickly when you consider traveling with young children is that of enjoying every meal at sit down restaurants.  This was just as well for us this day because we had too much to see and too little time. But in general, be prepared to eat on the go when traveling with young children.  

Lucky for us, we love hole in the wall type places because it allows for more authentic experiences, and we found a couple of gems during our visit.  El Pescato Cucinato was highly recommended on TripAdvisor and was just the type of place we needed after making our way uphill.   Italian style fish and chips, plus a few extra treats from the sea, quick and fresh, allowed us to refuel quickly before continuing on our way.  

After strolling through the rest of the town, we made our way back to the ferry which took us to Manarola.  A similar scene of carrying strollers up a labyrinth of stairs commenced with strangers playing the part of hero to the crazy Americans traveling with twin toddler boys!  When we did not think we could not walk any further, we took respite in a restaurant with a view to the sea where the boys enjoyed sweet treats and the grown ups enjoyed different kinds of treats.  

Once back on the ferry, we realized we were starting to lose daylight and were quite exhausted from our literal ups and downs throughout the day.  It was with much sadness that we made the decision not to visit Vernazza. When I envision the Cinque Terre, it is photos of Vernazza that I see in my head.  It was the village I most wanted to visit, but it was just too much to fit in if we wanted to keep our sanity.

We saw Vernazza from the sea, but you cannot see the postcard view from the ferry.  However, when I really think about it, the photo I wanted to capture would have most likely required a hike to get to that perfect vantage point and that would have never been possible.  

Vernazza is supposed to be the most touristy of the villages, so it would have probably been the most difficult to explore with our strollers. It is not far fetched to say I will be there again one day and will be able to visit the villages more thoroughly.  As far as visiting it with toddlers, it is very doable with one and maybe even two if both parents are in perfect health. Our biggest mistake that day was not taking the train all the way to Riomaggiore, walking downhill through town to the port, then taking the ferry to Manarola and Vernazza ending in Monterosso al Mare.  The stairs would have still posed a challenge, but we would have started the day downhill and would have had the time needed to see all the villages.

Although I was disappointed to not visit Vernazza, I quickly made peace with it.   Connor and I sat outside on the front of the ferry letting the sea spray tickle our faces.  It was a rare one on one moment where he just sat still in my lap for a few minutes.

However, this calm did not last long and it turned out that my camera was not the only one of our belongings to find its way to the sea that day.  Without rhyme or reason, Connor threw his sippy cup into the sea. In an effort to not overpack, I only brought one sippy cup for each of the boys. This might not seem like that big of a deal, but sippy cups are not nearly as easy to come by in Italy.  Something you might not think about, unless you are a twin parent, is that you literally have to have two of the same thing or the twins will fight about it. We bought an Italian sippy cup that was not nearly as user friendly as the one we brought with us from home, and the rest of the trip was spent fighting over which cup each one would drink from.  The morale of this story is to always bring more than you need when traveling with toddlers!

Despite not visiting all the villages we intended to visit and losing both a camera and a sippy cup, I could not be upset.  I had crossed off a high priority item off of my bucket list and spent quality time with those I love most. You will always lose things or have to spend more due to some mistake you make while traveling, but when these things happen, we shrug it off as the cost of travel.  It is always worth the price. Our day ended in Monterroso where an on the go snack break was followed by time at a playground where our children frolicked with other children as afternoon became evening.  

A slow paced day to the Italian Riviera was the perfect follow up to our day in Cinque Terre.  Even though it was only a forty-five minute drive from our hotel, it seemed to last much longer since my eyes were glued to the road the whole time in an attempt to help Rob navigate the windy and often one laned road to Portofino.  

Of course, Rob may use another word than helping!  The drive made one thing obvious, one must really want to go to this village to make the trip, which has cultivated it into a resort town for the rich and famous.    

Portofino literally means the port at the end of the road, and that is exactly what it is!  The road spits you out into the town’s underground parking garage, and even though it was expensive, it was nice not to have to look for a place to park.  When we exited the garage, we were right in the middle of the action. Keeping to our pledge to take it easy this day, we just pushed the boys along in their strollers along the entire harbor while we marveled at the brightly colored buildings taking guesses on how much it would cost to purchase one.  We bought the boys some local sweets in the main square by the port and let them run around as the church bells chimed.

Even though we really did not do anything there, I really liked the feel of Portofino, mostly because it seemed like the kind of place my mom would have driven out of her way to show us while on a vacation simply because it was pretty.  As a child or adolescent, I would have teased her relentlessly for wasting our time. I am not sure if I truly appreciate these types of places now or if I simply appreciate them because they make me nostalgic. Either way, I am glad we made the effort to see a little slice of the Italian Riviera.

Our original plan was to eat lunch in Portofino, but the restaurants we saw did not look like the kind of places that would fancy our cumbersome strollers and our children running around the tables.  

We opted to keep our visit to Portofino to an hour so that we could save on the high parking costs and made our way back the way we came stopping for lunch in the town of Santa Margherita Ligure. This ended up being a much better option for us despite us learning the hard way that when you order a carry out meal at a restaurant with tables, you must declare whether you will eat there or take away. Apparently, they charge extra if you decide to grace their tables and chairs with your presence, so do not say take away and then sit down. You will be scolded! We took our food outside by the water which was a much better set up for us anyway. At that stage in the boys life, it was not worth taking a table at a restaurant if there were no high chairs available.

Luckily, our dinner spot that night did have plenty of high-chairs available.  On our last night, we ate where we saw the locals eating, I Due Forni Pizzeria, just a few steps away from our hotel.  We were seated next to another set of twins (these two were fraternal and Italian, gemelli), but even through broken English, we could relate with these parents trying to entertain their kids with toys and coloring books while preventing the young children from spilling the red house wine placed well within reach by the waiter who clearly did not have children of his own.  What better place to dine with Italian families than a pizza restaurant, a food that transcends all borders and is loved by children worldwide.

Were our first few days foolproof?  Absolutely not. We made many mistakes, but we also created memories that I can vividly relive almost four years later.  I cannot recall much of the day to day grind from the first two years of raising twin boys, but I remember fondly these two weeks that my family and our two strollers spent visiting some of Italy’s hilliest destinations.  


  1. I really liked the feel of Portofino, mostly because it seemed like the kind of place my mom would have driven out of her way to show us while on a vacation simply because it was pretty. As a child or adolescent, I would have teased her relentlessly for wasting our time. I am not sure if I truly appreciate these types of places now or if I simply appreciate them because they make me nostalgic.

    ❤️ This.