ITALY.

I’m going to keep this Italy blogpost as short, sweet and to the point as possible or else I’ll never get it done! 😂 I think I have close to 5k pics from this trip!? ha so as you can imagine, it’s been hard to sift through our memories from our 2 weeks in Italy to select only a few! With that said, I will do my best to highlight the best of it all.

Our hotels/airbnbs, noteworthy restaurants, and tips on surviving Europe with a VERY active 14 month old baby!

I’m going to kick off this blog FAQ style, in hopes that I answer some of your q’s right off the bat.

“Do you regret taking the baby? Was it hard?”

In short, I’d say we truly can’t imagine that trip without him. Was it tiring at times fighting the jetlag and navigating the unknowns of the trip with him? Sure. However those struggles don’t hold a candle to the joy that he brought and the family memories that were made. Truly.

“How was the flight over with him?”

Easy.

We took an evening flight (def recommend) that got us in around 9AM local time. If you have a connection, which we did, just make sure it connects in the states so that the long stretch is straight into your destination. He slept the entire way over as it was middle of his regular evening sleep.

We used the Flyaway bed, as Wilder had his own seat. I’ve also been eyeing this Jetkids by Stokke Bedbox Ride-On Carry-On Suitcase that’s on sale right now at Nordstrom. It seems like you get significantly more band for you buck. I posted it on my IG stories and had people raving about it. Not only does it include a fold up mattress, it’s also a little multi-purpose rolly suitcase! I actually think I’d prefer this so that we didn’t have to blow up the bed in flight! As long as you have something that extends so that your baby/toddler can lay down to sleep, that’s all you need. I don’t think Wilder would have had a mattress preference lol.

“How was the jet-lag!?”

Jetlag sucks whether you’re with a baby or not, it just comes with the territory of traveling abroad. I’d say the jetlag actually benefited us when it came to Wilder’s “schedule”, or lack-there of. I think the key is to never let them fully adjust to local time!? Italy is 7 hrs ahead.
As soon as we arrived, we simply let him nap on the go whenever he wanted and as long as he wanted. He slept a LOT during the day, which was great as we were going to lunches/wineries, etc. then he went to bed around our bedtime (11-12pm local time). So he ended up being more on our “regular” evening schedule, 11-8am.

This sounds all technical, but we really didn’t put much thought into it. We let him sleep when he was tired, brought him everywhere we went, and let him fall asleep with us in the evening. I will say he’s been conditioned since he was very young as we’ve always been a bit relaxed with his sleep, ie: allowing him to nap on the go, but I do think it’s doable for everyone. maybe with a little practice before you go!?

All in all, the sleep schedule / jetlag wasn’t perfect, but we made it work.

“Did you take taxi’s with Wilder?”

We did. I didn’t initially love the thought of this TBH, but at the end of the day it’s no different from taking an Uber with him in the states. We only took a taxi a few times and it felt quite safe when we were there. We brought a carseat and strapped him in with the buckles, just as we would back home if we were taking an Uber.

I should point out that TECHNICALLY/legally, you are supposed to use a carseat of “European standards”. With that said, everything I read online (and man I went deep into forums), says that your American carseat will work just fine, just as it would in the states. “I’ve never heard of anyone being stopped or ticketed for properly restraining their child in an American car seat”. Is what I kept reading over and over.

I’m not recommending one way or the other! Do your research with it. You can always opt for bringing a European carseat if you’re concerned about “not meeting European standards”! Maybe renting one is a possibility!?

“What was your main form of transportation to and from cities”

Trains, cars, and even a boat! I actually LOVE taking the trains, but only if it’s a long, DIRECT route— because hopping on and off trains with the baby + luggage isn’t exactly fun.

I also opt for business/first class if available. It’s worth the extra money $$ in my opinion and makes the trip so much more enjoyable. Like anything, you can choose what to budget for and this was definitely something that was important to me. The journey to and from felt more like a part of the vacation instead of simply a mode of transportation.

For booking trains, we used trailine.com . I downloaded the app so all of our tickets were on our phone! Super straightforward and user-friendly. I do recommend printing out physical tickets of everything just to have a copy in case phone dies, you lose it, etc.

TIP: when you get to the train station, often times your destination/train will NOT be on the board until about 15 mins prior. As we always arrived early, we didn’t know this and were slightly panicking that we f*cked up the reservation 😅 it might also have the FINAL destination of the train on the board, instead of the city you’re ticketed for, so just double check the train # and you’ll be good.

“Any regrets or lessons learned!?”

PACK LESS. Lol. Nothing will humble you quite like lugging multiple 50lb suitcases through the cobblestone streets of Europe. I’ve done Europe many many times over the years, you would think I have learned my lesson by now!?

In my defense, I packed for 2 this trip, and I did have to bring quite a bit of clothing for work-related content. However going back, I’m determined to make it LESS of a business trip in that sense and pack as little as possible. I think I can speak for Colleen and Landon as well ha.

Pack neutrals so you can mix and match, simple dresses you can transition to day-night, and comfy shoes you can wear with multiple outfits. Consolidate! As far as hair tools, we ended up having our hair slicked back 95% of the time because it was so hot. Your hotel will also likely have the essentials like soaps, shampoos, and blow dryer.

OK let’s visit the cities! 👇🏼

ROME

1x night

We flew into Rome, as it’s one of the main airport hubs and often cheapest to fly in and out of.
Rome is cool to see, specifically the colosseum, but I think 1 day is plenty. It’s more of a “city”, and a popular one at that, so you get more tourist than Italian charm.

I can’t recommend our Airbnb because booking.com royally f*cked up our reservation, and we ended up at a completely different one. It worked out fine, it was actually a great/safe location and all but the owner was a dick and it was all-around not the best experience.

Restaurant Recs

Before we left for our trip, we asked the restaurant manager at Yolan for Italy suggestions. He is from Rome, and he happens to manage the best Italian restaurant in Nashville, so we trusted his input! He gave us recommendations for each city we visit, so even if we didn’t get to visit each and every one, I’m still going to list them as a local* suggestion!

Osteria da Fortunata- allll about the pasta! I discovered this place on IG/TikTok and it lived up to the hype. They have ladies in the front of the restaurant making all the pasta by hand, which is cool to see.
Antica Pesa in Trastevere- local suggestion*
Perilli in Piramide area- local suggestion*
I Meloncini at Tor Di Quinto- local suggestion*

In the morning, we were off to Positano!

We took a train from Rome to Salerno, and then took a ferry from Salerno into Positano.

We booked our ferry tickets with ferryhopper.com

POSITANO

3x nights

Positano is a pinch-me town. It’s stunning and overwhelming and tiring and charming all at once. Sooo so memorable and worth the hype. We stayed 3 nights, and I would have loved 1 extra!

Positano is a little tricky to get to, as there isn’t a direct train into Positano. We opted for the ferry route as I had heard the views were beautiful. I’m so glad we did! It’s a relatively quick and enjoyable ride that gives you stunning views of the coast as you approach Positano.

We stayed at the beautiful Positamy— I did some extensive research to find the perfect spot for us, and this certainly lived up to my expectations! It was PERFECT. We got the 2 bedroom suite— pricey but worth it. It was walking distance to everything (an enjoyable 10 min walk to the main beach), the views from our balcony were stunning and the hosts were as kind and accommodating as humanly possible.

Here are a handful of recs! P.s if you want a visual, I cover this all in my IG Reel here.

1. Porter service!! Ask your accommodation to book this for you. We arrived by ferry, and the porter service was waiting at the dock ready to take our bags to our airbnb. I don’t think we physically would have been able to w/ the baby + all of our luggage!? 10-15 euro per bag & worth every penny.

2. Book the boat. Exploring the coast by boat was one of the most memorable days of our whole trip! We did a 1/2 day rental w/ @grassijuniorpositano , our cutie captain was Mario & it was all perfect! Most people opt to go to the island of Capri, which I have done before and definitely recommend if you have the time and energy, but having Wilder with us, we wanted our day to be super chill.

If you’re going all the way to Positano, you might as well budget for a boat to really get the full experience of this stunning coastal town. Do it, do it!

3. Snag a res ahead of time at one of the many Michelin Star restaurants. We went to Li Galli and it was an EXPERIENCE. The food. The views. The service. 12/10, like nothing I’ve experienced before.

4. Rooftop drinks at @radabeachpositano . It’s hard to imagine that there are better views of Positano!?! Like, wow. We were here for our friends vow renewal party, but I do know it’s open for food + drinks when it’s not booked out for an event!

5. Beach day at @pupettobeachclub . It was a bitch to get to (thx Google maps), BUT turns out there is a much easier route closer to the water, which we ended up taking back. We got lounge chairs, and ate at the cafe where we had pizza & too many aperols. This beach (Fornillo) was significantly less crowded and much more charming than the main beach IMO!

Restaurant Recs:

Li Galli- an intimate, wow factor Michelin star restaurant with out of this world views and service.
Da Vincenzo Positano 1958- we booked this in advance based off of (top!!) recommendations and we loved it! It was just as enjoyable as Li Galli but in a much more casual way.
La Zagara- casual cafe in the heart of Positano with a charming little patio. We came here almost every day for “breakfast” aka coffee and pastries, which happened to be included with our hotel stay!
Il Tridente- local suggestion* and one that I heard about over and over prior to our trip. We simply ran out of time, but I would have LOVED to have snagged a res here.
Bistro F.lli Pansa- OK best carbonara of my life!! This was in Amalfi, but if make your way over there during your stay in Positano, come here solely for this carbonara!

UMBRIA/TUSCANY

4x Nights

We headed to the Tuscan Hills (via private car transfer), and stayed at Villa Cozzano for 4x nights. *Located about 15 mins from the Castiglione del Lago train station* The only reason we opted for private car service is because by the time we looked at train tickets, the times were horrible with multiple stops. It would have taken a full day to get to where we wanted to go, opposed to the car service which was about 4.5hrs straight shot. This is definitely the more expensive route, and if I were to do it again, I would have booked our train tickets way in advance to secure the best time slots.

But OK, back to Villa Cozzano because what a hidden(ish) GEM of a place. It’s actually hard to put into words how much we adored staying here!? The room, the people that ran it, the food, the views. Everything about it was straight out of a fairy tale and everything we could have wanted for a stay in the countryside.

Also, everything I could have wanted in a proposal 🥲 A little more on how that went down…

We toured the grounds of the hotel with the owner, as he told us all about the fascinating history of the building and land. Our final stop was in the olive groves— where there was a stunning table setup with candles and flowers and music. Again, straight out of a fairy tale.

Nervously giggling walking up to it, Landon grabbed my hands and asked, “do you know why I set this up?” I replied, “I think so?”. He gave a beautiful, simple speech before getting down on one knee and asking me to marry him.

The proposal wrapped up with a stunning brunch at our table, with Wilder and Colleen nearby ready to join in on the celebration. There was a drone flying above capturing video content, and Wilder was FASCINATED. It was such a special day that I will cherish forever.

We used Cortona Wine Tours to take us around to a couple different wineries, and I couldn’t recommend enough. Alberto is SO kind and knowledgable, and he went out of his way to make our private tour feel so special and unique. He even took us to the grocery store so that I could cook us dinner in our villa when we got back!

Other than the wine tour, we really just chilled at our hotel which was REALLY nice after the fast pace of Rome + Positano. Our hotel offered a lot of “activities”, which we booked in advance. We drank, ate a lot of good food, did a cooking class, wine-tour, private movie night, private candle-lit dinner in the olive groves, rented a vintage car, got engaged (nbd) and just thoroughly enjoyed everything that the hotel and surrounding area had to offer.

I’ll wrap this up with a few (a lot) of pictures from our time here… because no words will do it justice.

FLORENCE

2x nights

OK I LOVE Florence. I had been a couple times prior, and I always underestimate how much I love it and wish I allocated more time to spend here. It’s more “city” than Tuscany obviously, but nothing like Rome IMO! It’s buzzing with young people, bars, cool restaurants and lots of shopping. It’s charming and FUN. 3x nights here would have been ideal.

Our Airbnb was perfect, we stayed at Serristoria Palace Residence and really enjoyed everything about it. It’s a bit of a walk from the “city center”, but we actually preferred being a little out of the hustle. There’s also a cute local market a block away that has tons of wines (priority), pastries, deli food, basic groceries, etc. There is also a handful of non-touristy cafes just a couple blocks away!

Restaurant + Bar Recommendations:

Hosteria del Bricco: a hole in the wall spot behind our Airbnb! With a hand-written menu of Italian classics, this place was a real treat. I forget exactly what we ordered, as it was a LOT, but I do remember the ‘gnudi’ dish was out of this world. I still dream about it.

I' Girone De' Ghiotti: sandwich shop! This was a top recommendation that we sadly never made it to, but I had enough recommendations to suggest this place.

La Ménagère: another top recommendation that we DID made it to, and it’s definitely worth the hype. A chic bistro selling flowers, gifts and elevated food & drinks!

Rasputin: a hidden cocktail bar near Santo Spirito, the first of it’s kind in Florence! It’s a moody, sexy, elevated vibe and it was definitely worth staying for a couple drinks! We got lucky with seats at the bar, but reservations are strongly encouraged!

MILAN

1x night
Since we were flying OUT of Milan, we took a train from Florence to Milan the night before our flight, so we could spend a day/evening exploring everything Milan has to offer. Just like Rome, it’s definitely “city”, and I probably wouldn’t go out of my way to make a separate trip to see it. However if you like fashion, the concentration of high-end shopping is quite impressive! The Duomo di Milano was also pretty cool to see up close and personal.

Restaurant recommendation:

Landon and I snuck away for a date night and ate at Il Salumaio di Montenapoleone which we booked about a month in advance (from recommendations). We sat on the patio and had a really great experience!

OK I think that’s all she wrote! All in all, it was truly a once-in-a-lifetime trip, and I can’t wait to do its every year! lol. No but really, Landon and I talked about budgeting and planning for a family trip every year moving forward. It doesn’t have to be this extravagant, it could be somewhere closer to home in the states, but just something to look forward to every year! A new place to explore as a family.

Travel is such a passion of mine, it always has been, and having babies and a family will never stop me from doing that. I know it seems intimidating, especially if you haven’t embarked on that first journey with your babe yet, but I sure do hope you take the leap!

If you have any questions at all, please feel free to drop them below! I’m happy to answer any and all questions!

Ciao,

Jen x

ITALY RECAP: 2 Weeks in Italy (with a 1 yr old!).