Almost two years after our wedding, my husband Jeremy and I decided on a belated honeymoon to Italy. While it was his first time going, this trip would be my 4th time visiting Italy! I had the incredible privilege to visit the country 3 times while in college as part of my Art History minor and the incredible professors that made it possible.
The story goes something like... "I found great flights to Rome. You have 5 minutes to tell me no." And sure enough, I purchased our flights and got to work on our itinerary. Having visited previously and to many areas of Italy, I knew what I wanted our *first* trip to look like. I got to work the old fashioned way with maps and spreadsheets. Many of our trips are very go-go-go, and I was trying with all my might to keep this a little bit more relaxing (I was only so successful on this part). I also downloaded Babble and became diligent in learning more of the beautiful language.
College-aged Rachel somewhere between 2010-2012 on a bus in Rome.
After arriving home, we had so many requests to learn more about our itinerary so I'm happy to share our plan in 2 parts! First up – it's time to board your plane!
Arrivederci New York!
Thanks to the help of a great friend, we were whisked off to JFK for an overnight flight. Our flight was substantially delayed, so much so that our car rental was cancelled (we didn't have any wifi, it was down), and we missed our very first tour in Rome. Armed with our international driver's licenses, we were able to book another car and had to suck it up with our missed (and expensive) tour. Very quickly we learned about the ZTL – for the love of all things Italian, DO NOT DRIVE into the ZTL. Your photo will be taken, you'll receive a ticket in the next few years, and you will be laced with fear. Only those with a permit are allowed to drive in these forbidden areas.
Our first night, we navigated to an incredible Airbnb and parked our car in a nearby garage (still waiting on this ticket). Claudio's apartment was centrally located and just steps from the Trevi Fountain. We fought our sleep and made our way out to dinner, casually walking past the Pantheon. Osteria da Fortunata was our dinner choice for the evening where they make fresh pasta right in the window. We sat outside, listened to fun music, and savored each and every bite.
The Pantheon was hoppin' – this photo was taken around 10:30pm and the piazza was full of both adults and kids.
The next morning, we headed to Tuscany, and seeing my husband's genuine awe was truly wonderful—I could tell this trip had captured his photographer's heart, ensuring it wouldn't be our last! Our Airbnb, once a convent, boasted a charming medieval church on-site— Abbadia Sicille was the most perfect location. With an oversized room (we were kindly upgraded to the honeymoon suite!), convenient parking, picturesque grounds, and a delicious breakfast that I still reminisce about, our stay was perfect. We spent a few nights there, exploring Pienza, Montepulciano, and Siena, each town offering its own unique charm and hidden gems between them.
Our charming Airbnb in Trequanda.
Dinner in Pienza.
Exploring Siena.
Piazza del Campo - Siena. Truly the place to be for people-watching, gelato-eating, and cocktail-drinking.
A great way to purchase tickets with guided tours, itineraries, and more is by using the app/website, Get Your Guide. We purchased tickets that allowed us to skip long lines and fit more in than we thought we could, like touring the Siena Cathedral.
We fell in love with the gorgeous hilltop top of Montepulciano. Watch out for the ZTL! P.S. – Do you know what famous movie scene was filmed here?
Aperitivo – a necessity for tired legs and parched mouths. We caught the most beautiful sunset at this Montepulciano restaurant, Romantico.
There's a unique charm in savoring moments, embracing the sounds and scents, relishing hot bread dipped in olive oil, and sipping on wine—lots of it. We laughed with the kids playing in the piazza, listened to distant church bells, indulged in plenty of gelato, and ended our meals with espresso or limoncello.
Photo break!
As we said our farewells to Trequanda, we drove to our next day-stop in Volterra. While I had visited Volterra several years ago, we decided to purchase the Volterra Tour Pass to get as much in as we could in a short time. Some of the spots included the Etruscan museum, the Roman Theater, Piazza del Priori, and the Alabaster Museum. The rolling hills and small alleys were beautiful and dramatic all at once. After getting in all the steps possible, we took a much needed lunch break before once again hitting the road.
Lunch break – I could go for a panino right now!
Our next stop and our Airbnb for the night was in picture-perfect San Gimignano. Jeremy teased me about all of my research and my Rick Steves' book, but I found us the absolute parking which saved our backs for this part! You can not drive in San Gimignano but parking is available in several lots. With our bags and camera gear, we made our way up the hill to our Airbnb overlooking the central Piazza Duomo. One of our favorite and most ridiculous parts (in the best way) was getting used to the various keys, old doors, and winding staircases.
Our absolute best dinner was again thanks to Rick Steves' suggestion at La Vecchie Mura. While many restaurants required reservations including this one (which we didn't have), we were sat right away at a stunning table overlooking the Tuscan hills and caught the end of a sunset. If I could have any dinner again, it would be this one.
Stay tuned for part 2!
