I’d been planning this trip for a while. I presented the idea on my laptop in the middle of a Longhorn Steakhouse during my dad’s birthday dinner in September 2023. Initially, it was 13 days, and we would stay in 4 different cities. After considering some logistics, I narrowed it to 10 days, with two different accommodations and two day-trip excursions.
This was not my first time in Italy, which made deciding what to see a little easier. However, it still took a long time to figure out the best way to see as much as possible. Thankfully, a lot of people love Italy and have recommendations that I was able to sift through.
Friday, November 22
Today was easy; most of us worked at least half a day and then went to the airport for our red-eye flight to Rome.
Saturday, November 23
The cheapest way to travel was to book a round-trip flight in and out of Rome. However, we wanted to start our vacation in Florence, so we also booked a one-way flight from Rome to Florence. We spent a few hours in FCO waiting for our next flight, and it was a long few hours, but eventually, we ended up in Florence. There were seven people in our group, and when we got our luggage, we got in a taxi that fit all of us, which was very convenient.
During our stay in Florence, we stayed at the Rivalta Florence Hotel. They were great from the very beginning. When I emailed them to let them know we had a large group, they helped me book the correct number of rooms. Although it was colder during our stay, the hotel has a great outdoor seating area and rooftop terrace. It’s located right on the Arno River, and all the sights are within a twenty-minute walk. We ended most nights at the hotel bar before retiring to our rooms.
After checking into the hotel, we had dinner reservations at Buca Mario. Our waiter, Aldo, was excellent—he had a song for everything we said. The food was delicious. My dad and brother got a Florentine steak, which was the biggest cut of steak I’ve ever seen. On our way out, the hostess gave my mom and aunts’ aprons and my sister and me a tote bag.
Sunday, November 24
Fun fact: Today was the Florence Marathon. I found out about this through the hotel about a week or so before our trip. Coming from Boston, I was a little panicked about what this could mean, but it didn’t disrupt our day very much.
We didn’t have anything booked for today but knew we wanted to see the Duomo and Accademia Gallery, so we started walking that way. For breakfast, we ate at Caffe Gilli, which was delicious, before making our way to the Cathedral of Santa Maria del Fiore. You can climb the Duomo if you want, but there are many stairs, so our group decided not to and just took pictures from the outside instead.
Outside the Accademia Gallery are different lines based on which ticket you buy. There was also a QR code to purchase the tickets, which resulted in us accidentally buying tickets for the Uffizi Gallery. Thirty feet away from us was a ticket office we went to and wished we noticed in the first place. The Accademia Galley is home to the Statue of David, but my favorite part is the half-finished works leading up to David. I find it so impressive that Michaelangelo took a rectangular prism of marble and was able to make intricate sculptures.
We walked through the Piazza Della Signoria while deciding what to do next. We were tired and a little hungry but didn’t want to return to the hotel, so we had “A Sit & A Snack” at Cacio & Pepe to regroup.
My sister’s most anticipated museum was the Gucci Garden, so we walked through that next before using our accidentally bought Uffizi Gallery tickets. Gucci Garden is a quick museum, but it’s very fun. One room has mirrors on all of the walls, so the bags look like they go on forever.
Nobody cared that the time on our Uffizi tickets was incorrect. This Gallery is ginormous. Every room seems to lead to three more rooms, and the building is horseshoe-shaped, which I overlooked from the outside. A person could probably spend an entire week deciphering all of the bible depictions.
We ended the day testing our luck at the Fontana del Porcellino, pre-dinner drinks at Cavallino, and dinner at Mama Eat.
Monday, November 25
Since we had done so much on Sunday, we had nothing planned for Monday morning, so we decided to walk across the Ponte Vecchio to the Piazzale Michelangelo. For anyone who hasn’t been, it’s uphill and upstairs—lots of hills and lots of stairs. However, the view is worth it.
Our A Sit & A Snack for the day was at Ditta Artiganale. Then we crossed the river and looked around Scuola del Cuoio. I wish I were more of a pocketbook person because the bags were beautiful. Around the corner was the Christmas Market in Piazza di Santa Croce, which was a fun surprise.
For dinner, we participated in the Fresh Pasta and Gelato Authentic Cooking Class. We made two types of pasta and enjoyed wine and gelato. The cooking class was a lot of fun, and the food was delicious.
Afterward, we walked around the Gucci Store, the Palazzo Strozzi, which showcases “Drift Art,” and back over the Ponte Vecchio before calling it a night.
Tuesday, November 26
We made our way to Venice! We got up early and walked to the train station. The woman at the desk was very helpful in getting us our tickets.
Once in Venice, we walked to the Libreria Acqua Alta, which, for some reason, I thought was a bookstore on a gondola. However, it’s a whole store.
After a quick coffee at Illy, we did the Murano, Burano, and Torcello Half-Day Sightseeing Tour. We saw a demonstration at the Gino Mazzuccato Glass Factory in Murano. Then we went to Torcello and took a picture on the Ponte del Diavolo before walking to Basilica di Santa Maria Assunta. My brother, sister, dad, and I climbed the bell tower. After seeing the colorful houses on Burano, we grabbed a snack at Fritto Misto. Our tour boat dropped us off right by the train station, so we grabbed a drink at Olimpia before getting on the train.
That night, we had dinner at Oliviero in Florence.
Wednesday, November 27
I purposefully booked an afternoon bus from Florence to Rome in case we had any last-minute sights. We wanted to see nothing new, so we enjoyed one last day in Florence.
We started the day with breakfast at Riviore, which has a delicious hot chocolate. Then, we returned to Scuola del Cuoio and the Christmas Market in Piazza di Santa Croce. Before getting to the bus station, we had some bellinis at Battipalla and gelato at Vivoli.
Once we arrived at our Airbnb in Rome, we had dinner down the street at Le Tavernelle. Our waiter, Bill, played the song "More Than a Feeling" when he learned we were from Boston. That’s one of my dad’s favorite songs, so he was thrilled.
Thursday, November 28
My dentist told me about a great private tour company called My Best Tour. We booked them for a day and a half of tours. Although their website was a bit tricky to navigate, once we started an email chain, it was easy to book everything.
The first one we did was a 4-hour private Golf cart tour around Rome. Our driver was Chiara, and she brought us to Heart Park, Spanish Steps, Santa Maria Minerva, Pantheon, Trevi Fountain, and Santa Maria Maggiore. She gave us some facts at every location so we could get out and walk around.
After a quick lunch at Pizza Della Madonna, we started a second tour with Pino as our guide. This was a three-hour walking tour of the Colosseum and Roman Forum. We also talked a lot about Palatine Hill. Pino was very knowledgeable.
A Sit & A Snack was on the San Clemente terrace's rooftop. Dinner was at La taverna dei monte. My sister and I got gelato at Glauco, and then we walked back up to Santa Maria Maggiore. We thought the Christmas tree would be lit up, but it wasn’t.
Friday, November 29
We ate breakfast at Caffe del Commari before meeting Pino again for a walking tour of the Vatican Museums, Sistine Chapel, & St. Peter’s Basilica. The Sistine Chapel is a must-see, but I also really liked all of the tapestries in the museums.
We grabbed lunch at Ristorante Giovanni before checking out Sant’Ignazio of Loyola Church. It’s one of the churches with a mirror to see the ceiling and film it as a TikTok trend. The line was really long, though, so I didn’t wait. I watched some people go through it.
After going back to the Airbnb to relax for a little bit, we walked back to the Trevi Fountain and Spanish Steps. Italy is planning for their Jubilee, so the fountain has scaffolding for cleaning, but they’ve added a bridge that allows you to get closer to the statues than you would normally.
We ate dinner at Ristorante Alla Rampa, located by the Spanish Steps. The waiter hated us in the most comical way. He judged everything we ordered and made faces.
Saturday, November 30
Our last day in Italy was spent on the Citywonders tour: a day trip to Pompeii, the Amalfi Coast, and Positano from Rome.
The most extended stop was a private tour of Pompeii. I've been before and know the history from Latin class, but it’s astounding to see the plaster casts of people trying to outrun their fate from Mount Vesuvius.
Before arriving in Positano, we walked through the Limoncello Dicapri Factory. By the time we reached the Amalfi Coast, we didn’t have much time to explore, but we took photos by the Tyrrhenian Sea and sat in the church of Santa Maria Assunta.
Sunday, December 1
We woke up and headed to the airport to go home. It was an easy travel day because the direct flight was seven hours long. However, anything more than five hours is very long for me.
