The Highlights from Our 12 Day Trip to Italy

Last week Finn & I returned from our 12 day trip to Italy. To say it was amazing would be quite the understatement. I honestly think it was the best trip of my life and I can’t wait to share all of the details with you guys today!

I took countless photos during our vacation and I have so much to talk about…so I hope this post isn’t all over the place. Tomorrow I plan to chat all about what I packed and wore for this trip, and next week I’ll have a post with tips on planning your own international vacation. So I’ll keep those tidbits out of today’s recap.

Destination 1 – Rome

Travel: In order to save on costs, we decided to fly in and out of the same city with a non-stop round-trip flight to Rome. We took the overnight flight from Chicago and landed in Rome at 9 am on a Saturday….leaving us 2 full days to explore this ancient city. Once we got to the airport, we took the Leonardo Express train to the city (super quick, cheap, & easy!). 

Accommodations: We stayed at the Rome Life Hotel which ended up being a great location for us and close to a lot of quaint dinner and lunch spots. The room wasn’t huge, but it worked out well for our short stay. 

Activities: We did our best to pack as much as possible into our 48 hours in Rome. Because we arrived on a Saturday, we had to see the Vatican that day (it’s closed on Sundays). So we booked our tickets in advance (highly recommend you do that!) in order to skip the line. It was incredibly overwhelming and way larger than I ever could have dreamed. So fascinating to see all of the artwork and The Sistine Chapel. We didn’t do a guided tour, but instead just purchased the audio headset so we could do everything in our own time. Definitely give yourself a few hours here as it’s massive! 

That day we also snuck in a few more must-see spots including The Pantheon, Spanish Steps, & the Trevi Fountain.

It poured (and boy do I mean poured!) on our 2nd day in Rome. We had tickets to go to the Colosseum, so we trekked over there in our rain gear and checked it out for about 25 minutes before we were evacuated due to the storms. We did our best to see as much of the city as possible even with the rain and it ended up being a magical day! 

Food: Boy did we eat! Every meal was absolutely fantastic and we made sure not to miss one. Plus lots of Peronis, proseccos, and cappuccinos too! Here are some of our favorite places we ate and drank…

  • Da Simo Pane e Vino: Quick & cozy lunch spot
  • Ai Tre Scalini: Went here for dinner…amazing pasta dishes!
  • La Bottega Del Cafe: Split a bottle of wine & a huge cheese plate.
  • Il Bacaro: The sweetest outdoor spot tucked away on a cobblestone street. Plus the food was fantastic!

Overall Thoughts: Rome was a whirlwind, but we managed to squeeze a lot into 2 full days there. We really liked it, but it wasn’t our favorite stop on the trip. Instead, our next destination claimed that title…

Destination 2 – Florence

Travel: We took a high-speed train from Rome to Florence. It only took a bit over an hour and was a breeze!

Accommodations: We stayed at the most amazing AirBNB I’ve ever been to. Honestly. Not only was it in the best location, but it was modern, spacious, and had the best rooftop terrace. Here are some views from the roof…We met my brother Ryan & his girlfriend Sarah (you guys might remember them from their master bedroom makeover!), so we needed a space with at least 2 bedrooms. Activities: Because we had 4 days in Florence, we didn’t feel quite so rushed and we were able to really relax and enjoy our time there. The 2 main things we planned were a trip to the Duomo and a wine tour through Tuscany. 

The Duomo was absolutely breathtaking. So colorful and full of detail. We booked our tickets in advance, along with a reservation to climb to the very top. This is a must! Even though it is quite the journey up (holy leg workout!), it is not to be missed. Plus once you get to the top you get these views of the entire city! 

Our 2nd big adventure was a full day exploring wineries in Tuscany. My friend passed along the information for a private driver she used and we ended up booking her for the day. It was a bit of a splurge, but it was the highlight of our trip! Our driver, Monika, drove us all over the entire region and answered all of our questions along the way. The day was really relaxed and we made stops based on what we had a taste for. She took us to boutique wineries so every stop was a unique experience without a tourist in sight! It was by far the biggest highlight of our trip, and I recommend everyone check out the wineries in Tuscany if you’re heading to Italy. 

Our final 2 days were filled with shopping (lots of leather!), eating (sooooo much food!), and visiting adorable markets throughout Florence. 

Food: If we weren’t exploring, chances are you would find us eating and drinking! Florence is amazing because there are so many small non-touristy places to stop in and get a bite. We’d often grab a panini and cappuccino to go during the day, and then at night have long dinners with plenty of table wine. Oh and gelato…you can’t forget the gelato!

  • Gusta Pizza: Best pizza in Florence! Grab a couple pies and sit outside with a bottle of wine. Perfection!
  • Mangia Pizza Firenze: Quick stop for pizza here.
  • Antico Noe: Our apartment was actually right above the best sandwich stop in all of Florence. Their paninis are insanely good, but the line gets long throughout the day. Get there early!
  • Aqua Al Due: Traditional Italian spot for dinner.
  • Osteria Cinghiale: Loved this restaurant…my favorite dinner of the trip.
  • La Prosciutteria: Had the best panini of my life here and we came back another night for their large charcuterie board to split amongst the 4 of us. Heavenly. 

Overall Thoughts: We absolutely fell in love with Florence and it was by far our favorite city. It’s not as touristy as Rome and you can find so many quaint spots tucked away on the cobblestone streets. I would have spent 10 days in this city if I could!

Destination 3 – Sorrento

Travel: We took a high-speed train from Florence to Naples and then a sketchy small train from Naples to Sorrento. This train is known for pickpocketing so be on high alert.

Accommodations: We stayed at the Grand Hotel Capodimonte. It was a gorgeous hotel at the top of a hill overlooking the town of Sorrento. The views were incredible and the pool was the icing on the cake. This place felt a bit “fancy” for us, and we were by far the youngest people there. But it was still a delightful stay! Activities: This last leg of the trip was a lot more relaxing than the first 2 cities, so we didn’t squeeze in tons of sightseeing. Our big activity for the trip was a boat ride to Capri and a hike up the mountain to see the entire island. 

The hike all the way up was exhausting (especially after not working out and eating everything in sight for 10 days), but it felt good to get our bodies moving. Plus the views were incredible. Once we got to the top, we took a chairlift to the tippy top. That was quite the ride up. Not for the faint of heart. 

But the views were worth it! 

Other than that day trip, we spent a lot of our time exploring the small town of Sorrento and lazing by the pool. 

Food: It’s all about seafood in Sorrento and we ordered it every chance we got. Here are some of our favorite restaurants from the trip. 

  • Porta Marina Seafood: Local spot (cash only!) right in the marina.
  • Ristorante Lo Zodiaco: This was on the island of Capri and we had a wonderful seafood lunch here.
  • Ristorante Soul & Fish: Located right on the water and the cutest decor.

Overall Thoughts: Sorrento was gorgeous, very colorful and quaint. It was incredibly different from the other cities on our trip and was the perfect relaxing way to end our vacation.

And that is it! This is by far the longest post I’ve ever written here on the Playbook, but there was just so much to cover! If you have any specific questions as you plan your own Italian vacay, don’t hesitate to ask them in the comments. I’ll be back tomorrow with what to pack for your September trip to this gorgeous country!

Ciao for now!

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The Year of Casey

Hey there!

I’m Casey Finn, the voice behind The DIY Playbook. I’m a Chicago gal teaching you how to design, DIY, and maintain your home…by yourself! Learn more about me right here.