Take a 10-Day Italy Road Trip with Window Seat Coffee

Hi, I'm Kristen, and my husband, Tom, and I are the founders and owners of Window Seat Coffee.

Window Seat Coffee was born from a love Tom and I have for both coffee and travel. What better place to experience both than Italy? Tom and I were fortunate enough to take a road trip through much of Italy (and two other countries!) in April of 2019, less than a year before Window Seat opened... and travel shut down. I'm going to share that trip with you now, in hopes of inspiring your own dream trip!

I absolutely love to travel. I love the planning, the anticipation of the trip, the journey, and definitely the destination. My favorite way to visit a place is to hit the highlights and tourist attractions, but also to live like a local. We were really able to do all of this and more on this 10-day trip. We rented a car in Milan and then drove to Cinque Terre, Pisa, Florence, Siena, Rome, San Marino, and Venice before ending back in Milan.

Driving in Italy

We rented a car in Milan and drove from there. I was a little nervous before arriving, especially about accidentally driving into restricted zones, or ZTLs, but it ended up being much easier to navigate than I anticipated. The highways (or autostradas) were awesome and there were really nice, convenient stations pretty frequently where you could fill up your tanks and your stomach! A tip for driving somewhere new, especially if you don't anticipate having cell service, is to download the Google Map before you leave home. This will allow you to view the area and even use the directions function without wi-fi.

Milan: Fashionable and Fantastic

I was blown away by our very first city. Beautiful architecture, beautiful people, and a place I could see myself living. We had delicious coffee and pastries at Panettoni Giovanni Cova. Don't try to order your coffee the same way you order it here in the States, though! Latte, for example, just means "milk" so you will literally get a cup of milk if you order this. And a caffè is usually just two shots of espresso. You can't ever go wrong with a cappuccino, though! Tourist highlights in Milan include the Duomo and Leonardo da Vinci's mural "The Last Supper". Take the climb (or elevator) up to the roof of the Duomo; pictures do not do it justice. Pro tip: book your tickets FAR in advance to see "The Last Supper". We chose to do a full guided tour of Milan, which included this famous site, and it was perfect.

Cinque Terre: Five Lands

This region is actually made up of five different towns, each with their own unique feel. We stayed on the side of a cliff just outside Riomaggiore and the trek up and down each day was worth it for the view and the remoteness, but I would recommend staying in one of the towns or even La Spezia, which is just outside and a short train ride away from Riomaggiore. We loved hiking the trails between the towns, but even if you don't plan to hike, bring good shoes and be prepared to walk! It was a good thing we were walking, as we ate WELL. I highly recommend Kepris for pizza in Riomaggiore. Not only was the pizza delicious, but the owner made it while we waited and then shared some local beers with us. For dinner, Nessun Dorma in Manarola is everything you could ask for. The view from the line is quintessential Cinque Terre. We waited for about 45 minutes and it was WORTH IT.

Pisa: More Than a Leaning Tower

Okay, so that lean is real! But this cute little city is definitely more than "just" the Tower! The Field of Miracles itself is enough to warrant a day trip. We actually visited on Easter Sunday, which was very special. I wish we would have done some sort of guided tour to find out more about (and enter) each building in the field, but we were here for a very quick stop, which means we'll have to return!

Florence and Tuscany: Food, Art and Wine

One of the most surprising things to me about Florence is how small the city itself is. We walked from one end to the other in less than an hour. I loved that because it meant we were able to leave the car at the hotel and really get to see the city. Most of Florence was extremely crowded, but for good reason - the city has beauty at every turn and is very easy to navigate. Things not to miss? The Duomo, which is really unique and worth a climb to the top; Piazzale Michelangelo for the view; the Galleria dell'Accademia, which is home to the David as well as lots of other amazing pieces of art. The meat and cheese board pictured here can be found at I' Girone De' Ghiotti and I swear was worth the trip to Florence in itself. We also took a wine tour through Tuscany that I cannot recommend enough. We still order wine from one of the wineries we visited and have it shipped to Texas!

Siena: Hills and Horses

One of the most recognizable plazas in Italy, PIazza del Campo in Siena is still the site of a twice-yearly horse race, famously seen in James Bond: Quantum of Solace. We spent a good portion of our day here, sitting and watching people go by. Something we found to be true just about everywhere we went in Italy? People (especially at restaurants) are not in a hurry! So we took advantage of that and enjoyed a long, relaxing lunch in the sun. The city is fairly small but very hilly so the walking around was a lot of fun (and great exercise after that nice meal!).

Rome: The Capital

We needed about a month in this city alone, with historical sights around every corner. We did a walking tour that included inside the Colosseum, the Roman Forum, the Capitoline Museum, and the site where Julius Caesar was assassinated. It's hard to believe that, not only do these sites exist in one city, but are within walking distance of each other. Do the tours and eat gelato as many times a day as possible. When in Rome... go to Frigidarium!

The next day, we went to the Pantheon, the Trevi Fountain, Spanish Steps, and our second country, Vatican City. Again, the fact that all of these sites are doable in one day is amazing to this Texan! The Vatican Museums and St. Peter's Basilica are truly must-sees. Be sure to reach out and ask me for the best tip ever to avoid the line into the Baslica!

San Marino: Another Stamp in the Passport

Why stop at two countries when you can visit three? The drive up to San Marino was one of the scariest rides of my life, but WORTH IT. Truly a country up in the clouds. The views especially at sunset were everything.

Venice: City on the Canal

Without a doubt, Venice is the most unique city I have ever had the pleasure to visit. It is odd and wonderful and falling apart and beautiful and expensive and worth every penny! My one regret is that we didn't actually stay on the island of Venice. It was very easy to get there from our hotel, but definitely took some time! While there, visit the Doge's Palace and leave yourself plenty of time to get lost (for fun) in all the alleyways.

Conclusion

I cannot say enough good things about the Italian countryside, people, food, and (oh yeah) coffee! The culture of coffee there is different, but it still brings people together. Plan to pay extra if you want to sit and drink your espresso... or just do as the Italians do and drink your caffe at the bar before being on your way!

Let me know when you go to Italy; I can't wait to hear how you experience it!