Expert Recommendations for Amazing Itineraries

The Cattedrale di Santa Maria Assunta, towering proudly over Montepulciano, is a breathtaking testament to Gothic and Renaissance architecture. As the heart of the city, the Piazza Grande unfurls before the cathedral, offering a picturesque setting steeped in history and charm. Flanked by ancient palaces and adorned with a timeless well, the piazza serves as a lively gathering place, where locals and visitors alike converge to soak in the atmosphere and marvel at the cathedral’s beauty.

Listed as one of “i borghi più belli d’Italia” (“The most beautiful villages of Italy”), this walled town is a so picturesque that when you look at your photos, you’ll have to tell friends “this is a real place!” When we arrived by car, we parked in a small parking lot at the base of the hill. We boarded a city bus that drops you up at the top. Keep in mind that the walk to the Civita is long and steep and may not be suitable for all travelers, but I promise that it is worth every drop of sweat to get there. Inside the city walls, you’ll find the typical piazze and churches. Not large at all, this is a the perfect stop if you are in Tuscany and are heading to Rome or south. Don’t miss it…

This hotel on the edge of the Monti neighborhood is a great central spot that is not in the more touristy area.

The building housing the Comune di Montepulciano stands as a stately symbol of civic pride and heritage in the Piazza Grande. Originally constructed during the medieval period and subsequently renovated in Renaissance style, the Comune di Montepulciano building embodies the enduring spirit of the community. Its halls have witnessed centuries of decision-making and community affairs, making it not just an administrative center but also a living repository of Montepulciano’s collective memory and identity. For a unique perspective, visitors can ascend to the roof for a nominal fee, offering panoramic views of Montepulciano’s enchanting surroundings and a closer look at the architectural details that grace this historic landmark.

Da Felice in Testaccio is one of the most famous Roman restaurants for the Roman Classic “spaghetti cacio e pepe.” You do have to plan in advance for this one as it is hard to get a day-of reservation. The Testaccio neighborhood is a little away from the main tourist attractions and it feels very Roman. There are plenty of shops and gelaterias for after your meal!

“Da Oio a casa mia” in Rome’s Testaccio neighborhood is a true gem of traditional Roman cuisine. From the moment you step in, the warm ambiance and friendly staff make you feel like family. The menu features a delightful array of classic Roman dishes, each bursting with flavor and prepared with care. Whether it’s their perfectly al dente pasta dishes, tender meat courses, or heavenly desserts, every bite is a culinary delight. The restaurant’s commitment to using fresh, high-quality ingredients shines through in every dish. With its cozy atmosphere and mouthwatering cuisine, “Da Oio a casa mia” is a must-visit for anyone craving an authentic taste of Rome.

This lovely little enoteca is right on the Piazza San Donato looking at the church and is a wonderful place to people watch while enjoying a delicious meal. There are a few local cats hanging out in the square as well though they don’t seem friendly enough to pet. We enjoyed the polenta bolognese and this delicious contorno of Tuscan beans with toasted bread. Perfetto!

Dar Poeta in Rome’s Trastevere neighborhood is a cozy pizzeria with rustic charm and delicious pizza. The inviting atmosphere sets the stage for a memorable dining experience, while the pizzas, whether classic Margherita or creative specialties, are always fresh and bursting with flavor. With friendly service and reasonable prices, Dar Poeta is a favorite spot among locals and tourists alike for authentic Roman pizza.

De’Ricci Cantina in Montepulciano offers a unique wine tasting experience set within ancient Tuscan caves. Located in the heart of the historic town, these atmospheric caverns provide the perfect backdrop for sampling a curated selection of local wines. As you descend into the cool depths, you’re transported back in time, surrounded by centuries-old stone walls that echo with the stories of generations past. The knowledgeable staff guide you through the tasting, sharing insights into the region’s winemaking traditions and the characteristics of each vintage. With its historic charm and dedication to showcasing the best of Tuscan viticulture, De’Ricci Cantina’s old Tuscan caves offer a truly memorable wine-tasting journey.

Don Nino’s is a chain Italy — you’ll see them in Rome, Florence and other big cities and for a good reason, as they make delicious cannoli for you while you wait. Cannoli should not be filled ahead of time as it makes the shell soggy. Don Nino’s makes your cannoli while you wait and is the perfect place for a sweet treat while touring Florence.

Obviously one of the main tourist sites in Florence, this imposing group of buildings deserve a whole day, if you have it. Do check the tourist information offices found on both sides of the Piazza to make sure the Basilica is open (they don’t allow tourists on Sundays) and if you plan to climb Bruneschelli’s dome or the campanile, you’ll need a timed ticket. The ceiling of the Baptistery is under construction in 2023/2024 but it’s still worth it to see the building and the amazing gold doors. Keep your eye open for scammers and pickpockets in this piazza but don’t miss it.

The first stone of the city’s cathedral was laid in 1099 and the construction continued until 1184. The church is a beautiful example of Romanesque architecture and a UNESCO World Heritage site. We enjoyed touring the inside of the church and it’s magnificent bell tower, known as the Ghirlandina. The carvings on the outside of the church are intricate and unique, well worth the visit alone.

This great enoteca is at the top of the hill and has a huge variety of wines to try. You can select the amount of your pour as well. Since it’s at the top of the hill, it’s a quick walk to the Comune building, the Piazza Grande and the Cattedrale.

The Ferrari Museum was a fun stop when we visited Modena. It’s easy to walk to from the train station and we enjoyed touring the slick, modern museum and seeing all the famous cars. We had a quick bite to eat in their lobby cafe which we enjoyed! It’s a fun stop in Modena.

If you leave the city out of the Porta Berarda, walking down the Via Guiseppe Maffei, you’ll come to a beautiful church and park, just outside the city gates.
This park is a quiet place to sit for a minute and enjoy the lovely views.

There is a legend that if you can roll a coin down the Porcellino’s tongue, you’ll have good luck. You can tell it is a well known story as the bronze statue’s nose is shiny from people rubbing it for luck! The statue is at the end of one of the big famous leather markets in town, so make sure to take time to peruse the stalls for a new wallet, purse or belt. In the evening, when the stalls are closed, there is space for musicians to setup and serende the evening crowd.

This tiny gelato shop is my exception to the rule. I normally say not to stop at the places right in the tourist areas, but this gelato is so delicious it makes sense to grab a double on a cone and find a spot in the piazza to enjoy it and people watch.

This small ristorante in the Monti neighborhood of Rome has the most delicious Cacio e Pepe pasta. Their cute tables outside are perfect for a nice dinner!

This amazing restaurant is an Instagram phenomenon. Set in a cave, every table has the view of a lifetime. The menu is extravagant and expensive but worth every penny. The food is delicious, the service is impeccable and it will definitely be a memorable evening. Reservations are hard to get so plan accordingly but if you have a special occasion while in Italy and are putting Puglia on your itinerary, this restaurant will be perfect for your celebration!

Yes, there is a picture of Guy Fieri on the wall. But it makes sense because the pizza is delicious. 10/10 — definitely recommend and can’t wait to go back. It’s right by the Piazza di Santo Spirito so don’t miss that when you are there.