Expert Recommendations for Amazing Itineraries

Pisa is a quick and easy afternoon trip from Florence. About 45 minutes on the fast train and a 20 minute walk and you are at the famed leaning tower. There is a cathedral, a baptistery, extra creepy graveyard where you walk on the grave (unless you are me and you walk on the edges the whole time). It’s really well worth the trip if you have extra time in Florence.

This pizza place right down from the Piazza Grande makes traditional pizza but they also offer some interesting non-traditional styles. We tried the pizza fritte and enjoyed it very much. Interestingly, they also sell wine from Sting’s nearby Tuscan vineyard.

If you are in the mood for a little luxury shopping + food, Rinascente is right near the fountain. The basement has an ancient aqueduct and the sixth-floor is a food hall. It includes an outlet of the Michelin-starred Neapolitan pizzeria Gino Sorbillo. This store is ultra swanky with amazing brands like Gucci, Loewe, Louis Vuitton, and many more. There is also a rooftop terrace for some food, if you want to sit and enjoy a nice day in Rome.

In 2007, we visited this restaurant and were very much looking forward to returning. We were not disappointed. Sitting right next to the Comune building, this restaurant has a nice outdoor seating area if you are there on a nice day! They serve traditional Tuscan dishes and have warm, friendly service!

We happened on this restaurant during our day in Perugia and definitely felt like part of the family. Filled with locals at lunch (even a graduation party!) the Italian Nonna running the place was the picture of warmth and hospitality. While waiting for our entrees, she brought us a small taste of their house specialty, beans in a warm sauce with a piece of crusty bread, and they were one of the best dishes we ate in Italy.

Ristorante Da Constantino in Positano is a beloved family-run restaurant offering a fantastic dining experience with a stunning view of the Amalfi Coast. Nestled on a hillside above the town, the restaurant serves traditional Italian cuisine, with a strong emphasis on fresh seafood and local specialties. The terrace dining area provides a breathtaking backdrop of the coast, making it the perfect place to enjoy a relaxed, authentic meal. With its welcoming service and delicious dishes, including homemade pastas and regional wines, Ristorante Da Constantino is a must-visit for anyone seeking a true taste of Positano.

PRO TIP: Your hotel can arrange a car to come and get you for dinner and bring you home at the end of the evening!

This restaurant is just outside the gates of Pienza and it has the most spectacular view (and food!) We enjoyed a long lunch here and look forward to going back!

Ristorante Nomade in Viareggio is a popular spot offering a delicious mix of meat and seafood dishes, made with fresh, high-quality ingredients. Located near the beach and the vibrant promenade, it provides a spacious and welcoming environment for both casual diners and those celebrating special occasions. The restaurant is known for its versatile menu and excellent service, making it a great choice for both intimate meals and larger events. Whether you’re enjoying lunch or dinner, Ristorante Nomade offers a relaxed atmosphere to savor authentic Italian cuisine.

Ristorante Santa Croce is a charming and rustic eatery located in the small village of Nocelle, perched above Positano on the Amalfi Coast. Offering breathtaking views of the Mediterranean, the restaurant is known for its delicious traditional Italian dishes, with a focus on fresh seafood and locally sourced ingredients. The outdoor terrace provides a perfect setting to enjoy a leisurely meal while taking in the stunning vistas. Whether you’re enjoying fresh pasta or savoring a glass of local wine, Ristorante Santa Croce promises a memorable meal in a spectacular setting.

In Castiglione del Lago, there is a medieval fort which is open to the public.
Walking on top of the walls of the fort is a very entertaining way to spend the afternoon. You’ll go through the walls of the town and walk all the way to the end, where you will see a small museum which costs a few Euro for admittance. After walking through a few rooms in the museum, you head down a staircase that leads to the walls of the fort. The main passage is very narrow and long. At the end, you come out to towers and walls which you can walk around and have a spectacular view of the lake. I highly recommend this one!

This was one restaurant we booked well in advance of our trip. We’d heard good things and were not disappointed. We booked our table in the wine cellar and since it was a rainy, chilly night – that was perfect. The meal was delicious, the service was impeccable, the wine choices were so vast it was a bit overwhelming and we enjoyed every minute of it. Turns out we were not alone, as we were leaving, we realized that we shared that cellar with Chef Amanda Frietag a Food Network chef.

At this Salumeria, the star of the show is the porchetta. Sliced to perfection, each bite is a delicious taste of tender meat infused with aromatic herbs and spices, encased in a crispy, golden exterior. Pair it with the delectable Parmesan chunks, drizzled with the rich sweetness of balsamico di Modena, and you have a match made in culinary heaven. The vibe here is great too — lots of folks enjoying an apertivo and cocktail, sitting on bar stools on the sidewalk – it’s a great spot to spend some time in the evening.

Construction of this church was started in 1741 and this was place for women who wanted to spend their life in prayer. Now, it is a the end point of the longest covered portico (the Portico di San Luca), which stretches about 2.4 miles from the city to the hilltop sanctuary. This portico features 666 arches, making it the longest in the world. Pro Tip: Take a taxi there, then walk home. Down the hill (and steps) is much more enjoyable that up!

If learning Italian is on your bucket list, I highly recommend taking some classes if you have time while in Italy. I enrolled in Scuola Parola for three weeks at the beginning of my last trip to Italy and I was so happy I did it. The students are all “stranieri” (foreigners) and classes are just in the morning from 9am to 1pm so you have time in the afternoons and evenings to tour the city. Taking the time to learn the language gives you the opportunity to have real interactions with Italians and get to know this magnificent country better. Now, when we plan a trip, I make sure they have a school in their town so I can keep learning!

The Spanish Steps, located in the heart of Rome, are a renowned landmark and popular gathering spot for tourists. Constructed in the 18th century, the steps connect the Piazza di Spagna at the base with the Trinità dei Monti church at the summit. The elegant design, featuring a series of terraces, 135 steps, and the iconic Barcaccia fountain at the foot, reflects the grandeur of Roman architecture and urban planning. Over the years, the Spanish Steps have served as a backdrop for various cultural events and are celebrated for their beauty and historical significance in the Eternal City.

We booked a cooking class in Bologna to learn to make authentic Bolognese and tortellini. The class was hosted at a women’s home in Bologna where we made three kinds of pasta, two kinds of sauces and then enjoyed a delicious dinner!

The Terrazzo Infinito at Villa Cimbrone is one of the most breathtaking viewpoints on the Amalfi Coast. Perched high above the cliffs, this “Infinity Terrace” offers panoramic views of the coastline, the sparkling Mediterranean Sea, and the lush surrounding hills. The terrace is framed by elegant marble busts and lush gardens, creating an atmosphere of tranquility and beauty. It’s the perfect place to take in the stunning scenery, whether you’re visiting the historic Villa Cimbrone or simply walking around the gardens. With its spectacular vistas and serene surroundings, the Terrazzo Infinito is a highlight of any visit to Ravello.

The Arch of Augustus, often referred to as the gate in Rimini, was built in 27 BC and it served as the western entrance to the city of Ariminum, which was a crucial point along the Roman road network. The Arch of Augustus is the oldest preserved arch in Italy

The great thing about Bologna is all the Colonnades. These archways are everywhere in this city and it makes it a nice place to visit when it’s raining but also just architecturally so interesting.

The contrade of Siena are 17 historic districts that form the heart of the city’s identity, each with its own symbol, colors, and traditions. Originally established in the Middle Ages as military and administrative divisions, they have evolved into deep-rooted communities that foster local pride. Twice a year, the contrade compete in the famous Palio di Siena, a thrilling bareback horse race held in Piazza del Campo. The rivalry is fierce, but the sense of belonging and tradition runs even deeper, with each contrada hosting events, festivals, and gatherings year-round. Whether you’re visiting during the Palio or simply exploring Siena’s streets, learning about the contrade adds an extra layer of meaning to the city’s unique character.