Expert Recommendations for Amazing Itineraries

Dominating the main piazza in Ariccia, Santa Maria Assunta in Cielo is a striking example of Baroque harmony and elegance. Designed by Bernini, the church’s circular form and luminous interior create an immediate sense of balance and calm. Its location—anchoring the town’s civic and social life—makes it more than just a religious site; it’s the heart of Ariccia itself. I always suggest stepping inside even if only briefly, then lingering in the piazza afterward to soak in the rhythm of daily life. It’s a perfect stop for travelers who appreciate architecture, atmosphere, and the quiet beauty of small-town Lazio.

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!

When people say “Sirmione,” they’re referring both to the town and the entire narrow peninsula that extends about 4–5 kilometers into the lake. The peninsula’s tip is famous for its thermal springs and scenic views, while the base connects to the mainland near the town. We took the train from Milan and it drops you at Desenzano del Garda, from there we took a taxi to Sirmione. Only a few cars are allowed over the drawbridge so the taxi dropped us and we walked the last few minutes. Sirmione is a crowded tourist destination most of the year, and it certainly was in late September. The land on the tip of the peninsula is quite small so you notice the masses. But once we walked out away from the Castle, the crowds thinned and we enjoyed the views and walks. Most hotels have thermal spas and spending an afternoon poolside with views of the lake is a lovely way to pass the time.

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.

There’s a beach at Lake Albano, and it’s one of the Castelli Romani’s best-kept surprises. Set along the shores of this ancient volcanic lake, the lido areas offer a relaxed, local escape just outside Rome. Clear, cool waters make it especially refreshing in the warmer months, while sun loungers, cafés, and casual restaurants line the waterfront. It’s the kind of place where Romans come to unwind—swimming, sunbathing, or lingering over a long lunch with a lake view. I love recommending Lake Albano’s beach as a balance to sightseeing: after exploring Castel Gandolfo above, head down to the water for an easy, unpretentious afternoon that feels worlds away from the city.

We were staying close to the Milan Malpensa airport and had a few extra days to explore so we headed out to Stresa on Lake Maggiore. You can easily take the train from Malpensa to the town of Arona, then hop off and get a ferry the rest of the way. Stresa is a cute little lakeside city with nice piazze and cafes. We strolled around, found a lovely little piazza and stopped for lunch. After lunch, we hopped on the next ferry to take us a bit further north in the lake to the Borromean Islands and Isola Bella.

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! We also have taken pizza making class in Rome which was also so fun! I highly recommend taking a cooking class anywhere in Italy as it’s a great way to learn traditional recipes!

The Terrazza degli Innamorati—literally, the Lovers’ Terrace—is one of Nemi’s most romantic viewpoints, and it fully lives up to its name. Set along the edge of the village, the terrace opens onto sweeping views of Lake Nemi below, its dark waters reflecting the surrounding forested crater walls. Benches invite you to pause, take in the scenery, and enjoy the stillness that defines this hill town. Whether visited at midday or as the light softens toward evening, the terrace captures Nemi at its most poetic—a quiet moment suspended between sky, water, and legend.

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 and we enjoyed walking around the grounds for a few moments as we were leaving the city. It’s well worth the stop!

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 Portico di San Luca is the world’s longest covered walkway, stretching approximately 3.8 kilometers (2.4 miles). This historic portico connects Porta Saragozza in the city center to the Santuario di San Luca, a sanctuary situated atop the Colle della Guardia hill. We actually took a taxi to the sanctuary then walked back so we would have a down-hill walk.

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.

Starting at the Circus Maximus, you can walk up Aventine hill, stopping at the lovely gardens along the way, Giardino degli Aranci. At the top of the hill, there is a huge green door. There will likely be a line there, so just get in line with the rest of the people. The door has a keyhole that has a picture perfect view of the Vatican.

This Palazzo in the Piazza della Repubblica is the main square in Cortona and is a lovely place to sit and have a café and people watch. The famous Christmas market scene in “Under the Tuscan Sun” was set here in this piazza. We loved sitting on the steps and watching the world go by!

The Pantheon is one of my favorite buildings in Rome, with its ocular hole in the roof and the way the sun streams in at certain times of the day. The piazza out front will be crowded so be alert to scammers and pickpockets. Centrally located among the other tourist sites, this one is not to be missed.
There are lots of spots for gelato or a meal, if you need a break.

I can’t think of one person visiting Rome who doesn’t know that the Colosseum is a “must see” so instead of describing it, I’ll offer a bit of advise. If you have it in your budget, hire a local to give you a walking tour of the Colosseum and the Forum because there are so many interesting things to see and learn. The stories the local tour operators know make the cost of hiring one well worth it.

Talk about a cafe with a view! This cafe has tables in the street and on the sidewalk under the colonnades. Turn your chair towards the view of the le due Torri and enjoy an Aperol spritz along with some porchetta and tigelle! The vibe in the promenade was so nice, we didn’t even check the inside of the restaurant. But why would you with a view as iconic as that?!?

The Vatican, a city-state within Rome, is the spiritual and administrative center of the Catholic Church. St. Peter’s Cathedral is one of the most renowned examples of Renaissance architecture and serves as a symbol of the Church’s grandeur. Its iconic dome, designed by Michelangelo, dominates the skyline of Rome and attracts millions of visitors each year. Inside, the Sistine Chapel, famous for its stunning ceiling painted by Michelangelo, is open to the public but tours/tickets must be arranged well ahead of time.

The street in Modena known for its colorful hanging umbrellas is Via Cesare Battisti, often referred to as “The Way of the Umbrellas.” This charming alley, located in the heart of Modena, is adorned with vibrant umbrellas suspended overhead, creating a whimsical and picturesque atmosphere. The installation was conceived by local traders and supported by the city as part of an initiative to enhance the city center

The tastiest little sandwiches, made with a variety of Italian fillings, from Bolongese to Procuitto and Parm. Tigelle are small, round breads from Emilia-Romagna, traditionally cooked in clay molds. Soft inside with a lightly crisp crust, they’re usually sliced open and filled with cured meats, cheeses, or classic cunza—a spread of lard, garlic, and rosemary. Tigelle are a delicious, authentic taste of Modena’s rustic culinary tradition. We make Tigelle at home all the time now!