Expert Recommendations for Amazing Itineraries

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!

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 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.

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.

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.

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 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.

Right in the heart of Trastevere, there are multiple sites of this restaurant. We ate at the one right in the Piazza della Scala by our apartment and it was really tasty. Good red wine by the caraffe, we each had a tasty pasta and then split saltimbocca and it was excellent.

If you are missing your cat, this spot is perfect to see some ancient ruins and to pet a few cats. The Torre Argentina is the remains of four Roman temples and is thought to be the place where Caesar was murdered. It was found during an excavation in the 1920s and now is a protected site. Within the ruins is also a cat sanctuary. You’ll see lots of cats roaming the ruins and in the grass but you also can walk down a small flight of stairs to a basement where there are cats you can interact with. Some are old or blind and they are all lovely to sit with for a few minutes. It doesn’t smell great in there, but it was worth it for me to visit. Be a good citizen and leave a few euro to donate to help these cuties.

By far, this was one of the top dinners we had in Italy. This is a small family run trattoria, but you do need to get reservations because it is so popular. I had the small ravioli with parmesan inside and pea cream with sausage.

This tiny restaurant is in the Mercato Sant’Ambrogio so it is only open for lunch. The market closes at 2pm so be sure to plan to be there around noon for lunch. The tables are open to everyone so you may share a table (and a carafe of wine) with some folks taking their lunch break. The scene is a little chaotic but they restaurant knows what it’s doing so just ask for a table for your party and roll with everything else. The food is delicious and clearly made with care and love.