Expert Recommendations for Amazing Itineraries

This vineyard, run by a local woman and her two daughters, is full of Sangiovese grape vines and olive trees. They make delicious wine and exception olive oil. The tour is informative and the tasting is a lovely way to enjoy a tasting of their exceptional Brunello di Montalcino. We had a little bite of traditional Tuscan meats and cheeses while we tried the variety of Brunello!

If you watched the Netflix special called Chef’s Table: Pizza, there is an episode about Franco Pepe and his pizza place in Caiazzo — about an hour east of Naples. Franco is said to be the best Pizzaiolo in the world. The restaurant is called Pepe In Grani and they make the traditional and non-traditional pizzas along with antipasti and dolci.

The Perugia Mini Metro is a modern and efficient transportation system serving the city of Perugia. Consisting of small, driverless electric trains, it connects the historic city center with the nearby parking lots, helping to avoid a lot of uphill/downhill walking. Its eco-friendly design and minimal impact on the city’s historic architecture make it a model of sustainable urban transportation. We loved using the MiniMetro to get from the parking areas to the top of the town!

Perugina Chocolates, originating from Perugia, are renowned for their taste and quality craftsmanship. Founded in 1907 by Giovanni Buitoni, Perugina quickly gained fame for its iconic Baci chocolates, which are small, hazelnut-filled chocolates wrapped in a poetic love note. The brand’s dedication to using only the finest ingredients and traditional chocolate-making techniques has made Perugina a symbol of Italian excellence in the world of confectionery.

Piazzale della Pace in Parma is a serene, beautifully restored green space in the heart of the historic center. Once the devastated site of wartime bombings, the square now features sweeping lawns, a reflective fountain by Mario Botta, and two evocative monuments—the Monument to the Partisan and the Ara Verdiana honoring Giuseppe Verdi. Framed by the majestic Palazzo della Pilotta and nearby heritage palaces, it’s a peaceful cultural hub ideal for relaxing, contemplative walks, and enjoying public events.

Piazza della Repubblica in Perugia is a central square that embodies the city’s vibrant spirit and rich history. Lined with charming cafes, shops, and historic buildings, it serves as a gathering place for locals and visitors. At its heart lies the Fontana Maggiore. This elegant fountain, carved in the 13th century by Nicola and Giovanni Pisano, is adorned with intricate panels symbols of Perugia and representations of life in medieval times. The square itself is surrounded by Renaissance palaces and elegant porticoes. It is a beautiful backdrop for an afternoon espresso or evening aperitivo.

From here, narrow streets radiate out into Perugia’s historic center, inviting you to wander and discover hidden artisan shops, small trattorias serving hearty Umbrian dishes, and quiet corners steeped in centuries of history.

The piazza is also a hub during Perugia’s many festivals, including Umbria Jazz and the Eurochocolate festival.  Whether you are admiring the architecture or simply people-watching under the Umbrian sun, Piazza della Repubblica captures the timeless beauty and daily life of this hilltop city. It’s the perfect place to pause and soak in the essence of Perugia before continuing your exploration through its storied streets and panoramic viewpoints.

Piazza delle Signoria, situated in the heart of Florence, is an iconic square steeped in history and grandeur. Flanked by magnificent Renaissance buildings and close to the Uffizi, the piazza serves as an open-air museum of Florentine art and architecture. At its center stands the imposing Palazzo Vecchio, a symbol of civic power and authority since the medieval era. This majestic fortress-palace boasts an intricate facade adorned with sculptures and family crests. In the piazza there is a replica of Michelangelo’s David standing tall, offering a glimpse of the masterpiece that once graced the square. As the political heart of Florence for centuries, Piazza delle Signoria and Palazzo Vecchio continue to captivate visitors with their timeless beauty and significance in the cultural tapestry of the city.

Arezzo’s Piazza Grande is one of Tuscany’s most charming squares, with its sloping pavement and mix of medieval and Renaissance buildings. Fans of *Life is Beautiful* will recognize it as the backdrop for many scenes from the film. The square comes alive during the monthly antique market and certainly at Christmas for its famous Mercato di Natale. Cafés and restaurants line the edges, perfect for soaking in the atmosphere with a coffee or aperitivo. Whether you’re here for history, film, or just a leisurely stroll, Piazza Grande is a place that feels straight out of a storybook.

This beautiful Piazza, full of people and surrounded by shops and cafes is a great place to spend an afternoon. If you have time to tour the large Basilica, you can take a tour this church which was built between 1390 and 1663 and is an excellent example of Italian Gothic architecture. In the evening, the lights come on and you’ll find people just sitting on the church’s steps. Some times there will be people playing guitar and singing and often the crowd feels compell

Piazza Navona is a captivating public square renowned for its Baroque beauty and lively atmosphere. Adorned with stunning fountains, including the iconic Fontana dei Quattro Fiumi (Fountain of the Four Rivers) by Gian Lorenzo Bernini, the square is a masterpiece of architectural and artistic splendor. Beneath its cobblestones lies an archaeological site, a testament to its rich history as the site of ancient Roman games and festivities, which you can tour for a few euros. Surrounding the square are elegant palaces, bustling cafes, and charming shops, creating a vibrant ambiance day and night.

Make sure to check the weather for the clearest day and then plan to spend sunset at Piazzale Michelangelo. You can walk there from central Florence but it is uphill so a taxi might be a good option too! Once there, you can tour the Chiesa di San Salvatore al Monte until the sun is setting, then grab a drink and watch the show. There are often artists and entertainers there too.

Pienza is a Unesco World Heritage site which has been referred to as a “Renaissance utopia.” In the late 15th century, native son Pope Pius II hired an architect to create a town-planning model which was later used throughout the region. Pienza is quaint and lovely, with many beautiful streets to walk down and unbelievable views of the Val D’Orcia.

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.

No trip to Florence feels complete without strolling across the Ponte Vecchio. This medieval stone bridge, lined with glittering gold and jewelry shops, has spanned the Arno River since 1345. As you wander, you’ll notice its unique architecture with overhanging shops and shuttered windows, giving it a village-like charm suspended above the water. At sunset, the bridge glows in warm light, creating an unforgettable view of the river and city. Don’t forget to pause at the center to admire the Vasari Corridor above you and the timeless beauty of Florence reflected below. It’s pure Italian magic in every step.

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. The day we were there was a bit overcast, but they do have outside seating on beautiful days.

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! We enjoyed a traditional Fiorentine steak and a plate of pasta along with the most gorgeous pastry for dessert! What a view!