Expert Recommendations for Amazing Itineraries

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.

Piazza Raffaele De Ferrari is the vibrant heart of Genoa, a grand open square where the city’s historic grandeur meets its modern energy. Anchored by its iconic bronze fountain—whose cascading arcs of water shimmer day and night—the piazza sits at the crossroads of Genoa’s most important landmarks, from the ornate Palazzo Ducale to the elegant Teatro Carlo Felice and the stately Palazzo della Regione. Lined with 19th-century buildings and buzzing with locals, students, and visitors, it’s the perfect place to feel Genoa’s unique mix of old-world elegance and contemporary life.

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.

Traditional Neapolitan pizza in Liguria! Spaccanapoli is a well known neighborhood in Naples and the restaurant in Sanremo definitely feels authentic. The pizza crust was light with many bubbles. We had two pizzas; one traditional margarita (as we always do) and one with prosciutto, fresh cherry tomatoes and arugula. The staff was friendly and the service was quick. We noticed a line of people waiting for their pizzas to go as well, so it’s clear folks in Sanremo love this spot.

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.

The Port of Genoa blends centuries of maritime heritage with a modern, revitalized waterfront. Once the power center of the Genoese Republic, the port today stretches from bustling cruise terminals to the vibrant Porto Antico area redesigned by architect Renzo Piano. Here, you’ll find a lively mix of museums, cafes, panoramic walkways, and landmarks like the Bigo lift and the Genoa Aquarium. Fishing boats, ferries, and sleek yachts all share the same horizon, creating a constant sense of movement and life.

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 charming new restaurant came highly recommended by our VRBO host. The menu is small but every dish is packed with flavor. The coastal-inspired vibe is cozy, and the space is intimate, so reservations are a must. We started with a delightful pasta primi—a perfectly executed aglio e olio—followed by secondi of fresh fish and tender chicken, complemented by a lovely bottle of Tuscan Chianti. Dessert was a homemade masterpiece from the owner: a lemon cake with a limoncello filling that was both light and indulgent. We lingered over every course, savoring the meal and the relaxed, welcoming atmosphere.

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!

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.