Expert Recommendations for Amazing Itineraries

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City: Siena
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Key Largo Bar is a perfect spot for a casual drink or a quick bite. Located on Il Campo, it boasts a beautiful terrace overlooking the Piazza and the Torre del Mangia, offering stunning views of the iconic square. The bar serves a variety of coffee, cocktails, and snacks, making it an ideal place to relax and people-watch. Whether you’re enjoying a morning espresso or an evening aperitivo, the laid-back atmosphere and friendly service make it a favorite among locals and tourists alike.


We had a lovely dinner here — it’s delicious Puglian food, so of course, we had to try the orecchiette. Make sure to make a reservation. It’s right inside the city’s gates and perfect for a nice evening out. Make sure to try a Puglian Primitivo with dinner!

City: Siena

La Locanda dei Tintori is a cozy restaurant nestled in the heart of Siena, honoring the city’s rich history of textile and leather dye artisans. The name pays tribute to the neighborhood’s past, once bustling with renowned dyers like Jacopo Benincasa, father of Saint Catherine of Siena. The menu showcases traditional Sienese cuisine, featuring dishes such as pici pasta with aglione sauce and wild boar ragù. Guests can enjoy the warm ambiance indoors or opt for outdoor seating along the charming Via dei Pittori. Located just a short stroll from the Sanctuary of Saint Catherine, it’s an ideal spot to savor authentic Tuscan flavors while exploring Siena’s historic center.

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This hotel sits right on the bluffs overlooking the quaint town of Vietri Sul Mare on the east side of the Amalfi Coast close to Salerno. The hotel has a lovely restaurant, is walking distance to the town and even has a few parking spaces. We especially loved the kind staff who greeted us each morning for breakfast and in the evening for aperitivo!

City: Bologna

This red wine from Emilia-Romagna is quite different than tradition Italian red wine. We were in Bologna in May and it was getting warm, so we enjoyed Lambruscho quite often as it’s fizzy and served chilled. We highly recommend trying a bottle if you are in this region.

City: Bologna

In the 12th century, when Bologna was a city of power and wealth, the construction of these towers indicated the status of the family — at one point in history, there were likely almost 200 towers in Bologna. These towers are part of the UNESCO World Heritage sites. They serve as a reminder of the city’s rich past and the rivalry between noble families.

City: Rome
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This lovely French bakery is a quick walk from Trastevere and the perfect spot to pick up a nice celebratory treat. The cafe and quiche lorraine for lunch which were delicious. Highly recommend.

City: Florence

Right next to the Piazza Santa Croce, this small sandwich shop is the perfect spot for lunch. They make the traditional Schiaccia sandwiches and you can sit in their spots on the sidewalk to enjoy your lunch — or walk down to the benches in the Piazza. The food is delicious!

City: Arezzo

Lo Spaccio Focacce Panini in Arezzo is a beloved spot known for its delicious focaccia and panini, perfect for a quick and tasty bite. Located near the historic center, this casual eatery is popular with locals and visitors alike. The menu offers a variety of fresh, flavorful sandwiches made with quality ingredients, and it’s especially known for its creative focaccia combinations. Its popularity has grown significantly on Instagram, where food lovers share photos of their mouth-watering meals. If you’re in Arezzo and craving something casual yet delicious, Lo Spaccio is a must-visit.

City: Rome
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Literally everywhere you go, there is something amazing above you. Inside, it’s a 14th century fresco on the ceiling in your school. Outside, it’s amazing architecture and sculpture. Just look up…. so you don’t miss a thing.


This pastry shop has the most beautiful desserts and they are just as delicious as they are pretty. They serve a tasty espresso and seem to stay open late for the folks walking home.

City: Matera
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Matera is just an hour away and well worth the visit. It is known for its unique architecture and fascinating history. Carved into the rugged landscape, Matera is famed for its “Sassi” districts, where dwellings are built into the rock cliffs, creating a strikingly picturesque scene. Visit the Museo della Civiltà Contadina “Casa Grotta” (Museum of Peasant Civilization “House Cave”) to get a fascinating glimpse into the daily life of Matera’s inhabitants throughout the centuries. These cave dwellings, some dating back to prehistoric times, have earned Matera recognition as one of the world’s oldest continuously inhabited settlements and a UNESCO World Heritage Site since 1993. You may also recognize it as the backdrop in the James Bond movie “No Time to Die.”

City: Florence
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The first floor of the mercato centrale is a vibrant bustling market with fresh food, fruits, veggies and the like. Like. The upstairs is a very interesting and entertaining dining hall. There are many different types of food to choose from, all prepared by local vendors and all delicious. You can get a glass of wine with a delicious plate of pasta or a big Florentine steak. It’s an absolute stop for any foodies while in Florence.

City: Rome
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The Mercato di Testaccio in Rome is a lively food market in the heart of the Testaccio neighborhood. Here, visitors can explore stalls filled with fresh produce, artisanal cheeses, and Roman street food delights. From supplì to porchetta sandwiches, the market offers a taste of authentic Italian cuisine amidst a bustling atmosphere, making it a must-visit destination for food enthusiasts and travelers alike.

City: Florence
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The Mercato Sant’Ambrogio is a fresh food market with stalls of all kinds of different foods. There are stalls for fish, meat, pasta, veggies, fruit, spices and more. It’s so fun to walk through the stalls checking out all the interesting local ingredients. If you are a foodie and don’t want to brave the crowded of the Centrale Market, try this one instead!


Nestled amidst the rolling hills of Tuscany, Montalcino exudes a timeless charm that captures the hearts of visitors from around the world. This picturesque hilltop town is renowned for its stunning views of the surrounding countryside and its rich cultural heritage. Montalcino is perhaps best known as the birthplace of Brunello di Montalcino, one of Italy’s most esteemed wines. Here, visitors can wander through the narrow cobblestone streets, lined with ancient stone buildings and charming artisan shops, or explore the imposing fortress that dominates the town’s skyline. With its idyllic setting, centuries of history, and world-class wine, Montalcino offers a quintessential Tuscan experience that is as captivating as it is unforgettable.

City: Rome
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Also known as the Victor Emmanuel II Monument, this imposing white building just before the Coliseum and the Roman Forum is the perfect place for a great view of the city. You can pay a few Euro to ride the elevator to the roof. Of course, you still have to make it up all those white marble steps, but I promise – it’s worth it! The elevator takes you to the top and from there, you can see all of Rome. You can see the roof of the Pantheon, the Coliseum and so much more. It’s a nice modern elevator with a quick ride to the top, we highly recommend this stop.

City: Pisa
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The Mura di Pisa (Pisa City Walls) are a historic and impressive set of fortifications that once protected the city. Stretching over 5 kilometers, the walls date back to the 12th century and were built to defend the city from invaders. Today, much of the walls remain intact, offering visitors the opportunity to walk along parts of them and explore their historical significance. The Mura di Pisa also provide beautiful views of the city, especially as you stroll through the green spaces that now surround the walls. Whether you’re a history enthusiast or simply looking for a scenic walk, the Mura di Pisa offer a unique perspective of the city and its past.

City: Rome
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The Museo delle Mura in Rome is dedicated to the history and preservation of the city’s ancient walls, offering a fascinating glimpse into Rome’s past. Located near Porta San Sebastiano, one of the best-preserved gates of the Aurelian Walls, the museum showcases artifacts, maps, and models that highlight the evolution of the city’s defensive structures. Visitors can explore the history of the walls from ancient times through the Middle Ages to the Renaissance, and even walk along parts of the preserved walls. With its blend of history, archaeology, and stunning views, the Museo delle Mura provides a unique perspective on Rome’s development and its lasting impact on the city’s architecture.

City: Florence
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The Museum of the Duomo is spectacular and can be included on your ticket to the Duomo. There is an open air balcony where you can see some amazing views of the dome.

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