Expert Recommendations for Amazing Itineraries

Dar Poeta in Rome’s Trastevere neighborhood is a cozy pizzeria with rustic charm and delicious pizza. The inviting atmosphere sets the stage for a memorable dining experience, while the pizzas, whether classic Margherita or creative specialties, are always fresh and bursting with flavor. With friendly service and reasonable prices, Dar Poeta is a favorite spot among locals and tourists alike for authentic Roman pizza.

De’Ricci Cantina in Montepulciano offers a unique wine tasting experience set within ancient Tuscan caves. Located in the heart of the historic town, these atmospheric caverns provide the perfect backdrop for sampling a curated selection of local wines. As you descend into the cool depths, you’re transported back in time, surrounded by centuries-old stone walls that echo with the stories of generations past. The knowledgeable staff guide you through the tasting, sharing insights into the region’s winemaking traditions and the characteristics of each vintage. With its historic charm and dedication to showcasing the best of Tuscan viticulture, De’Ricci Cantina’s old Tuscan caves offer a truly memorable wine-tasting journey.

Don Nino’s is a chain Italy — you’ll see them in Rome, Florence and other big cities and for a good reason, as they make delicious cannoli for you while you wait. Cannoli should not be filled ahead of time as it makes the shell soggy. Don Nino’s makes your cannoli while you wait and is the perfect place for a sweet treat while touring Florence.

Obviously one of the main tourist sites in Florence, this imposing group of buildings deserve a whole day, if you have it. Do check the tourist information offices found on both sides of the Piazza to make sure the Basilica is open (they don’t allow tourists on Sundays) and if you plan to climb Bruneschelli’s dome or the campanile, you’ll need a timed ticket. The ceiling of the Baptistery is under construction in 2023/2024 but it’s still worth it to see the building and the amazing gold doors. Keep your eye open for scammers and pickpockets in this piazza but don’t miss it.

The first stone of the city’s cathedral was laid in 1099 and the construction continued until 1184. The church is a beautiful example of Romanesque architecture and a UNESCO World Heritage site. We enjoyed touring the inside of the church and it’s magnificent bell tower, known as the Ghirlandina. The carvings on the outside of the church are intricate and unique, well worth the visit alone.

Siena’s Duomo is a stunning mix of black-and-white marble that stands out in the heart of the city. Inside, its striped columns and intricate mosaic floors make it one of Italy’s most beautiful churches. The Piccolomini Library, with its colorful frescoes, is a hidden gem worth exploring. For an incredible view over Siena, climb up to the panoramic terrace. Whether you love history, art, or just a great view, this cathedral is a must-see.

This great enoteca is at the top of the hill and has a huge variety of wines to try. You can select the amount of your pour as well. Since it’s at the top of the hill, it’s a quick walk to the Comune building, the Piazza Grande and the Cattedrale.

This wine tasting room is in the basement of the Wine Museum in the castle in Barolo. There is an enomatic machine which dispenses tastings of over 30 wines, all from the region. The staff is kind and helpful in explaining about the wines, the region and the production of the regional king, the nebbiolo grape. This organization also has shops in Barbaresco, Grizano Cavour,

The Ferrari Museum was a fun stop when we visited Modena. It’s easy to walk to from the train station and we enjoyed touring the slick, modern museum and seeing all the famous cars. We had a quick bite to eat in their lobby cafe which we enjoyed! It’s a fun stop in Modena and if you feel like spending a few euro, you can even sit in one of the new Ferraris for a photo.

If you leave the city out of the Porta Berarda, walking down the Via Guiseppe Maffei, you’ll come to a beautiful church and park, just outside the city gates.
This park is a quiet place to sit for a minute and enjoy the lovely views.
We saw children playing and people with dogs walking which made it feel just like home!

There is a legend that if you can roll a coin down the Porcellino’s tongue, you’ll have good luck. You can tell it is a well known story as the bronze statue’s nose is shiny from people rubbing it for luck! The statue is at the end of one of the big famous leather markets in town, so make sure to take time to peruse the stalls for a new wallet, purse or belt. In the evening, when the stalls are closed, there is space for musicians to setup and serende the evening crowd.

This tiny gelato shop is my exception to the rule. I normally say not to stop at the places right in the tourist areas, but this gelato is so delicious it makes sense to grab a double on a cone and find a spot in the piazza to enjoy it and people watch.

This small ristorante in the Monti neighborhood of Rome has the most delicious Cacio e Pepe pasta. Their cute tables outside are perfect for a nice dinner! I enjoyed having a solo dinner there while waiting for the rest of my group to arrive and the folks at the restaurant were attentive and kind. Just ate my dinner while reading my book and watching the world go by.

This amazing restaurant is an Instagram phenomenon. Set in a cave, every table has the view of a lifetime. The menu is extravagant and expensive but worth every penny. The food is delicious, the service is impeccable and it will definitely be a memorable evening. Reservations are hard to get so plan accordingly but if you have a special occasion while in Italy and are putting Puglia on your itinerary, this restaurant will be perfect for your celebration!

Yes, there is a picture of Guy Fieri on the wall. But it makes sense because the pizza is delicious. 10/10 — definitely recommend and can’t wait to go back. It’s right by the Piazza di Santo Spirito so don’t miss that when you are there. They offer lots of different toppings and the vibe is very friendly and warm!

This hotel is the perfect place to spend your first or last night in Italy if you are using FCO airport in Rome. You can literally walk to the hotel from the airport, the rooms are safe and clean, and they have the best breakfast buffet I’ve ever seen. After a good night sleep, you can wake up refreshed and head to the train station at the airport. There is a connection to Roma Termini where you can get to almost anywhere in the country quickly. There is a direct train from FCO to Santa Maria Novella in Florence (it does stop in Termini but you don’t change trains) and in 2 hours, you’ll be at the Duomo!

Hotel & Ristorante Pupetto, located in Positano on the Amalfi Coast, is a charming and picturesque spot offering stunning views of the Mediterranean. The hotel provides a cozy and relaxing atmosphere, with rooms that feature traditional Mediterranean decor and breathtaking views of the sea and surrounding cliffs. The restaurant, renowned for its delicious seafood and classic Italian dishes, offers an ideal setting for a meal by the water. Guests can enjoy fresh local ingredients, including the catch of the day, while taking in the panoramic vistas.

This is our “Home away from Home” on the Amalfi Coast of Bella Italia. We have stayed there 20 Times over the last 26 years and 14 members of our family and many friends have joined us there.

This small and beautiful hotel is truly family run and has been since 1968 when the Cinque family converted it from a 17th century palazzo.

We have always been treated as part of the family and consider ourselves that way. The included colazione is delicious and several years ago the family opened a chic high end Ristorante, “Don Giovanni” on their picturesque terrace overlook the sea. The hotel is quite popular and there are just 16 rooms, most with sea view terraces, so reservations during peak season must be made very well in advance.

Hotel Plaza e de Russie is a luxurious seaside hotel known for its elegance and impeccable service (it’s a Relais & Chateaux property). Located along the stunning promenade, it offers beautiful views of the Mediterranean and easy access to the beach. The hotel is home to the Michelin-starred restaurant L’Assaggio, where guests can indulge in gourmet dishes crafted from fresh, local ingredients, providing an unforgettable dining experience.

Located in Trastevere, this boutique hotel has spacious rooms and gorgeous courtyard. Breakfast is delicious and they even serve a happy hour for guests! They also have family friendly rooms where your kids can have their own beds. The location is really perfect if you want to stay in Trastevere. If you are travelling with kids, they have some great options for suits with a master bedroom and a second spot with bunk beds for the kids.