12-Day Rome, Florence & Milan Itinerary: City Highlights & Tuscan Countryside

The legendary founders Romulus and Remus established Rome as a city in 753 BC. The city developed into the central point of the Roman Republic followed by the Roman Empire before it established itself as the religious hub of Christianity. The present-day capital of Italy exists in the current era but its historical past continues to dominate the city more than any other place. The city has received its first 2,500 years of historical influence from emperors, popes, artists and common Roman citizens.

Ancient ruins, art-filled churches and the treasures of the Vatican all compete for your attention. At first, Rome feels large and overwhelming, but the more you walk, the more it reveals its village-like side.

This is Rome: beautifully chaotic, full of contradictions and endlessly alive.

This morning, discover Rome from a fresh perspective as you explore by e‑bike. The city's famous monuments have a short driving distance to several peaceful streets which contain multiple secret areas that tourists typically miss. Your guide will lead you through these serene neighborhoods which lead to Rome's most recognizable landmarks: the Colosseum (outside), Trevi Fountain, Spanish Steps, Pantheon (outside) and Piazza Navona.

The tour also takes you into Trastevere and the Jewish Ghetto, two lively neighborhoods rich in history and local character, often described as the true heart of the city. Riding an electric bike keeps the pace relaxed while allowing you to cover more ground than on foot.

Please note that the route covers around 14 km (9 miles) and is considered leisure level, becoming intermediate when using a child seat or child extension. During official or public events in central Rome, the itinerary may be adapted and some locations replaced. Infants and children up to 22 kg (48 lbs) can join in a child seat, while those over 22 kg (48 lbs) and under 140 cm (4 ft 7 in) use a child extension.

*Inclusions: 4-hour private experience with an English-speaking guide, Pick-up from a designated meeting point, Electric bike and helmet*

A private food tour through Trastevere and Campo de’ Fiori allows you to experience Rome's authentic tastes while avoiding the typical tourist areas. The atmospheric neighborhoods of your exploration will lead you to experience local specialties which present the city's traditional food heritage through its street food and traditional dishes.

Along the way, your guide will share insights into Italian gastronomy, ingredients and cooking techniques, as well as the stories behind the dishes you taste. Between tastings, there’s plenty of time to enjoy the history, architecture and everyday life that make these quarters such beloved parts of the Eternal City.

The walk is at a relaxed pace but takes in some uneven surfaces, so comfortable shoes are recommended for this delicious exploration of Rome’s food culture.

*Inclusions: 2.5-hour private guided experience with a licensed guide, Pick-up from a designated meeting point, Tastings of local delicacies*

Today you head south for a full day discovering Naples and Pompeii, two of Italy’s most fascinating destinations. Set off from Rome in the comfort of a private vehicle for the three-hour drive to Naples, where you’ll meet your local guide.

Visitors to Naples should visit Piazza del Plebiscito, the Royal Palace, Teatro San Carlo and Galleria Umberto I which represent the city's historic landmarks. The city of Naples presents a unique blend of historical landmarks which coexist with the active daily activities of its residents.

The archaeological site of Pompeii stands as one of the world's most significant historical sites which we will visit next. Your directions will lead you through the historic streets of ancient times while you enter both residential areas, commercial spaces and community facilities which Vesuvius eruption protected from destruction. The discovery allows us to observe how people lived their daily lives in a Roman city which exists in a state of permanent preservation. The evening brings a chance to relax during your return journey to Rome while you understand the historical and cultural significance of southern Italy.

*Inclusions: 11-hour private experience with a licensed guide, Hotel pick-up and drop-off (vehicle), Entrance tickets to the archaeological site of Pompeii*

The city of Florence developed its economic and cultural status through the Medici family who controlled the area during the 15th and 16th centuries. The city developed humanist and Renaissance principles because people rediscovered classical Greek and Roman knowledge.

The historic city walls contain an exceptional collection of artistic works. The world's most valuable artistic treasures amount to more than one-third of its total collection which includes Michelangelo's David and Caravaggio's Medusa and Botticelli's Birth of Venus. The architectural design of Florence displays Renaissance principles which include harmony  and beauty through its symmetrical domes, its graceful courtyards, arcades and fountains that fill the historic center.

A short walk takes you past museums and churches that include the world’s largest collection of Renaissance art, including the Uffizi Gallery, Galleria dell’Accademia and Il Duomo di Firenze. This is Florence! The symbol of the Renaissance and an open-air museum in its own right.

A private walking tour should start your introduction to Florence by showing you its essential landmarks and its traditional squares today. Meet your expert guide in your hotel lobby and continue through the streets of the historic center.

Admire the Cathedral of Santa Maria del Fiore, or Duomo, crowned by Brunelleschi’s remarkable dome, the largest brick dome ever built. Pause by the Baptistery of St. John, dedicated to the city’s patron saint and enjoy its famous bronze doors. Learn the story behind Giotto’s Bell Tower, a masterpiece that still defines the skyline.

Cross the Ponte Vecchio, the medieval bridge lined with jewelry workshops and feel the energy of Piazza della Repubblica, a lively square with deep roots in Florence’s past. Continue to Piazza della Signoria, an open-air gallery of statues that tell the story of the city’s political and artistic life.

Finish at the Basilica of Santa Croce, final resting place of Michelangelo, Galileo and other Italian greats. On your way back think of how much this city has affected Western art, science and culture.

*Inclusions: 3-hour private guided experience with a state-licensed guide, Hotel pick-up within city limits (on foot)*

The private tour of today explores two Tuscan attractions which are Pisa and Lucca while showing their individual historical characteristics. Your driver will meet you at your hotel lobby before you begin your journey to Pisa which used to be a maritime republic of Italy and now hosts the famous Scuola Normale Superiore.

The Piazza del Duomo in Pisa contains the Campo dei Miracoli which is an extraordinary place. The UNESCO World Heritage Site unites the famous Leaning Tower with the Cathedral and the Baptistery and the Monumental Cemetery to form a unique collection of medieval buildings. The Lungarno offers a walking experience where visitors can see historic buildings including palaces, towers and churches which face the Arno River. The former political hub of the city Piazza dei Cavalieri welcomes visitors to see Vasari’s Palazzo della Carovana and the historic Palazzo dell’Orologio.

Continue to Lucca, often called the “city with a hundred churches” thanks to its many religious buildings. Walk along the impressive 14th-century walls, now a tree-lined promenade with wonderful views and explore Piazza dell’Anfiteatro, a lively square having the shape of the ancient Roman amphitheater. Visit some of Lucca’s churches and basilicas and see the Torre delle Ore, a medieval clock tower that still keeps time, before returning to Florence.

*Inclusions: 8-hour private experience with a licensed guide, Hotel pick-up and drop-off (vehicle)*

Set out on a full-day small-group “Grand Tour” of Tuscany, taking in classic hill towns, rolling vineyards and some of the region’s most famous landmarks. The tour starts in Siena where visitors can follow a guided route to discover the medieval charm of Piazza del Campo and learn about the Palio horse race and the historical customs of the Contrade districts. Narrow streets, stone palaces and hidden courtyards bring the city’s layered history to life.

The town of San Gimignano awaits visitors who want to see its historic medieval towers and experience the breathtaking views from its elevated position. The town offers visitors to walk through its streets while they can taste traditional food and experience the eternal charm of the place.

 From there, head into the Chianti countryside to a boutique winery, where you’ll tour the cellars, learn about winemaking and sit down to a traditional Tuscan lunch paired with selected wines. On the way back, stop in Impruneta, known for its ancient terracotta craftsmanship, before continuing to Pisa.

The drive toward Florence offers you to see vineyards and olive groves and hill towns which create a memorable goodbye to the Tuscan landscape.

*Inclusions: 12-hour small group experience (max 8 pax) with a professional English-speaking guide, Pick-up from a designated meeting point, Lunch in a Chianti boutique winery, Wine tasting*

**Exclusions: Pisa Leaning Tower tickets**

Welcome to Milan which serves as the active capital of Lombardy and stands as Italy's second-largest urban center. The city of Milan served as the capital of the Western Roman Empire before it became the Duchy of Milan and later the Kingdom of Lombardy–Venetia thus establishing its position as a vital European historical center. The metropolitan area of the city now spans across its original boundaries to become one of Europe's biggest and most powerful urban areas within the European Union.

Milan is recognized as a global hub for fashion, design, finance, media and arts. International events such as Milan Fashion Week and the Salone del Mobile furniture fair draw visitors and professionals from all over the world. The city is also home to major cultural institutions, academies and universities, as well as museums and galleries that house important works, including masterpieces by Leonardo da Vinci.

Beyond its modern skyline and designer boutiques, Milan offers historic neighborhoods, grand churches and elegant piazzas, inviting you to explore both its modern energy and its rich past.

Today you escape the city and spend a day by Lake Garda, Italy’s largest lake, which touches the regions of Lombardy, Veneto and Trentino. Meet your private driver in your hotel lobby and set off toward one of northern Italy’s most scenic areas.

Your first destination should be Sirmione which is a beautiful peninsula that extends into the lake. The town features its enchanting pathways which lead visitors to Scaliger Castle which stands as a perfectly conserved fortress that dominates the surrounding water. Visit the Grottoes of Catullus which represent the remaining structure of a luxurious Roman estate while experiencing the dual appeal of Sirmione through its archaeological sites and its natural hot springs. A private boat tour during your visit will provide you with panoramic views of Lake Garda while you take in its beautiful waters and surrounding mountainous landscape.

The town of Desenzano leads to a lakeside community which provides a warm welcome to visitors who want to experience its ancient heritage. Visit Piazza Malvezzi and the historic harbor of Porto Vecchio before exploring the artistic and archaeological history of the town which dates to Roman civilization. The hilltop location of Desenzano Castle provides visitors with a spectacular view which ranks as one of the lake's most stunning vistas.

This day offers a well-balanced mix of history, lakeside atmosphere and scenery, giving you a true feel for the charm of Lake Garda.

*Inclusions: 10-hour private experience with a licensed guide, Hotel pick-up and drop-off (vehicle)*

Discover Milan’s historic center with your private guide, combining grand monuments with insights into the city’s role as a modern cultural capital. Meet the guide at a designated point and set off on foot through the streets of this stylish metropolis.

Your visit begins at the Duomo, Milan’s extraordinary cathedral and a masterpiece of Gothic architecture that took more than five centuries to complete. Admire its elaborate façade, spires and statues as your guide explains its construction and symbolism.

The Sforza Castle serves as our next destination because it started as a defensive stronghold which evolved into an elegant Renaissance palace. The text provides information about its historical significance in Milan and its current status as a cultural institution. The Galleria Vittorio Emanuele II presents itself as an elegant 19th-century arcade which features glass roofing, iron structures and high-end shops that display Milan's status as a fashion and design center.

As you move through the historic core, your guide will put together the stories of artists, rulers and innovators who helped shape Milan into one of the world’s leading creative and economic hubs.

*Inclusions: 3-hour private guided tour with a licensed guide, Pick-up from a designated meeting point*

Today your Italian journey comes to an end, but the cities you’ve explored, the flavors you’ve tasted and the people you’ve met will stay with you. Your Italian journey has taken you through Rome's historic roads and Florence's Renaissance masterpieces and Milan's contemporary style and the natural beauty of Tuscany and Lake Garda.

Your mind will start to picture your future vacation when you browse through photos, examine your travel souvenirs and recall your most cherished travel experiences. Once you arrive at the airport, check in for your international flight and prepare to head home.

Although this trip is ending, the idea of planning your next Tailored by Locals adventure will be ready to come back to life whenever you are.