Discover the best of Italy's northern regions, starting in the medieval city of Florence, with guided walking tours and wine tastings in Tuscany. Make your way through San Marino and the coastal cities of Riccione and Ravena before heading into Emilia-Romagna for a culinary exploration through Bologna and Parma. Take a cooking class and learn how to identify wine with a sommelier, then enjoy exploring the extravagant shores of Lake Como and the fashion-focused streets of Milan.


  • Sip Chianti wine and taste traditional food in Tuscany
  • Enjoy a culinary road trip tasting the best of Emilia-Romagna
  • Discover Florence, Bellagio, and Bologna on guided walking tours
  • Climb the hills of San Marino and stroll the beach of Riccione
  • Relax along the shores of Lake Como and tour its extravagant villas

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Florence - Explore the city Florence
Day 2 Discover Florence on a guided walking tour Florence
Day 3 Tour Chianti with olive oil, wine, and beer tastings near San Gimignano Florence
Day 4 Drive to Marradi - Visit a local farm for wine and food tastings Marradi
Day 5 Visit Brisighella and San Marino on your way to Riccione Riccione
Day 6 Explore Ravenna and Bologna Bologna
Day 7 Enjoy a culinary tour through Emila-Romagna, ending in Parma Parma
Day 8 Day trip to Piacenza - Enjoy an optional opera performance Parma
Day 9 Transfer to Lake Como - Enjoy a boat trip to Bellagio Bellagio
Day 10 Enjoy a private tour of the elegant villas on Lake Como Bellagio
Day 11 Transfer to Milan - Explore the city's culture of fashion and art Milan
Day 12 Depart Italy via Milan  

Detailed Itinerary

Day 1: Arrive in Florence - Explore the city

Florence at Night
Florence at Night

Welcome to Italy! After arriving at Florence Airport, you'll transfer to the city center and settle into your accommodation. If you have time after your arrival, enjoy the rest of your day exploring the city.

Florence is the regional capital of Tuscany and its most populous city. Long considered a cultural capital, Florence is home to many masterpieces of Renaissance art and architecture, including the iconic Duomo and the Galleria dell'Accademia, where you'll find Michelangelo's famous statue, David.

Although you'll enjoy a guided tour of Florence tomorrow, take some time to stroll by its top sites, which include the Piazza della Repubblica, one of the city's main squares since Roman times. The Piazza della Signoria, the city's political center since the Middle Ages, is where ceremonial events, rallies, and festivals are held. Here you'll find several iconic Florentine landmarks, such as the town hall at Palazzo Vecchio and the Uffizi Gallery, home to works by Michelangelo and Leonardo da Vinci. The square's centerpiece is the Neptune Fountain, a popular meeting place for locals and tourists alike. 

As you stroll along the cobbled streets, you can't miss Ponte Vecchio, a covered medieval bridge that's been a symbol of Florence's power for over seven centuries. The bridge houses buildings and shops, which have been occupied by merchants and shopkeepers since the Middle Ages. A short walk away, the Gothic Florence Cathedral and Giotto's Bell Tower rise above the surrounding city buildings.  

For dinner, find a restaurant in a lively piazza, or grab a seat at a quiet bistro along one of the many hidden side streets.

Day 2: Discover Florence on a guided walking tour

Florence's Famous Ponte Vecchio Bridge
Florence's Famous Ponte Vecchio Bridge

After breakfast, you'll meet your guide for a walking tour of the city's top sights. Even if you saw some of these monuments last night after arriving in the city, your guide will take you through their centuries-old history.

You'll start at the Piazza della Repubblica and the nearby Cathedral of Santa Maria del Fiore, the symbol of the city which is known for its terracotta dome. The picturesque cathedral is flanked by Giotto's Bell Tower and the Baptistery with impressive bronze doors. Get lost in its exterior tile, or head inside to admire its sculptures, art, and crypt.

Next, you'll enjoy a guided tour of the Galleria dell'Accademia, where you'll see Michelangelo's David. Your final stop is the San Lorenzo Church, the former parish church of the powerful Medici family which houses a library designed by Michaelangelo. You'll finish your half-day tour with an aperitif and a light lunch.

For the rest of the afternoon, you can continue your exploration of the city at your leisure. Some suggested activities include:

  • Head to Studio Artemisia, located steps away from the Ponte Vecchio for a class in ancient fresco-painting techniques.

  • Visit the Mercato Centrale, a 19th-century open-air market, to browse for a wide selection of vegetables, fruits, meats and cheeses, and a variety of street food. 

  • Take a walk through the peaceful Boboli Gardens to see the oval-shaped Isolotto, a small island surrounded by various sculptures and lots of greenery.

In the evening, stroll around the Piazza della Signoria in front of the Palazzo Vecchio. Enjoy some gelato and people-watching, followed by dinner and drinks in the hip Sant'Ambrogio neighborhood.

Day 3: Tour Chianti with olive oil, wine, and beer tastings near San Gimignano

Medieval Streets of San Gimignano
Medieval Streets of San Gimignano

In the morning, you'll meet your driver for a day exploring the region of Chianti. Located between Florence and Siena, Chianti is famous for its unparalleled beauty, peaceful countryside, and, of course, its renowned wine of the same name. Each part of the region is full of vineyards, wineries, medieval towns, and winding rural roads. 

You'll start your tour with a drive through the beautiful scenery, ending at an agriturismo (an agricultural village) to taste wine, olive oil, and beer that's produced in the area. Your guides will walk you through the process of producing the products, teaching you all about the soil, climate, and culinary culture behind these endeavors. 

Next, you'll have lunch at a winery just outside of San Gimignano, a UNESCO World Heritage Site famous for its many medieval stone towers and terraced cafes. Chianti's unique characteristics and local climate have made the area ideal for growing wine grapes. While enjoying lunch, you'll taste the local staple of Chianti wine, which is made primarily of Sangiovese grapes. Afterward, you'll have some free time to explore San Gimignano before returning to Florence.

Day 4: Drive to Marradi - Visit a local farm for wine and food tastings

Countryside of Emilia Romagno
The countryside of Emilia Romagna

Today you'll trade the bustling streets of Florence and its rolling hills for the gastronomic region of Emilia-Romagna. After breakfast, you'll collect your rental car from Florence Aiport and drive 1.5 hours to the hillside town of Marradi. This village is surrounded by trees and sits on the Lamone River, near the border of Tuscany and Emilia-Romagna. 

After settling into your accommodation at Palazzo Torriani, a boutique hotel set in an old villa, you'll enjoy a welcome drink with a traditional appetizer, plus a quick tour of the property. You'll then head out into the town for lunch at a typical restaurant. 

In the afternoon, a local guide will join you for stories of the area's history, geography, and people. You'll also enjoy a visit to the Dino Campana Museum, featuring both contemporary and non-contemporary art exhibits, as well as a beekeeper's farmhouse with wine and food tastings.

In the evening, take some time to rest in your room before dinner at the hotel.

Plan your trip to Italy
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Day 5: Visit Brisighella and San Marino on your way to Riccione

Rocca della Guaita in San Marino
Rocca della Guaita in San Marino

After a gourmet breakfast at your boutique hotel, you'll make your way to the town of Brisighella. This village is famous for its clock tower, Torre dell' Orologio, which dramatically protrudes from a rocky cliff and is part of the castle known as the Rock of Brisighella. Upon arrival, you'll meet a local guide for a food tour through Brisighella, which is known in particular for its oils, salt, and chocolate.

Afterward, you'll start your drive to the seaside city of Riccione. Along the way, you'll stop in the town of Faenza, where you'll enjoy its heritage of ceramic art with visits to the International Museum of Ceramics and workshops. You'll also visit the Republic of San Marino, a small country enclosed by Italy. In its hilly capital, enjoy climbing the stairs of Guaita Tower, one of the three hills overlooking San Marino. 

By late afternoon, you'll arrive in Riccione. After settling into your accommodation, you'll join your host for a traditional dinner of piadina (traditional Italian flatbread), fish, and local wine.

Day 6: Explore Ravenna and Bologna

Rooftops of Bologna
Rooftops of Bologna

Enjoy a leisurely morning in Riccione, with breakfast by the sea and stroll along the city's long, sandy beach. You'll then head north toward the city of Ravenna in the Emilia-Romagna region. The city was the capital of the Western Roman Empire for over 70 years during the 5th century. It's known for its colorful mosaics from both its Roman era, as well as its time under the Byzantine Empire.

You'll have some free time to stroll the city's streets and admire its Roman and Byzantine architecture. You'll find many mosaics in the Baptistery of Neon, which is next to the city's central cathedral, the Duomo and the Archiepiscopal Chapel of Sant'Andrea. You can't miss Dante's Tomb, where the poet is buried, or the Roman mosaics in the Mausoleo di Galla Placidia. For lunch, enjoy a traditional restaurant in the city center, such as Osteria Passatelli, where you can try local and regional seafood.

In the afternoon, you'll arrive in Bologna, the capital of Emilia-Romagna. After settling into your hotel, explore the city, starting with an aperitif in the city's main square, Piazza Maggiore. Here you'll find several cafes and shops under arched collonades, plus must-see sites such as Basilica di San Petronio, the 13th-century Palazzo Re Enzo, and the town hall complex, Palazzo d'Accursio.

You can't miss the Two Towers, the symbols of Bologna that offer views over the city. Other recommended sites include the Sanctuary of the Madonna di San Luca and the art galleries of Palazzo Fava.

In the evening, you can find dinner along the lively, charcuterie-lined street of Via degli Orefici.  

Day 7: Enjoy a culinary tour through Emila-Romagna, ending in Parma

Piazza del Duomo in Parma, Italy
Piazza del Duomo in Parma, Italy

Today you'll make your way to the city of Parma, passing through the picturesque Italian countryside in the heart of Emilia-Romagna. Your drive will act as a culinary road trip through one of the most gastronomically-rich regions of Italy. 

As you make your way to Parma, you'll stop at farms, bistros, and vineyards, where you'll enjoy tasting the best of the region. You'll partake in a cooking class, discovering the secrets behind some of the most traditional dishes in Italy. You'll also enjoy blind tastings of the region's famous products, such as Parmigiano Reggiano, prosciutto di parma, and balsamic vinegar, plus a wine course with a local sommelier. 

Today's food tour can be personalized, with potential stops in historic towns like Castell'Arquato and Vigoleno, where you can enjoy a meal inside the Castle of Di Vigoreno. You can also opt for lunch in a beautiful farmhouse with a private wine tasting near the town of Rivergaro.

By the late afternoon, you'll arrive in Parma, where you'll settle into your hotel before exploring the city.

Day 8: Day trip to Piacenza - Enjoy an optional opera performance

Medieval Village of Grazzano Visconti
Medieval Village of Grazzano Visconti

Today you'll explore the city of Piacenza, set on the bank of the Po River. Start in the heart of the city at its main square, Piacenza Piazza Cavalli. Here you'll find Palazzo Gotico and the Governor's Palace. Other sights include the 13th-century Piacenza Cathedral, the Romanesque architecture of the Basilica of Sant'Antonino, and the Gothic-style church, San Giovanni in Canale.

Near the main square, you'll find the street Via XX Settembre, a popular pedestrian area known for its international shopping. Enjoy some free time meandering the shops and strolling the city's side streets.

The region of Emilia and the city of Piacenza are both known for their opera performances by the likes of Giuseppe Verdi, Antonio Stradivari, Luciano Pavarotti, and Arturo Toscanini. The cities of the region have all been graced with the talents of these popular composers, singers, and violinists. After your walking tour, you'll enjoy a traditional Giuseppe Verdi lunch based on cold cuts and cheese, plus local wine.

In the afternoon, you'll return to Parma via the medieval town of Grazzano Visconti, which was built in the 10th century. In the evening, you can attend an optional opera performance of Nessun Dorma.

Day 9: Transfer to Lake Como - Enjoy a boat trip to Bellagio

Botanical Garden on the Lakeshore
Botanical Garden on Lake Como

Spend the day exploring the beautiful lakeside town of Bellagio, which sits on Lake Como in northern Italy. After breakfast in Parma, you'll drive to the city of Como, where a scenic boat trip will take you the rest of the way to Bellagio. After settling into your accommodation, your local guide will lead you on a 3-hour walking tour to discover the vantage points and sights of the beautiful town. Stroll around Punta Spartivento and gaze out at Lake Como. Walk to the village of Aureggio to see rare 19th-century Larian gondola boats in a traditional fishing harbor.

In the afternoon, you'll tour the neoclassical Villa Melzi and the surrounding botanical gardens, which are filled with rare and exotic plants, as well as a Japanese pond. The residence was built for Francesco Melzi d’Eril, vice president of the Italian Republic during Napoleon's time. Head inside his elaborate home to see works by Antonio Canova, Andrea Appiani, Giovan Battista Comolli, and Giuseppe Bossi. Then step into the adjacent Orangery to view a small museum of Napoleonic memorabilia. Spend some time here enjoying the views of Lake Como from the elegant terrace and gardens.

Day 10: Enjoy a private tour of the elegant villas on Lake Como

The City of Como
The City of Como at Sunset

After breakfast, enjoy a full day on Lake Como, Italy's third-biggest lake. The area is known for its upscale resorts, dramatic landscapes, and views of the Italian and Swiss Alps. The lake's unique location gives it consistently favorable weather conditions, with most of the cold winds blocked by the mountains to the north. 

Thanks to the mild weather, the lake has long been a popular place for the rich and famous to build extravagant summer villas and lakefront palaces. You'll spend the day exploring a few of the following villas, as well as other sights:

  • Villa Carlotta in Tremezzo, which boasts Japanese style gardens

  • Villa Melzi in Bellagio's beautiful English gardens along the lake with a wealth of historical Napoleonic relics

  • Villa D'Este, a hotel of international renown, with an elegance and charm that reminds visitors of older times 

  • Villa Balbanello in Lenno, an elegant and refined villa with a manicured garden that drapes over the rocky lakefront terrace 

  • Villa Monastero, located between the towns of Varenna and Fiumelatte, which has an eclectic style and a garden full of exotic trees, balustrades, and Venetian wells

Continue your tour in the city of Como, which lies on the southwest branch of the lake. You'll visit the Gothic 14th-century Cathedral of Como, sprawling Villa Olmo park and exhibition halls, and the Museo Didattico della Seta (Museum of Silk) with your local guide.

In the afternoon, you'll ride on the funicular railway and enjoy the views from the top of Mount Brunate. End your day with a stroll on Como's waterfront promenade before returning to Bellagio.

Day 11: Transfer to Milan - Explore the city's culture of fashion and art

Galleria Vittorio Emanuele II, Milan
Galleria Vittorio Emanuele II, Milan

Enjoy your final morning along the shore of Lake Como, then transfer to Milan. The city is known as the non-official capital of Italy, a vibrant, international metropolis brimming with business, shopping, fashion, and culture, as well as medieval art and beautiful architecture.

After settling into your accommodation, set out to explore the city. Many of Milan's old monuments and buildings were destroyed during WWII and the new construction and modern architecture give Milan a sophisticated vibe. Because of this, Milan is known as Italy's "new" city and represents modern Italy. 

Spend the afternoon exploring Milan's art and culture. Choose from the following options to make the most of your time:

  • Learn about Leonardo da Vinci's works in the Leonardo da Vinci National Museum of Science and Technology 

  • Visit the Pinacoteca di Brera fine art gallery located in the Palazzo Brera

  • Stroll around the bohemian Brera District to see art academies, galleries, and fine dining restaurants and bars
  • Go shopping for luxury brands at the Via della Spiga, Via Sant’Andrea and Via Montenapoleone shopping streets 

In the afternoon, you can visit the 16th-century Royal Palace, a sprawling neoclassical dwelling turned art museum. Although the building suffered great damage during World War II, it has been beautifully restored and is now a renowned cultural center. 

In the evening, head to the Navigli at Porta Genova, Milan's ancient network of canals and passages used for transporting goods and supplies across the city. Then find dinner in one of the restaurants in the city center.

Day 12: Depart Italy via Milan

Milan Cathedral
Milan Cathedral

Today is your last day in Italy. After breakfast, you'll transfer to the airport in Milan for your flight home, or onto your next destination.