Spend two weeks exploring northern Italy at your own speed with this self-drive itinerary that allows you to choose the stops. You'll start off in the northern lakes, with Lake Como and Lake Garda offering boat tours past villas and amusement parks alike. Then make your way into Tuscany, where you'll ride a horse-drawn wagon through the countryside and explore the medieval walled city of Siena and famous art of Florence. Finish your trip in the Italian Riviera and colorful five villages of Cinque Terre.


  • Cruise past the luxury villas of Lake Como
  • Ride a horse-drawn wagon through Tuscan hills
  • Experience history in the medieval city of Siena
  • Relax on a sunset boat tour of colorful Cinque Terre

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Milan, Transfer to Lake Como, and Como, Bellagio & Villas Boat Tour Lake Como
Day 2 Free Day in Lake Como Villages Lake Como
Day 3 Lake Como to Lake Garda, West Lake Garda & Sirmione Boat Tour Lake Garda
Day 4 Free Day on Lake Garda Lake Garda
Day 5 Lake Garda to Chianti, Chianti Wagon Ride & Picnic Chianti
Day 6 Explore Tuscany Chianti
Day 7 Chianti to San Gimignano & Monteriggioni San Gimignano
Day 8 Day Trip to Volterra San Gimignano
Day 9 San Gimignano to Siena & Explore Siena Siena
Day 10 Day Trip to Florence Siena
Day 11 Siena to Italian Riviera & Explore Genoa Italian Riviera
Day 12 Free Day on the Italian Riviera Italian Riviera
Day 13 Sunset Boat Trip & Cinque Terre Villages Italian Riviera
Day 14 Italian Riviera to Milan & Depart  

Detailed Itinerary

Day 1: Arrive in Milan, Transfer to Lake Como, and Como, Bellagio & Villas Boat Tour

Enjoy views of Lake Como
Welcome to Italy! Start your trip with a scenic drive from Milan Malpensa Airport to Lake Como, which takes between 45 minutes and 1.5 hours, depending on your location and traffic.

Once you arrive, set out on a guided tour starting at Piazza Cavour, in Como’s historical center, before taking a semi-private cruise around the lake. You'll see why Lake Como has been attracting nobility since Roman times when Julius Caesar founded Novum Comum (Como city). Your guide will lead you through tales of fortresses and castles, furious naval battles, and crowned monarchs who built villas with large Baroque or Romantic gardens. Take in the views of these villas, such as Villa Olmo, Villa D’Este, Villa Versace, Villa del Balbianello, and Villa Carlotta, as well as the towns of Cernobbio and Tremezzo.

Then, board your vessel for a look into the lake's secret corners. No trip here is complete without some time on the water. Enjoy breathtaking views over the lake as well as its architectural wonders and villas, before you disembark in famous Bellagio, the area's most-visited town.

In Bellagio, you'll learn from your guide about key sights like Punta Spartiviento, the Romanesque Basilica of San Giacomo, and Via Roma. The town has been drawing visitors since the Renaissance when it was a center of industries—particularly silk—thanks to its ideal location. Stop at a hidden 18th-century cellar for local charcuterie tasting, then take a stroll through the boutiques to see how it still excels in silk products today.

Get lost in the colorful streets of the old town and enjoy the views over the lake. Then pay a visit to the gardens of Villa Melzi, where you'll be greeted by Moorish architecture, water lilies, and even more lake views before your tour ends.

Day 2: Free Day in Lake Como Villages

Springtime in Bellagio,
Springtime in Bellagio
Enjoy your breakfast and head out for a full day on Lake Como, Italy's third-biggest lake. The area is known for its upscale resorts, villas owned by celebrities, dramatic landscapes, and views of the Alps. In Como town center, you'll find the Gothic 14th-century Cathedral of Como and the 12th-century Basilica di San Fedele. Overlooking the lake are Piazza Cavour square and the sprawling Villa Olmo park. 

Explore other villages to the north by ferry or car. The resort town of Bellagio is north of Como and sits on a promontory that juts into the lake. Lake Como splits three ways at this spot, offering spectacular scenic views. Varenna is another picturesque village to the east of Bellagio. A short ferry ride brings you to the town's promenade along Lake Como, and the chance to visit Villa Monastero and the botanical gardens. If you have the time, consider visiting Lecco and Menaggio.

Day 3: Lake Como to Lake Garda, West Lake Garda & Sirmione Boat Tour

Castle in Sirmione
Castle in Sirmione
Enjoy a scenic drive from Lake Como to Lake Garda, which takes about 2.5 hours. Northern Italy is full of fascinating cities, beautiful towns, charming villages, and stunning landscapes, making it an ideal region for a road trip. Along the way, consider stopping at some of the area’s famed cities, such as Milan and Bergamo. You can also visit some of the quieter villages or explore castles, churches, and museums. 

Once you reach Lake Garda, immerse yourself in the local history and nature with a relaxing private boat cruise. As you glide through the calm waters surrounded by beautiful scenery, you’ll view Salò, Garda Island, and Gardone, plus enjoy swimming from the boat.

Departing from the Sirmione Peninsula, you’ll head toward the impressive outcrop of Rocca di Manerba and pass the island of San Biagio. Next, cruise near the enchanting Isola del Garda, the private residence of the counts of Borghese-Cavazza. Lastly, make your way to the magnificent Costa Romantica, which boasts spectacular villas overlooking the lake and surrounded by lush vegetation.
The Costa Romantica is the lakeshore between Toscolano Maderno and the Gulf of Salò. This area still bears traces of the Republic of Salò, declared during the Fascist period, and the architecture is a perfect reflection of its style, with the occasional Liberty touch to enhance its vintage charm. After the tour, you will return to Sirmione and pass under the two bridges of the Scaligero Castle.

Day 4: Free Day on Lake Garda

Sunset over Lake Garda
Spend a day exploring Lake Garda on your own schedule. Garda is known as the most family-friendly Italian lake, with plenty of activities both in nature and at the many water and theme parks. Hike easy, fun paths, visit different villages, or learn about science and local crafts in the museums. Theme parks like Gardaland and outdoor activities such as the Monte Baldo cable car await.

Day 5: Lake Garda to Chianti, Chianti Wagon Ride & Picnic

Enjoy a Wagon Ride with the Horses
Enjoy a wagon ride with the horses
Enjoy a scenic drive from Lake Garda to Chianti, which takes about four hours. Driving from Lake Garda through Tuscany is the perfect way to explore the area since it is less accessible by public transport. You’ll find Chianti slightly south of Florence, most famous for the red wine (Chianti Classico) produced in the region. The area is home to many small towns and villages, including Castellina, Radda, Gaiole, and Greve. 

Along the way, you’ll pass several fascinating cities worth a stop. Enjoy Verona for its romantic setting in Romeo and Juliet, Mantua for its Renaissance history, and Modena and Bologna for their gastronomy, including the famed balsamic vinegar. You can also explore some of the area’s hilltop towns and vineyards.
Once you reach Chianti, explore the Tuscan scenery at a peaceful, relaxed pace as your private guide leads you through the picturesque and aromatic Chianti region on a wagon. You’ll end your tour with a fresh picnic lunch and panoramic views, enjoying a truly unique way to experience Tuscany.

You’ll meet your driver and guide and board your wagon. As you make your way through the Chianti countryside, enjoy breathing in the clean, fresh, and aromatic air in an open-air wagon. Two powerful horses lead you, crossing panoramic routes and historic castles. Your guide will entertain you with stories, interesting facts, and local myths.

Take a break at a shaded spot amongst Tuscany’s vineyards, enjoy a fresh picnic lunch of local products, and take in the panoramic views of this iconic landscape before heading back through more scenic Tuscan countryside.
Plan your trip to Italy
Chat with a local specialist who can help organize your trip.

Day 6: Explore Tuscany

Montepulciano and Views of the Valley
Montepulciano and views of the valley
Tuscany is vastly known for its vineyards, but it has so much more to offer. If you are not fond of wine-tasting and winery visits (or just not of age), you will still be amazed by the castles, small towns, and villages as you drive through magnificent nature and countryside. The landscape is famous as a setting for many iconic films including Under the Tuscan Sun. Today you'll feel like a local as you explore this region and the places of most interest to you.  

Visit family-friendly spots in the Chianti Valley like Val D’Elsa around San Gimignano, and Val D’Orcia around Pienza and Montepulciano. Throughout the incredibly scenic drive, you’ll be surrounded by olive groves and vineyards that make up the typical hilly landscape. The route is a combination of main roads and winding hilltop lanes as you make your way through the Tuscan countryside, and can take between a half and a full day to complete depending on how many stops you make.

Day 7: Chianti to San Gimignano & Monteriggioni

Old Town Monteriggioni in Tuscany

Enjoy a scenic drive from Chianti to San Gimignano, which takes about one hour. Along the way, enjoy your time exploring the beautiful landscape, hilltop towns, charming villages, and, of course, the vineyards. Stop to visit some of the region’s acclaimed castles and museums.

San Gimignano is famous for its tall, medieval towers. A UNESCO World Heritage Site since 1990, the charming hilltop town once housed 72 tower-houses, built as symbols of wealth and power of aristocratic families during the 13th and 14th centuries.

Be sure to make a stop to visit the impressive medieval fortress of Monteriggioni. The intact castle walls surround this town perched on a hillside and are a sight to behold. Take in the views, have a coffee, and enjoy wandering around the porticos and piazzas in the charming historic center.

Day 8: Day Trip to Volterra

Beautiful Tuscan Villages at Sunset
Beautiful Tuscan villages at sunset
Explore the Tuscan countryside by venturing into the town of Volterra on a self-drive day trip. Drive through scenic countryside and reach the hilltop town with magical views. This walled town has deep roots in Etruscan history, and to this day visitors can still see parts of its protective walls and ancient gates to enter the town. Start off in the center square and in Palazzo dei Priori, whose bell tower offers impressive views. Apart from its historic importance, Volterra is also known for its alabaster production.

Day 9: San Gimignano to Siena & Explore Siena

Torre del Magnia in Piazza Campo
Torre del Magnia in Piazza Campo
Enjoy a scenic drive from San Gimignano to Siena, which takes about one hour. After leaving San Gimignano, head northwest toward Colle di Val d’Elsa, with interesting stops along the way like the region’s famed medieval villages, churches, and museums.
Siena, located southeast of San Gimignano, is known as Italy’s "open-air museum," rich in medieval monuments, museums, palaces, and churches. As cars aren’t allowed in the historic city center, you’ll need to park in an adjacent lot and walk up to the town. Siena is set on a steep hill, so be prepared to walk a lot as you visit spots like the Natural History Museum.

Day 10: Day Trip to Florence

Dome of Basilica di Santa Maria del Fiore
Dome of Basilica di Santa Maria del Fiore

Pop over to neighboring Florence for the day. You’ll find some of the world’s most recognizable art and architecture here, from Michelangelo’s "David" and Botticelli’s "Birth of Venus" to the 1,000-year-old Ponte Vecchio medieval bridge. If you're looking for something more hands-on, visit the Leonardo da Vinci Museum, which is as interactive as the man himself would want, or consider the celestial spheres at the Museo Galileo, where you can peer through ancient telescopes.

The charms of Florence aren’t just found in its museums. Check out the many parks and gardens, including the Iris Garden that holds 250 endangered species, rambling markets, and celebrate the city’s status as the capital of gelato with as many scoops as you can handle.

Day 11: Siena to Italian Riviera & Explore Genoa

Royal Palace Museum
Royal Palace Museum
Enjoy a scenic drive from Siena to the Italian Riviera, which takes about three hours. Traveling between Tuscany and the Italian Riviera by car is an excellent option if you want more flexibility and freedom to enjoy the natural landscapes and scenery. In particular, you’ll pass near the Mediterranean coast and through the hilly region of Liguria, both offering many options for interesting stopping points.
The city of Genoa is full of beautiful historic palaces and monuments from the 12th century onward. With a full day to explore at your own pace, you have an array of stunning buildings, interesting museums, and iconic streets to wander. There are two sides of this city, both worth seeing: the historic center and the waterfront harbor and port. 

Via Garibaldi is the most famous street in Genoa, with many extravagant and luxurious Renaissance palaces open to the public. You can purchase a ticket to enter all the Rolli Palaces, which together make up the Strada Nuova Museums. Each one is unique and spectacular and together, they are a UNESCO World Heritage SiteDown by the port, you can spend time at the Maritime museum before heading into the historic city center.

Day 12: Free Day on the Italian Riviera

Colorful Summer Villas in Portofino
Colorful summer villas in Portofino
Explore the Italian Riviera from Sestri Levante to the Portofino National Park, Genoa, and the pristine beaches of the West Riviera. Walk the fishing villages of Santa Margherita Ligure, Rapallo, and Camogli, and taste local treats, such as homemade pesto Genovese, focaccia di Recco or stuffed Pansotti pasta.
Enjoy a walk from Santa Margherita Ligure to Portofino, another nearby picturesque and compact coastal village, with colorfully painted houses tumbling down to a historic fishing port. For adventurers, there are hiking trails suitable for different abilities in Portofino and around the San Fruttuoso Abbey. If relaxation is on your mind, then discover the sandy beaches that stretch along this side of the Mediterranean Sea.

Day 13: Sunset Boat Trip & Cinque Terre Villages

Narrow Alley in Corniglia
Narrow alley in Corniglia
Spend a full day exploring the towns of Cinque Terre, a section of the Italian coast famous for its medieval villages, stunning cliffs, and beautiful hiking trails. Cinque Terre is a rugged strip of the Liguria coastline made up of five old fishing villages—Monterosso al Mare, Vernazza, Corniglia, Manarola, and Riomaggiore. The coast, villages, and surrounding hillsides are all part of the Cinque Terre National Park and are a UNESCO World Heritage Site. The region is renowned for its beautiful natural surroundings and its abundance of Mediterranean plants, covering the scrubby hillsides that tumble down to the turquoise water.
Today you'll be discovering the historic villages and breathtaking beauty of the region. The well-preserved towns prohibit vehicles so as not to destroy the traditional charm, and they are small enough to walk around without a guide. In this way, you'll avoid large groups and can find your own favorite places and make the most out of your day. Hiking is also a possibility as there are many routes through the national park with spectacular views.
In the evening, experience the beauty of Cinque Terre with a boat tour at sunset, when the landscape glows and romantic light washes over the charming villages. This activity is truly one of the most scenic tours you can experience when visiting the area.
You’ll depart from the pier in Monterosso and admire the five famous coastal villages from the sea. As you glide through the water and catch glimpses of colorful harbors, enjoy a traditional Italian aperitif with local products. Sip prosecco and listen to music as the sky starts to shift colors. In the warmer summertime months, you can stop to swim in the crystal-clear waters of the National Marine Park.
Take a short break in picturesque Vernazza to taste typical Ligurian specialties in the town’s central piazza, then set sail toward the sunset. Enjoy nature’s performance in a romantic and peaceful setting and with the best views of the sea.

Day 14: Italian Riviera to Milan & Depart

Plaza in Milan
Enjoy a scenic drive from the Italian Riviera to Milan Malpensa Airport (MXP), which takes about 2.5 hours through the hilly Liguria region, before you head home or onto your next adventure.


Map of Family Road Trip: Northern Lakes, Tuscany & Italian Riviera - 14 Days
Map of Family Road Trip: Northern Lakes, Tuscany & Italian Riviera - 14 Days