Highlights
- Take a day trip to Switzerland and ride the iconic Bernina Express train
- Admire extravagant villas while on a private Lake Como boat tour
- Spending a day tasting sparkling wines in the Prosecco Valley
- Glide along the canals of Venice in a private gondola
- Day trip out to the islands of Murano and Burano in the Venetian lagoon
Brief Itinerary
| Day | Highlights | Overnight |
|---|---|---|
| Day 1 | Arrive in Milan, Explore the City | Milan |
| Day 2 | Self-Guided Day in Milan | Milan |
| Day 3 | Full-Day Bernina Express & St. Moritz Tour | Milan |
| Day 4 | Collect a Rental Car, Drive to Lake Como | Lake Como |
| Day 5 | Private Lake Como Boat Tour, Explore Bellagio | Lake Como |
| Day 6 | Free Day on Lake Como | Lake Como |
| Day 7 | Drive to Lake Garda, Free Afternoon to Explore | Lake Garda |
| Day 8 | Day Trip Around Lake Garda | Lake Garda |
| Day 9 | Self-Drive Prosecco Wine Tour | Lake Garda |
| Day 10 | Drive to Venice, Private Gondola Ride | Venice |
| Day 11 | Guided Murano & Burano Excursion | Venice |
| Day 12 | Depart Venice |
Detailed Itinerary
Day 1: Arrive in Milan, Explore the City
Say ciao to Italy! You've landed in Milan, Italy's capital of fashion, design, and finance. On arrival at the airport, a private driver will meet you for the transfer to your accommodation in the city. Drop your bags at the hotel so you can go explore. The rest of the day is yours to tick off Milan's highlights. Start at the iconic Duomo di Milano, where you can admire the Gothic architecture and take in panoramic city views from its rooftop terraces. Then, just steps away, visit the Galleria Vittorio Emanuele II, an elegant 19th-century shopping arcade and a symbol of Milanese style.
Continue to the famous Teatro alla Scala, one of the world’s most prestigious opera houses. Then head to Sforza Castle to stroll through its beautiful courtyards and visit the museums inside, which house works by Michelangelo and da Vinci. Finish the day with an evening aperitivo tour in trendy Navigli. As the sun begins to set, the locals step out for a predinner ritual of classic cocktails and delicious bites.
Day 2: Self-Guided Day in Milan
Today is yours to experience Milan like a local. After ticking off the major sights yesterday, today you can go deeper and discover some lesser-known attractions and explore more of Milan's art and culture. Start the day shopping in the fashion district, where you'll find beautiful things on the Via della Spiga, Via Sant'Andrea, and Via Montenapoleone shopping streets. Then, learn about Leonardo da Vinci's works and scientific and technological advancements in the Leonardo da Vinci National Museum of Science and Technology.
Stop for lunch, or keep up the pace with an on-the-go snack of arancini (deep-fried risotto balls). In the afternoon, visit the 16th-century Royal Palace, a sprawling neoclassical palace turned art museum. It's a beautiful place that combines history and art. Finally, stroll the cobbled streets of the bohemian Brera district. Here, you'll find art academies, galleries, restaurants, and bars. For dinner, find a nice osteria or trattoria to try Milanese specialties, such as rich risottos and osso buco.
Day 3: Full-Day Bernina Express & St. Moritz Tour
Today, you'll ride one of the most spectacular railways in the world, so pack your passport and board a 2.5-coach to neighboring Switzerland. Your day trip takes you on a memorable journey through the Swiss Alps aboard the Bernina Express. The adventure starts in Tirano and climbs over the breathtaking Brusio Arches before cutting through the 2,253-foot-high (687 m) Bernina Pass, offering stunning views of plunging gorges, glaciers, and snowcapped peaks. The 2.5-hour ride is any keen photographer’s dream, with every turn revealing alpine forests, crystal-clear lakes, and more.
Finally, the train will pull into St. Moritz, a luxury mountain town. Here you'll step into a glamorous hilltop world set against a backdrop of striking natural beauty. Take time to explore the local cafés, chocolate houses, and luxe boutiques frequented by VIPs and movie stars. As the day draws to a close, you'll board a comfortable, air-conditioned bus for the scenic three-hour drive back to Milan.
Day 4: Collect a Rental Car, Drive to Lake Como
After breakfast, collect a rental car and set off north for magnificent Lake Como, Italy's third-biggest lake. This charming Italian region is home to upscale resorts, quaint lakeside villages, and dramatic landscapes. Located just an hour north of Milan, Lake Como has long been a retreat for aristocrats and celebrities who chase the allure of this sophisticated and romantic lake destination. It's not hard to see why—the lake sits at the foothills of the Alps, with deep blue waters framed by lush green hills and colorful Italian villas and villages.
On the way here you could stop at the Alfa Romeo Museum and the famous Spina Verde Regional Park. If you're heading toward Bellagio or Varenna, pass by Monza and the world-famous Autodromo Nazionale Monza Formula 1 racetrack. Once you arrive at your accommodation, drop your bags and set out for a gentle stroll by the water, then find a lakefront restaurant for a taste of the regional dishes.
Day 5: Private Lake Como Boat Tour, Explore Bellagio
Any visit to Lake Como must include an aquatic adventure, and today you'll set off on its turquoise waters to explore the most famous sights. From the water, you'll get a much better view of some of the extravagant villas that border the lake (including one owned by George Clooney), as well as the lush gardens that surround them. A private skipper will guide you between Torno and Blevio, where small villages line the shore, many with beautiful bell towers reflected in the water.
Chat with a local specialist who can help organize your trip.
Day 6: Free Day on Lake Como
There's a lot to see and do with a free day at Lake Como. You could start with a spot of local history, visiting the Museo Archeologico in the town of Como to browse ancient artifacts. Then, tour the Gothic 14th-century Cathedral of Como, take a leisurely stroll through Villa Olmo's sprawling park and exhibition halls, and step into the Museo Didattico della Seta for a look at the region's past as a producer of silk. Then take the funicular to Brunate, perched high in the mountains above the lake, for breathtaking views and a relaxing walk along the waterfront promenade.
Or, jump in the car and follow the curves of the lake northward. Venture to the elegant Villa Balbianello in Lenno to wander the terraced gardens and elegant interiors. From here, you could continue north to the charming town of Menaggio, or rent an electric bike for a scenic ride along the lake. Or, return to Como and jet off in a seaplane with Aeroclub Como to catch panoramic aerial views of the mesmerizing northern Italian landscape.
Day 7: Drive to Lake Garda, Free Afternoon to Explore
Jump behind the wheel again this morning and travel 2.5 hours east to the expansive Lake Garda, Italy's largest lake. En route, you could detour to the charming small city of Bergamo, known for its art and antiquities. Explore the charming Città Alta (Upper Town) with its medieval streets, ancient city walls, and the impressive Piazza Vecchia. A visit to the Accademia Carrara, one of Italy's premier art galleries, is also a must for art enthusiasts. After, continue your drive to Lake Garda, arriving in the early afternoon.
Use the rest of your day to unwind by the lake and soak up the picturesque scenery. You'll likely stay in or near the lakeside town of Sirmione, famous for its Roman ruins and the romantic Castello Scaligero. Stroll along the waterfront promenade and relax at a lakeside café. If you're itching to explore, jump on a boat tour of the lake to enjoy its crystal-clear waters and panoramic mountain views.
Day 8: Day Trip Around Lake Garda
Today you'll set off for a self-guided drive around Lake Garda, taking in various sights and Mediterranean scenery. Starting in Sirmione, head along the west bank, traveling north. You'll pass through Desenzano, the lake's most populous town, before stopping at Salò, arguably the lake's most beautiful town. Appreciate the medieval achitecture and ancient gates, including the Town Hall and Church of Saint Mary the Annunciation, which date back to the Venetian era. Wander along Salò's long lakeside promenade, then continue north.
Your next stop is Gardone Riviera, a favored destination for the bourgeois in the late 1800s. As you drive along the scenic Riviera dei Limoni, you'll reach the gorgeous village of Limone sul Garda, renowned for its terraced lemon groves and lakeside views. Stop for a delicious lunch in Riva del Garda, the head of the lake, where you can experience a blend of Italian and Austrian influences. Then, it's time to return south along the eastern bank of Lake Garda. Make time to visit Malcesine and explore its medieval hilltop castle before returning to the hotel.
Day 9: Self-Drive Prosecco Wine Tour
Get ready to pop some bubbles today when you explore La Via del Prosecco (The Prosecco Road), which runs between Conegliano and Valdobbiadene. The wines here are as delicious as the scenery is delightful, so even if you're the designated driver, you'll have a great day out. The adventure begins with a two-hour drive from Lake Garda to Valdobbiadene, entering the gentle foothills of the Dolomite Mountains, which rise from the Venetian plain with pretty villages atop many of the hills.
Day 10: Drive to Venice, Private Gondola Ride
It's time to drive to your final destination—Venice, Italy's famous floating city. The scenic drive from Lake Garda will take around two hours, and along the way, you can detour to a couple of charming highlights in the Veneto region. The city of Padua is a beautiful stop with its world-famous botanical garden; Vicenza is known for its architectural masterpieces; and the quaint town of Soave is famous for its wines. Once in Venice, return the rental car and take a water taxi to navigate the Venetian canals to your accommodation.
This afternoon, you'll get a true taste of Venice and tick off your bucket list when you board a gondola. The gondola is as unique as Venice itself—each with a crescent-shaped hull and forcole, which allow the gondelieri to position their oars in many different ways. This is how they navigate these slender craft along the network of canals. On your 30-minute private ride, you'll glide back in time, passing soaring Venetian palaces and passing under bridges through the narrow back canals of San Marco. Afterward, enjoy the rest of your afternoon exploring the "Floating City."
Day 11: Guided Murano & Burano Excursion
The Venetian Lagoon is home to dozens and dozens of islands. Two of the most populated ones—away from the main city of Venice—are Murano and Burano. You'll need to board a boat to reach these two, and along with a guide, you'll pass the island of San Giorgio Maggiore, the tip of Sant'Elena, and the Lido as you head toward Murano. If that name seems familiar, it's because Murano is a renowned glassmaking island. Step ashore to visit a glassblower to learn about the process and marvel at the intricate pieces, including elaborate, extravagant, and colorful chandeliers.
After exploring Murano, you'll cruise over to Burano, famous for its elegant lacework and colorful houses (the brightly-painted homes are said to have helped the island's local fishermen find their way home through the infamous Venetian mists). Snap pictures with the rainbow of houses that line the canals, then explore the art of lace-making, passed down for generations, which continues at the island's workshops and lace museum. After, return back to Venice.
Day 12: Depart Venice
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