Two Week Road Trip in Northern Italy

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Advisor - Hannah Kratz
Curated By

Hannah Kratz

  • Road Trip Travel

  • Arts & Culture

  • Food & Wine

  • Luxury Travel

  • Milan

  • Venice

  • Italy

  • Barefoot Luxury

  • Sightseeing

A beautiful view of Lake Como from Villa Monastero.
Curator’s statement

Sometimes it seems Rome and Florence get all the Italian "amore." Sure, there is the timeless allure of Rome and Sicily, effortlessly captivating hearts with their romantic charm for centuries. But amidst their spotlight, Northern Italy quietly awaits in the shadows, brimming with its own treasures. From masterpieces of art to the vast expanse of the world's largest alpine meadow, from meandering canals to the soul-stirring Prosecco countryside, there's a wealth of experiences waiting to be discovered. Many of these spots require access to a rental car, so go get that international driver's license and get ready for an unforgettable Italian road trip.

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Days 1-2: Milan

People shopping inside of Galleria Vittorio Emanuele II in Milan.

Milan typically has better flight deals compared to its southern counterparts! Take the speedy Malpensa airport transport from the airport (MXP) straight into the heart of Milan. Lucky for you, your luxurious hotel, The Excelsior Gallia, is right across the street from the Milan Central train station, so you'll be relaxing in its world-class spa and luxurious rooms in no time. Take the evening to recharge your batteries and eat at the hotel's Michelin-starred restaurant, Terrazza Gallia, which offers innovative Italian cuisine paired with an extensive wine list. Additionally, the hotel boasts a stylish bar and lounge area, perfect for cocktails and socializing.

You are going to pack it in today, but trust me, you will see so much! Before heading out, don't miss out on breakfast. The Gallia’s breakfast buffet is a stunner, and the homemade pastries are not to miss. Your rate includes free breakfast, so take the time to enjoy all that it offers. You'll start off the day with a small group tour of the Milan Duomo, including the rooftops. The tour will take you walking through all the main sights including the Duomo, Sforza Castle, the Vittorio Emmanuel II, the oldest mall in the world and a serene viewing of Leonardo Da Vinci’s "The Last Supper."

In the evening, grab a vino and delectable pasta at Ristorante Galleria. Squeeze in one last window shopping at Vittorio Emmanuele II, and then catch an opera at the famous Milan Opera House – Teatra alla Scala. Other restaurant options: Maio Restaurant or LaRinascente Rooftop (both with incredible views of the Duomo).

Days 3-5: Lake Como & Dolomites

A view of the stunning Mandarin Oriental, Lago di Como Hotel with a sailing boat, mountains in the background, right before dusk.

In the morning, take a private transfer to Lake Como – (trust me, so much easier to watch someone else take those windy roads and narrowly avoid other speeding cars.) It’s just a short ride, and you will feel like you are in a whole new world. There are plenty of gorgeous hotels dotting the outline of the lake, but my favorite is The Mandarin Oriental, Lago di Como. Spend your first day soaking up the sun on the pool deck, which is floating IN the lake. Swim in the pool with a Campari spritz in hand, relax in the spa area and walk the grounds.

The following day, you’ll take an afternoon boat ride around the sights of Lake Como, and have your driver drop you off in Bellagio for a most picturesque day of shopping in the quaint town. Make sure you’ve made dinner reservations for the hidden gem of Dispensa 63. It’s a small restaurant with an exposed kitchen. The chef and servers feel like family from the moment you enter.

On your last day in Lake Como, enjoy one last cappuccino as you look out over the lake and then head back to Milano Centrale Station, where you’ll board your train to set off for the Dolomites. The train from Milano Centrale to Bolzano is three hours. You’ll rent a car in Bolzano or hire a private driver to bring you to your hotel in the Dolomites.

Day 6-9: Dolomites

A stunning view of the raw and rugged landscape atop the Dolomites on a sunny day.

The Dolomites, a UNESCO World Heritage Site in northeastern Italy, show off their breathtaking alpine landscapes and rich cultural diversity – merging German, Swiss, Austrian and Italian influences. The region offers unparalleled opportunities for outdoor activities like hiking, skiing and rock climbing, alongside a culinary experience, blending Alpine flavors with Italian and Austrian influences.

Alpenroyal Gourmet (Selva di Val Gardena): Located in the charming village of Selva di Val Gardena, Alpenroyal Gourmet is a one-Michelin-starred restaurant renowned for its creative interpretations of traditional South Tyrolean and Mediterranean cuisine. Chef de Cuisine Mario Porcelli combines innovative techniques with high-quality ingredients to create memorable dining experiences.

Anna Stuben (Bressanone): In the historic town of Bressanone, Anna Stuben is a one-Michelin-starred restaurant housed in a charming Alpine chalet. Chef Reimund Brunner showcases his culinary skills through a menu that blends traditional Tyrolean flavors with modern techniques, resulting in dishes that delight both the palate and the senses.

Hotel Tyrol (Santa Maddelena): This quaint hotel offers a phenomenal prix fixe dinner each evening with stunning views of the valley in which it resides. If you arrive mid-day, take the time to visit the church of St. Johann (a very Instagrammable spot). Or take a moderate six-mile loop on the gorgeous Adolf Munkel trail in the Puez Odle Nature Park.

Hikes/Cable Cars:
Ortesei (Val Gardena): Take the Mont Suec cable car ride up for hiking trails, and panoramic views of the surrounding Dolomite mountains along the way. The journey provides visitors with a breathtaking perspective of the rugged peaks, lush valleys and picturesque villages that characterize the region. Don’t miss an al fresco lunch with an Aperol or Hugo spritz at the Mont Suec restaurant, located at the top of the cable car run.

Seceda: The hike to Seceda offers stunning panoramic views of the Odle Group, one of the most iconic mountain ranges in the Dolomites. Start from the Seceda cable car station and follow well-marked trails that lead to viewpoints overlooking the rugged peaks and verdant valleys below.

Alpe di Siusi (Seiser Alm): Alpe di Siusi is the largest alpine plateau in Europe and offers a network of hiking trails suitable for all levels. Wander through lush meadows dotted with wildflowers, past rustic mountain huts, and enjoy panoramic views of the surrounding peaks.

Puez-Odle Nature Park: Explore the pristine beauty of Puez-Odle Nature Park with its rugged peaks, deep valleys and lush forests. Choose from a variety of trails that wind through this protected area, allowing you to discover its diverse flora and fauna while soaking in the majestic scenery.

Days 10-11: Dolomites & Vicenza

An open square, Piazza dei Signori in Vicenza, showcasing the town's architecture, clock tower and people out and about.

This day is all about a scenic drive. Your ultimate goal is Vicenza, a hamlet that has Shakespearean lore, but is better known for its bubbly - more specifically, Prosecco. The quaint bed and breakfast you will be staying at the next two nights hosts one of these famous vineyards. Beyond the walls of your sweet hotel are many more vineyards to choose from. But you can do that on the next day. Spend the rest of the day lounging by the pool or the Turkish baths at Relais d’Arfanta, and book an in-room massage. While they don’t have a full restaurant, the breakfast and lunch options are fantastic, and the staff provides excellent recommendations for dinner off-site.

Your second day in Vincenzo is your day to sip Prosecco from the famous region of Valdobienne. Visit some of the top wineries in the Valdobbiadene region: Nino Franco, Adami, Valdo Spumanti, Villa Sandi, and Mionetto. Sample a variety of Prosecco wines, learn about the production process and soak up the picturesque vineyard landscapes. Explore Vicenza: Take some time to explore the charming city of Vicenza. Visit architectural stunners such as the Palladian Basilica, stroll through the historic city center and discover hidden gems tucked away in its winding streets.

Days 12-14: Vicenza & Venice

Venetian gondolas and gondoliers transporting tourists through Venice's canals, with classic architecture and buildings to view along the way.

You are finally going to ditch your car. Because, well, Venice prohibits them. Only gondolas from this point forward. Drop your car near the Mestre train station, from there, take a short jaunt into the splendid city of Venice. No visit to Venice is complete without a gondola ride along its iconic canals. Relax as you glide past historic palaces, picturesque bridges and bustling piazzas. Soak up the magic of Venice from the water. You will gondola from the train station to St. Mark's, where you will board a speedboat to your hotel for the next three nights. The JW Marriott Isola della Rose offers an unmatched experience, one where you have Venice at your fingertips, yet feel like you are on a luxury vacation on a private island (which it is!). The hotel offers so much more than a hotel in Venice. Grab a bike (they are free for guests) and ride around the island – you’ll see multiple swimming pools (heated, and one on the rooftop offering stunning views of Venice), outdoor games, an old chapel, a luxurious spa offering a range of treatments and pool area, a Michelin-starred restaurant (Dopolavoro) and special events organized weekly by the JW team. Boats run all day and late into the evening so you can hop on and be back in Venice in less than thirty minutes.

Spend your last days in Italy exploring the enchanting city of Venice. Take a leisurely stroll through its labyrinthine streets, visit iconic landmarks such as St. Mark's Square, the Rialto Bridge and immerse yourself in the city's unique atmosphere. Set off to find the famous Bansky art that changes the way you see it as the water rises throughout the day. Take a boat ride to Murano and explore the artistic scene of glass blowing or to Burano to see the finest lacemaking and colorful houses. Experience Venetian culinary culture by dining in a bacaro, a traditional Venetian wine bar. Sample cicchetti, small plates of local specialties, paired with regional wines. Join locals at bustling bacari in neighborhoods like Cannaregio or Dorsoduro for an authentic taste of Venetian cuisine. And don’t miss the opportunity to get lost in the Venetian streets around sunset time, the light casting magical hues on the buildings and water around you.

Day 15: Fly Home

A plane taking off at Venice Marco Polo Airport (VCE), on a sunny day.

Fly out of Venice airport, or take a train back to Milan if you booked a round trip out of MXP. Start dreaming of your next trip back to this amazing country.

Advisor - Hannah Kratz

Travel Advisor

Hannah Kratz

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This itinerary is part of our ongoing series on travel to Italy. Looking for more travel inspiration? Check out my itinerary, North Lake Tahoe Ski-Week.