Milan · Lake Como · Lake Maggiore
Your northern Italian journey begins in Milan — Italy's capital of fashion, design, and contemporary culture. A private driver meets you at Malpensa Airport and delivers you to your hotel in the Brera district, Milan's artistic quarter of galleries, boutiques, and aperitivo bars.
The rest of the day is yours. Walk the Galleria Vittorio Emanuele II, one of the world's oldest shopping arcades, and stand beneath the spires of the Duomo as the evening light turns the marble pink. Find a traditional Milanese restaurant for risotto alla milanese — saffron-gold, creamy, and unmistakably Lombard.
The morning's centrepiece: a reserved viewing of Leonardo da Vinci's Last Supper at Santa Maria delle Grazie. Access is limited to 25 people every 15 minutes, and your specialist has secured your entry months ahead. Standing before this fresco — the brushwork, the geometry, the drama of the moment — is one of Europe's great art experiences.
Afternoon, explore the Duomo rooftop terraces for panoramic views across the city to the Alps. Visit the Pinacoteca di Brera for Raphael and Caravaggio, then walk through the Quadrilatero della Moda — Milan's fashion district where Versace, Prada, and Armani have their flagship stores. This evening, aperitivo on the Navigli canals — Milan's waterside nightlife district.
Your driver takes you north from Milan into the foothills of the Alps. Within an hour, the city gives way to the southern shore of Lake Como — a body of water so dramatically beautiful that George Clooney, Versace, and generations of European aristocracy have called it home.
Check into your lakeside hotel — many properties have private boat docks, terraced gardens falling to the water, and views across to the mountains on the far shore. Afternoon, a private boat tour along the western shore: villa after villa, each more extravagant than the last, the water a deep impossible blue beneath you. Stop in the village of Torno for espresso, or swim from a quiet cove. This is Lake Como at its most intimate.
Ferry across to Bellagio, the so-called Pearl of the Lake, where the two arms of Como meet. The town climbs steeply from the waterfront in a cascade of stone staircases, silk shops, and terrace restaurants. Visit Villa Melzi and its extraordinary lakefront gardens — the neoclassical architecture reflected perfectly in the still water.
Take the ferry onward to Varenna, a quieter village on the eastern shore. Walk through Villa Monastero's botanical gardens, stretching along the lakeshore for nearly a kilometre. Lunch on the waterfront: fresh lake fish, local olive oil, a glass of white from the Valtellina. Return to your hotel by private boat as the mountains turn purple at sunset.
A morning at leisure on Lake Como — swim, walk the shore path, or visit the silk museum in the town of Como itself (the region has produced silk for centuries). Late morning, your driver takes you west through the pre-Alpine foothills to Lake Maggiore, the largest of the Italian lakes and the one that feels most like a secret.
Arrive in Stresa, the elegant resort town on Maggiore's western shore, with views across to the Borromean Islands. Check into your lakeside hotel. Late afternoon, walk Stresa's Liberty-style waterfront promenade — the architecture, the palm trees, the mountains rising directly from the far shore create a landscape that feels almost tropical despite being in the shadow of the Alps.
The day belongs to the Borromean Islands — three jewels floating in the centre of Lake Maggiore. A private boat takes you first to Isola Bella, where the Borromeo family's baroque palace rises from terraced gardens filled with white peacocks, exotic plants, and statues. The palace rooms are lavishly decorated; the gardens descend in ten terraces to the water's edge.
Continue to Isola dei Pescatori, the fishermen's island, where narrow lanes lead to waterfront restaurants serving lake perch and risotto. Lunch here is unhurried and perfect. Finally, Isola Madre — the largest and quietest island, with a 16th-century palazzo surrounded by the oldest botanical garden on the lakes. Your boat returns you to Stresa as the late afternoon light gilds the water.
A final morning on the lake — perhaps a walk to the botanical gardens on the hillside above Stresa, or a cable car to the summit of Monte Mottarone for views stretching from Monte Rosa to the Po Valley. Your driver collects you and heads south toward Milan, with a stop in Bergamo.
Bergamo's upper town — the Città Alta — is one of northern Italy's best-kept secrets. Encircled by 16th-century Venetian walls (UNESCO-listed), this medieval hilltop town has its own piazza, cathedral, and basilica, plus restaurants that rival anything in Milan at half the price. A guided walk connects the architecture to centuries of history. Farewell dinner in the Città Alta, looking out over the Lombard plain.
A final northern Italian breakfast, then your private driver takes you to Milan Malpensa Airport for your departure flight. The drive from Bergamo or Milan takes about an hour, and your specialist has timed the transfer to your flight.
You leave carrying northern Italy with you: the spires of the Duomo catching morning light, the impossible blue of Lake Como seen from a private boat, the white peacocks of Isola Bella, and the stone lanes of Bergamo's hilltop town. This is a different Italy — refined, alpine, unhurried — and it stays with you.
This is a sample custom route — a starting point, not a fixed package. Many clients travel something very close to this. Book a free consultation and a specialist will build from here.
Your specialist pre-arranges the right luxury experiences based on your interests and travel style. These are the custom experience types available on this route — specific choices are made with you, not for you.
Activities are selected and pre-booked with your specialist based on your interests — not all activities are included in every trip version. Availability varies by season.
You work directly with a specialist who knows Italy deeply — not a call center or booking agent. Every consultation is with someone who has been there, stayed in those hotels, and knows the country inside out.

Florence and Austria-based, Lexi brings on-the-ground expertise across Southern Europe’s most sought-after destinations. Every recommendation comes from personal experience — the right lakeside hotels on Como, the Last Supper entry months in advance, the private boat operators who know the lakes properly.
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25 years designing European trips, with a deep network across Italy’s regions. CMSC certified and former Peace Corps. Ideal for multi-country trips combining Italy with Ireland, Scotland, or beyond.
Book a Consultation“Juniper Tours did an amazing job booking our vacation to Italy. Lexi Blade helped us schedule our dream vacation from Venice all the way to Sorrento on the Amalfi coast, with stops in Florence and Rome. Lexi was phenomenal and made changes for us many times to assure we got the most out of our trip.”
Nikki Walls · Milan & the Italian Lakes Tour · Verified Google Review
30 minutes, completely free. Walk away with a clear picture of what your luxury custom Italian Lakes trip could look like — dates, route, 4 and 5-star accommodations, and all.