City Chic to Lakeside Luxe: A 4-Day Northern Italy Itinerary You’ll Never Forget
Curated By
Patricia Caruso
Curator’s statement
Milan and Lake Como are the perfect contrasts—and together, they create a truly unforgettable escape. In Milan, centuries of art and architecture meet modern elegance. Then, just a short train ride away, Lake Como welcomes you with cinematic beauty: shimmering waters, grand villas draped in wisteria, and charming towns like Tremezzo, Bellagio, and Menaggio that feel suspended in time. Gliding across the lake on a classic wooden boat, with the Alps in the distance and the golden hour light catching the hills, feels like stepping into a dream.
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Day 1: Arrive in Milan
Duomo di Milano
Start your Italian escape in the cosmopolitan city of Milan, where haute couture meets centuries-old art and architecture.
Head to Brera District: My favorite area of Milan, a maze of cobblestone streets lined with elegant boutiques, galleries, and ivy-covered cafes. It’s where classic Milanese style meets bohemian soul, home to the renowned Pinacoteca di Brera and some of the city’s best aperitivo spots. Whether you’re browsing art, shopping for curated fashion, or just people-watching, Brera captures the romantic heart of Milan.
Quick Italian lunch: Stopping by Luini, just steps from the Duomo, is a delicious Milanese rite of passage. Opened in 1949, this family run bakery introduced the panzerotto—Puglia’s iconic fried turnover stuffed with gooey mozzarella and tomato—to Milan. Do yourself a favor and wait in line for one. This savory, street food masterpiece has become a cherished Milanese must-try!
Visit the Duomo di Milano: Marvel at this gothic masterpiece and trek to the panoramic rooftop.
Stop at Galleria Vittorio Emanuele II: Make sure to stop and spin three times with your heel on the bull—legend has it that is brings good luck! End your afternoon with an aperitivo at Camparino Bar, a beautiful bar serving the classic campari aperitif and snacks!
Day 2: Journey to Lake Como & settle into timeless Tremezzo
Checking in to the Grand Hotel Tremezzo
It’s time to leave the city behind and transition to Lake Como’s tranquil luxury.
Check into your lakeside hotel and enjoy the serenity and beauty of the lake views—incredible from every angle!
Tour the Botanical Gardens of Villa Carlotta: Perfectly manicured and lush, this is one of the prettiest villas on the lake—well worth the visit.
Dinner with a view at Belle Ile: Try the lamb ragù pappardelle!
Day 3: Explore Lake Como
Beautiful Bellagio
Today is all about exploring the central triangle of Lake Como, hopping by ferry to the most romantic towns on the lake.
Morning ferry to Bellagio: Wander the “Pearl of Lake Como,” known for its boutique-lined alleys, villas, and waterfront cafés. Spend time getting lost in the maze of the cobblestone streets and enjoying the artisan shops. One of my favorites is Quelli della Pelle—their leather products are incredible!
Lunch at La Punta: Have lunch where the lake splits, with panoramic views of the lake and Tremezzo and Menaggio on the other side.
Evening in Menaggio: One of my favorites—this small town is so charming! If you are lucky, there will be an event in the main square and all the locals will come out to enjoy! Stroll the promenade, enjoy gelato, and admire the views from every angle!
Day 4: Charter a boat
Enjoying the day on Lake Como on our private chartered boat
No trip to Lake Como is complete without time on the water. Today is your moment to live the dolce vita.
Charter a classic Venetian-style boat or book a self-drive boat rental from Tremezzo or Menaggio. Cruise past:
Villa del Balbianello (The James Bond and Star Wars Villa!).
The pastel villages of Lenno and Varenna.
If the water is warm enough, spend some time swimming in the lake.
Farewell dinner: Treat yourself at La Terrazza at Grand Hotel Tremezzo, a tribute to legendary Italian chef Gualtiero Marchesi. Make sure to have the famous Risotto Oro e Zafferano!
Need to know
Best time to visit Milan & Lake Como
The best time to visit Milan and Lake Como is in late spring (May–June) and early autumn (September–October). These months offer:
Mild, pleasant weather.
Blooming gardens and lush lakefront landscapes.
Fewer tourists than in peak summer.
Cultural events in Milan and open villas around Lake Como.
July and August can be hot and crowded, especially in Milan, and many locals go on holiday (some shops may close in mid-August). Winter is peaceful on the lake, but many restaurants and ferries operate on limited schedules.
How to get from Milan to Lake Como
The train from Milan to Lake Como is fast and scenic.
For the mid-lake area (Tremezzo, Bellagio, Menaggio), take the train from Milano Centrale to Varenna-Esino (approximately one hour). From Varenna, catch a ferry across the lake.
Private transfers or rental cars offer flexibility, especially if staying in Tremezzo or exploring lesser-known villages.
Getting around Lake Como
Ferries are the easiest and most scenic way to explore towns like Bellagio, Menaggio, Varenna, and Tremezzo.
Choose the “navigazione laghi” mid-lake ferry for frequent service between central towns.
For a luxurious experience, book a private wooden boat tour with a skipper or rent a self-drive boat for a few hours.
Travel Advisor
Patricia Caruso
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