Fashion capital, banking powerhouse, and Renaissance treasure chest—Milan is a city that rewards curiosity. From the Gothic lacework of the Duomo to da Vinci’s enigmatic Last Supper, history and modern design live side by side. Evenings belong to aperitivo: golden-hour cocktails with thoughtful snacks that turn a square into a living room.

Just an hour north, Lake Como unfolds in deep-blue curves beneath steep, forested mountains. Liberty-era villas, camellia gardens, and storybook towns like Bellagio and Varenna dot the shore, best explored by ferry or a classic wooden boat. The Como-Brunate funicular lifts you into the clouds for sweeping views from terrace cafés.

Practical notes: book Last Supper tickets weeks (often months) ahead, and pack for microclimates—Milan runs urban and fast; Como is breezier by the water. Trains between Milan and Como are frequent and inexpensive, and ferries connect lake towns year-round. Expect standout Northern Italian cuisine: saffron risotto and ossobuco in Milan; lake fish, alpine cheeses, and mountain herbs on Como.

Milan

Milan’s core is compact and walkable: Duomo, Galleria Vittorio Emanuele II, La Scala, and the Sforza Castle frame the center, while Brera’s cobbled lanes hide ateliers and the Pinacoteca’s Caravaggios. The Navigli canals hum at dusk with bars, design studios, and trattorie. Fashion temples line the Quadrilatero della Moda, but don’t miss indie boutiques in Isola.

• Top sights: Duomo (and rooftop terraces), Santa Maria delle Grazie (The Last Supper), Sforza Castle & Parco Sempione, Brera district, Fondazione Prada.
• Food & drink: classic risotto alla milanese at Osteria del Binari; seasonal Milanese cooking at Trippa; pastries at Marchesi 1824; inventive cocktails at Nottingham Forest; aperitivo at Camparino in Galleria.
• Fun fact: Milan’s Duomo took nearly six centuries to complete and hosts one of the world’s largest collections of marble statues.

Stay in Milan: Browse stays on VRBO Milan or Hotels.com Milan. Specific picks: Hotel Principe di Savoia (classic grand-dame), Room Mate Giulia (steps from the Duomo), UNAHOTELS Cusani Milano (between Brera and the Castle), or budget-chic Ostello Bello.

Getting to Milan: For flights to/from Europe, compare on Omio (flights). If arriving by rail from nearby cities (Venice, Florence, Zurich), check schedules and fares on Omio (trains) or Trip.com (trains).

Como

Como town, the lake’s southern gateway, blends medieval lanes with a luminous waterfront. From Piazza Duomo to the 14th-century Broletto, stone and stucco glow at sunset. The funicular climbs to Brunate for terrace views; boats fan out to Cernobbio, Bellagio, Varenna, and Lenno’s Villa del Balbianello (a film favorite).

• Top sights: Como Cathedral (Duomo), Como–Brunate Funicular, Villa Olmo, Bellagio’s Villa Melzi gardens, Varenna’s Villa Monastero, lakeside promenades.
• Food & drink: lake fish (lavarello), pizzoccheri buckwheat pasta, alpine cheeses. Try Osteria del Gallo (cozy Como classic), La Colombetta (Sardinian seafood), Terrazza 241 (sunset cocktails).
• Fun fact: Como was Europe’s silk capital; you’ll still find exquisite scarves and ties in town.

Stay around Lake Como: Explore options on VRBO Como or Hotels.com Como. Standouts: Hilton Lake Como (rooftop pool/bar), Hotel Engadina (great value near lake), or splurge on Grand Hotel Tremezzo. In mid-lake, consider Hotel Belvedere Bellagio, Hotel Olivedo (Varenna), or Hotel La Darsena (Tremezzina).

Getting from Milan to Como: Trains run 3–4x/hour. Milano Centrale → Como S. Giovanni (Trenitalia, 40–50 minutes, ~€5–€12) or Milano Cadorna → Como Lago (Trenord, ~1 hour, ~€5). Check and book via Omio (trains) or Trip.com (trains). Ferries between towns: see routes and passes; for broader European ferries use Omio (ferries).

Day 1 — Arrive in Milan, Duomo Glow, and Aperitivo

Afternoon: Land in Milan and check into your hotel. Shake off jet lag with an espresso and a cannoncino at Marchesi 1824 near the Galleria. Stroll the Galleria Vittorio Emanuele II—note the mosaics and polished bull for good luck—then admire the Duomo’s façade as the marble shifts from pearl to rose.

Evening: Embrace the aperitivo ritual at Camparino in Galleria or Terrazza Aperol (views of the cathedral included). Dinner near the center: reserve at Nerino Dieci Trattoria for silky tagliatelle and veal Milanese or try Trippa for nose-to-tail dishes that have locals queueing (book weeks ahead). Cap the night with gelato at Cioccolati Italiani.

Day 2 — Duomo Rooftops, Brera, and The Last Supper

Morning: Start with pastries at Pavé (buttery veneziana, excellent filter coffee). Then take a guided rooftop visit of the Duomo for flying buttresses and skyline views. Tour option:

Milan Super Saver: Skip-the-Line Duomo and Rooftop Guided Tour (fast-track entry, elevator access, and expert insights). Expect 1.5–2 hours.

Afternoon: Wander Brera’s lanes to the Pinacoteca (Mantegna, Raphael, Caravaggio). Lunch at Ratanà (Isola) for risotto made with Carnaroli and bone marrow or a lighter stop at Eataly Smeraldo’s pasta bar. Time your visit to Santa Maria delle Grazie for da Vinci’s masterpiece; tickets are scarce—book a guided slot:

Milan Last Supper and S. Maria delle Grazie Skip the Line Tour (priority access, art-historian guide).

Evening: Head to the Navigli canals—peek at the Vicolo dei Lavandai washhouse—and grab aperitivi at Mag Café or Backdoor 43 (minuscule “micro-bar” with big flavors). Dinner at Osteria del Binari for ossobuco and saffron risotto, or try Al Pont de Ferr for contemporary takes. Nightcap at Nottingham Forest for theatrical, award-winning cocktails.

Day 3 — Morning Train to Como, Funicular Views, and Old Town

Morning: Depart Milan after breakfast. Milano Centrale → Como S. Giovanni (40–50 minutes, ~€5–€12) or Cadorna → Como Lago (~1 hour, ~€5). Compare and book on Omio (trains) or Trip.com (trains). Check in, then enjoy a light lunch at Osteria del Gallo (tiny, homey, daily chalkboard menu).

Afternoon: Explore Como Cathedral’s blend of Gothic and Renaissance façades and the adjacent medieval Broletto. Ride the Como–Brunate Funicular (every 15–30 minutes; RT ~€6–€8) and take the short viewpoint walk for lake-wide panoramas. Espresso break at Pasticceria Monti for fruit tarts or hazelnut cake.

Evening: Sunset cocktails at Terrazza 241 (rooftop at Hilton Lake Como) with a plate of lake-fish crudo. Dinner choices: La Colombetta (Sardinian seafood in an elegant former chapel) or Il Pinzimonio (seasonal Italian classics). Gelato by the water at Gelateria Lariana.

Day 4 — Ferries to Bellagio & Varenna, Gardens, and a Private Wooden-Boat Cruise

Morning: Board a ferry from Como to Bellagio (regular ~2 h; hydrofoil ~1 h—hydrofoil costs a bit more but saves time). In Bellagio, wander Salita Serbelloni’s stone stairways, stroll the lakeside promenade, and meander through the romantic Villa Melzi gardens (seasonal opening). Coffee and a brioche at a café on Piazza della Chiesa.

Afternoon: Hop the ferry to Varenna (15 minutes). Walk the “Lover’s Walk” promenade and visit Villa Monastero’s terraced botanic gardens bursting with citrus, palms, and wisteria in season. Lunch at Trattoria San Giacomo (Bellagio) or La Pergola (Varenna, by the water) for lake fish and homemade pasta.

Evening: Return to Como (consider a fast ferry). Celebrate with a one-hour private wooden-boat cruise—golden hour is magic, passing villas and cypress-lined shores:

Private Tour by Classic Wooden Boat on Lake Como (heated/covered in cool seasons). Afterwards, dine back in Como at Ristorante Sociale (near the Duomo; hearty Lombard dishes) and finish with cocktails at Fresco Cocktail Shop.

Day 5 — Villa Olmo, Silk Shopping, and Departure

Morning: Stretch your legs along Passeggiata Lino Gelpi to Villa Olmo, a neoclassical villa with landscaped park and lakefront lawns (exhibits vary; the park is free). Browse Como’s silk heritage—look for Mantero 1902 scarves or elegant ties along Via Vittorio Emanuele II and Piazza San Fedele. Brunch at L’Orologio Bistrot for eggs, salads, and good coffee.

Afternoon: Train back to Milan for your onward journey: Como S. Giovanni → Milano Centrale (~45 minutes), then Malpensa Express to MXP (~50 minutes, ~€13) or metro M4 to reach LIN if you’re staying in the center. Check times and tickets on Omio (trains) and consider Omio (flights) for your return.

Optional full-day add-on from Milan (if you swap a day): Ride the iconic Bernina Red Train into the Swiss Alps for glacier views and St. Moritz. It’s a long but unforgettable day from Milan:

Bernina Red Train, Swiss Alps & St Moritz From Milan.

Where to book stays quickly: Milan—Room Mate Giulia, Hotel Principe di Savoia, Ostello Bello. Como—Hilton Lake Como, Grand Hotel Tremezzo, Hotel Engadina.

In five days you’ll taste Milan’s creative pulse and Lake Como’s serene rhythm—rooftops and Renaissance art giving way to ferries, gardens, and sunset boat rides. With easy trains, memorable meals, and time to linger, this Lombardy itinerary balances headline sights with local moments you’ll want to revisit.