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12-Day Winter Itinerary Exploring Milan's Best Attractions and Day Trips

Viewed by 242 travelers

Day 1: Arrival & City Orientation

Milan, Italy on December 17, 2025

9:00am

Breakfast at Pasticceria Marchesi

Start your Milan adventure with traditional Italian pastries and coffee at this historic café, renowned for its elegant atmosphere and quality. Opens at 7:30am.
EUR10, 1h0m

10:30am

Visit the Duomo di Milano

Explore Milan's iconic Gothic cathedral, including the rooftop for breathtaking views of the city. Entry fee applies and the cathedral opens at 9am.
EUR15, 1h30m

12:30pm

Lunch at Luini

Enjoy a quick but iconic panzerotto, a must-try street food in Milan located just near the Duomo.
EUR8, 0h45m

2:00pm

Galleria Vittorio Emanuele II

Wander through this elegant 19th-century shopping gallery filled with luxury boutiques and cafes, perfect for a leisurely stroll and some shopping or people watching.
Free, 1h

3:30pm

Pinacoteca di Brera

Discover Italy’s finest collection of Renaissance and Baroque art in the Brera district. Open 8:30am-7:15pm.
EUR12, 2h0m

6:00pm

Dinner at Trattoria Madonnina

Enjoy authentic Milanese dishes such as risotto alla Milanese in a cozy, traditional setting.
EUR40, 1h30m
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Day 2: Sforza Castle & Parks

Milan, Italy on December 18, 2025

8:30am

Breakfast at Pavé

Indulge in freshly baked pastries and excellent coffee at this popular bakery, which opens from 7:30am.
EUR12, 1h0m

10:00am

Sforza Castle

Explore this historic fortress with its museums and art collections; it is a key symbol of Milanese history. Open 9am to 5:30pm.
EUR10, 2h0m

12:30pm

Lunch at Paper Moon Giardino

Savour upscale Italian cuisine in a charming garden atmosphere, near the castle.
EUR35, 1h15m

2:00pm

Parco Sempione

Relax or take a stroll in Milan’s most famous park located right behind the castle.
Free, 1h0m

3:30pm

Museum of Ancient Art

Visit part of the Sforza Castle museums with art and sculptures from the medieval period. Included in castle ticket.
Included, 1h0m

6:30pm

Dinner at Osteria del Binari

Try Milan’s signature ossobuco and other local dishes in this quaint and atmospheric osteria.
EUR40, 1h30m
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Day 3: Day trip to Lake Como

Lake Como, Italy on December 19, 2025

7:30am

Breakfast at hotel or nearby café

Enjoy a light yet energising breakfast before your day trip, many Milan cafés open from 7am.
EUR10, 0h45m

8:30am

Train to Lake Como (Como city)

Travel by train from Milan Centrale to Como San Giovanni station, journey approx 40 minutes. Check Trenitalia schedules.
EUR10, 0h45m

9:30am

Villa Olmo

Visit this neoclassical villa with beautiful gardens overlooking Lake Como, open 9am-5pm in winter.
EUR5, 1h0m

11:00am

Boat tour on Lake Como

Take a scenic boat ride along the lake to admire charming lakeside towns. Boats run every hour; check local timetables.
EUR15, 1h30m

1:00pm

Lunch at Ristorante La Darsena

Dine on fresh lake fish and Italian classics with a superb lake view, located in Torno village.
EUR45, 1h30m

3:00pm

Explore Bellagio town

Stroll the picturesque streets of Bellagio, known as the pearl of Lake Como, visiting shops and lakeshore promenades.
Free, 2h0m

5:30pm

Return to Milan by train

Take the evening train back to Milan Centrale, relax after a full day of sightseeing.
EUR10, 0h45m

7:30pm

Dinner at Eataly Milano Smeraldo

Sample a range of Italian regional dishes and fresh produce from this expansive Italian market and food hall near the city centre.
EUR35, 1h30m
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Day 4: Shopping & Art Galleries

Milan, Italy on December 20, 2025

9:00am

Breakfast at Marchesi 1824

Enjoy a refined breakfast with exquisite pastries in one of Milan’s most famous patisseries, open from 8am.
EUR15, 1h0m

10:30am

Shopping in Quadrilatero della Moda

Visit Milan’s premier fashion district featuring high-end boutiques like Prada, Gucci, and Versace.
Free to browse, 2h0m

12:30pm

Lunch at Nobu Milan

Experience contemporary Japanese-Peruvian fusion cuisine in a stylish setting, perfect for a luxurious lunch.
EUR50, 1h30m

2:30pm

Visit Museo del Novecento

Discover a vast collection of 20th-century Italian art, beautifully housed in a historic building near the Duomo. Open 9:30am-7:30pm.
EUR10, 2h0m

5:00pm

Coffee break at Caffè Napoli

Relax with a coffee and a sfogliatella pastry in a charming café known for Neapolitan specialities.
EUR8, 0h45m

7:00pm

Dinner at Ristorante Berton

Dine on innovative contemporary Italian dishes in a sleek, minimalist restaurant.
EUR60, 1h30m
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Day 5: Day trip to Bergamo

Bergamo, Italy on December 21, 2025

8:00am

Breakfast near hotel

Grab a quick Italian espresso and brioche before your day trip.
EUR8, 0h45m

9:00am

Train to Bergamo

Board the train from Milan Centrale to Bergamo, journey about one hour. Check Trenitalia schedules.
EUR12, 1h0m

10:15am

Explore Città Alta (Upper town)

Walk through Bergamo’s medieval old town, with its Venetian walls, Piazza Vecchia, and historic churches.
Free, 2h30m

12:45pm

Lunch at Da Mimmo

Enjoy traditional Bergamasco and Lombard cuisine in this cosy trattoria famed for polenta and local cheeses.
EUR30, 1h15m

2:15pm

Visit Accademia Carrara

Tour this art gallery featuring Renaissance paintings from Italy’s great artists. Check winter opening hours 9am-6pm.
EUR8, 1h30m

4:00pm

Return train to Milan

Head back to Milan via train, relax after a cultural day out.
EUR12, 1h0m

6:00pm

Dinner at Il Luogo di Aimo e Nadia

Indulge in Michelin-starred modern Italian cuisine highlighting seasonal, local ingredients.
EUR85, 2h0m
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