6 Days in Northern Italy; Milan, Lake Como, & Venice Winter Itinerary + Travel Tips & Mistakes to Avoid

Italy in December is pure magic, twinkling lights, crisp air, warm bowls of pasta, and cobblestone strolls wrapped in scarves. I traveled with my family (a group of 6) through Milan, Lake Como, and Venice, soaking in everything from bustling piazzas to serene ferry rides.

For our family of six adults, it was essential to maximize our PTO and make every moment count while creating lasting memories.

This was our 6-day winter itinerary, complete with highlights, must-know tips, favorite meals, Google Map pins, and some moments I wish I could do over.

P.S. here is the method I use for planning our itinerary

BLUF

(bottom line up-front)

❌ Things I’d Do Differently

• Spend more time in Varenna

• Download Trenord app to track train delays or changes

• Add more buffer time than you think when it comes to transportation, finding your train, etc.

• Don't go on on Gondola ride. If you really want to then remember to bring cash

📅 Day 1: Arrival in Milan

BLUF:

📍 Milan

🚆 Transit: Malpensa Express + Metro (~1.5 hr)

🍽 Dinner at Via Pasteria

💡 Pro Tip: La passeggiata (evening stroll) is the best way to recover from jet lag.

Travel Log Notes:

🛬 Landed in Milan at 3pm.

🚆Caught the 4:13pm train to the city center then took the subway to our hotel. It was ~1.5 hour ride.

🛏️ We booked "BB Hotels Smarthotel Duomo" since it was walking distance from a metro stop. After checking in, we freshened up and headed to dinner.

🍝 Even though we didn't have a reservation, Via Pasteria, welcomed our party of 6. This was one of our family's favorite meals:

• Carbonara (if you like cream + bacon)

• Spaghetti Aglio (if you prefer a lighter sauce and something unique)

  
  

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Lastly, we enjoyed a post-dinner walk, la passeggiata. We did this every single night and I really hope to take this habit back home. It literally means "a walk" and is especially associated with the walk after the evening meal to socialize and enjoy the community.  It's not about getting to a specific destination but about the act of walking, talking, and being seen. 

Bonus points: walking after eating aids digestion, helps regulate blood sugar, and promotes better sleep.

We took a gander at:

• The Gothic cathedral, Duomo di Milano, which took nearly 600 years to complete

• The Galleria Vittorio Emanuele II, a stunning shopping gallery. Here, we gazed up at the 4 women that represented the different parts of the world and saw the famous bull mosaic

📅 Day 2: Day Trip to Lake Como

BLUF

📍 Como → Brunate → Bellagio → Varenna

🚆 Transit: ~3 hrs total (2 trains + 3 ferries + 1 cable car)

🍕 Pizza at Ristorante Carillon

💡 Pro Tip: Do not wait in line to buy ferry tickets to Varenna at the first booth when you dock in Bellagio. Walk south, down the block, to the correct one.

Travel Log Notes:

🚆We rose early for breakfast at the hotel and then day trip to Como, ~1 hour picturesque train ride.

🎟️ Once we got to Como at around 10:30, we walked straight to the Ferry Terminal to buy tickets to Bellagio. The next availability wasn't until 1pm.

🚠 To kill time we went to the cable car, "Funicolare Como-Brunate." Not getting the earlier 12pm ferry was a blessing in disguise because we got to see a breathtaking view of the mountains, lake, and even Switzerland from the top of the mountain.

Pictures of the view just don't do it justice, well worth the ticket cost €6-7

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Learn from us: do NOT walk up any hills to get to the entrance! We thought we had picked the correct location on google maps and meandered through the town for about 15 minutes up several very steep hills until we realized something was wrong. The ticket entrance is on the main street right along the lake, Lungo Lario Trieste. Right next to Ox Pub and Grill Como.

⛴️ We descended the mountain in the cable car in ~10 minutes and caught the ~45 min ferry ride to Bellagio, known as the "Pearl of the Lake."

We queued up for the ferry ~30 min earlier than the departure time and was able to get a seat at the window. The ferry stopped at a few smaller towns on both sides of the lake on the way to Bellagio.

We only got to spend ~2.5 hours in Bellagio before taking another ferry to Varenna, but it was enough time walk around the town, eat lunch and walk around on a beautiful promenade, "Lungolago Europa," alongside the lake.

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When you disembark in Bellagio you might think "oh I'll just buy our next ferry tickets to Varenna here since there is a ticket office." Don't do it! We waited in line for 15 minutes only for them to tell us to walk further down the street, to buy the tickets at a different counter.

🎟️ Here is where you actually buy your tickets and board the ferry for Bellagio to Varenna:

🍕 Once we got our tickets for the next ferry ride, we walked around looking for lunch. We found a lakeside café, Ristorante Carillon, where we enjoyed pizza. Mostly because that was what was open, had decent reviews, could seat 6, and had a view.

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We noticed lots of places close between lunch and dinner. There were also quite a few restaurants closed for the season.

⛴️ Around 4pm, we boarded a ~20 minute ferry to Varenna. It’s standing room and mostly open-air, so be prepared. It was absolutely freezing and windy when we went in December. That said, the exposure made the views even more dramatic, with the winter light hitting the lake and mountains just right.

To get to the towns center you walk along a sidewalk that is alongside (and sometimes overhangs) the lake. See 2 vertical pictures below. Only kind of scary, but very enchanting. We only had about ~45 minutes in town since we were trying to catch the 5:35 train back (which didn't happen)..

🚆After getting more steps in exploring the town we walked ~20 minutes back to the Varenna train station. We took the train back to Milan and went straight to our reservation for dinner at 8pm. We were not impressed with dinner so I will not be recommending it here.

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We wanted to take the 5:35pm train back to Milan, per the companies timetable, but it never showed up! We (and hundreds of others) had to wait an hour outside (in the cold) for the next train. Lesson learned - check the train website for updates rather than cluelessly standing around.

↪️ If I could re-do this day I would spend more time in Varenna. It had the best small town charm and reminded me of a town you would see in Pixar's movie "Luca."

📅 Day 3: Morning in Milan + Travel to Venice

BLUF

📍 Milan → Venice

🚆 Transit: 2.5 hr train

🧁 Breakfast at Starbucks Reserve

💡 Pro Tip: Keep backpacks under your seat — thefts happen fast.

Travel Log Notes:

We checked out, checked our bags with the hotel, and had a final wonder around Milan.

• Starbucks Reserve for breakfast. IDC if I sound basic but the pastries were chef's kiss and their drink menu was unique, definitely worth a stop.

• Duomo di Milano. We had seen the Duomo from outside but wanted to see the inside as well. To do so, we bought our tickets online the night before. Another must see.

• Sforzesco Castle. We walked the grounds and stopped by the cafe for a quick snack. We didn't get to walk inside due to our itinerary.

  • If I were telling a friend what to see I would tell them they could skip this.

🚆Next we went back to the hotel to grab our bags, took the subway to the Milan's main terminal, bought our train tickets at a kiosk, then boarded a 2.5 hour train for Venice. As soon as we stepped off the train, the enchanting canals and historic buildings welcomed us.

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Lesson learned: keep your backpack and any valuables in the chair under your seat. I had kept my backpack in the overhead bin area because that is what everyone else had done, and it was relatively crowded. As we were rolling into one of the stops I woke up and noticed a man hesitantly grabbing my backpack and kind of just standing there. I stood up and politely told him that was mine and I could move it out of his way. He said something angrily in Italian and got off at the stop. Later on we noticed a man a few rows in front of us talking to the police, apparently someone had stolen all the cash from their backpack.

⛴️ As soon as you leave the Venice train station you are facing a canal. We were off to find the ticket counter for the ferry that got us closest to our hotel. Again we purposefully chose a hotel that was close to a ferry dock. There were 4 counters to choose from. Ferrovia A, B, C and D. Once you have your tickets, be prepared to be overcrowded and amazed at the buoyancy of the boat with the number of people crammed on.

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Ferry stops are quick. Start making your way to the exit during the stop before so you can "scusi" yourself to the front...& this was our experience when we went during an off season.

🛏️ We stayed at the Ca'pagan Hotel. Before we got there I was a little worried it looked outdated but this became my favorite hotel on this Italy vacation. The drama of each room was fun and unexpected.

After freshening up we had dinner (wasn't worthy of a recommendation) and then a stroll to Rialto Bridge, which was more beautiful at night and the perfect way to end the day.

📅 Day 4: Discovering Venice

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📍 Venice

🏛 Museo Correr, Doge’s Palace, Basilica della Salute

🍝 Lunch at La Piazza

💡 Pro Tip: Step past Basilica della Salute near sunset for panoramic lagoon views.

Travel Log Notes:

Our second day in Venice was dedicated to exploration. It was a long day with a lot of walking, so be prepared! (I bring 2 different shoes to rotate between each day)

• Museo Correr: large collection of artifacts from Venice and beyond. Really learned about how Venice changed from a fishing village, to a merchants paradise, to just a tourist destination over the ages.

• Doge's Palace: impressive large empty rooms with informative signs to learn about the previous government. This was a place I remember learning about in Art History and seems bigger on the inside.

🍝Lunch reservation at 1:30 La Piazza

🚶🏽‍♀️Walk across Ponte dell'Accademia

☕️Stop for espresso along the Grand Canal with an amazing view. Here are the coordinates since this is the patio since I couldn't remember the name. (my parents went back to the room for a nap)

• Basilica Della Salute: another beautiful church but this one has a circular floorplan and a gold Papal throne for the priest, dedicated to St. Pius X, a former Patriarch of Venice. & yes e really enjoyed trying to take a picture of each other trying to make it look like we were seated on it.

  

Don't be these types of tourists:

• Walk a little past the church to get to the end of the island and be rewarded with a beautiful view of other islands and boats criss crossing over the water then went back Hotel to freshen up

  

  

  Venice lagoon at sunset

🍝For dinner I was able to reserve our party of 6 a spot at Trattoria Al Gazzettino. Listen all pasta is better in Italy, but was this our favorite? No. But for a party of 6 somewhat last minute with a menu that had something for everyone, it was fit the bill.

📅 Day 5: Venice Exploration + Milan Spa Night

BLUF:

📍 Venice → Milan

🚆 Transit: 2.5 hrs

🧖🏽‍♀️ Evening at QC Termemilano

💡 Pro Tip: Reserve QC Terme early, perfect end-of-trip reset. Remember to back a bathing suit if you go.

Travel Log Notes:

I purposefully planned for another 1/2 day in Venice and it turned out to be the perfect amount to see and experience 5 more stops that we hadn't gotten to on our list.

Saint Marks and museum. It is pretty small but it was worth it to get to see the ceilings up close, go onto the balcony, and see the iconic ancient bronze horses that graced the Hippodrome of Constantinople ~ the 2nd or 3rd century,

Venetian arsenal : we were interested in this since they used to build ships here but we couldn't see much since it's still used by the military.

🍝Lunch at La Nuova Perla - no reservation was needed. Had a view of the canal if you sit outside.

⛴️Ferry ride from this stop: "arsenale" back to Saint Marks stop. We got to sit at the very front on this ferry and it was amazing! We loved feeling the wind on our faces and the view of Venice go by.

🛶Gondola ride: beware you will most likely need cash!

↪️If I could redo this I wouldn't spend the cash on a Gondola ride (it was about $120). It did not beat getting to sit on the front of the ferry and cost 10x more 🤑

⛴️Then we went back to the hotel to grab our bags and take the ferry to train station. Bought 1st class tickets online whilst on the ferry and only had ~1 minute to spare. We made it luckily, probably only because 1st class is near the front of the train. We got on board and put our bags down and the train started to move.

🚆4:48 Train to Milan (2.5 hour ride). Check into hotel, then take the Metro to the spa.

🛏️We chose this hotel, "B&B Hotel Milano Central Station" because it was close to Milan's main central terminal since we would need to get up early and go ot the airport. If I were to re-plan this trip I would choose one even closer!

🧖🏽‍♀️8pm reservation at QC Termemilano. Change into your bathing suit, put on a robe, and enjoy cold plunges, hot baths, saunas or steam rooms, just like the ancient Romans did. The PERFECT way to have a mini vacation from your vacation, soak up the memories, and decompress before getting back on a plane.

Afterwards we had a late night snack at Trapizzino Milano across the street from the spa.

📅 Day 6: Leaving Milan

📍 Milan → Airport

💡 Pro Tip: keep your liquid toiletries easily accessible and in a proper-sized clear bag so it's easy to pull out for security.

Travel Log Notes:

🛫Pack up, savor your last moments, go souvenir shopping, and get your butts to the airport early! It seems a bit more chaotic than traveling in the states, because of a language barrier and everything is slightly different than the states.

• There are multiple passport checks, sometimes you have to go to the gate agent before they start calling boarding groups

• 3 of 6 of us got our bags searched at the airport but luckily only added about 15 minutes to the 30 minute security line.

• Europeans really care about what size plastic bag your toiletries are in and some airports even provide the clear bag if your don't meet requirements.

• They don't typically announce your gate until 20-30 minutes before boarding. So everyone is forced to stay in a larger waiting area, find a seat at a restaurant or a lounge before heading onto your gate. Where there is typically limited food / drink options.

Marco Polo's Last Will & Testament designates only women as universal heirs; his wife & 2 daughters. He also wished to free a servant from slavery. 🤯

💌 Final Reflections

This trip reminded me of something bigger:

🕰️ How rare it is to slow down, to really use your PTO, and to share uninterrupted time with family. As adults, you can probably count the number of times you get to explore new places with people you love.

We saw beauty and learned about the sights, yes, but we also had 2-hour dinners, ferry rides where we all just stared at the mountains, and moments where time didn’t feel so fast.

That’s what I’m bringing home: the magic of shared wonder, and the importance of pressing pause. Also, the food in southern Italy was better. I said what I said, it's my truth!

If you’re considering a similar journey, embrace the challenge of efficient travel and make the most of your time in these amazing cities. Check out my Travel Log; it's an all in one planner / journal! Or checkout my Free Travel Bingo

Have you been to Italy in the winter?

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P.S. You may have noticed we didn't get to visit 1 of the main attractions of Milan. Lesson learned: book your tickets for The Last Supper Viewings months in advance! They open up the website for future tickets every 3 months. We tried to book it about 2 weeks in advance and none of the time slots worked, or there weren't availabilities for all 6 of us.