Highlights From Our Trip to Milan and Venice, Italy

A few weeks ago, I returned home from a trip to Italy. My visit didn’t go quite as I planned and I had to head home early. (More about that here.) However, I thought it would be helpful to share our Milan and Venice itinerary here on the blog in case you have your own trip to Italy planned.

Our Milan and Venice Itinerary

Our Milan and Venice itinerary

I planned this group vacation with the help of Trova Trip, so everything we did was organized by them. We had a group of 14 women and it was nice knowing that everything was already planned for us. Not only was our itinerary planned, but we had a guide, Vincenzo, to lead us every step of the way. We could just show up and have fun!

Our Milan and Venice itinerary

If you’re planning your own trip, the DIY way, I’m hopeful that today’s blog post will give you some ideas on what to do during your visit so you can fill your days with activities that interest you!

2 Days in Milan

Exploring the city of Milan

Accommodations: We stayed at the DoubleTree by Hilton, on the outskirts of Milan. It was a very nice hotel with spacious (for Europe) rooms. However, it was a bit too far from town and we had to take cabs to get to all of the action. I would recommend finding a hotel closer to the center of the city.

Meeting my amazing group of friends
  • I’m sure seeing the Duomo di Milano will be at the top of your list. It’s ginormous, beautiful, and over 600 years old! We didn’t tour it as a group, but one of our travelers braved the long line and loved her experience touring this magnificent icon, especially the rooftop.
  • Next to the Duomo, you’ll find lots of luxury shopping including the gorgeous Galleria Vittorio Emanuel II. We also visited the Rinascente which was multiple floors of shopping. We even had lunch here one afternoon and we could see the Duomo from our table.
Going through the park
  • We did lots of walking around Milan (it’s a big city!) and walked through the Castello Sforzesco di Milano, a medieval castle, and through Sempione Park. It reminded me of Central Park – a large gorgeous park right in the middle of the city.
Exploring the city via bike
Exploring the city of Milan by bike
  • On our second day, we explored the entire city by bike. I highly recommend doing a bike tour! The city is so large and it can be hard to explore it all by foot. We had an amazing guide who took us through so many neighborhoods around the city. This was my favorite part of our Milan trip.
  • Breakfast each morning was a big buffet, with European and American favorites on the menu, provided by the hotel.
Our delicious dinner in Milan
  • Il Tavolino: We had a wonderful group dinner here, with delicious pizza and wine.
  • Cantina della Vetta: Here, we not only had a delicious Italian meal, with lots of courses and lots of wine, but the chef gave us a cooking demonstration. We learned how to make risotto and veal cutlets.
Checking out the Brera neighborhood in Milan
  • The Brera neighborhood ended up being the group’s favorite area to dine, with lots of non-touristy restaurants and outdoor dining options. Imagine cobblestone streets, bistro tables, and people-watching…yes, please!

1 Day at Lake Como

Our group visiting Lake Como

Lake Como is only about 45 minutes from Milan and we journeyed by bus to this magical destination.

Our Milan and Venice itinerary included a trip to Lake Como

Whoa, I can’t even describe the beauty! Just imagine a glistening lake with picturesque little towns surrounding it.

Dining in Bellagio

We had a walking tour of the town of Como and then we traveled to Bellagio by boat. This was just about the cutest town you ever did see, with lots of shopping, restaurants, and breathtaking views of the lake. Most of our group enjoyed shopping and eating, but one of the ladies took the time to walk to a beautiful park above the city, where she was surrounded by beautiful plants, walkways and panoramic views.

exploring the gorgeous town of Bellagio

I wish we had more time in Lake Como because it was such a magical place! Someday, I’d love to return.

As you read a few weeks ago, at this point of the trip, I had to head home. My mom and the rest of the group continued on and had the most amazing time in Venice.

I’ll let my mom, Jan, take it from here!

Journey to Venice

Journey to venice

We boarded a big, luxury bus early in the morning and headed to Tenute la Montina, in the wine region of Franciacorta, where a local family has made the most delicious sparkling wines for generations. One of the owners gave us a tour of their operation, explaining each step in great detail. We saw the complete process of winemaking, from the crushing of the grapes, to the bottling of the sparkling wine.

Wine tasting in Venice

After we explored the gorgeous grounds and completed our tour, we were treated to a wine tasting, which included a lovely snack of bread, prosciutto, and cheese. We compared two of the La Montina sparkling wines and the owner kept pouring and pouring. Needless to say, it was a fun afternoon!

Wine tasting in venice

We piled back in the bus and most of us took the opportunity to enjoy a little snooze on our two-hour ride to Venice.

2 Days in Venice

Our Milan and Venice itinerary

Our bus took us to the outskirts of Venice, where we met two water taxis that took our group and our luggage across the lagoon and into the canals of Venice. None of our group had ever been to Venice, so we were all surprised that travel by boat is not just an option for travel, but the only option for travel in Venice. There are absolutely no cars in the city.

Our Milan and Venice itinerary

Accommodations: We stayed at the Hotel Carlton on the Grand Canal which is a very old, but elegant hotel on the main canal. The rooms were smaller than the DoubleTree in Milan, but they had an old-world elegance to them. The hotel has a rooftop bar that overlooks the canal and we all enjoyed hanging out there. The only complaint about the hotel is that the location is at the far end of the Grand Canal, as far from the center of Venice, St. Mark’s Square, as possible. What that meant is that we either had a long, meandering walk over lots of bridges or a water taxi ride to take us from our hotel to St. Mark’s Square. If I were to have the opportunity to go to Venice again, I would probably find accommodations that are closer to the square.

Seeing the sights in Venice, Italy
  • Guided tour of Venice: We spent a couple of hours with our knowledgeable tour guide, Michael. He took us all around St. Mark’s Square, explaining the history of the city and pointing out the various churches, buildings, and historical sites. We learned so much from Michael, like the fact that Venice is actually built on 118 small, man-made islands, with more than 400 bridges connecting them. I highly suggest finding a competent guide if you decide to visit Venice. There is so much history here and it’s helpful to tap into the knowledge of an expert.
A gondola ride in Venice
  • Gondola ride – No trip to Venice would be complete without a gondola ride through the canals. The gondoliers, with their striped shirts, straw hats, and long oars, expertly guide the traditional boats through the narrow canals for an up-close view of the city.
Exploring Venice
  • Islands of Venice boat tour – Our group embarked on a half-day tour of two of the three major islands of Venice. We stopped in Murano first and watched a demonstration of glass blowing, an art that has been passed down from generation to generation. After the demonstration, we had the opportunity to meander through rooms full of beautiful glass pieces for sale. Our second stop on this tour was on the island of Burano. This island is known for its colorful buildings and cute shops featuring locally made lace. We all wished we had had a little more time to explore this lovely place.
  • Guided nighttime tour of St. Mark’s Basilica – A couple of ladies in our group decided to do this tour on their own and they loved it, describing it as “spectacular”.
  • Harry’s Bar – A few of us made our way to this local bar, which is famous for inventing the drink, the Bellini. The bar, itself, is a very small cramped space, packed with people who all have the same idea. The Bellini was quite delicious, but a tad overpriced if you ask me. 22 Euro for one small drink seemed a little steep, but when in Venice…
Trip to Venice, Italy
  • Once again, breakfast was included in our stay and provided by the hotel.
  • Trattoria alla Rivetta: When we were in Bellagio, we met an American who gave us a recommendation for this restaurant, his favorite. Our whole group went to dinner there the first night in Venice and it was wonderful. Great pasta and delicious wines, along with great service!
  • Osteria Ae Scoste: We chose this restaurant for lunch on the spur of the moment and we all loved it. We were treated to wonderful pasta, amazing calamari, and again, lots of great wine.
  • Da Bruno: This is where we had our farewell dinner, the last night before our departure. We were treated to delicious lasagna, chicken, spinach, and tiramisu. And of course, more wine!

One of the best parts of this trip was the fact that we had lots of scheduled activities that we all did together, but we also had plenty of free time, as well. That meant that the people who were interested in history could take extra tours and explore on their own. It also meant that others could spend time shopping, wine tasting, meandering down small walkways to take photos, and observing local people in their home city.

And finally… Who would imagine that a trip to the airport to head back to the US would be worthy of mentioning? Well, when in Venice, a trip to the airport means a ride in a water taxi, which made our send-off seem extra special. It was our last opportunity to take pictures and admire this amazing city and we made the most of it. I wonder how many other airports have a dock for their passengers’ arrival?

Our Special Group

Our amazing group of women in Italy

Casey here. I can’t finish this post without a shout-out to our amazing group of travelers. You can be at the coolest place in the world, but if you’re with the wrong people, your trip isn’t quite the same. All of these women signed up for this trip without really knowing me in person and I now consider each and every one of them a friend. We had a phenomenal group of easygoing women who were down for anything!

Our group of women in Italy

One of the women has two teenagers at home and said she is always talking to them about being safe and not talking to strangers on the internet. She said she couldn’t possibly tell them that she was heading to Italy with people she met on the Internet. Ha! We all got a kick out of that one! But, in all seriousness, I’m so grateful for this group and especially their support when I had to leave our vacation a few days early. I’m not quite ready to leave our time zone right now, but when I do, I would love to do it with this group again!

More to Come

What to wear on an april trip to italy

I have one more Italy post for you. This one will dive deep into what to pack for a trip to Italy in the springtime. I even polled our entire group to get their #1 items that they brought and I got some really great answers. Stay tuned for that…

Check Out More Italy Posts

In the meantime, here are some posts from my previous trip to Italy…


The Year of Casey

Hey there!

I’m Casey Finn, the voice behind The DIY Playbook. I’m a Chicago gal teaching you how to design, DIY, and maintain your home…by yourself! Learn more about me right here.