City Essentials: First Day • 3 hours 5.0
(251)

Kickstart your trip to Milan

Pizza, pastries, and picnics – yes, please! Castles, cathedrals, and cobbled cafes

Don't forget to bring a compact umbrella as it can quickly turn from a blue-sky morning to a rainy, drizzly afternoon with little warning.

What makes this experience special

Key highlights

  • Find your feet and learn to navigate your way through the bustling streets of Milan
  • Learn how to use public transport and avoid any potential first-day hiccups
  • See the most famous attractions in the city center, and those off the beaten track
  • Get insider tips and tricks from your local host – like where to find the best restaurants in the city!
  • Taste some of the city’s most popular food, whether you grab a quick bite at a cafe or settle in for sunset aperitivo

What to know before you go

Here’s everything you need to know before your day unfolds.

3 hours
Fully tailored to your preferences
English Other languages may be requested

What’s included

A private and personalized experience
3 hours with a Host
Walking experience
Hotel meet-up (available on request for central location)

What’s not included

Food and drinks
Tickets to any attractions
Transportation costs
Gratuities (optional)

Meeting point

Your hotel/apartment or any other central location

Cancellation

Free cancellation up to 24 hours before the experience

What to bring

  • We recommend wearing comfortable shoes and carrying a light bag for your essentials.
  • Public transport may be used during the experience - please bring a travel card or small amount of cash for fares.

How your day could unfold

A flexible, unscripted experience designed entirely around your interests. Your host will adapt the day based on what excites you most

What you’ll do

In Milan, the city that needs no introduction, you’ll get, well... a pretty great introduction! Think of it as a crash course in all things Milanese from your knowledgeable host, from learning how to navigate the city’s network of buses and trams to discovering the best local haunts for sunset aperitivo and a perfectly prepared risotto. You’ll weave through the backstreets of the city’s central districts, making mental notes of where to stop off again tomorrow, and even squeeze in some sightseeing – landmarks like Sforza Castle and Duomo di Milano cathedral are along the way! When you’re feeling snacky, grab an opportunity to pop into a cafe and ask your host any questions you might have over an extra-strong espresso. 

1. Select a date
2. Select start time
3. Tailor your experience
Answer a few quick questions to help your host craft the perfect day tailored to you.
1. What’s your preferred hosting style?
2. How would you like the pace of your day?
3. What’s your walking comfort level?
4. Are you celebrating something special?

Real Stories, Real Connections

See our hosts and guests creating memories

Roberta_Perandini_Milan_BR-1246925233

Roberta_Perandini_Milan_BR-1246925233

Joyful Trio Exploring Historic Castle Grounds

Joyful Trio Exploring Historic Castle Grounds

Capturing Moments in Front of a Majestic Estate

Capturing Moments in Front of a Majestic Estate

Cherished Moments in the Heart of History

Cherished Moments in the Heart of History

25,413+ 5-Star Reviews and Counting

Trusted and recommended by travelers worldwide, including 99% on Google and TripAdvisor.

recommended by 99% of travelers on google
recommended by 99% of travelers on tripadvisor
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Aldo Nov 2025

Silvia was absolutely amazing! She gave us the perfect mix of history and local insight — making the walking tour both memorable and meaningful. It never felt like just sightseeing; every stop had a story and a connection to Milan today. Her passion for the city really comes through, and she has a great way of keeping everyone engaged without it ever feeling rushed or rehearsed. I highly recommend Silvia to anyone looking to spend a few hours with a local who truly knows Milan — the places worth seeing, and the stories worth hearing. Five stars, without question!

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Robin Nov 2025

Daniela was a fabulous guide. She was not only extremely knowledgeable, but she very kind, personable and a lot of fun. She showed me so many interesting places and I learned so much about Milan that I never could have done on my own with the short amount of time I had in the city.

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Jennifer Nov 2025

Our guide organized the tour with no insight from our group. She was very knowledgeable of Milan and took us to all the tourist spots and other hidden spots along the way.

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Eric Nov 2025

Alex was incredibly knowledgeable about Milan and all of the places that he showed us. He was super nice and even changed our tour after he found out we had already looked at one of the places we were supposed to go. 10/10 recommend Alex and this tour!!

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Robin Oct 2025

Daniela was spectacular. She was extremely knowledgeable about so many things of Milano and I leaned so much! She was also so kind, considerate of what I wanted to do and a lot of fun! I highly recommend Daniela!

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Todd Oct 2025

We had such a wonderful time on our tour with Connie. We walked around the city and got detailed information about so many of the buildings and the history of Milan. It was a perfect tour for us to get a glimpse of Milan in our short period of time! Thank you Connie for all that wonderful things you showed us.

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