City Essentials: First Day • 3 hours 5.0
(238)

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

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Trenton Oct 2025

Silvia was a special guide. She made a great itinerary for a two hour tour based on things we wanted to see and do. She was very clear with communication and directions on how to meet her from our hotel. As soon as we met her, it felt like we were meeting up/visiting with a friend. At the end of the tour, she walked us to our tram stop so we could head to a cooking class. When it looked like we would be late due to a delayed tram, she called the restaurant to notify them that we would be late. Additionally, as she was familiar with Como, she found us a parking garage near our upcoming boat tour. Thankful she went above and beyond to help us feel comfortable our first day in the city. Thanks for a fabulous time!

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Dale Oct 2025

Lisa is an excellent guide and sensitive to our needs. We appreciate her expertise and knowledge. We highly recommend Lisa!

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Kelly Oct 2025

Lisa was a wonderful guide!!! She provided us with the best highlights on our 2 hour tour and was so knowledgeable!!! Highly recommend!

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Dale Oct 2025

Lisa is professional, thoughtful and insightful. We thoroughly enjoyed our experience with Lisa in Milan

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Joanna Oct 2025

Massimo was excellent! I would recommend

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Kathy Oct 2025

This was a fantastic tour. Bibi was extremely knowledgeable and friendly. She met us at our hotel and planned a 3 hour tour that took us to many hidden gems we would have never seen. Her enthusiasm was refreshing and she hit the spots of our interest and gave us many recommendations for shopping and dining.

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