Episode Overview

The 2026 Winter Olympics are just days away, and Milan is already buzzing. But long before the medals, lights, and flags, this Italian city has been preparing in its own way—for centuries. In this episode, David and Tim explore Milan between the events: where to stay, what to eat, and how to really experience the fashion capital of Italy.

From stylish hotel rooftops to wood-fired pizzas at sunset, they share first-hand tips for exploring the city beyond the stadiums. Whether you're headed to the Games or planning a future summer trip through Northern Italy, this guide is packed with local insight.

What You’ll Hear in This Episode

Where to Stay

1. Excelsior Hotel Gallia (Luxury Collection, Marriott)
2. A favorite of David’s, this hotel features a rooftop spa with Himalayan salt rooms, a massive breakfast spread, and skyline views. It once had Maseratis as its shuttle vehicles—now it’s black vans, but still iconic.
3. Radisson Collection Palazzo Touring Club
4. Tim’s pick for elegant old-world charm with a twist—think lobby bookstores, functioning travel agencies, and travel-themed design.
5. Radisson Collection Santa Sofia
6. A bold, stylish transformation of a former insurance building. Rooftop dining and luxury finishes make this a standout stay.
7. Vico Milano
8. Chic and affordable (~€150–300 per night), this boutique hotel in the fashion district offers rooms with a story—and strong design credentials.

What to Do

1. Duomo di Milano & Galleria Vittorio Emanuele II
2. The heart of the city: Gothic grandeur meets historic shopping arcade.
3. Villa Necchi Campiglio
4. A house museum filled with vintage Milanese charm—and original Picasso and Matisse sketches hidden in the bathroom.
5. Fondazione Prada
6. An avant-garde art complex with rotating exhibitions, performance spaces, and a “Haunted House” wrapped in 24-karat gold.
7. Naviglio Grande District
8. Canals, cobblestones, and aperitivo hour—this area comes alive at night with trattorias, studios, and great people-watching.
9. DMAG Fashion Outlet
10. For fashion fans (or just the fashion-curious), this off-season designer outlet is part shopping destination, part street-style theater.

Where to Eat

1. Dedici Gaddi Rooftop Pizzeria
2. David’s can’t-miss: Located above the Galleria, this sunset pizza spot offers unbeatable views of the Duomo—and some of the best wood-fired pies in the city.
3. Issei Rooftop (Santa Sofia Hotel)
4. Tim’s pick: A Peruvian-Japanese fusion speakeasy vibe, with nori tacos and sake cocktails overlooking the city skyline.
5. Peck & Piccolo Peck
6. Part gourmet grocery, part in-store bistro, this iconic food emporium is a go-to for Milanese flavors. Try the ravioli di carne pomodoro or build your own charcuterie from the deli.
7. Eataly Milano
8. The flagship location of this Italian food hall chain, offering classes, groceries, and restaurants under one massive roof.

Can’t Miss

1. Dedici Gaddi Pizzeria – Sunset pizza and Negronis with views of Milan’s most famous cathedral.
2. Villa Necchi Campiglio – A rare peek into Milanese aristocratic life, and yes, the Picasso bathroom is real.
3. DMAG Fashion Outlet – Where locals hunt for designer deals—and where the people-watching is just as good as the shopping.
4. Olympic Atmosphere – Even without tickets, Milan during the Games will be full of free concerts, pop-ups, and global energy.

Olympic Tips

1. You don’t need a ticket to experience the excitement. Sponsor activations, concerts, and cultural events will fill the city.
2. Milan is a gateway to Northern Italy: Lake Como, Venice, the Alps, and even southern France are just a few hours away.
3. Book early—but don’t rule out last-minute deals. Sometimes supply ends up outpacing demand.

Listen & Subscribe

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