Before We Dive In…A Few Words about Flight Prices

For summer flights to Europe, when flying Economy, $1500+ per person is the new $800 per person. I know it seems crazy. And yes, sometimes you can do it for less. But…assume $1500+ per person.

Also remember you don’t have to fly in/out of the same airport. Sometimes a roundtrip into/out of Rome is a false economy if you are ending in Lake Como or Amalfi. (Sure, the roundtrip might be cheaper but you still have to pay for trains, transfers, an a repositioning night in Rome for your flight home.) Try flying home from Milan or Naples instead!

If you are looking for really great flight prices, you almost have to let the flight prices dictate your holiday destination. Search Google Flights for flights to Anywhere. Also consider subscribing to Going (the old Scott’s Cheap Flights).

And then remember, there’s also my service Point.me that can help you maximize your frequent flyer miles and credit card points.

Now Let’s Talk Milan…

Milan gets a bad reputation. Ask most travelers and they'll tell you two days is plenty, maybe less. They're mostly wrong — but I get it. Most people fly in, see the Duomo, wander for an afternoon, and take the first train out. They miss the city entirely.

I was just in Milan the other week, brushing up on all things Milanese (including the risotto) and here’s how I would recommend spending your time…

Book the Last Supper before you book anything else (this is where I come in)

The Last Supper is non-negotiable — Leonardo's fresco inside Santa Maria delle Grazie, viewed in 15-minute timed entries. Tickets sell out months out, so book this before you book your hotel. (My guide, when I was there in August, told me they were pretty much sold out through December.)

This is exactly the kind of thing I exist for. Between waitlists, resale sites, and third-party markups, trying to book the Last Supper yourself six months out — while also juggling flights, hotels, and everything else — is a genuine headache. I secure this along with other private, skip-the-line, and after-hours experiences across Milan and Lake Como that you simply can't book on your own once the calendar fills up. Beyond the Last Supper, the Pinacoteca di Brera holds one of Italy's best collections and draws a fraction of the crowds you'll fight in Rome or Florence — and I can arrange a private guide there too, if you want the context behind the art instead of just the walls. Ready to talk private touring in Milan? Book a complimentary vacation consultation here

Shop like you mean it

Start at the Galleria Vittorio Emanuele II, the glass-domed 19th-century arcade linking the Duomo to La Scala. It's less a shopping center and more a cathedral to commerce — mosaic floors, Prada's original flagship, over a century of Milanese history under one roof.

From there, walk to Via Montenapoleone. This is the street: Armani, Gucci, Versace, Prada, every Italian house you've heard of and a few you haven't, anchoring the Quadrilatero della Moda. Have a plan. Window shopping here turns into real shopping fast.

Have a spritz or two

While you're under the glass dome of the Galleria, stop for a spritz. Camparino in the Galleria has been pouring drinks on that corner since 1867 — order the Campari, obviously. Sivini, a few steps over, is the quieter option with the same view and less of a wait. (Along with very nattily dressed servers.) Either one works as a break between shopping and everything else on the list. (Aperol Spritz is the spritz of Venice. Campari Spritz is the spritz of Milan. Personally, this bitter orange is not for me but when in Milan…or Venice…)

Hang out in Brera

Brera is Milan's quiet side — cobblestone streets, no cars, and an art-school energy that comes from the Accademia di Brera at its center. The Pinacoteca di Brera anchors the neighborhood, with Caravaggio and Raphael on the walls and a fraction of the crowds you'd fight in Florence or Rome. Wander Via Fiori Chiari and Via Madonnina for antique dealers and small design shops, then stay for aperitivo — Brera's bars spill onto the sidewalks and the whole district turns into an outdoor living room, without Navigli's crowds.

Eat where Milan actually eats

Skip the trattorias circling the Duomo and head to Navigli. The canal district wakes up at aperitivo hour — a Negroni arrives with a full spread of snacks, and the whole neighborhood exhales after work.

I did a food tour through Navigli and it's one of the best few hours I've spent in this city. A local guide, five or six stops, and more risotto Milanese and bone marrow than I could finish. If you want the neighborhood explained rather than just walked through, this is where I come in. If you’re a foodie, I can set you up with a private foodie guide to help you experience Milan like the locals do.

AI made me this image of Milan taxis in Milan. Milan taxis are fantastically well-run.

Getting around Milan

I used to go to Milan for work back when I worked in the investment management industry, and I was always so impressed by the taxi system. It’s still just as fantastic. You can ask any hotel or restaurant to call you a cab and they will hand you a little ticket with the approximate arrival time of your cab, along with the name and number of your driver. Alternatively, head to a taxi rank (they're all over the city center) or book through IT Taxi or appTaxi. You can also book city cabs via Uber but my friends in Milan explained that taxis are more likely to cancel when booked via Uber as Uber takes a larger cut of revenue.

Where to stay in Milan

I'm a Virtuoso advisor, and all three of these Milan properties are Virtuoso hotels — which means when you book through me, I can typically add room upgrades, resort or spa credit, daily breakfast, and early check-in/late check-out, at no extra cost to you.

Four Seasons Hotel Milano — a 15th-century convent turned hotel, steps from the fashion houses on Montenapoleone. As a Four Seasons Preferred Partner, I can add room upgrades, resort credit, and daily breakfast for two.

Mandarin Oriental, Milan — four connected 18th-century buildings near La Scala, home to one of the city's most complete spas.

Park Hyatt Milano — the closest of the three to the Galleria, with the Duomo practically at the door.

Lake Como

Twenty-five minutes from Milan, and it feels like a different country. Como is drama — mountains dropping straight into water, villas that have been hosting the same families for four hundred years, ferries crisscrossing between towns that all claim to be the prettiest. Plus, cooler air in summer!

Now I want to be clear…Lake Como is very chill. It’s great if you like a boat ride. But if you are looking for museums and nightlife, this is not the place for you. It’s more a relaxing (but crowded) end to your summer vacation. It’s great if you want to just hunker down at a 5 star hotel.

Where to Stay in Lake Como

As with Milan, all four of these are Virtuoso properties — booking through me means upgrades, credits, and perks that you won't get booking direct. Ready to talk about Lake Como hotels? Book a complimentary vacation consultation here

Passalacqua (Moltrasio) is the one everyone's talking about — a restored 18th-century villa with a lake-view infinity pool and only 24 rooms. Book it if you want the property to be the destination. Best for: clients who want the most talked-about hotel in Italy right now.

Mandarin Oriental, Lago di Como (Blevio) has the most reliable service of the group — a real asset if this is your client's only Como stop and everything needs to run smoothly. Best for: first-time-to-Como travelers who want zero surprises.

Grand Hotel Tremezzo (Tremezzo) is the classic — floating pool, Bellagio views across the water, old-school glamour. This is the property for clients who want the postcard. This is the property for clients who want the postcard. Best for: romantic getaways and anniversary stays.

Grand Hotel Villa Serbelloni (Bellagio) puts you in the town itself, cobblestones and gelato outside your door, with the private beach and gardens to retreat to when the crowds show up. Best for: travelers who want to walk out the door into an actual town, not just a lakefront estate.

Getting Around Lake Como

Most people assume the train is the way to see Como — it isn't. The train gets you to Como town; it doesn't get you to Bellagio, Varenna, or any of the villas tucked along the water, and once you're there, connections between towns mean ferry schedules and walks from the station.

A vetted private driver solves this entirely. Door-to-door between Milan and your hotel, then on call for day trips to Bellagio, Varenna, or across to Villa del Balbianello — no schedules, no transfers, no lugging bags down to a dock. For a lake built around water, most of your best days are actually spent on it — but the driver is what gets you there and back without losing half the day to logistics. This is where I can be of tremendous help to your trip. I’ll make it all seamless for you.

And if you want the trip to feel seamless from the moment you land, I can also arrange VIP meet-and-greet service at Milan's airport — someone waiting at the gate to walk you through passport control and straight to your driver, no lines, no lost time

Other Ways to Experience the Lake Como Area

There's more than one way to do this lake, and honestly, that's where I earn my keep — figuring out which version of Como actually fits the trip you're building, not just the one that's easiest to book.

Many river cruise lines add Lake Como as a pre- or post-cruise extension, and it can be a smart value play if you're already booked on a cruise — I can tell you which lines make this seamless and which ones leave you scrambling for transfers. If you're into the outdoors, Backroads also has a fun walking and hiking tour of the region, great for clients who want to move through Como rather than just sit and look at it. Lake Garda can give you Como vibes without the Como price tag. If you are up for a group tour, CIE Tours has a great itinerary that covers this part of the world.

None of these is a one-size-fits-all answer, which is exactly why it's worth a conversation instead of a checklist. Tell me what you're picturing — a quiet week at one villa, a whirlwind through three towns, a hiking trip, a group celebration — and I'll tell you which version of Como gets you there.

Ready to Plan Your Trip to Milan and Lake Como?

Want me to build this itinerary for you? Everything above — the Last Supper tickets before they disappear, the Virtuoso upgrades at Passalacqua or the Four Seasons, the private driver who knows Como's back roads, the food tour that actually gets you into Navigli's kitchens — is the kind of thing that's a lot harder to pull off on your own than it looks from the outside. It's also exactly what I do for a living. Let’s talk all things Italy! Tell me your dates, your must-haves, and your must-nots, and I'll build you a Milan-and-Como itinerary that's built around how you actually want to travel — not a template. Let's make it happen. Book a complimentary vacation consultation here

About Krista

I’m a Virtuoso travel advisor based in Palm Beach, Florida. I attended the University of Notre Dame for undergrad and I have my MBA from the University of Chicago. Before building my travel business, I spent 20 years in the investment management industry and over a decade living and working in London, England. I’ve personally traveled to 80+ countries and now design thoughtful, highly customized trips for travelers who value expertise, access, and a seamless experience.

I offer a complimentary 30-minute consultation for travelers considering a custom itinerary or luxury cruise. Book a complimentary vacation consultation here.

For travel inspiration and real-time updates, you can follow along on Instagram or connect with me on Facebook. I also share a curated list of travel products I genuinely use and recommend in my online Amazon store.

What I Offer…

Custom itinerary design for complex, multi-stop trips
VIP hotel benefits through Virtuoso and preferred partner programs (including complimentary breakfast, hotel credits, and priority for upgrades where available)
Luxury ocean, river, and expedition cruises with added onboard credits
Vetted villa rentals with concierge services worldwide
Private guides, small-group touring, and unique local experiences
Private aviation and yacht charters through trusted partners
Airport transfers, VIP arrival and departure services, and full ground logistics
Travel protection and support when plans change

I work best with travelers who want expert planning, trusted partnerships, and someone in their corner from start to finish. That’s what I am best at! Ready to talk travel? Book a complimentary vacation consultation here.

Milan and Lake Como, Done Right