Italy Travel Guide
My husband Jared and I have wanted to go to Italy forever. So for our 20th anniversary, we made it happen. When we finally sat down to plan the trip, we originally thought Rome and a few other cities, but the more we talked about it, the more we knew we wanted something slower. We ended up with Portofino, Milan, and Lake Como, and honestly it was the perfect mix. A little of everything: relaxed resort days, museum days in the city, and some of the most beautiful scenery either of us has ever seen.
A huge part of why this trip felt so seamless was our travel agent. We worked with Wagner Bespoke (not sponsored, I am just genuinely singing their praises). Booking through our agent got us suite upgrades at every hotel plus welcome amenities at each stop. If you're doing a multi-city trip like this, book through someone who knows these properties. It makes such a difference.
Like I always do after a trip, I put together a guide of what we did, where we stayed, what we loved, and what I wore. I hope this inspires you if Italy is on your list!
Portofino
Portofino is tiny. I was genuinely stressed before we arrived, trying to figure out what we were going to do for three days in a city this small. We saw the entire village in one afternoon. And it was perfect, because the whole point of Portofino is to slow down. It's a little fishing village on the Italian Riviera—colorful buildings stacked on a hillside, boats in a harbor that looks too perfect to be real. You go there to be there, not to sightsee. It was so nice to just lay by the pool and relax.
Our Hotel
Splendido, A Belmond Hotel
Now, I am known for staying in a nice hotel because I love to take inspiration from the design and hospitality to bring that into my own work. So when I tell you that this was the best hotel I have ever stayed in, I mean that. The design is extraordinary—it was designed by one of my favorite designers, and everywhere I turned I would find a new detail I was in love with.
But what sets it apart from other beautiful hotels is the service. Every night during turndown, they left something different — a chocolate one night, face masks another. On our last night, because it was our anniversary, they drew us a bath with rose petals. The staff knew our names, asked about our days, remembered things. It felt genuinely personal in a way that is very hard to pull off at scale. The minibar was complimentary, which at this level feels right. I am still dreaming about this hotel.
Restaurants
La Terrazza (Located in the Splendido)
Elizabeth Taylor got engaged at the Splendido, and the hotel has a spaghetti dish named after her. This might have been my favorite meal of the entire trip. I say might because it's hard to choose, but there's something about the setting and the history of that dish that makes it unforgettable.
Langosteria Paraggi
Right on the water at Paraggi beach, about ten minutes from Portofino. Incredible seafood. We ate a lot of fish on this trip because we were on the coast, and as someone who usually goes for red meat, it was a refreshing change.
Things To Do
Bagni Fiore Beach Club
We had our own spot—sun beds, shade, food and drinks ordered right there. One of those afternoons that disappears faster than it should. I wish we'd had more time here. We scheduled our massages the same day, which meant we had to cut it short, so if I were doing it again I'd separate those two things.
Dior Spa, Splendido
The Splendido partnered with DIOR on their spa experience, and I am still dreaming about it. We did a couples massage and the whole thing from the products, to the setting, to the way it's designed felt incredibly special. If you're staying at the Splendido, book this.
Castello Brown
Pay the entry fee and go up to the castle. The views are incredible, and the castle itself is worth seeing. This is worth the climb.
The Lighthouse
It's a lot of steps, it's hot, you can't go inside, and the view doesn't pay off. Not worth it.
What I Wore in Portofino
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Milan
Milan has a completely different energy. It's a real city known for its fashion, design, food, and culture. Where Portofino is slow and all about the resort experience, Milan is go-go-go. It was Jared's first time, so we wanted to see as much as possible, which meant early mornings and more ground covered. The shopping alone could take days.
Where We Stayed
Four Seasons Hotel Milano
I'll be honest—after the Splendido, it was hard for anything to compete. The Four Seasons is a beautiful hotel, housed in a 15th-century convent in the middle of the fashion district. It's stunning architecturally. But the magic of the Splendido is hard to replicate. That said, the double upgrade we got through our travel agent made it feel very special, and the welcoming amenities were a nice touch.
Restaurants
La Gioia San Marco
Our first night in Milan and one of the best meals of the trip. I got a cacio e pepe with truffle that I am still thinking about. If you're in Milan, go here.
Things To Do
Duomo di Milano—Rooftop Access
One of the most beautiful buildings I have ever seen. As a designer, the level of detail is almost impossible to process in person. Get the rooftop access — walking among the spires up close is an experience you don't forget. It’s worth paying for the elevator for this because it’s so many steps.
Da Vinci's Last Supper
So worth it. We did a private group tour, which meant a guide walked us through the history and the symbolism behind the painting. There is so much in that painting that you would never notice on your own, and having someone explain it changes the whole experience. I didn't know how much meaning was packed into it. Book this in advance because it sells out far ahead.
Shopping
The fashion district, known as the Quadrilatero della Moda, is everything you'd expect with every major luxury brand. I could spend days here.
I especially love the Galleria Vittorio Emanuele II, one of the oldest shopping centers in the world, right next to the Duomo. Even if you're not shopping, the architecture alone is worth seeing.
What I Wore in Milan
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Lake Como
Lake Como is huge. I didn't realize before we arrived that it's not just one town. There's Como, Bellagio, Varenna, Moltrasio, and a dozen other little villages along the shore. Each one is its own thing. We stayed in Moltrasio, which is quieter and more removed from the crowds, and it was the right call.
Where We Stayed
Passalacqua
Named one of the best hotels in the world, and it earns it. The property is a historic villa converted into a boutique hotel with only a handful of rooms, and the whole ethos is that you're a guest in someone's home. Breakfast is served in the villa kitchen with the chef preparing everything right there. It has a charming, Downton Abbey vibe, in the best possible way.
The bathroom haunts me in a good way. The best bathroom I have ever had in a hotel. Marble everywhere, beautiful shutters, the most incredible toiletries. I loved how they carried their branding across the robes, slippers, and gift wrap. So luxurious. The mini bar was complimentary here as well. This hotel will be hard to top.
Restaurants
Restaurant Passalacqua
At a property this special, the food follows. Dinner here felt personal, beautiful, and memorable. Someone is playing the piano, and it is so charming and romantic.
Ristorante Una Finestra Sul Lago
The name means "a window on the lake." The views over the water at dinner make the whole experience.
Ristorante La Baia di Moltrasio
Right on the water in the village. A more casual night, which after a few very beautiful dinners felt like exactly the right pace.
Things To Do
Private Boat Tour
One of our favorite days of the entire trip. Our guide took us along the shore and showed us the villas, stopped at what he swore was the best gelato on the lake (he was right), and let us jump in and swim. We made it to Bellagio and explored the shops there. We had lunch in Varenna and had some of the best pizza of the trip. If you're going to do a boat tour, do a private one because the flexibility to go at your own pace is worth it.
What I Wore in Lake Como
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Final Thoughts
Portofino or Lake Como? We've debated this since getting home. My honest answer is that I'm not sure we can compare them fairly because we went to Portofino first, and there's something about arriving somewhere for the first time when you don't know what to expect. We wonder if we'd gone to Lake Como first whether that would've been the favorite. Both are equally beautiful and equally worth your time.
If you're planning something similar and want help putting together an itinerary, I cannot recommend using a travel agent enough—especially for hotels at this level. The upgrades and amenities alone made every stop feel more special than it already was.
If you end up at any of these places, send me a message on IG. I'd love to hear what you think.
