Yes, I’ve been to Italy 5 times. No, it does not ever get old.

Where To Stay

Villa D’Este

If you’ve ever been on Pinterest, you’ve seen photos of the ultra-glamorous Villa D’ Este. Just like the moodboard-inspired photos, the stunning hotel sprawls across an expansive estate, manicured to perfection. They take the saying “no leaf unturned” to a new level. When you arrive at this iconic pied-a-terre, you’ll be greeted with smiling bell-hops donned in white gloves. The property itself is old, but they’ve maintained the building’s natural foundation externally. Once you step inside, though, there’s no question – you’re in a five-star, glitzy, upper-echelon establishment. Kourtney Kardashian and Travis Barker were guests of the hotel the week before we arrived. I guess it’s safe to assume that their people have vetted out the location sufficiently: If it’s good enough for Mason, it’s good enough for me!

Mandarin Oriental

Situated above the coastline of Lake Como, The Mandarin Oriental stands tall above the rest of the surrounding establishments. You can see it from just about any angle if you’re along the water. In the center of the hotel sits a 19th Century Villa Roccabruna which has been maintained and skillfully renovated with Italy’s charm and subtleties of oriental design. They proudly tout that their spa is the largest spa on Lake Como. Dine at L’aria to get that picture-perfect meal like your favorite influencers.

Armani Hotel – Milan

This ultra-sleek hotel is right in the heart of Milan. It’s the perfect place to hang up your (Louboutin) boots for the night. if you’re looking to be quasi-located, but still, feel like you’ve got some privacy, be sure to check into a room with a balcony, so you can peek out onto the locals during your stay. The hotel itself is modern and sexy, but in the “I’m not even trying,” way. The in-room amenities will make you nerd out, like the sound systems in the shower. If you’re not technologically savvy, this hotel isn’t for you.

Where To Eat

Villa D’Este

VDE offers a whopping six dining options on the property.

The Sundeck is where we had our first lunch on that trip, and my God, one glass of wine and a glance up at the glistening lake, your jetlag is gone. Be sure to put in your food orders before you’re actually hungry, though. It may take a while to get your food, but you’ll forget you even ordered it after you take a dip in the pool.

The Veranda is a more formal dining setting, but be sure to sit outside for lunch. The entire seating area is littered with glamorous couples who are on their honeymoon, families with tiny perfect kids, and then there was us. We were there for a wedding, and most of the wedding attendees stayed at VDE, so there was much fun to be had. We certainly had a laugh or two here.

Canova Bar

This is the perfect setting for your rowdy nightcaps with friends. Yes, you might be the only people in there after 9 pm, but that makes it even more fun. The bartenders will be cheeky and play mixologist if you’re nice. Mostly, this is where you go when you’re too tired to go anywhere else but too rowdy to call it a night.

Giacomo Arengario

Described as a “Designer Italian spot for bistro fare,” Giacomo Arengario is without a doubt, a must for your next trip to Milan. Yeah, I had a breakup there, but it seemed like everyone else was really enjoying their meal. Even if your tears do fall into your plate of freshly made Risotto Alla Milanese, between the decadent saffron and the breathtaking view of the Duomo di Milano you won’t even notice. If you’re looking to snap an envy-worthy Insta, take it here. Just wipe your tears first.

Paper Moon Milan

This restaurant was posed to me as Milan’s “Sexiest Restaurant” by a friend of mine. At first, I thought he was kidding, because truthfully, when any New Yorker says something is “sexy,” it could be left open to interpretation. Alas, I must concede, because he was right. After losing yourself in the cobblestone streets of Milan, if you’re lucky, you might stumble upon Papermoon, which is tucked into a quiet cul de sac along the bustling streets of Milan. The hostess will lead you to the back, where you’ll sip on Negronis amongst the trees, and devour Cacio e Pepe and luxuriant Italian homages that will make you see stars. It is a difficult table to book, so be sure to make this reservation in advance.

What To Do

Take a Boat to Bellagio

If you’re staying at Villa D’Este, be sure to ask the concierge to lend you a boat for the day – they’ll do it. If you don’t want to operate a motor vehicle, take a guided tour to Bellagio. We took the tour so we could enjoy an Aperol Spritz or two while we took in the scenery that is, Lake Como. If you’re with a guide, they’ll be sure to point out where they filmed “House of Gucci,” Richard Branson’s massive estate, and even George Clooney’s ‘humble abode’. Plan to take the day to walk around the shops of’s an hour boat ride there and back – make the most of your time on land!

Walk Through The Gardens, Villa D’ Este, Tivoli

As I mentioned before, Villa De’ Este’s property is one of the most beautiful landscapes I’ve ever seen, and I should know, my dad is a botanist. When you’re looking for a moment of serenity, or romance, grab your partner’s hand and go for a long walk through the ethereal 10-hectare gardens. Don’t be afraid to literally stop and smell the roses.

Treat Yourself

One of the many things Villa D’Este has to offer is a fantastic spa treatment menu. If you pride yourself on being a spa connoisseur, you won’t be disappointed. Those small Italian women may look relatively subdued, but you’ll quickly learn just how strong they are. It should be noted that VDE has been accredited as being one of the world’s best luxury hotels. They might know what they’re doing.