🍷 My Escape to Italy: Como, Rome, Ischia, and Amalfi Magic

Written By Krista Nannery

View from Como, the city, of the eponymous lake

But First, A Note about Black Friday Travel Deals

I learned a long time ago that there’s no such thing as a free lunch! During the Thanksgiving period, don’t get hung up on heavily promoted travel deals. You know the best time to book a trip? Way in advance! If you can plan two years in advance for a cruise (deposits are low!) or 330 days ahead for a hotel, that’s when you’re going to get the best pricing. Some exceptions apply — newer cruise lines, newer hotels, super luxury properties — which I’ll talk about next week in my newsletter. But hey, I get it, everyone wants a deal. Ready to talk to a travel professional who stares at the numbers all the time? Book a complimentary vacation consultation here.

Now, Let’s Talk about My Time in Italy

Every so often, I like to put myself in my clients’ shoes. Last month, that meant heading to Italy for a few days to test-drive an itinerary that I’d happily send to any of my travelers looking for a quick European recharge: Lake Como followed by two nights in Rome, two nights in Ischia, and two nights in Amalfi. Easy, elegant, and logistically smooth.

✈️ Arrival in Milan & Transfer to Lake Como

I flew Delta into Milan Malpensa (FLL to JFK to MXP) and was met right outside baggage claim by my driver holding a sign with my name — my favorite thing! A sleek Mercedes E-Class whisked me north to Como — just a 45 minute drive with no traffic — where I checked into the 4-star Albergo Terminus, a historic lakefront hotel with a mix of Belle Époque charm and modern polish. This hotel has new owners who are reportedly upgrading the property to a luxury 5-star in 2026 so watch this space.

I’m very pleased with this photo of Captain Mario and Hotel Tremezzo

🚤 A Private Morning on Lake Como

The next morning, I set out on a private half-day Lake Como cruise. My skipper met me at the pier near Como’s Bar Lario, and for the next few hours we glided past ornate villas, cypress-lined gardens, and sleepy lakeside villages. In Bellagio, I hopped off the boat for a cappuccino (it was still early—no cappuccinos after 11 am please!) and some retail therapy. All-in-all, a wonderful morning. My boating partner in Como operates some of the lake’s most beautiful and classic boats.

🍷 Wine Tasting in Como

That evening, I joined the Como Wine Tasting Experience — five Italian wines, each paired with regional cheeses and charcuterie. It wasn’t stuffy or pretentious; it was exactly what wine tasting should be: generous pours, good conversation, and a crash course in what makes Lombardy’s wines fascinating. If you think Italy is all about Chianti and Barolo, this tasting will set you straight.

🍴 Food Tour of Como

The next day, I took a Lake Como Food Tour. It’s one thing to walk the cobblestone streets of Como — it’s another to do it while eating your way through them. From silky prosciutto to risotto al pesce persico (local perch from the lake), I felt like I’d stumbled into a secret progressive dinner party hosted by nonnas.

🚄 South to Rome and The Hotel de Russie

After two perfect days in Como, my driver took me to Milano Centrale for the Italo high-speed train to Rome. First class, naturally — comfortable seats, Wi-Fi, and espresso on demand…as long as you can catch someone’s attention!!! (Frustrating.) Three hours later, I was stepping off the train into the chaos of Termini Station, where I was met by my trip concierge. She took my luggage and walked me out of the chaos and straight to my driver. (Honestly, this was so fantastic. So many travelers were trying to find cabs or Ubers and I didn’t have to worry about any of that.) Rome traffic was heavy, but I barely noticed as we made our way to the beautiful Hotel de Russie.

The courtyard at The Hotel de Russie

Travel isn’t always easy, and I experienced that at Hotel de Russie. A political delegation was refusing to check out of the hotel. I am not kidding when I tell you it was something like 30 rooms, all with their Do Not Disturb signs on at 3 pm. It was WEIRD. The check-in delay was so bad that the Hotel de Russie comped our late lunch and delivered us many, many treats. I was honestly so frustrated — I was still in my travel clothes and we had hotel inspections a 4 pm, 5 pm, and 6 pm. With 5 star luxury properties! So bad was the check-in delay that my colleague and I missed the first two site inspections and only had time for the last inspection at the Bvlgari Rome, which I’ll write about in the new year. BUT…as I always quote with Anthony Bourdain…

“Just be nice,” he said. “Getting angry and frustrated in much of the world doesn’t help at all. It’s incomprehensible, you lose face, it makes you look ridiculous. Have a willingness to try new stuff. Be grateful for any hospitality offered. And be flexible in your plans, because a rigid itinerary is lethal to a good time.”

Once checked-in though, the hotel was beautiful. Very very busy, but beautiful. Thank you, Hotel de Russie, for a wonderful stay.

🎨 A Busy Day in Rome

I kicked off my first full day in Rome with a walking tour and a watercolor workshop—yes, watercolor. As in—me trying to paint while surrounded by layers of ancient stone and Vespas buzzing past. I used to be very artistic but life got in the way. This was my attempt of rediscovering my artistic side. I somewhat succeeded.

That evening I took a gastronomic pasta-making class that turned into a three-hour celebration of carbs and chaos. We rolled, stuffed, and sauced our way through the classics, with a few glasses of wine to keep spirits high. Everyone should do a cooking class in Rome.

Autogrill excitement! Look at what you get for those prices!

🌊 South to Ischia

The next morning, our driver picked us up for the journey south—Rome to Ischia. Along the way, we stopped at an Autogrill and admired all the food options. (Italian rest stops are amazing.) Once in Naples, we enjoyed a quick seaside lunch. My vongole was simple and perfect.

View from my hotel room at San Montano, Ischia

Then came the ferry across the Bay of Naples to Ischia, the quieter, more local cousin of Capri. My home base was Hotel San Montano Resort & Spa, perched above the sea with views that make you question every life decision that doesn’t involve the Mediterranean.

I really loved this hotel. It has the largest spa on the island. My aesthetician didn’t speak English, but weirdly she spoke some basic German, so we got along well. (I joke that I’ve been studying German my entire life but will never be fluent. My German is about 80%. Grammatically imperfect but with a perfect accent, apparently!)

🚗 Ischia Vintage Day

If you’ve ever wanted to feel like you’re in an old Italian movie, Ischia delivers. I joined a vintage car tour that took us winding through island villages, past lemon groves and crumbling watchtowers. The cars were pure nostalgia—bright colors, loud engines, zero power steering—and we capped it off with a visit to a local wine cellar. These are the types of unique experiences that I can organize for you and yours.

Positano

🛥️ The Amalfi Coast by Boat

The next morning was straight-up cinematic. I am always a sucker for a boat cruise and this was the most amazing day. A 60 foot yacht and a full-day Amalfi Coast cruise!. We left Ischia behind as we traced the coastline past Capri, Positano, and Amalfi. Every turn revealed another postcard view—terraced lemon trees, pastel villages clinging to cliffs, and water so blue it looked fake.

We stopped for a swim and a light lunch on board (because Italy), then disembarked in Amalfi for a wander. If you’ve ever wondered whether all those Instagram photos of the Amalfi Coast are exaggerated—nope. It really is that beautiful.

That evening, we checked into a lovely hideaway at the Grand Hotel Furore, a lovely property about a 10 minute drive from Amalfi,

Villa Cimbrone, Ravello

🌸 Ravello Magic

Honestly, the weather during our only full day in Amalfi was terrible. Pouring, pouring rain. All our plans were ruined. But later in the afternoon, we headed up the mountain to Ravello, which I’d somehow never visited before. It’s one of those places that feels suspended in time—quiet and elegant. We wandered through Villa Cimbrone, which was lovely and peaceful but a little…boring. Afterwards, we met the locals (and the local cats) in the piazza for local beer and local snacks which was much more interesting. People-watching is always fun.

Romeo Naples, the most comfortable bed I’ve slept in that’s not my own! Plus great linens.

🚆 Ciao, for Now

My final morning was the usual bittersweet travel goodbye: one last espresso overlooking the coast before heading back to Naples to Hotel Romeo, right across from the cruise port. Weirdly, despite all our extravagance during this trip, the Romeo has the best bed and best linens of the entire trip. The hotel also had a great rooftop pool. It’s not in the center of things, but the hotel is great for a pre- or post-cruise stay if you are okay with taking taxis to get around.

Need hotels, experiences, train tickets, and drivers in Italy? I’m ready for you. Book a complimentary vacation consultation here.

About Krista

I’m a Virtuoso travel advisor based in West Palm Beach, Florida. I attended the University of Notre Dame for undergrad, and have my MBA from the University of Chicago. Prior to moving to Florida to take care of my elderly mom with Parkinson’s Disease, I spent over 11 years living and working in London, England. My background and 20 year career in the investment management industry have taken me all over the world. To date, I’ve been to 78 countries. Now I bring the joy of travel to others as a Virtuoso travel advisor. I offer a 30 minute complimentary vacation consultation to anyone looking to plan their next trip.

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Krista Nannery
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