Just Back From

Just Back From: Rediscovering the Magic of Italy

For her first international trip since 2020, Indagare’s Madeline Case traveled to Italy, one of her longtime favorite destinations. During her two weeks experiencing la dolce vita, she ventured from the shores of Lake Como to the coast of Tuscany, stopping in Florence and the countryside along the way. If there’s one thing you take away from this article, know this—Italy is back. Long gone are the days of having the Colosseum essentially to yourself, as the country braces for a tourism boom after two years of relative quiet. It’s easy to read that sentence and immediately groan, imagining the hordes of tourists, but the truth is, now is an excellent time to visit Italy, one of Indagare’s top-booked destinations. The energy isn’t anxiety or trepidation, but rather earnest excitement, as if the whole country has been waiting behind the couch to jump out and yell “surprise!” as you walk through the door.At one hotel in Florence, a new employee donned a pin reading “I’m in training and I’m trying my best.” I kept that sentiment with me throughout my travels, reminding myself to approach this year of travel with patience and compassion. Everywhere I went across Italy, from Lake Como to Tuscany, I was met with warm Italian hospitality that we know and love, and a sense of anticipation and eagerness for what’s to come.Contact Indagare or your Indagare Trip Designer to start planning a trip to Italy. Our team can match you with the accommodations, reservations and activities that are right for you.

A Lake Como Favorite (and its New Sister Property)


I started my saga in Lake Como at the iconic Grand Hotel Tremezzo. The storied Italian lake’s reputation speaks for itself, and yet even with all of the fanfare surrounding the destination, nothing could quite prepare me for the ultimate wow that the natural landscape of the region provides. Yes, the historic glitz and glamour of the hotels alone justifies a visit, but the splendor of the lake—with steep, green pre-Alpine slopes rising from its shores—is a wonder to behold.

The highlight was getting a sneak peak at Grand Hotel Tremezzo’s new sister property, Passalacqua. A true labor of love from owner Valentina De Santis and her family, the newcomer already feels like it’s been an establishment on the lake for decades. And in some ways, it has: it’s inside an immaculately restored 18th-century villa that once welcomed the likes of Napoleon and Churchill. De Santis and her family have left no stone unturned in designing the hotel—everything from the gorgeous art collection to the custom-designed pool umbrellas has their fingerprints on it.

Passalacqua offers a different experience from Tremezzo and the other Lake Como properties like Villa D’Este or Mandarin Oriental, Lago di Como. At only 24 rooms and suites, spread across three buildings and five acres of land, the hotel masterfully strikes the balance between elegant and cozy, making good on De Santis’s promise that guests will feel like they’re staying in a home rather than a hotel. There are seemingly endless gardens and grounds for guests to explore and relax in while soaking up the views of the iconic lake. Without spoiling all the surprises, take note—the stunning bones of the property combined with the De Santis family’s impeccable taste makes for a hotel that you’ll be dreaming of long after you check out.

Falling for Florence

Moving south to Florence, I thought it would be impossible to top my experience in the northern lakes district. And yet, as I was reminded time and time again throughout my trip, Italy will never disappoint you. Walking through the bustling historic streets, I remembered what it was like to travel pre-pandemic, bumping into kind strangers eager to share their city with incoming visitors. Some pandemic changes, though, have stuck around for the better. Enforcing timed-entry requirements for museums to reduce crowds proved to be a useful tool for managing crowds, and while the major sites were far from empty, I was able to get prime views of Michelangelo’s David and Botticelli’s Venus in the usually packed Uffizi. Art lovers and history buffs will love “Donatello: The Renaissance,” a new exhibition shared between Palazzo Strozzi and the Bargello National Museum. On view until July 31, this once-in-a-lifetime exhibit showcases Donatello’s remarkable career with more than 100 works, including sculptures, paintings and drawings. For something more contemporary, I also loved the “Archetypes,” exhibit at Gucci Garden (the fashion house’s museum, boutique and restaurant inside the historic Palazzo della Mercanzia). The show provides an immersive, multimedia deep-dive into Gucci’s recent ad campaigns from Creative Director Alessandro Michele.With a relatively quiet few years, hotels had time to think about their visions of the future, and how they want to leave their mark on their beloved city. One notable development to come out of this is The Place Firenze’s (formerly J.K Place Firenze) Place of Wonders program. To celebrate Florence’s roots as an artistic capital of the world and to support its creative future, the initiative offers exclusive guest experiences that connect them with local artisans, from ceramicists to jewelers. Proceeds go directly towards a fund that sponsors the education and apprenticeship of young local craftsmen, ensuring that these arts don’t become relics of Florentine history.

To the Tuscan Countryside


Following my cultural tour of Florence, I transitioned to the slower pace of the Tuscan countryside (with a knot growing in my stomach knowing that my time in Italy was soon coming to an end). First stop was Borgo Santo Pietro, a dreamy property planted on over 300 acres of rolling hills. I could smell the property before I saw it. Lilacs and other fragrant blooms fill the property, and they announced something that I hadn’t felt when I left New York behind a week ago: Spring had sprung. 

With only 22 rooms, the footprint of the hotel is small compared to the massive estate it inhabits. Areas to explore include the many vegetable and flower gardens—whose bounties you can find both on your plate and at the centerpiece of your table. And the floral arranging class was a surprise highlight of my visit. In the 90-minute session, I learned how to arrange and rearrange flowers until their very last day, rather than toss them aside once they look a bit wilted. The farm to table ethos of Borgo Santo Pietro is ubiquitous here, from the Seed to Skin skincare line made on property to the Michelin-starred dining experience. This is a place for people who need to be reminded to stop and smell the flowers.

My next stop in Tuscany was Rosewood Castiglion del Bosco, which overlooks the Val d'Orcia, a UNESCO World Heritage site. I was immediately struck by the variety of the Tuscany landscapes on view: Standing in one spot on Rosewood’s 5,000-acre estate, I could see vineyards, forests and golden hills, all begging to be explored. I had planned on going out to explore the charming neighboring towns of Montalcino and Pientza, but there was so much to enjoy around the property, I didn’t want to leave! Between touring the vineyards and tasting their world-renowned Brunello and exploring the forests in Castiglion del Bosco’s backyard (complete with a wild boar sighting), I barely had time to enjoy my book by one of resort’s two infinity pools, which look out over quintessential Tuscan landscapes.

The Ferragamo family was the creative force behind Rosewood Castiglion del Bosco, and the result is, unsurprisingly, a sublime balance of traditional Italian and modern. And last year, the hotel unveiled 19 new suites, bringing the total room count to 42 rooms and 11 villas. But for loyal visitors concerned the expansion would make Castiglion del Bosco too crowded, I can happily confirm the placement of the new accommodations felt so natural, it’s hard to imagine that a year ago they didn’t exist.

A Dream-worthy Coastal Escape

At this point in my trip, the inkling of homesickness started to tug at my heartstrings. I had been gone for nearly two weeks (my first international trip since the pandemic began), and I remember thinking as I packed my bags into the car leaving Castiglion del Bosco that I wished I was heading to the airport. Just one more stop, I reminded myself. Within 15 minutes of arriving at Il Pellicano, on Tuscany’s Mediterranean coast, I was ready to stay forever. Once a playground for Hollywood elite such as Charlie Chaplin and Sophia Loren, the hotel maintains the glamour of a bygone era without feeling stuffy or overly historic. It feels exclusive but homey, and it’s easy to imagine sitting at its beach club, looking over at the chair next to you, and seeing an Old Hollywood movie star. During my stay, New Hollywood was there instead: actress and director Olivia Wilde and singer Harry Styles had also checked in. There isn’t all that much to do on the small peninsula Il Pellicano calls home, but I can’t imagine wanting to do anything other than sit along that rocky coastline with a book, getting up only to cool off in the sea or order another Aperol spritz. In the month since I’ve returned, not a day has gone by where I haven’t dreamed of Il Pellicano, mentally preparing to someday return.Though I’ve worked in the travel industry for many years, and my travels have taken me across the globe multiple times over, I felt like a newborn deer finding my footing as I ventured out into the world for the first time since 2020. Everything felt doubly exciting, even things that I’d experienced before, like seeing David up close. The trip wasn’t without “hiccups,” from slower service to larger snags like being denied my rental car when I arrived in Florence (Note: Italy is now enforcing its policy of requiring international driving permits). But in a way, all of that reminded me of the joys of exploring. I had become so accustomed to a manicured, overly polished version of travel, and in this post pandemic world I was able to peek behind the curtain and see the more authentic version of all of the people and places I encountered. Not only was I reminded to practice patience and compassion towards our recovering industry, but also gratitude for being able to experience it all, even the slightly messy parts.Contact Indagare or your Indagare Trip Designer to start planning a trip to Italy. Our team can match you with the accommodations, reservations and activities that are right for you.

Published onJune 1, 2022

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