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Checking In

I checked into The Fifth Avenue Hotel on a beautiful spring morning for a one-night staycation with a friend. We were attending a wine event on property that would be held in The Grand Salon and The Conservatory. The stay lasted just one night, but it lingered longer than many lengthier stays. 


Grand King Bed
Grand King Bed

The Stay

 

Set inside a landmarked mansion stitched to a modern glass tower, The Fifth Avenue Hotel in Manhattan feels less like a property and more like a stage set for beautifully dressed mischief. The design is layered, maximalist, and unapologetically dramatic. Every surface seems considered. Every object feels placed with intention, because they are. Most of the interiors were custom-made for the hotel. 


 

We had booked a City King and were upgraded to a Grand King, which came with a full room orientation from our butler, a sentence that still feels almost too indulgent to type. There was a sense that the staff truly enjoyed the theater of hospitality, as no interaction felt forced. 

 

The room itself surprised me with its size. New York hotels often require spatial compromise; this one did not. A proper wardrobe framed the entry, opening into a sitting area with a bistro table and a separate desk beyond the bed. My brain immediately started running rampant with thoughts of how to recreate this space at home. 


Grand King Sitting Area
Grand King Sitting Area

 The vibrant greens and blues gave off a jewel-box rich aesthetic with layered textiles, deep tones, lacquered finishes, and clever lighting that kept everything glowing. 

 

But what stayed with me most wasn’t the room, it wasn’t the staff, or the dining. It was how the hotel reveals itself slowly through each moment spent wandering its halls.

 

My Favorite 90 Seconds


Portrait Bar
Portrait Bar

 Sitting down with a cocktail at Portrait Bar, and glancing around the room at all of the other guests was just a moment. The wood-paneled alcove located past the elevator bank has a carved stone fireplace and walls covered in eclectic portraiture. 

 
Our phones were put away in our bags and we just giggled over cocktails like we did a decade ago when I first moved to New York. It was one of those moments that took me back to being 24 and enamored by all of the possibilities promised by the city outside.  

 

The Moments That Make It


The Conservatory
The Conservatory

 

One of the “wow” moments of our stay at The Fifth Avenue Hotel was when we were whisked into The Conservatory for a masterclass on wines from Southern Italy. The room almost seems out of place in New York City, something more like you may find in West Palm Beach. It was like stepping into the most beautiful and elaborate greenhouse I could have ever imagined. The room itself is stunning with mirrors everywhere, reflecting light, and color and making the room seem infinitely larger, with a vaulted glass ceiling, dramatically draped in white. Again, I was wondering how to recreate this feel, or what kind of party I could throw here. 

 

Dining at Café Carmellini is not to be missed. The room is full of grandeur. More vaulted ceilings, crushed velvet banquets, living trees breathing life into the center of the room, as if it needed more energy than the guests themselves bring. Starting with oysters and champagne, we settled in for a long, luxurious dinner filled with people watching and delectable bites crafted in the open kitchen. 

 

Who This Hotel Is Actually For


The Grand Salon
The Grand Salon

 This hotel is for luxury travelers who want a scene, but also one they may not have stepped foot in before. It’s for someone who appreciates art, vibrant baubles, and little details. 

 

It’s for aesthetes, romantics, celebrators, and anyone who believes the environment affects emotion. It’s ideal for milestone weekends, cultural travelers, design lovers, and couples who want their hotel to feel like part of the story. 


I found myself lingering as I strolled through each room, finding something different to be enamored by every time I walked by. The hotel gives you a sense of wonder. In a city like New York, that’s a great quality to have. 

 

Practical Stay Notes


Cafe Carmellini. Images courtesy of  Jacqueline Zonkowski
Cafe Carmellini. Images courtesy of Jacqueline Zonkowski

Visited: for a spring overnight and again in summer for dinner and drinks


Length of stay: 1 night


Room: Grand King (upgraded from City King)


View: City view


Purpose: Staycation + on-property wine event

 

Reader Takeaways


Best time to visit: It’s a 5-star stay any time of the year


Can’t-miss experience: Cocktails at Portrait Bar by the fireplace


Best for: Design lovers, romantic stays, celebration trips, cultural traveler


Nearby Points of Interest


Eleven Madison Park: The world-renowned tasting menu destination just a few blocks south, ideal for a landmark New York dining experience.


Rezdôra: A Michelin-starred favorite celebrated for its refined takes on Northern Italian cuisine, just west of the hotel.


The Morgan Library & Museum: A serene cultural gem housing rare manuscripts, rotating exhibitions, and one of the city’s most beautiful historic interiors, an easy walk north.


SVA Galleries: Showcasing contemporary exhibitions and emerging artists through the School of Visual Arts’ rotating gallery program.


Eataly Flatiron: A world-renowned Italian marketplace for espresso stops, gourmet provisions, and casual dining opposite the Flatiron Building.


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Jacqueline Zonkowski is a writer and marketing professional drawn to places, people, and experiences that linger long after the moment has passed. Her work focuses on travel, hospitality, and lifestyle storytelling with heart and intention.


Updated: 5 hours ago


Tucked away in the serene Maremma countryside, Castello di Vicarello is your escape in the heart of Tuscany that holds every amenity you could desire in a luxury boutique property. This high-end boutique hotel combines luxury, history, and nature, creating the perfect destination for your unforgettable Italian getaway. Whether you're planning a family vacation, a romantic retreat, or a special event like a wedding, Castello di Vicarello delivers a personalized and enchanting experience just for you.


Credit: Victor Fitz
Credit: Victor Fitz

Suites and Villas


At Castello di Vicarello, you can choose from ten beautifully designed suites and one villa, with a second separate villa currently under construction. Each suite offers its own unique charm, blending rustic Tuscan architecture with modern amenities such as Wi-Fi, air conditioning, and heating.



In the main house, six suites feature exposed wooden beams, stone walls, and cozy lounges. Some, like the Suite Giardino Segreto, include a private garden, while others, such as the Suite Mezzatorre, boast Italian marble bathrooms and stunning outdoor terraces.




The four garden suites give you even more privacy and comfort, with private entrances, terraces, and fireplaces. For a truly special stay, the Villa La Vedetta offers two luxurious suites, a private heated pool with a jacuzzi, and a spacious outdoor terrace.


Relax at one of the estate’s three pools, including two private infinity pools, where you can unwind and soak in the beauty of the Tuscan landscape. With the new villa on the horizon, you’ll soon have even more space for larger groups and special occasions.






Dining


At Castello di Vicarello, you’ll enjoy farm-to-table dining with organic ingredients sourced directly from the estate’s gardens and olive groves. With over 50 varieties of vegetables and 30 aromatic herbs, their chefs craft authentic Tuscan dishes that highlight the freshest local flavors. Start your day with a breakfast made from the estate’s own produce, including eggs you can collect yourself!



For lunch and dinner, choose from several memorable settings, from candlelit dinners on the castle’s grassy terrace to romantic meals in the glass verandah. La Terrazza offers breathtaking views of the Maremma countryside, and dining under the stars is a must. Whether you’re sampling small bites by the pool or indulging in a gourmet multi-course dinner, the culinary experience will be unforgettable.


You could even purchase their own wines and tasting gift boxes!



Experiences


Your stay at Castello di Vicarello goes beyond relaxation. Immerse yourself in the true essence of Tuscany with a range of unique activities. As a wine lover, you’ll appreciate guided tours of the estate’s vineyards, where you can sample award-winning wines and even participate in the grape harvest. If you’re passionate about food, their cooking classes will teach you traditional Tuscan recipes, from homemade pasta to delicious desserts.


Explore the surrounding countryside in the Tuscan Maremma with hiking, an e-bike tour, or horseback riding along private trails that weave through vineyards, forests, and olive groves. For a truly special adventure, join a truffle hunt with an experienced guide and savor the flavors of this prized Tuscan delicacy.



Ever wanted to create your own leather bag or belt? Castello di Vicarello offers a one-day leather crafting course. Guests may learn the art of Italian leather, visit the leather tannery, and create a handmade belt or simple leather bag. For those interested in creating their own bag, they offer a 2-day immersive course.



Credit: Victor Fitz
Credit: Victor Fitz

My Favorite 90 Seconds


My favorite moment at Castello di Vicarello happened almost immediately upon arrival. It was a welcome lunch set beneath a vine-covered grape pergola, overlooking the sweeping Maremman hills. The stillness, the peace, and the food. This lunch was the highlight of my trip, and some of the best Italian food I have ever tasted. Every bite was bursting with fresh, just-harvested flavor.


My guest and I shared homemade pasta and seasonal vegetables, lingering over Vicarello’s house wine as the landscape unfolded endlessly before us. This moment was an introduction to the rhythm of the estate itself, unhurried, generous, and unforgettable.



Who This Hotel Is Actually For


Castello di Vicarello is for travelers drawn to thoughtful luxury that feels intimate rather than showy: romantics, food lovers, design appreciators, and anyone seeking to slow down and truly absorb the essence of Tuscany. Spend the afternoon taking a dip in one of the estate’s infinity pools, where you can bask in the panoramic views of the valley, or unwind in the more secluded pool nestled among olive trees for complete privacy.



Nearby Points of Interest


Explore the beauty of Tuscany beyond the estate with these nearby attractions:


Siena


Visit this UNESCO World Heritage Site, famous for its medieval architecture and the Palio horse race.


Monte Argentario


Discover scenic beaches and a vibrant coastal atmosphere in this charming seaside town.


Pitigliano, Sorano, Sovana


Wander through these ancient towns, famous for their unique volcanic landscapes and medieval history.




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