Late Checkout: This Tuscany Resort Is a Monastery-Turned-Magic Spot for Anyone Serious About La Dolce Vita

Getting There:

If you’re coming from the U.S., fly into Paris or Milan before making your connection to Florence. If coming from Europe, chances are there’s a quick and easy flight or train (ideal) into Florence. Once in Firenze, it’s just over an hour drive to the property. I would only recommend driving if you’re a confident driver (European hillside roads are their own breed!) and are eager to explore the surrounding area. Otherwise, the hotel can organize a private transfer from the train station or airport.

The Property:

Driving through the rolling hills of Tuscany is like the perfect visual appetizer before getting to Pieve Aldina. After driving up its gravel-y driveway, there’s suddenly a charming expanse of sandy-hued stone buildings and lush greenery. Inside is a rustic and artsy feel, which holds true inside any of the 22 suites. The dining room (which is the breakfast room in the morning) has high ceilings with wine racks to remind you at every hour what you could be indulging in. The spa, with its sauna and steam room, is buoyant with natural light, which was lovely to experience after a sleepy massage. The grounds are big enough to get your steps in while admiring Pieve Aldina’s olive groves (you can and should buy their homemade olive oil and wines!) The pool, tucked away around the corner from the dining room, is serenely bordered by tall trees.

Food really matters at a hotel like this one. Thank goodness Pieve’s culinary team is A1. The breakfast is superb, from American options to more local ones. For dinner, I never had issues, which is rare for me in Italy (I’m vegetarian and allergic to tree nuts). In the past, this has meant eating the same three things and still ended up being fed nuts. The kitchen didn’t just accommodate my vegetarian and nut-free dietary restrictions; they adapted and evolved at every moment when someone else might have given up and offered me an unsatisfying salad. 

There's a chapel on-site, which is where I heard guests throwing weddings at Pieve host their ceremonies; it's a 10th-century structure that used to be the Romanesque church of Santa Maria Novella.

The Room:

Despite having just 22 suites scattered across the property, each has a sense of grandeur. My room was enormous and made me question living in New York. I had a dedicated patio—which would be great to share on a girls trip or romantic getaway. My suite was outfitted with a couch, upholstered chair, and coffee table, in addition to a desk and chair on the side of the room which is exactly where I got work done the few times I opened my laptop. The bathroom had a rocketship of a shower (by which I mean there were several ways to get water out of the faucet). The cherry on top? My welcome gift, which included fresh berries and a handwritten note, is exactly the kind of green flag I’m looking for when experiencing a new hotel. 

I can’t talk about the room without giving a spotlight to the king bed. It was the kind of comfy you quickly sink into then slumber off into your best travel sleep. (I don’t know about you, but the first few days of any big trip, I tend to struggle sleeping and be a little cranky. I slept like a baby in this bed, whether for a siesta or at night.)

The Spa & Fitness:

If I can help it, I’m getting a massage when I’m on vacation. I’d never had a massage like I had at Pieve Aldina. Yes, it was relaxing… but the audio wasn’t rain sounds or energetic bells. It was Gregorian chants. The property really leaned into its history with this one. I still enjoyed my massage—facials are offered too—and a session bouncing between the sauna and steam room after. The spa is private, which is great news for introverts (me) and having a quiet moment to take in the beauty around.

Let’s talk fitness. If you’re someone who quips that calories don’t count on vacation, then you shouldn’t be too bothered that the hotel doesn’t boast the most modern fitness facilities. The main option is yoga. While I maintain a weekly strength routine, I leaned into la dolce vita with some days away from dumbbells, with yoga mats and longer walks instead. After all, morning yoga overlooking Tuscany is worth missing a couple weight sessions. 

What to Do While Staying at Pieve Aldina:

While I suggest exploring the surrounding area a bit (more on that in the next section), I recommend treating the hotel like a resort for most of the time that you’re there. Trust me, there’s enough programming to keep you entertained if long afternoons at the pool and aperitivos in the garden aren’t enough.

My all time favorite was a cooking class with chef Niccolò Pini, who is the executive chef of the hotel’s Le Rondini restaurant. We made bruschetta, homemade pasta, homemade pasta sauce, and tiramisu (which I have since remade at home). It’s worth booking a wine and olive oil tasting class, too. You’ll never experience olive oil in the same way, nor wine. I am no sommelier, but I left Tuscany with a better vocabulary and understanding for grapes.

It'd be remiss if I didn't mention there are options to rent bikes and cycle, go horseback riding, and get on a hot-air balloon. 

Around the Area:

One of my favorite things about Pieve Aldina is that it is tucked away and as intimate as it is serene. Note, it’s not totally isolated. There’s plenty to do in the nearest town, Siena, and there’s plenty to do in Florence, which is likely the city you’ll be routing through regardless.

I’d start in Siena and spend a day there. If you’re able to walk, I’d wear my best walking shoes and plan to see everything on foot. Visit the city’s insanely detailed gothic cathedral, Duomo di Siena. Take a stroll around Piazza del Campo, appreciating the architecture and people watching, but don’t eat at one of the cafes on the perimeter, unless you don’t mind a little tourist trap. Instead, walk a few winding roads over and have lunch at Michelin Guide-recognized Osteria Le Logge. Venchi is an easy pick for an afternoon gelato. But if you’re in a Carrie Bradshaw mood, skip dessert and go next door to Aloe&Wolf, a vintage shop with a curation of luxury options, including harder-to-find Fendi baguettes and archival Pucci pieces.

If you’ve traveled as far as Tuscany and are spending time in the countryside, it’s absolutely worth spending at least a couple days in Florence. Stay somewhere central like the newly reopened W Florence for a more modern feel or Sina Villa Medici for something more mature and classic. Make sure you see Florence’s Duomo, climb up to Piazzale Michelangelo, cross the iconic Ponte Vecchio, drink an Aperol Spritz at Harry’s Bar, and have a nightcap at Locale Firenze, a Michelin guide restaurant with a charismatic bar full of creative cocktails. 

The Verdict:

I dream of getaways like this one. Pieve Aldina was a fanciful feast for the senses—rolling hills for the eyes, the scent of a Tuscan summer, the taste of handmade pastas and chianti, the peacefully quiet sounds at night—and a sweet spot to relax. I often get woefully bored at remote resort type spots, but I appreciated all the activity options that kept my boredom at bay. Even better, you can go “off campus” for a bit and explore historic cities like Siena. I understand why I saw so many couples and families there, and why people book it out for weddings.

The hotel closes November 1, 2026 for the season—and usually ends its season around then—before reopening mid-March. This leaves the door open for an early spring, peak summer, or early autumn visit. Pieve, I’m coming back!