Everyone knows that person who spends weeks sniffing around travel blogs, going deep into Tripadvisor rabbit holes, collecting Google docs from friends of friends, and creating A Beautiful Mind–style spreadsheets to come up with the best vacations and itineraries possible. In this recurring series, we find those people who’ve done all the work for you and have them walk us through a particularly wonderful, especially well-thought-out vacation they took that you can actually steal.
Tommaso Mardegan finds himself in Tuscany multiple times a year — his travel company, N2S, specializes in bespoke experiences and events throughout Italy. But Mardegan admits that his own travel style leans a bit more spontaneous. “Most of my clients require a formal plan, but I like to go with the flow, improvising most of the time.” And that’s how a recent road trip in April unfolded when he and his girlfriend, Tatiana, took advantage of the low season’s affordable prices and access to grand villas turned B&Bs. “The spring and fall are some of my favorite times to visit,” Mardegan says. “It’s less packed and rates start dropping. The fall, specifically, is when you’ll start to see all these products from the recent harvest — white truffles, olive oil, and all of the new wines of the season.”
Plus, it’s all here, Mardegan says: “Charming villages, a sprawling countryside, and the coast. Just don’t stop once you reach Siena. Most travelers do, and they’re missing out.” On this trip, which made a circle around the southern and lesser-known part of Tuscany, Mardegan met with the region’s best artisans, farmers, winemakers, chefs, and art historians, and discovered secret spots, like a hidden winery in a former watchtower and a sculptor’s personal studio in the backyard of his gallery. And no matter how many times he’s been, the energy of Mount Amiata at dusk is like experiencing it for the first time. “It was a lot of kilometers and emotions.”
Day 1
11 a.m.: Fly to Florence and visit a sculpture gallery
I live between Milan and London, and this time I was traveling from London with my girlfriend. So we flew from London Heathrow to Florence Airport with British Airways. If traveling from Milan, I would have taken the high-speed train (Frecciarossa or Italo), and in two hours you’ll arrive in the Renaissance capital, Florence, which is the starting point to explore the region. On this trip, we rented an old Defender from Noleggio Chianti 500 — they have tons of vintage cars. But first: quick ciao to our friend Raffaello, the fourth-generation sculptor in the Romanelli Gallery (Borgo S. Frediano, 70). I love to visit him while at work in his workshop in Florence; I’m always inspired by the sculptures in the gallery and studio. Some of them have been there for centuries!
12 p.m.: Grab lunch at a classic trattoria before hitting the road
Since we were in the neighborhood of Oltrarno, we couldn’t resist a quick bite at my favorite spot in the South Bank: Cammillo (Borgo S. Jacopo, 57/r). We enjoyed some seasonal artichokes (raw and baked), a pecorino brûlée, tiramisu, and a glass of Nobile … then we hit the road!
5 p.m.: Make an overnight pit stop near Casole d’Elsa
Our first overnight was a logistical stop, as it is midway to the deeper Val d’Orcia. We stayed at my friend Meraud’s house, near Casole d’Elsa. His mother is an antiques dealer, so the house is incredible and uniquely decorated, using only recycled materials. The name is Podere Le Porciglia (Unnamed Road, 53034 Colle di Val d’Elsa SI), and it is rentable by emailing [email protected]. We had dinner here with friends and ate pici, the typical Tuscan pasta. It’s a handmade pasta made using water and flour only, no eggs! Poor ingredients, rich in flavor.
Day 2
11 a.m.: Visit a winery in a former watchtower
After a coffee and breakfast at the Podere, it was time to travel south. We were headed to Castello di Argiano (Castello di Argiano, 53024 Montalcino SI), one of the chain of castles that originally served as watchtowers and is now a winery run by Elisa Sesti. We came to visit the renovated tower and taste some of the best Brunello di Montalcino produced in the area, called Sesti wines, and were greeted by Elisa Sesti herself. After climbing to the top of the tower, we headed down to the cellar, where we tasted eight different wines. Giuseppe, Elisa’s father, is an astronomer and dedicated all the labels from their Phenomena Brunello di Montalcino Riserva to different constellations to honor a significant astronomical event that occurred during the year of harvest. The tasting ended with some olive oil; when it’s organic, it’ll surprise you how good it is to sip (a well-known technique in Italy for avoiding hangovers!).
1:30 p.m.: Have a fresh misticanza salad for lunch
Finally, time to eat! The estate cook prepared a simple but extremely delicious meal. And I was so happy to see a great bowl of misticanza salad coming from the kitchen garden. Misticanza is a salad with a mixture of bitter greens from the garden. I go crazy for it. This was served with a bowl of pasta with fresh ingredients from the kitchen garden.
5 p.m.: Drive to Castello Di Vicarello
With full bellies, we drove to our second stop, Castello Di Vicarello (Via Vicarello, 1, 58044 Poggi del Sasso GR), in the Maremma area. It’s a family-owned boutique hotel, and it doesn’t get more Tuscany than this. After check-in, dinner was served on the grassy rooftop.
Day 3
10 a.m.: Enjoy a slow morning at the hotel
We didn’t rush to get up, as it’s one of those places where you can sleep deeply.
11 a.m.: E-bike through the Tuscan hills, then hit the pool
We had breakfast on the property. Afterward, we rented e-bikes from the hotel, rode around the surrounding hills, and came across a farm with donkeys. We stopped for some photos, then headed back to Vicarello to spend the afternoon at the pool.
9 p.m.: Stargaze with a pro
We had the pleasure of meeting with Alessandro Marchini, a professor at the Siena Observatory. If you contact him with a little notice, he’d be happy to meet you wherever you are (providing that you are not farther than 80 kilometers from Siena) and bring his telescope for amazing stargazing. To book, contact [email protected]. After sipping Castello Di Vicarello’s delicious wines, stargazing was even more enjoyable.
Day 4
11 a.m.: Head to the Tuscan coast
After the two magical nights at CDV, we realized we were close to the Tuscan coast, so at the last minute we decided to check out the Talamone area — it’s less known than Argentario nearby, but in my opinion, even more laid-back and with a proper Maremma vibe. We drove about an hour to the port, which had an incredible view of an imposing castle on the edge of the sea.
1 p.m.: Spend the night in a seaside villa
We arrived at our next stop, Villa Talamo (Via Gaetano Carotti, 8, 58015 Fonteblanda GR), and were immediately greeted by the owner, Max. It was a beautiful day and we had an aperitif under the palms with some fritto misto, a fried medley of fresh seafood and veggies. This villa is a B&B during low season (April, May, October, and November), where you have the opportunity to book individual rooms, and during high season (June, July, and August), it can only be rented as a whole villa. Since it was the low season, we rented a room and stayed the night.
Day 5
8 a.m.: Check out the Tarot Gardens
We woke up excited to finally get to our final destination, the green and wild Val d’Orcia. I couldn’t wait to see Mount Amiata in all its magnificence. But before making our way, we quickly stopped at the Tarot Gardens, an open-air museum garden in Capalbio (58011 Capalbio, Province of Grosseto), since we had never been and had always wanted to visit. The “Giardino dei Tarocchi” is a massive artistic installation created by renowned artist Niki de Saint Phalle. Wild, vibrant, and truly out of this world.
10 a.m.: Arrive at Val d’Orcia
After a two-hour drive from the gardens, we finally approached Val d’Orcia, and the view felt surreal. We just drove around, taking in the surroundings and stopping multiple times for photos.
1 p.m.: Have a quick Tuscan lunch
We stopped for lunch at Dopolavoro La Foce (SP40, 90, 53026 La Foce SI), now with new management and a menu that I find fresh and innovative while still respecting Tuscan traditions. We ordered the steak tartare, creatively served on the bone with capers and mustard. As a primo dish, the famous pasta all’aglio. We got back in the car after lunch and had fun driving around, getting lost, taking photos of the iconic dirty roads and cypress trees.
6 p.m.: Enjoy golden hour by the pool
Finally, we arrived at Follonico (Località Casale, 2, 53049 Torrita di Siena SI), a beautifully run B&B that’s probably the best value for your money in this part of Tuscany. You can get brilliant rooms for €200/night. We enjoyed golden hour by the pool with a great glass of natural wine.
Day 6
11 a.m.: Visit a local cheese farm
After a simple but incredible breakfast with mostly food from the farm, we explored the area leading up to Pienza. We visited the cheese farm Podere Il Casale (Via Podere Il Casale 64, 53026 Pienza), where the owner Sandra took us on a tour (book by emailing [email protected]). They are from Switzerland and fell in love with this area over 20 years ago. Back in the day, there were more sheep than humans here; now it’s becoming pretty touristy. She showed us all the animals and explained their very strong biodynamic agriculture, as well as the cheese-making process. We sat for a cheese tasting and long lunch in one of the most panoramic and breathtaking terraces of the region. No rush here.
3:30 p.m.: Explore the village of Pienza
From the terrace, you could see medieval Pienza, so we decided to check out this nice hamlet and its beautiful cathedral. Pienza was the birthplace of Pope Pius II, and it was rebuilt as an ideal Renaissance town in the 15th century by applying architectural theories of the Florentine humanist Alberti.
4:30 p.m.: Stop for coffee in town
We picked up some gelato at Buon Gusto Gelateria (Via Case Nuove, 26, 53026 Pienza SI), which should not be missed. There is also a great restaurant in Pienza called La Bandita Townhouse (Corso il Rossellino, 111, 53026 Pienza SI); we weren’t able to eat there since the kitchen was closed at that time, but we had a coffee. We headed back to our lovely B&B for the night.
Day 7
11 a.m.: Take a familiar detour
It was time to make our way back north. But instead of passing through the very known Siena and Chianti area, we decided to travel through Lucignano (not far from Arezzo). We stopped at our friend Selvaggia’s Castello del Calcione (Strada Provinciale del Calcione, 101, 52046 Lucignano AR) for our last night — and some horseback riding. Selvaggia is one of the few female horse jockeys in Italy, and she is extremely talented. Castello del Calcione is a B&B and also has villas in the estate that can be rented for events. These walls have seen great parties …
12 p.m.: Go horseback riding, then have a picnic lunch
We headed to the stable, Scuderie Del Calcione, and immediately jumped onto the saddle and galloped off. Disclaimer: Only experienced riders are accepted by the very selective Selvaggia. Afterward, we had a picnic lunch on the grounds.
9 p.m.: Have one last (incredible) dinner
After a dose of adrenaline and some nourishment, we went back to the Castello to relax and get ready for dinner, where a surprise awaited us: That day, Paolo Parisi, a legendary cook, farmer, and food-and-beverage guru, happened to be cooking for Castello’s guests. It was an amazing way to wrap up this Tuscany adventure.
Day 8
12 p.m.: See some art
We left after breakfast for our late-afternoon flight back to London, but before reaching Florence Airport, I took Tati, who loves art, to visit Castello Di Ama (Località Ama in Chianti, 53013 Gaiole in Chianti SI), one of the most sophisticated wineries in Chianti. They have contemporary art installations all around the estate.
6 p.m.: Drive off-road into the sunset
We off-roaded a bit and enjoyed the last golden hour. Until next time, Toscana.
Tommaso’s Tuscany Packing List
These are multitasking boots — great for a hike in the woods or jumping onto the saddle and horseback riding.
For me, this is the Bible. We are always updating the N2S must-do guides, and restaurants are a huge component. In Osterie d’Italia, you’ll always find the best places to eat locally. Even when you’re in the middle of nowhere, this guide might just suggest the most unbelievable spot for lunch in the smallest village up in the hills.
[Editor’s note: This guide is updated annually in Italian, while the most recent English copy is from 2007. There is also an app version.]
I just love colorful beanies and always wear them while traveling.
My cargo vest is now an inseparable travel companion. One pocket for my passport, one for my wallet, another for headphones and sunglasses. I’ll never again look for items lost in the bottom of my bag.
The Strategist is designed to surface the most useful, expert recommendations for things to buy across the vast e-commerce landscape. Some of our latest conquests include the best acne treatments, rolling luggage, pillows for side sleepers, natural anxiety remedies, and bath towels. We update links when possible, but note that deals can expire and all prices are subject to change.
