Luxury experiences in Tuscany are best measured in moments: a glass of Brunello sipped in a centuries-old cellar, dawn light spilling across the Val d’Orcia, a Michelin-starred meal served aboard a historic train. They linger in memory because they distill Tuscany’s beauty into rare, unforgettable moments. I’ve curated this collection as an insider’s guide to Tuscany at its most refined—an edit designed to elevate your journey beyond the expected and into the extraordinary.
A Legendary Journey: The Venice Simplon-Orient-Express Luxury Train to Tuscany
There are train rides, and then there is this—Belmond’s legendary Venice Simplon-Orient-Express, now running a Paris-to-Tuscany route. It’s the ultimate luxury train journey in Tuscany: polished wood paneling, a personal butler at your call, and candlelit dinners by Michelin-starred chef Jean Imbert as the Italian countryside drifts past your window.
“For me, the journey is just as important as the destination—and no journey is as evocative as this.”
Book it: Belmond Venice Simplon-Orient-Express
Private Yacht Charter Along the Tuscan Archipelago
Most travelers never see Tuscany from the water. Charter a private yacht in Tuscany and set sail through the Tuscan Archipelago, where hidden coves and quiet islands (Elba, Giglio, Capraia) await. Swim, snorkel, or simply sip chilled prosecco as the coastline unfurls like a Renaissance painting. This is Tuscany at its most glamorous and secluded.
Book it: Luxo Italia or Tenuta Torciano
Exclusive Horseback Riding in Val d’Orcia
The Val d’Orcia is the Tuscany of your imagination—rolling hills, lone cypress trees, and hilltop villages that seem to float in the distance. Now imagine experiencing it on horseback, one of the most intimate exclusive experiences in Tuscany. There’s something timeless about moving at this pace, as if you’ve slipped into a Renaissance painting. I’ve always believed that travel should be about changing your perspective—sometimes all it takes is the gentle rhythm of a horse’s gait.
Book it: Luxo Italia
Market-to-Table Cooking in Montepulciano
Step into a Tuscan market with a local chef, basket in hand, choosing the ripest tomatoes, bunches of basil, and fresh pecorino. Then retreat to a historic farmhouse kitchen where you’ll craft regional dishes like pici pasta or ribollita—an unforgettable highlight of private culinary experiences in Tuscany. This isn’t a cooking class—it’s a conversation with tradition, and it ends in the best way possible: eating under the pergola with a glass of Chianti in hand.
To learn more about the history of these humble yet profound recipes, delve into the story of cucina povera (“poor cooking”) in our Tuscany Travel Guide.
Book it: Flow Traveling
Private Wine Tours at Hidden Tuscan Estates
Yes, Tuscany is known for wine tastings—but few get to sip Brunello in a centuries-old cellar while a family winemaker shares stories of the land. At Colle Bereto, a 60-hectare organic vineyard in Chianti, you can taste nine different wines before sitting down to a bistecca lunch among the vines. At Corzano e Paterno, tastings include estate-made cheeses, olive oil, and honey—often followed by a four-course farm dinner. These intimate vineyard visits are the epitome of private wine tours in Tuscany.
Book it: Flow Traveling
Bespoke Luxury Experiences in Tuscany
Sometimes the most exclusive luxury is access. Bespoke Tuscany and Tuscan Secret Experience design fully customized luxury experiences in Tuscany. Think Ferrari drives through Chianti, artisan workshops in Florence, or a private dinner in a medieval tower. When I travel, I want to feel like every moment was designed just for me—these agencies deliver exactly that.
For a complete list of our trusted specialists, planners, and private guides who can bring these bespoke moments to life, visit our Tuscany Travel Resources edit.
Book it: Bespoke Tuscany or Tuscan Secret Experience
Ancient Healing: The Thermal Baths of Saturnia
For centuries, Romans and Renaissance nobles soaked in Tuscany’s natural hot springs, and the tradition endures. Saturnia remains the crown jewel of luxury thermal baths in Tuscany, with steaming turquoise pools cascading over travertine rock. Yes, you’ll find luxury spa hotels nearby, but there’s something magical about slipping into the open-air pools at dawn, when the mist rises and the countryside is still. This is Tuscany’s answer to time travel.
Book it: Terme di Saturnia Spa & Golf Resort
Crafting Your Own Tuscan Story
What I love about Tuscany is that no two journeys ever look the same. One traveler might arrive on a luxury train journey to Tuscany and spend their days yachting the archipelago, while another finds magic in a farmhouse kitchen or a glass of Brunello sipped straight from the barrel on a private wine tour in Tuscany.
“For me, luxury in Tuscany isn’t about excess—it’s about intimacy. A private moment in a place where time slows down, and beauty feels personal.”
To further inspire your plans and connect with the region’s romantic soul, explore our curated list of Books & Films Set in Tuscany that have immortalized these landscapes.
These are the luxury experiences in Tuscany I’ve curated to inspire your own journey—the kinds of moments that linger long after you’ve unpacked your bags.
Your Tuscan Story Doesn’t End Here
Ready to keep exploring? Let’s make your journey even richer:
- Where to Next? → Wander medieval towns and rolling vineyards in our Tuscany Destination Guide.
- Travel Through Story → Let our Books & Films About Tuscany transport you into the region’s art, history, and romance before you even board the plane.
- Pack Like a Pro → Steal my insider tips from the Style & Packing Guide for Tuscany so you’ll blend in effortlessly (while still standing out).