Destination guide · Italy
Tuscany,
hotel by hotel
Restored medieval borghi, hilltop castles and a 5,000-acre wine estate — the Tuscany hotels I recommend, and which one is right for your trip.
Destination guide · Italy
Restored medieval borghi, hilltop castles and a 5,000-acre wine estate — the Tuscany hotels I recommend, and which one is right for your trip.
In Tuscany the hotel is the trip. Pick the right one and you’ll barely want to leave it.
The countryside stays here fall into two families. The borghi are whole medieval villages restored and run as one hotel — you sleep inside the village. The castles and estates are grander, with the vineyards, golf and Michelin dining to fill a week.
I’ve stayed at Borgo San Felice and Borgo Pignano, toured Il Borro, and visited Castello del Nero and Castello di Casole. The three borghi are all Fora Reserve, and all three are fantastic — for three different travelers. That’s the heart of this guide.
Three restored borghi for three different travelers, then the castles and estates.
Restored medieval borgo among the vineyards (Fora Reserve)
One of my favorite stays so far, and the most well-rounded of the borghi: a perfectly restored hamlet in the Chianti hills with fantastic service and food, tennis, a gym and a spa. It just feels like home.
Keith’s notes
You’ll want a car (or a driver). The borgo sits in the Chianti hills a short drive from Siena, and Florence is an easy day trip. I arrange drivers who know the back roads, and can link it with my other Tuscany estates.
Book dinner in the piazza. In summer, tables go out in front of the chapel with live music as the sun goes down. Tell me your dates and I’ll make sure you have one of those nights.
Stay longer than one night. This is a place to settle into. Plan for at least three nights so Siena, the vineyards and a slow day at the spa don’t compete.
The verdict
A truly perfect gem near Siena — the most well-rounded borgo in Tuscany, and one of my favorite stays so far.
Restored hilltop borgo (Relais & Châteaux, Fora Reserve)
The country stay — close to a farm stay, and a bit remote. Great for couples who want quiet, with the best pool of the three borghi and dinner under a pergola facing the valley; around nine private villas make it the pick for families and groups.
Keith’s notes
It’s a bit remote — you’ll want a car (or a driver). That’s the point: this is a country, farm-stay kind of Tuscany. It’s about an hour and a half from Florence. Volterra, San Gimignano and my other Tuscany estates are all within easy reach; I arrange drivers who know the back roads.
Traveling as a family or group? Ask about the villas. They run from two to five bedrooms and vary in layout, privacy and view. Tell me who’s coming and I’ll match you to the right one.
Stay longer than one night. This is a place to settle into. Plan for at least two or three nights so the pool, the dinners and the drives out don’t compete.
The verdict
A quiet stone borgo on a Tuscan hilltop — the dinner view alone is worth the drive.
Restored medieval borgo and estate (Relais & Châteaux, Fora Reserve)
The Ferragamo family’s medieval village, where the whole borgo is the hotel — it reminded me of Aman Sveti Stefan. Honeymooners sleep in the original borgo; more modern rooms are a two-minute drive away. Stunning pools, and competitive rates.
Keith’s notes
Pick your stay before you pick your dates. Honeymooners and couples chasing atmosphere should be in the original borgo; if you want a more modern room, the newer accommodations are a two-minute drive away. Tell me which sounds like you and I’ll match the room.
You’ll want a car (or a driver). Il Borro sits in the countryside between Florence and Arezzo, so it pairs easily with a few nights in the city. I arrange drivers who know the back roads, and can link it with my other Tuscany estates.
Three borghi, three different travelers. Borgo Pignano, Borgo San Felice and Il Borro all offer a different stay for a different traveler, and all three are fantastic. Tell me who’s coming and what you want from Tuscany, and I’ll tell you which one is yours. Here are my side-by-sides: Borgo San Felice or Il Borro and Borgo Pignano or Il Borro. Or see all three side by side.
The verdict
A whole medieval borgo turned hotel — very authentic Tuscany, and for honeymooners, the original village is the place to sleep.
Countryside estate (Rosewood, Three Michelin Keys)
The big estate: 5,000 acres, a Brunello winery and golf, built for four-plus nights where you never need to leave. I’m a preferred partner of Rosewood, so the upgrade and credits compound across a longer stay.
Keith’s notes
Commit real nights to it. This is a multi-night countryside stay by design — my recommendation starts at four nights.
You'll want a car (or a driver). The Val d'Orcia's hill towns — Montalcino, Pienza, Montepulciano — are the day-trip circuit; I arrange drivers who know every back road.
Compare my Tuscany trio. Castello di Casole is the more traditional castle; Castello del Nero is the Chianti base for day trips. This is the estate for settling in.
The verdict
My top Tuscany pick for a countryside stay — 5,000 acres, a Brunello winery, and a week that never needs to leave the estate.
Converted castle retreat (COMO)
The smartest base on my list: a converted 12th-century castle between Florence and Siena, with a COMO spa to come home to after a day on the road.
Keith’s notes
It's the day-tripper's estate. If you plan to leave the property most days, this is the pick — if you plan never to leave it, look at Castiglion del Bosco.
Chianti versus Val d'Orcia. Chianti is vineyards and proximity; the Val d'Orcia is the wide-open postcard. Tell me which Tuscany you're picturing.
Wellness travelers, weight this one. The Shambhala programming is a genuine differentiator among Tuscan estates.
The verdict
A 12th-century castle that puts Florence and Siena both within reach — the smartest base on my Tuscany list.
Hilltop castle estate (Belmond)
The traditional castle, on a hilltop with sweeping views near Siena. As a Belmond preferred partner, I often book it as the countryside chapter of a Belmond Italy trip.
Keith’s notes
Traditional in feel is the brief. Stone, heritage interiors, classic service — if you want contemporary polish, that's Castiglion del Bosco.
It's remote by design. Plan a car or driver — the isolation is the luxury, and the hill towns are the excursions.
Belmond pairs beautifully. An hour from Villa San Michele above Florence — the two-stop Belmond Tuscany trip writes itself.
The verdict
A hilltop castle with sweeping views near Siena — for travelers who want their Tuscany slightly more traditional, this is the one.
Most Tuscany trips begin with two or three nights in Florence, then a drive out to the countryside. My Florence guide covers where to stay in the city or the hills above it.
“Tuscany in June, honeymoon” is a complete answer. I’ll take it from there.