A quick note before we get into it — calling this "Tuscany" is a little misleading. The region is enormous and wildly diverse, my husband likes to say it's roughly the size of New Jersey. So rather than try to cover everything, this is what I personally loved, plus a handful of recommendations passed along by people whose opinions I genuinely trust. Florence gets its own guide entirely, coming soon. One perk of doing this for work — I get to sit down with property owners and hear the history of these places first hand, and it changes how you experience them.
FIVE STAR HOTELS WORTH NOTING.
Borgo Santo Pietro
Genuinely one of my favourite hotels in the area, full stop. Originally bought by a Danish couple as their family home before they realised the property had so much more to give — they still own it today. No two rooms are alike and every detail feels personal rather than designed-by-committee. Two restaurants on site, one Michelin-starred and one trattoria built around the most magnificent tree you've ever seen. Most of the produce comes from their own gardens, plus their own cheeses and house-made ice cream — get the walnut, trust me. There's a real list of things to do here too: wine tastings, cooking classes, time with the bees and the sheep, even an apothecary. Ask for Adriana if you book, she takes wonderful care of guests and tells the story of the property better than anyone.
Rosewood Castiglion del Bosco
Two excellent restaurants, gorgeous grounds, a lovely boutique — any one of those would be enough reason to go. One of my favourite meals in the whole region was at their Osteria, which also holds a Michelin star. There's a golf course and cooking classes too. The winery is separate from the hotel and can be booked even if you're not staying — message me if you want the contact.
Il Borro
A massive property with its own vineyard, cooking classes, a pool, and multiple restaurants including a Michelin. Owned by the Ferragamo family, who still run a store on site. There's a medieval village within the property where you can shop for jewellery or even make your own shoes, plus a separate villa with its own pool that's perfect for a family or wedding party — I attended a friend's wedding there and it was stunning. Stables on site too if you ride. The wine and food are genuinely fantastic.
Belmond Castello di Casole
South of Florence, a Belmond so you know exactly what tier of experience you're getting. Restaurants with sweeping views over the Tuscan countryside, tennis courts that look like they belong in a coffee table book.
Casa Newton
Set in Pienza, a town locals talk about constantly and for good reason. This boutique hotel has its own winery, Fabbrica Pienza, which is also bookable separately.
Reschio
Technically nearer Umbria but close enough to mention. A genuine gem — Tom Holland was just there for an event, so make of that what you will.
Monteverdi Tuscany is also worth a mention if you're building out your shortlist.
As a Fora travel advisor I can book several of these properties with Virtuoso perks and preferred rates — message me before you book direct.
Genuinely one of my favourite hotels in the area, full stop. Originally bought by a Danish couple as their family home before they realised the property had so much more to give — they still own it today. No two rooms are alike and every detail feels personal rather than designed-by-committee. Two restaurants on site, one Michelin-starred and one trattoria built around the most magnificent tree you've ever seen. Most of the produce comes from their own gardens, plus their own cheeses and house-made ice cream — get the walnut, trust me. There's a real list of things to do here too: wine tastings, cooking classes, time with the bees and the sheep, even an apothecary. Ask for Adriana if you book, she takes wonderful care of guests and tells the story of the property better than anyone.
Rosewood Castiglion del Bosco
Two excellent restaurants, gorgeous grounds, a lovely boutique — any one of those would be enough reason to go. One of my favourite meals in the whole region was at their Osteria, which also holds a Michelin star. There's a golf course and cooking classes too. The winery is separate from the hotel and can be booked even if you're not staying — message me if you want the contact.
Il Borro
A massive property with its own vineyard, cooking classes, a pool, and multiple restaurants including a Michelin. Owned by the Ferragamo family, who still run a store on site. There's a medieval village within the property where you can shop for jewellery or even make your own shoes, plus a separate villa with its own pool that's perfect for a family or wedding party — I attended a friend's wedding there and it was stunning. Stables on site too if you ride. The wine and food are genuinely fantastic.
Belmond Castello di Casole
South of Florence, a Belmond so you know exactly what tier of experience you're getting. Restaurants with sweeping views over the Tuscan countryside, tennis courts that look like they belong in a coffee table book.
Casa Newton
Set in Pienza, a town locals talk about constantly and for good reason. This boutique hotel has its own winery, Fabbrica Pienza, which is also bookable separately.
Reschio
Technically nearer Umbria but close enough to mention. A genuine gem — Tom Holland was just there for an event, so make of that what you will.
Monteverdi Tuscany is also worth a mention if you're building out your shortlist.
As a Fora travel advisor I can book several of these properties with Virtuoso perks and preferred rates — message me before you book direct.
siena
Restaurants I enjoyed
Osteria San Martino was a real standout for me.
Recommended to me, not yet personally vetted
Osteria Permalico, Locanda Dell'Oste, and Ristorante Campo Cedro have all come highly recommended — do your own due diligence on these since I haven't eaten there myself yet.
Osteria San Martino was a real standout for me.
Recommended to me, not yet personally vetted
Osteria Permalico, Locanda Dell'Oste, and Ristorante Campo Cedro have all come highly recommended — do your own due diligence on these since I haven't eaten there myself yet.
BOLGHERI & MONTALCINO
Bolgheri
A fantastic wine region and genuinely one of my favourite parts of Tuscany for wine. I don't have a specific restaurant or winery to point you to here yet, but it is absolutely worth building into your route.
Montalcino
Restaurants: Osteria Grotta del Brunello, Re di Macchia, Alle Logge Di Piazza
Where to stay: Le Chiuse
Wineries I recommend
Casanova di Neri — my personal favourite producer for Brunello and Rosso di Montalcino.
Castiglion del Bosco — the winery tied to the Rosewood property. Excellent wines, great experience, and it showcases the more northern, mountainous side of Montalcino. Casanova di Neri sits on the warmer southern side, which in my opinion makes a juicier Rosso and Brunello.
Antinori — Massive operation, almost like Disney World for wine. Book well ahead.
Recommended to me, not yet visited: Azienda Agricola Losi Querciavalle, San Giorgio a Lapi, Le Potazzine, and Tenuta Corte Pavone have all come from trusted sources.
A fantastic wine region and genuinely one of my favourite parts of Tuscany for wine. I don't have a specific restaurant or winery to point you to here yet, but it is absolutely worth building into your route.
Montalcino
Restaurants: Osteria Grotta del Brunello, Re di Macchia, Alle Logge Di Piazza
Where to stay: Le Chiuse
Wineries I recommend
Casanova di Neri — my personal favourite producer for Brunello and Rosso di Montalcino.
Castiglion del Bosco — the winery tied to the Rosewood property. Excellent wines, great experience, and it showcases the more northern, mountainous side of Montalcino. Casanova di Neri sits on the warmer southern side, which in my opinion makes a juicier Rosso and Brunello.
Antinori — Massive operation, almost like Disney World for wine. Book well ahead.
Recommended to me, not yet visited: Azienda Agricola Losi Querciavalle, San Giorgio a Lapi, Le Potazzine, and Tenuta Corte Pavone have all come from trusted sources.
SERRE DI RAPOlANO
Castello delle Serre — a friend of mine owns and runs this property, and if you want something uniquely Tuscan and genuinely authentic rather than a big name brand, this is where I'd send you. She and her husband do a beautiful job and it's perfect for a romantic, personal experience rather than a polished hotel chain feel. I can personally vouch for her as a host.
pienza
Credit where it's due — these came from one of my contacts at Borgo Santo Pietro, whose own favourite town is actually Montalcino.
Abbazia di Sant'Antimo — a beautiful church, understated rather than ornate, and stunning because of it.
Ciacci Piccolomini d'Aragona, Mastrojanni, and Podere Le Ripi are all worth seeking out here too.
Casa Newton, Lupaia are wonderful 5 star hotels, then you have Hotel San Gregorio & Tenuta Santo Pietro
Abbazia di Sant'Antimo — a beautiful church, understated rather than ornate, and stunning because of it.
Ciacci Piccolomini d'Aragona, Mastrojanni, and Podere Le Ripi are all worth seeking out here too.
Casa Newton, Lupaia are wonderful 5 star hotels, then you have Hotel San Gregorio & Tenuta Santo Pietro
FORTE DEI MARMI
A beach town where everyone gets around by bike, no questions asked. Completely different energy to the rest of this list — relaxed, breezy, very Italian summer.
Restaurants & bars: Bistro for beachfront, CasaMare Forte dei Marmi for seafood with a lively main square atmosphere, Caffè Sambo for aperitivo, Enoteca Giulia for the atmosphere alone, and Alex Ristorante Enoteca — a bit of a bike ride but worth it, Michelin Guide-listed.
Beach clubs: There are honestly too many to count. Gilda is a favourite of mine. Alpemare is the trendy one in town, go for lunch or book a cabana. Most hotels here partner with a beach club too, and the space everyone gets is huge — cabanas for everyone.
Hotels: Pensione America, Villa Roma Imperiale (its sister property, which comes with its own beach club), and Hermitage — a well-priced option with a pool, bikes, and lovely service.
Restaurants & bars: Bistro for beachfront, CasaMare Forte dei Marmi for seafood with a lively main square atmosphere, Caffè Sambo for aperitivo, Enoteca Giulia for the atmosphere alone, and Alex Ristorante Enoteca — a bit of a bike ride but worth it, Michelin Guide-listed.
Beach clubs: There are honestly too many to count. Gilda is a favourite of mine. Alpemare is the trendy one in town, go for lunch or book a cabana. Most hotels here partner with a beach club too, and the space everyone gets is huge — cabanas for everyone.
Hotels: Pensione America, Villa Roma Imperiale (its sister property, which comes with its own beach club), and Hermitage — a well-priced option with a pool, bikes, and lovely service.
UMBRIA / ORVIETO
Technically not Tuscany anymore, but I still need to put together a proper guide for this area. It's been about a decade since I visited so take this with a grain of salt, but I loved Altarocca Wine Resort.
