It doesn’t take a genius to work out why Borgo San Vincenzo, a boutique bolthole with barrel-loads of charm, is named after the patron saint of wine. Widescreen vineyard views? Check. Cellar crammed with juicy Montepulciano reds? Natch. Regular tasting sessions? Now we’re talking. Take the edge off that morning-after feeling with a medicinal Penicillin 2.0 cocktail (gin, ginger, honey and lemon) sipped idly by the outdoor pool, where lofty cypresses provide shady spots for soaking up those endless panoramas of the hypnotic Tuscan landscape, and a spot of lounger-bound snoozing.
Get this when you book through us:
Two hotel-branded wine skins for toting bottles, tasting notebooks and a corkscrew
11am. Check-in, 3pm. Both are flexible if availability permits. Arriving and departing guests are welcome to store luggage and make use of the pool, bar and other common areas.
Double rooms from £155.57 (€180), including tax at 10 per cent. Please note the hotel charges an additional local city tax of €1.00 per person per night on check-out.
Rates include a continental breakfast served in the restaurant or garden. Hot à la carte dishes are also available on request.
Closed during winter, between early January and late March.
At the hotel
Bar, restaurant, outdoor pool, free WiFi, library with books and games, bicycles to borrow. In rooms: kitchenette with Nespresso coffee machine, flatscreen TV, free bottled water, luxury Frette linens and towels, Acqua dell’Elba toiletries.
Our favourite rooms
The wine theme looms large at Borgo San Vincenzo, where rooms and suites are named after different bottle sizes, in ascending order of square footage. At the top end, the Nebuchadnezzar weighs in at a whopping 520 square feet, with two en-suite bedrooms and traditional Tuscan-style decor that includes exposed brickwork, ceramic-tiled floors and rustic ceiling beams. A small pergola-shaded patio with views of the garden’s manicured lawns and olive trees provides quite the decadent spot for sipping a fruity vino nobile fresh from the local vineyards.
Pull up a lounger and dip your toes in the outdoor pool, open 8am–8pm daily. Frette pool towels and epic views of the Tuscan countryside come as standard. Poolside cocktails are optional, but highly recommended.
There’s an old-world feel about Borgo San Vincenzo that lends itself well to analogue pursuits. Just because the WiFi is free doesn’t mean you have to use it, right? Switch off with a well-thumbed paperback or two – how about Italy-and-England-set turn-of-the-century classic A Room with a View? Budding artists might want to consider a sketchpad and pencils for capturing the landscape from any one of the hotel’s dozens of excellent vantage points. And don’t forget the Alka-Seltzer, just in case the wine-tasting gets out of hand. You’ll thank us later.
Good old-fashioned push bikes are available to borrow for guests who fancy wobbling from vineyard to vineyard on two wheels, and e-bikes can also be arranged for an additional fee. A small selection of fitness equipment is also available on request.
Welcome but child-friendly facilities are sparse. There's limited availability, but extra beds can be added to the Imperial, Balthazar and Nebuchadnezzar suites (€75 a night); a cot can be added to the Methuselah Studio. Babysitting is €20 an hour.
Still and sparkling water is bottled on site (in glass, natch) to reduce plastic waste, and plans are afoot for solar panels to provide sustainable clean energy.
Chunky wooden tables on the terrace offer the best views through the cypress trees to the vineyards beyond.
Countryside chic is the order of the day here, so dig out your smartest swimwear for lazy days by the pool and think floaty florals and crisp, pressed linens for cocktail hour and dinner.
Meaning ‘little donkey’, Il Ciuchino serves up a seasonally changing menu using meat and vegetables sourced from local producers, regional seafood and farm-fresh cheeses. Expect a modern twist on Tuscan classics, with a menu of tapas-style small plates that includes octopus sliders, steak tartare tacos and a wild-forest-mushroom crème brûlée. Don’t leave without trying the near-infinitely moreish Tuscan pierogi at least once (though realistically probably twice or thrice). Wash down your feast with wines from vintners so local you’ve probably nodded hello to them on your morning constitutional.
Occasional special events at Il Ciuchino include Tuscan barbecues with meats grilled in the traditional brick oven and dinners hosted by local wine makers. The restaurant is open for breakfast, lunch and dinner.
Sure, there are some rip-roaring regional wines to be sampled in the hotel’s Flying Monk bar, but be sure not to neglect the cocktails. The menu includes a stack of boozy classics plus signature favourites like the Ramanier, a heady concoction of cacao nib-infused Ramazzotti, red vermouth and bourbon, topped with a theatrical smoke bubble, and Wayne Goes to Tuscany, with its triple-hit of bergamot liqueur, dry vermouth and gin. No wonder the monk was flying.
Breakfast runs from 7.30am to 10.30am, lunch from 11am to 2:30pm and you can catch dinner anytime between 7pm and 9.30pm. The Flying Monk bar serves cocktails and fine wines right until 11pm.
None, so be sure to fill up on those delectable Tuscan pierogi at dinner.
18th-century Borgo San Vincenzo occupies a delicious slice of southern Tuscan countryside, surrounded by vineyards, dreamy mediaeval hilltop towns and endless views of the Val d’Orcia hills, 15 minutes from Montepulciano.
It’s around 90 minutes from Florence Airport and two to three hours from Rome. Transfers start at an eye-watering €320 one way from Florence.
Handily located on the high-speed Florence–Rome railway, Chiusi-Chianciano Terme station is a 25-minute drive from Borgo San Vincenzo and can be reached in less than an hour from Rome. Transfers from the station to the hotel are a more palatable €50.
You’re going to want your own wheels for cruising Tuscany’s gentle hills, popping by vineyards and reaching those charming mediaeval and Renaissance villages that time forgot. Cars are available to hire at all of the airports and there’s free parking at the hotel.
Fancy kicking off your vacation with a thrilling bird’s eye view of Tuscany’s famous patchwork of wheat fields, olive groves and vineyards? Helicopter transfers can be organised on request.
Worth getting out of bed for
If you’re looking for postcard inspo that goes well beyond the usual ‘weather nice, wish you were here’ fare, then you’ve come to the right place. For example, you don’t have to cast out very far on your borrowed bike before hitting multiple quirky wineries. Il Conventino offers tastings in, as the name suggests, the picturesque grounds of a former convent, while Icario is all about those endless vineyard views (and the wine itself, of course), as well as regular art and photography exhibitions hosted in a modern space above the barrique cellar. Peer through the glass floor to where the state’s Vino Nobile di Montepulciano matures in great oak casks beneath your feet. La Ciarliana even runs a family-friendly tour with fun flashcards, worksheets and colouring pages for the kids, as well as a juice-tasting session to keep them entertained while parents get down to the serious business of sampling the wines.
Perched atop a hill with a great green patchwork quilt of vineyards spread out beneath it, mediaeval Montepulciano’s atmospheric cobbled streets and squares are chock-full of Baroque and Renaissance edifices, including churches, palazzi and a gothic-style 16th-century cathedral. Don’t miss the Renaissance paintings and monuments inside the cathedral and look out for the comical/sinister Pulcinella figure on the clock tower in the main square. Visitors lucky enough to be in town on the last Sunday of August can also bear witness to one of the country’s weirdest annual spectacles, Il Bravio delle Botti, in which colourfully dressed teams race uphill through the streets pushing 80kg wine barrels in front of them.
Cheese tasting, oil tasting, cookery classes and, heck, even truffle hunting can also be organised by the hotel’s dedicated experiences team, all but guaranteeing a riveting read for those lucky, lucky postcard recipients back home.
Montepulciano is very much where it’s at if you’re into moody vaulted cellars, exposed oak beams and traditional Tuscan flavours. Directly opposite the epic Renaissance confection that is the San Biagio church, La Grotta ticks many of the aforementioned boxes. Formerly a 16th-century stable, it’s now a popular dining room serving top-drawer Tuscan fare like pappardelle with rabbit ragu and mussels in white bean sauce with homemade tagliolini and pecorino. A tasting menu is available for those who find choosing just one or two dishes here impossible and there’s a leafy garden for al fresco summer dining.
Osteria del Borgo offers the best of all worlds: a location just off the monumental Piazza Grande, Montepulciano’s main square, an atmospheric pre-Renaissance barrel-vault dining room and a panoramic terrace with – and we don’t use the term lightly – jaw dropping views of the valley and Val d’Orcia hills. The food ain’t half bad either; we’re talking grilled Florentine steak, braised beef cheek in vino nobile sauce, tagliolini with porcini mushrooms and – be still my beating heart – homemade tiramisu. The wine list runs to some 600 labels, all hand-picked by this family restaurant’s sommelier brothers, Francesco and Giacomo. Expect local favourites including Brunello di Montalcino, Bolgheri Doc and Vino Nobile di Montepulciano, plus many more fine wines from across Italy and beyond.
You can’t stay this close to Montepulciano without stopping by Caffe Poliziano at least once. This grand dame of Tuscan cafés has been around since 1868 and – with its art deco interiors, potted plants, dainty desserts, and glass cabinets full of delicate china teacups – it wouldn’t seem out of place on the Champs-Élysées or Rome’s Via del Corso. What sets it apart is those sweeping views of the Tuscan countryside, best enjoyed from the terrace with an espresso and a crunchy cream filled cannoli or three.
You’re never far from the nearest bottle of wine in Tuscany, and Montpulciano is of course no exception. E Lucevan le Stelle combines those ubiquitous (but never boring) stone arches with arty black-and-white photos and bold, colourful canvases. Peruse a wine list that’s as long as your arm (if your arm happens to be unnaturally long, that is) and sip your chosen libation with splendid views of the Piazza di San Francesco. The bar even hosts occasional live jazz nights.
Nearby Opicifio 16 is an altogether less formal affair. Popular with locals, it’s set on a bustling shrub-lined sidestreet with apertivi and local wines advertised on handwritten chalkboards.
Every hotel featured is visited personally by members of our team, given the Smith seal of approval, and then anonymously reviewed. As soon as our reviewers have returned from this boutique borgo in the Tuscan countryside and unpacked (and uncorked) their stash of Vino Nobile di Montepulciano, a full account of their wine-fuelled break will be with you. In the meantime, to whet your wanderlust, here's a quick peek inside Borgo San Vincenzo in rural Tuscany…
It doesn’t get a whole lot more solitario than Borgo San Vincenzo, a restored 18th-century villa lost in the rolling hills and valleys of Italy’s top wine region, 15 minutes from the nearest town. The hotel blends into the undulating Tuscan landscape, all honey-coloured stone, rust-red rooftops, and an oh-so-enticing outdoor pool bordered by olive groves, cypresses and fairytale vineyard vistas.
Nothing of the borgo’s traditional Tuscan charm has been lost in its 21st-century makeover, which adds landscaped gardens, a firepit and, inside, vintage-look leather sofas, chests, suitcases and other quirky furnishings. Exposed oak beams, brickwork and terracotta-tiled floors retain a rustic olde worlde vibe while Frette linens and Acqua dell’Elba toiletries up the luxe factor in spacious rooms and suites.