On the Italian-romance meter, wine hotels in Tuscany are about as good as it gets!

If you’re not familiar with the concept of wine hotels (or “vineyard hotels,” as they’re often called), these are essentially properties that are either on or next to a vineyard.

Turns out, you can have your wine and drink it, too!

In an effort to help you make your wildest winery wishes a reality, I’ve cherry-picked 25 of the most romantic vineyard hotels in Tuscany for that vino-focused getaway of a lifetime.

So whether you’re craving some alone time with your partner or you’re looking to take the self-love up a notch on a solitary retreat, I’ve got you covered with these unbelievable wine hotels in Tuscany.

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From the moment my husband and I approached the entranceway of Borgo Tre Rose in our little Fiat, my expectations were exceeded. Just the parking lot itself felt like travel goals!

While Borgo Tre Rose is undeniably impressive, it’s definitely one of the more under-the-radar properties as far as wine hotels in Tuscany go.

In fact, when I was initially planning our two weeks in Italy and trying to figure out where to stay in Montepulciano, it took a bit of digging to find this gem; but boy, was it worth it! So if you’re also looking for Montepulciano accommodations beyond the old city, I cannot recommend it enough.

Perched on a dreamy hilltop, this historic hotel is surrounded by vineyards and boasts a whopping three wineries – one on the property, one in Montalcino, and one in Chianti.

The rustic guest rooms and apartments are spread out over the property and separated into mini villas, essentially. This creates a peaceful atmosphere and provides a sense of privacy, perfect for a Tuscan getaway.

Also, before I go any further, I want to clarify that our stay at Borgo Tre Rose was not sponsored in any way. Instead, we paid for the whole kit and caboodle out of pocket. Fortunately, it was worth every cent. I’d even go so far as to say that staying here is one of the best things to do in Montepulciano.

While I’ve been incredibly fortunate to collaborate with some wonderful hotels over the years – and I always disclose my honest opinions – I am under no obligation to provide my review for this one. In fact, I wasn’t even originally planning to write this article, as it was one of those rare occasions that my husband and I enjoyed a truly “anonymous” stay.

No one on the property so much as suspected that we were a blogger/photographer team. (Well, perhaps with the exception of that one maintenance guy who was trying to vacuum the pool during our sunset shoot! But I digress.)

In any case, that’s as good a segue as any to share that this property does, in fact, have a pool! I highly recommend heading here for sunset for the best view.

The pool is open seasonally from May until late September. My husband and I were here around mid-September and we enjoyed it all to ourselves!

We also stumbled upon this wooden swing on the property totally spontaneously, just as the sun was setting. It ended up being one of my favorite moments of the entire trip!

Although Borgo Tre Rose technically has a 3-star rating, you totally could’ve fooled me into thinking this was a 4-star property. Then again, with a 3-star price tag, this place is truly a hidden gem and one of the best hotels in Montepulciano, in my opinion!

Borgo Tre Rose offers an extensive buffet breakfast, which is included in the stay. Also, please know that I don’t take the term extensive lightly when it comes to Italian breakfasts; I don’t often see the locals having more than an espresso to start the day!

Fortunately, that’s far from the case here. You can expect a legitimately substantial and tasty hot breakfast including everything from eggs, to meats and cheeses, to breads, to pastries, to cereals.

Plus, you also have the option to incorporate dinner into the price of your stay if you wish.

In addition, wine tastings and cooking classes are offered on-site. You can read more about the tastings and classes here.

Also, free hotel parking is provided on-site, but the lot tends to fill up quickly, so keep that in mind.

Borgo Tre Rose is located at Via dei Palazzi, 5, 53045 Montepulciano SI. (You may also see the address listed as Loc I Palazzi 5, 53045 Valiano, Italy.)

While the hotel is essentially in Montepulciano, it’s technically located just outside of it in Valiano, about a 25-minute drive from Montepulciano’s old city.

Another 3-star gem to consider is the lovely Villa Medicea di Lilliano in Grassina, conveniently located just over a 20-minute drive from Florence. Tucked into the Chianti countryside and surrounded by certified organic vineyards, this property is perfect for everything from a romantic getaway to a wine retreat – or both!

Guests can select from a variety of wine tastings at the estate, ranging from a basic tasting to a private four-course dinner and tasting combination.

Beyond the tasting options, guests can enjoy the exclusivity and luxury of staying in one of the property’s six impeccably-restored private villas.

There are two main villa options to select from: the La Corte Villa and the La Torre Villas. The La Corte Villa sleeps up to a maximum of 12 people in five suites. These can be booked individually or as one collective party.

Alternatively, the La Torre Villas are comprised of five individual villas. Each mini villa has one to three suites with can be booked separately or in conjunction, just as with the La Corte Villa.

Regardless of where you choose to stay, each accommodation is conveniently located just a brief walk from the Villa Medicea di Lilliano wine estate.

The estate also has an outdoor pool that offers picturesque views of the rolling hills, one of the quintessential elements of the striking Tuscan landscape.

Some rooms include balconies that either overlook the pool or the property’s picturesque garden area.

Villa Medicea di Lilliano offers flexible terms for their guests. For instance, you can either rent a villa for your own personal use or for extended friend/family groups. You’ll be prompted to include this information at the time of booking in order to secure the appropriate cleaning services.

A continental/American breakfast is provided.

Villa Medicea di Lilliano is located at Via Lilliano e Meoli, 82, 50012 Grassina FI.

If an authentic farmhouse stay sounds appealing, Castello La Leccia offers the experience you’re looking for.

However, this isn’t the typical farmhouse property you may be expecting, not by a long shot! Instead, you can live like a king or queen in the property’s 11th-century castle!

Located on an organic farm in between Florence and Siena, this 12-room property produces its own organic Tuscan wine, including Chianti Classico, Toscana Rosso, and Toscana Bianco.

Guests can enjoy a relaxing stay directly in La Leccia Castle or in the 5-bedroom La Leccia House, the recently-renovated apartment adjacent to the castle.

Did I mention Castello La Leccia includes a panoramic swimming pool?

Open from May until September, the pool provides spectacular views over vineyards and olive groves.

Castello La Leccia includes a restaurant that serves everything from a breakfast buffet, to traditional Tuscan dishes, to tasty local wines.

Castello La Leccia is located at Località La Leccia, 53011 Castellina in Chianti SI.

From the moment I first saw pictures of Borgo Pignano, I haven’t been able to get it out of my mind. In fact, this is one of those wine hotels in Tuscany that seems too good to be a 4-star property!

First things first, the wine. At Borgo Pignano, guests can enjoy tasting an array of organic and biodynamic wines – given by a wine expert, of course – from the comfort of the property’s impressive 18th-century villa.

While there’s certainly something special about sipping wine in a historic villa, it definitely doesn’t stop guests from ordering an additional glass with a view later on!

Beyond grape goodness, the rooms here are such a vibe. (As you can see, I had a hard time limiting the photos to just one or two here…) There are a total of 14 rooms and suites – and none of them are average.

Oh, did I mention that the villa is located on a hilltop surrounded by traditional English gardens, olive groves, and woods?

Plus, this property has not just one, but two pools! The main one is a heated infinity pool that’s built into the hillside below the villa. Yeah, you guessed it. The views are insane.

Beyond this main pool, there’s also a smaller pool suitable for children, ideal for traveling families.

In case you weren’t already convinced, Borgo Pignano is all about relaxation and tranquility, as evidenced by the property’s spa and wellness center. Here, you can enjoy some R&R in the steam room, sauna, and hammam after a long day.

There’s also the Villa Pignano Restaurant, offering fresh, farm-to-table seasonal ingredients from the surrounding organic farm, vegetable garden, and terrain.

Borgo Pignano is located at Localita’ Pignano, 6, 56048 Volterra PI.

Nestled in the Maremma countryside and surrounded by vineyards, Wine Resort Conti di San Bonifacio challenges the status quo of traditional wine country hospitality.

In fact, the nectar of the Gods is truly the centerpiece of this impressive wine resort, which has been described as “Tuscany’s best boutique vineyard stay.”

In addition to an on-site garden vineyard, this award-winning wine resort also has a winery/shop which works alongside the Wine & Wellness Resort.

With all of these wonderful wine resources, Conti di San Bonifacio is able to offer their guests a variety of experiences, from tastings, to a decadent food and wine pairing dinner, to a complete wine workshop.

Beyond wine, guests can enjoy a variety of food experiences as well, from a Tuscan breakfast buffet to start the day, to Tuscan picnics with mountain/E-bikes, to conscious garden-to-plate cooking classes at Maremanna Restaurant.

In addition, guests can enjoy an exclusive stay in one of the property’s seven elegant rooms surrounded by timeless antique treasures.

Wine Resort Conti di San Bonifacio is located at Localita’ Casteani, 1, 58023 Gavorrano GR.

If you appreciate the traditional old-world charm that Tuscany is known for, then you’re sure to feel right at home at Relais & Châteaux Il Falconiere.

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Fortunately, this gorgeous 17th-century property is conveniently located just a one-minute walk from Barrachi Winery, located atop the rolling hills of Cortona. Here, hotel guests can enjoy sampling the estate’s very own Barrachi wines with a view of the incomparable Valdichiana Valley.

As far as cuisine goes, Il Falconiere – the former-orangery-turned-hotel-restaurant – places an emphasis on high-quality ingredients for a fabulous dining experience. This on-site restaurant also boasts a generous wine collection, should guests prefer to sip and savor here, particularly along the restaurant’s generous panoramic terrace.

Plus, with 34 refined rooms and suites strategically positioned around the estate, guests will enjoy a comfortable stay with Cortona’s countryside views as a pleasant backdrop.

In addition to dining at Il Falconiere, guests also have the option of enjoying breakfast from the comfort of their rooms, whether inside or along their private outdoor spaces.

The property also includes both indoor and outdoor pools as well as a wellness center for ultimate relaxation.

Relais & Châteaux Il Falconiere is located at Località S. Martino Bocena, 370, 52044 Cortona AR.

Borgo Scopeto Relais is a special 13th-century property housed within a medieval hamlet.

Enclosed by buildings and surrounded by vineyards and olive groves, a stay at Borgo Scopeto Relais feels protected from the outside world, yet it’s only a 20-minute drive from Siena.

Unsurprisingly, wine is the focal point of the property, and guests can either enjoy a tasting in Salla della Cisterna or from the cellars of Borgo Scopeto Relais and the surrounding vineyards.

In addition, each day also includes a daily “wine hour” from 6 – 7PM. This is a chance for guests to unwind with a glass in the cellars of Borgo Scopeto, Caparzo, Altesino or Doga delle Clavule.

Food is certainly an experience here as well, as evidenced by the property’s variety of eateries, from a restaurant, to a bistro, to a pool bar.

As for the accommodations, guests can expect a welcoming atmosphere in the property’s 52 total rooms, suites, and villas.

However, the charming interiors are just the beginning. Beyond each door is the romance of nature all around, from gardens and lavender fields filling the air with a heavenly scent to olive groves and vineyards delighting the senses.

If you’re looking for a refreshing dip, you’ll have plenty of options to choose from, between the indoor pool, hot tub, and Turkish bath, all available for an additional fee.

Borgo Scopeto Relais is located at Strada Comunale 14, 18, 53010 Vagliagli SI.

If you envision yourself in the heart of the Chianti Classico region with a glass of vino in hand, then look no further than Capannelle Wine Resort.

Part of the Capannelle wine estate, this property is completely surrounded by vineyards (and cypress trees). This is Tuscany, after all!

To give you a sense of the scale here, the estate is nearly 20 hectares (approximately 50 acres) and the vineyards account for nearly 40 acres! Pretty impressive, huh?

As for the property itself, the Capannelle Wine Resort consists of a fully-renovated cottage with five standard rooms and one suite.

But not to worry – the so-called “standard” rooms aren’t ordinary. Each lends its own Tuscan charm to your special stay. Plus, with the surrounding gardens, you can enjoy the beautiful vineyard views from the comfort of your room.

Alternatively, you can venture out to the gardens to enjoy the beauty all around you!

Capannelle Wine Resort is located at Località Capannelle, 13, 53013 Gaiole in Chianti SI.

Another wonderful option in the coveted Chianti Classico region – this one in the municipality of Radda and the Gallo Nero area – is Il Borgo di Vescine.

World-renowned for its array of vineyards and historic wine cellars, the Gallo Nero area is an ideal setting for a wine-friendly hotel experience.

However, what makes this property unique from the others on this list is its location in a 13th–century medieval village!

In particular, this storybook relais (which translates to countryside hotel) is perfect for a cozy and “homey” experience, as the property is aptly described as a “home away from home.”

As for the wine and culinary experiences, Il Borgo di Vescine places an emphasis on preserving the property’s medieval history and making the most of the surrounding land. For instance, they offer a weekly “medieval dinner” where you can enjoy a pleasant meal cooked right in front of you on the property’s impressive 700-year-old wood-fire oven.

Alternatively, guests can opt for a romantic picnic surrounded by the rolling hills of Chianti. With this selection, chefs will prepare a picnic basket with fresh local produce and provide a comfortable blanket for the spread. How charming is that?

And speaking of romantic, how would a candlelit dinner among the olive groves sound? This is another unique experience for couples to enjoy at Il Borgo di Vescine.

Personally, I find this to be one of the most romantic hotels in Tuscany, particularly if you prefer intimate, boutique properties.

And let’s not forget the star of the show: the wine! At the property’s Entoca Wine Bar, you can enjoy an array of fine wines from the surrounding vineyards and even join a tasting class to learn how to critique the best vintages.

In regards to accommodations, there are 21 total rooms and seven suites spread out over the property. Here, guests will enjoy a taste of the past in these original houses featuring fascinating period furniture.

Il Borgo di Vescine is located at Località Vescine, 53017 Radda in Chianti SI.

If you’d like to base yourself near Radda and surround yourself with Chianti hills but would prefer a more upscale experience, then I’d encourage you to consider a stay at Villa Campomaggio Resort & Spa.

However, you won’t have to worry about skimping on history if you’re still after an authentic Tuscan experience, as the property dates back to 1776!

Located just outside Radda, Villa Campomaggio Resort & Spa is contained within an aristocratic 18th-century villa and sits amidst an impressive and meticulously-kept garden.

This 20-room property offers classic and superior rooms as well as junior suites.

Each space either showcases the garden or provides a panorama of the surrounding vineyards.

In addition, guests can take a dip in the property’s lovely outdoor pool, which is open seasonally.

For the vino, guests can select from one of the area’s many surrounding wineries, and various guided tours are available.

In addition, a buffet breakfast is provided in the courtyard, surrounded by the beauty of a picturesque garden. While there’s technically no restaurant on-site, the wine bar is happy to provide a variety of lunches and other light dishes, such as cheese and cold cut platters, salad, and bruschetta.

Plus, if you’re looking to indulge in a relaxing holiday, you can treat yourself to a massage, a beauty treatment, or a soak in the Turkish bath at the resort’s wellness center.

The wine bar is open daily from 8AM – 11:30PM. It serves classic wine varieties ranging from Chianti Classico, to Chianti Riserva, to Super Tuscan (a variety of Bordeaux influence that combines French grapes with Sangiovese).

Villa Campomaggio Resort & Spa is located at Strada Provinciale 2bis, Radda in Chianti SI.

Hotel Poggio Piglia sits on a 150-year-old estate with 19 hectares (approximately 47 acres) of woods, vineyards, and olive trees.

This charming boutique farm hotel is known for its bold Sangiovese red wine. It pairs effortlessly with rich, savory foods, including red meats, thick soups, and dairy items. In addition to enjoying this (and several other wine varieties) at the property’s on-site restaurant and bar, guests are also encouraged to purchase wine to take back home. In addition to the characteristic Sangiovese red that the hotel is known for, Poggio Piglia also offers Brunello di Montalcino, Chianti, Vino Nobile di Montepulciano and, Super Tuscan varieties.

Plus, the hotel offers cooking classes if you’re interested in learning about the inner workings of Tuscan cuisine.

While the property offers only 9 suites in total, the rooms are spacious and offer luxurious bathrooms and spectacular panoramic views.

In addition, guests can take advantage of the lovely infinity pool and its natural surroundings.

Poggio Piglia is located at Frazione Macciano, 53043 Chiusi.

Relais Villa Olmo offers guests the best of both worlds – a relaxing Tuscan escape in a convenient location.

Located just under 30 minutes from Florence, this villa offers the beauty of the countryside while still in close proximity to a major metropolitan city. Sitting atop an ancient 15th-century hamlet, the property has been lovingly restored to provide the best possible experience for guests.

Relais Villa Olmo’s specialty wine is their Diadema red, which you can sip from the comfort of the property’s newly-restored wine cellar. Plus, wine-loving guests will appreciate the special perk of a free guided cellar tour!

Relais Villa Olmo also boasts an authentic Chianti Italian restaurant set amongst an idyllic scene of olive groves and vineyards. Here, you can enjoy everything from à-la-carte breakfast, to tasty lunch, to all-day dining menus.

In addition, Relais Villa Olmo has no shortage of accommodation options. In fact, the property boasts rooms and suites, a private villa, and even a farmhouse.

In addition, couples on a romantic retreat may consider booking one of the special suites for twosomes. These come with a private garden for the ultimate exclusivity.

Plus, for a relaxing time outdoors, you might just fancy a dip in the outdoor swimming pool with countryside views as your backdrop.

Relais Villa Olmo is located at Via Imprunetana per Tavarnuzze, 19, 50023 Impruneta FI.

If an ancient hilltop castle sounds like the ideal location to enjoy your wine, you should definitely have a look at Castello Vicchiomaggio.

Overlooking the valley of Greve in the heart of Chianti, Castello Vicchiomaggio offers tours of both their vineyard and historical cellars for an inside look at their award-winning wine.

The on-site castle restaurant serves up traditional Tuscan dishes leveraging timeless and beloved Italian recipes. This impressive space offers a historical feel with its beautiful vaulted ceilings and Renaissance hall setting. Hotel guests can also enjoy a buffet breakfast to start the day.

In addition, guests can expect a comfortable stay in Castello Vicchiomaggio’s elegant suites and apartments. Plus, there are spectacular countryside views for those lazy days by the pool.

Wine tours average 90 minutes and are offered by appointment only. Visitors are encouraged to follow up their tours with a wine tasting and lunch/dinner at the castle’s restaurant.

Castello Vicchiomaggio is located at Località Vicchio, 4, 50022 Greve in Chianti FI.

If a homey stay is your preference, then you should consider Villa Le Barone. This historic 16th-century manor house with its ivy facade is definitely storybook material!

With a romantic atmosphere and the intimate feeling of being in a private house, this beautifully renovated space is perfect for an elevated home-away-from-home experience.

In addition, with Villa La Barone’s ideal positioning in the heart of the Chianti wine-producing region, you can expect to taste some of the finest Chianti wines from the best local Tuscan wineries. All wines are carefully hand-selected for their ability to enhance the cuisine you’ll find at Il Torchio, the charming on-site restaurant.

From Super Tuscan varieties to the finishing Vin Santo, you’ll enjoy these wonderful varieties from the comfort and coziness of the villa’s own wine cellar.

In regards to accommodations, you can expect classic elegance, whether you’re staying in a charming room or a historic suite.

Plus, you can enjoy an inviting swimming pool amidst a lovely rose garden for a truly tranquil experience and oneness with nature.

Villa Le Barone is located at Località San Leolino, 19, 50022 Pieve di Panzano FI.

From the initial drive up to the entranceway of the estate, you’re sure to be wowed by the magnificence that is Il Borro Relais & Châteaux.

Located about 30 minutes from Arezzo, Il Borro Relais & Châteaux is a century-old hamlet spanning nearly 3,000 acres. Since 1993, the property has been lovingly restored to its current glory.

You can truly feel good about your stay on these organic vineyards, which have eliminated all chemical products and pesticides since 2012. Organized wine tours are offered in the property’s wine cellar, where you can sample reds, whites, rosés, and Vin Santos.

In addition, you can select from a variety of other wine combination tours depending on your interests.

Tour options include:

• Tour & bio
• Tour & picnic
• Wine tasting & spa
• Wine tasting & horseback riding
• Wine tasting & Tuscan bistro
• Wine tasting & cooking class
• Wine tasting & artisans

Plus, with two restaurants on-site –  Osteria del Borro and Il Borro Tuscan Bistro –  you’ll never go hungry at Il Borro Relais & Châteaux.

In addition, you’ll have plenty of options as far as accommodations go. Rooms are divided amongst three properties: the villas at Il Borro Relais & Châteaux, a manor house and villas at the Viesca Estate (located about 30 minutes away), and the three farmhouses of I Borrigiani (located just under one mile away).

In addition, make sure to take advantage of the nice outdoor pool with a view while you’re here!

Il Borro Relais & Châteaux is located at Località Borro, 1, 52024 Loro Ciuffenna AR.

Castello di Vicarello is more than a hotel – it’s an invitation to immerse yourself in the peaceful atmosphere of nature.

Nestled in the Maremma countryside and surrounded by organic vineyards, sprawling farmland, and olive groves, this award-winning property is perfect for a secluded getaway.

With fertile soil spanning over seven acres of organically-grown vineyards, Castello di Vicarello produce a uniquely delicious wine inspired by the wonderful wines of the Bordeaux region. The property specializes in four different wine varieties: Merah, Santaurora, Terre di Vico, and their own unique signature variety, Castello di Vicarello.In addition, Castello di Vicarello also offers convenient wine deliveries for those living in the EU.

In addition to their signature wines, Castello di Vicarello also takes great pride in serving organic cuisine made from farm-fresh, locally-sourced ingredients. Guests will have no shortage of dining venue options, from a romantic candlelit dinner atop the castle at Ristorante La Terrazza, to a terrace meal with spectacular views of the Maremma, to a relaxing poolside lunch.

Plus, the outdoor pool is like an escape unto itself.

For overnight guests, Castello di Vicarello offers nine unique suites that seamlessly blend modern and antique furnishings for a luxurious, yet authentic Tuscan experience.

Castello di Vicarello is located at  Via Vicarello, 1, 58044 Poggi del Sasso GR.

Recognized as one of the small luxury hotels of the world, Castello di Spaltenna Exclusive Resort & Spa is set within an ancient, 10th-century monastery in the charming Chianti’s Gaiole village.

This charming property produces its six exclusive wines from the surrounding vineyards, encompassing whites, reds, and rosés. Wines are available for tasting both in the Canteen or at the hotel’s Michelin-starred Pievano Restaurant. In addition, the hotel is home to La Terrazza Restaurant, offering light fare.

In addition to elegant rooms, suites, and villas, there are also exclusive spa apartments located just over half a mile away in picturesque Borgo Di Vertine, a storybook medieval fortified town.

Castello di Spaltenna also offers two pools – one outdoors and one indoors – to provide the ultimate in relaxation, regardless of the season.

In addition, you can take advantage of the Turkish bath, sauna, fitness center, tennis court, and billiard room for all your recreational needs.

Castello di Spaltenna is located at Via Spaltenna, 13, 53013 Gaiole In Chianti SI.

It’s not hard to see why Castel Monastero has earned the honor of one of the leading hotels of the world.

Located in a restored 10th-century medieval village, this impressive castle comes with a the works – a  pool, spa center, two wonderful restaurants, a tea room, and spectacular views over Tuscany, of course.

Specializing in Tuscan and Chianti wines, guests can sip and savor at the castle’s Wine Restaurant, located in the property’s medieval wine cellar. In addition to the Wine Restaurant, there’s also Contrada Restaurant, specializing in gourmet offerings made from local ingredients.

One of the largest properties on this list, Castel Monastero boasts 74 rooms and suites as well as one villa.

Castel Monastero is located at Loc. Monastero D’Ombrone, 19, 53019 Castelnuovo Berardenga SI.

Surrounded by vineyards in the heart of the Chianti wine district, Borgo San Felice is a luxurious wine resort and the singular relais and château in the Chianti Classico region, about 30 minutes outside of Siena.

The property’s vineyards are primarily dedicated to the harvesting of Sangiovese grapes, and Borgo San Felice is noted for its Il Grigio Riserva, Il Grigio, and Poggio Rosso.

In addition to the classics, Borgo San Felice is an experimental producer of indigenous Tuscan varieties, including Pugnitello.

In addition to an impressive wine production history, Borgo San Felice also has quite the extensive wine library – over 500 fine wines, to be exact – at Il Poggio Rosso, one of two on-site restaurants.

Alternatively, Osteria del Grigio, the property’s second restaurant, offers modern Tuscan cuisine for lunch and dinner in a more laid-back atmosphere.

As for accommodations, you’ll have 29 rooms and 31 suites to choose from. All are located throughout the palaces of the medieval hamlet, giving the sense that you’ve stepped back in time.

Borgo San Felice is located at Località San Felice, 53019 Castelnuovo Berardenga SI.

When it comes to luxury hotels in Tuscany, it’s hard to beat Castello di Velona.

Another property upholding the coveted leading-hotels-of-the-world status, Castello di Velona is a luxe destination for those after celebrity-level pampering.

Overlooking the stunning Val d’Orcia, this property is the true trifecta of hotel stays; it’s a resort, thermal spa, and winery all wrapped up in one immaculate package.

As for the wine, Castello di Velona specializes in a niche Brunello exclusive to the hotel and not found within wine shops. Fortunately, you may special-order bottles of your own from the property.

While the resort has a relatively modest vineyard area of just over 12 acres, the somewhat limited land allows for a higher-quality product and, ultimately, more coveted wines.

Beyond the wine, Castello di Velona boasts a remarkably impressive array of 11 restaurants! Three of these are located within the resort itself, while the remaining eight are partner restaurants located outside. In addition, as the only resort in Tuscany to offer a “Dine Around Program,” you can purchase an accommodation package to dine at one or more of the eight partner restaurants.

For the ultimate in relaxation, you can take advantage of the sauna, Turkish bath, and/or a beauty treatment at the hotel’s wellness center as well as swim in both the indoor and outdoor pool.

Castello di Velona will reopen in April 2022.

Castello di Velona is loated at Località Velona – Castelnuovo dell’Abate, 53024 Montalcino SI.

Toscana Resort Castelfalfi may as well be on its own private island in terms of how exclusive and elite it feels.

Set atop a hill surrounded by vineyards, olive trees, and a golf course, Toscana Resort Castelfalfi is the ultimate romantic escape.

Wine tastings at Toscana Resort Castelfalfi include the opportunity to sample the special labels produced by the Tentua di Castelfalfi and can even be paired with a delicious dinner. Wines may also be ordered online.

Plus, with three restaurants plus a bar, you can select the atmosphere most aligned to your sensibilities.

Toscana Resort Castelfalfi offers a range of rooms and suites from cozy and traditional to luxurious with spectacular views.

In addition, for a more secluded and private experience, you may wish to rent out one of the beautiful farmhouses or apartments located on the estate.

Of course, there’s also a pool with 10/10 views!

Toscana Resort Castelfalfi is located at Località Castelfalfi, 50050 Montaione, Metropolitan City of Florence.

However, while the address references Florence, keep in mind that this is a countryside property in Castelfalfi, located about 40 minutes from the center of Florence.

Perched atop a hill in a picturesque countryside-village-turned-heavenly-retreat, Hotel Le Fontanelle is perfect for nature lovers.

With expansive vineyards, Hotel Le Fontanelle produces a dozen exclusive wine labels, including Chianti Classico DOCG, Chianti Classico Riserva DOCG, and Chianti Classico Gran Selezione DOCG.

During your stay, you can visit the vineyards and winery as well as the barrel room and finish off with a fabulous selection of Vallepicciola varieties. In addition, private tours with the winemaker can also be arranged for a chance to learn the ins and outs of winemaking on the property. You’ll also have the chance to sample the different varieties along with local meats and cheeses.

In addition, guests can sip wines at their leisure at the Lounge Bar as well as bring home a bottle as a delicious reminder of a wonderful trip.

Hotel Le Fontanelle is also home to La Colonna Restaurant, a traditional Tuscan restaurant offering à la carte and tasting menu as well as sweet and savory breakfast options to start the day.

The elegant accommodations at Hotel Le Fontanelle range from classic rooms to spacious suites that operate as private residences apart from the main action.

Last – but certainly not least – is the gorgeous pool, of course!

Hotel Le Fontanelle is located at SP 408 km 14.7 Località, 53019 Pianella SI.

L’Andana Tenuta La Badiola in Castiglione della Pescaia is a pink-princess dream come true.

Set amidst the beautiful backdrop of Maremma and surrounded by olive groves and vineyards, this timeless luxury resort and former summer residence is simply awe-inspiring.

Wine is truly an experience at L’Andana and you can immerse yourself in the production process of Tenuta La Badiola on the impressive 1200+-acre estate.

In addition, you may also join a wine class and tasting focused on one of the most significant wine areas in the world – Montalcino. Choose between the “Road to Montalcino” experience (which includes any wines from the main list coupled with cheeses) or the “360° Brunello” featuring four Brunello glasses paired with local cheeses and cured meats.

During your stay, you can select from one of 33 rooms at “The Villa” or from one of the 14 rooms/suites at “The House.” Regardless of which you choose, you’ll be greeted by expansive views of the beautiful Maremma countryside.

The property’s main restaurant, La Trattoria Enrico Bartolini, is a Michelen-starred gem that combines classic Tuscan cuisine with experimentation for an exceptional culinary experience. In addition, The Villa restaurant offers an inviting atmosphere in a true home kitchen. Here, you can enjoy everything from a sumptuous breakfast to a tasty lunch and dinner.

A plentiful continental breakfast is also offered separately for guests staying at “The House.”

Alternatively, if you’d prefer to enjoy your meal amongst nature, a picnic on the property or by the beach can also be arranged.

In addition, you can enjoy extra time sunning yourself by the property’s lovely outdoor pool.

L’Andana Tenuta La Badiola will reopen on April 1, 2022.

L’Andana Tenuta La Badiola is located at Località Badiola, 58043 Castiglione della Pescaia GR.

Atop a magnificent 740-acre estate in the idyllic Chianti wine country sits 12th-century chateau COMO Castello Del Nero.

Here, you can sample the best the region has to offer, from wine, to olive oil, to honey. Wine tastings, in particular, run for one hour and introduce some of the best varieties in Tuscany, including Brunello di Montalcino and Chianti Classico. You’ll have a chance to sip and savor wines along with ham and pecorino cheese while learning about the estate’s own award-winning selections.

Beyond wine, you can’t miss a visit to Michelin-starred La Torre Restaurant set in the castle’s former stable. Here, you’ll select from an a la carte menu and a handful of local wines. In addition, for Tuscan specialties, you’ll have to try the estate’s second hotspot, La Taverna Restaurant.

COMO Castello Del Nero consists of 50 bright and airy rooms and suites, many of which offer views of the surrounding countryside and lakes.

In addition, there’s a lovely outdoor pool with wonderful hillside views.

COMO Castello Del Nero is located at Str. Spicciano, 7, 50028 Barberino Tavarnelle FI.

I’ve decided to include the spectacular Rosewood Castiglion del Bosco last on this list, as the property is temporarily closed. However, I hope this will serve as future inspiration!

Sitting on one of the oldest estates in Tuscany about eight miles from Montalcino, Rosewood Castiglion del Bosco is one of those wine hotels in Tuscany that truly immerses you in the winemaking process.

The property not only includes vineyards directly on the estate, but along the coast as well. In regards to wine tours and tastings, you’ll have the option of three:

• The Castiglion Del Bosco Wine Experience – This 90-minute experience provides a full overview of the art of winemaking, from vine to barrel. It includes a visit to the vineyards, cellar, and aging room, and concludes with a tasting of six Castiglion del Bosco wines.
• Cheese and Wine Pairing – This two-hour experience will demonstrate how to best pair various Italian cheeses with Castiglion del Bosco wines. It includes some limited production wines such as Brunello di Montalcino Riserva Millecento and a Vin Santo sweet varietal.
• The Vertical Tasting – This private 90-minute experience includes a visit to the property’s wine cellars with an experienced wine educator. It includes a tasting of the winery’s best vintages of Brunello di Monalcino alongside Pecorino cheese, Tuscan bread, and the property’s own olive oil and honey.

In addition to extensive wine tours and tastings, Rosewood Castiglion del Bosco also takes Tuscan cuisine to a new level within its restaurant, trattoria-style dining experience, bar, pool bar, and lobby area.

The property also includes 19 suites located within a new complex of the estate that still maintains a charming Tuscan character.

In addition, you can enjoy a relaxing afternoon at the hotel’s sauna and Turkish bath as well as swim in the beautiful panoramic swimming pool.

Rosewood Castiglion del Bosco is located at 53024 Castiglion del Bosco Province of Siena.

Well, that about does it for this handy guide to the most romantic wine hotels in Tuscany! I sincerely hope that you’re feeling the love and that you’ll be able to lock down one of these amazing properties for your next romantic getaway.

Have you had the opportunity to visit this magical region before? If not, which one of these romantic wine hotels in Tuscany is calling your name? Let me know in the comments below and cheers to la dolce vita!

Searching for fun activities to enjoy while in Tuscany? Check out my other guides:

• 15 Wonderful Wineries in Montepulciano
• 20 Awesome Things to Do in Montepulciano
• Breathtaking Landscapes of Tuscany: An Essential Photo Guide
• 20 Best Day Trips from Florence (Within Two Hours)