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Our Top 10 Romantic Lodgings in Chianti

Creating Fabulous Memories of Romance in Italy

A vacation for two surrounded by the picturesque vineyards of Chianti, the promise of fabulous sunsets, endless vistas, classic Italian meals, superb Chianti Classico wine and the exquisite Tuscan hospitality.  These are the undisputable ingredients for a romantic adventure of a lifetime.  

Our selection of the top ten romantic accommodations in Chianti below takes into consideration places that offer a special atmosphere with a historic setting or a whimsical decor including canopy beds and spa styled bathrooms. Not just the interiors but also exteriors that provide ample private nooks where you can hide away and indulge in some quiet moments making “forever” memories.

Romance is not just candle lit dinners on panoramic terraces, though as the Italians would say, “non guasta”. it doesn’t hurt to wine and dine under the Chianti stars. Romance can be found in those stolen moments walking around the Italian styled garden, visiting the cantina from yesteryear or lazing in a private jacuzzi with the sun at your back.

Dream your next romantic getaway with our selection of romantic holiday accommodations in Chianti.

1. Villa Dianella

Wine Cellar at Villa DianellaA private wine tasting at Villa Dianella

Where: Vinci, Florence

Everyone knows that romance and good wine go together, and we couldn’t think of anything more special than a winetasting to make the evening sparkle. At Villa Dianella not only will they dazzle your tastebuds but they will surround you with a glamorous setting just perfect for an amorous getaway.

2. Villa il Poggiale

Romantic bathroom at Villa PoggialeRomantic bathroom at Villa Poggiale

Where: San Casciano Val di Pesa, Florence

Not everyone will get as excited about this deluxe bathroom, but we couldn’t help imagine how a leisurely bath just seems so decadent. Villa il Poggiale combines the Chianti setting with typical Tuscan architecture to create a fairytale accommodation for a romantic vacation.

3. Palazzo Malaspina

Country styled decor at Palazzo MalaspinaCountry styled decor at Palazzo Malaspina

Where: San Donato in Poggio, Florence

Cosy and quaint, the typical Tuscan decor at Palazzo Malaspina creates a warm and welcoming atmosphere where you can sneak off and fall in love all over again. This idyllic palazzo set in a thriving town setting offers a quite atmosphere yet the possibility stroll the cobbled stone streets in Tuscany.

4. Borgo di Pietrafitta Relais

Romantic vista from Piertrafitta RelaisRomantic vista from Borgo di Piertrafitta Relais

Where: Castellina in Chianti

Created out of a small Tuscan town, Borgo di Pietrafitta Relais is a delightful mix of B&B and self catering apartments. Choose how you want to spend your holiday...being served delicious Tuscan treats with an early morning caffè latte or cooking together with the fresh ingredients from the market.

5. Villa Medicea di Lilliano

Night view of Medici villaUnder the stars at Villa Medicea di Liliano

Where: Grassina, Florence

Only a short distance from Florence, Villa Medicea di Lilliano will capture your imagination. This spectacular setting is perfect not only for your honeymoon...but why not your destination wedding as well. Catered parties or exclusive wine tastings for two, it is all possible.

6. Hotel Le Fontanelle

Indoor swimming pool at Hotel Le FontanelleIndoor swimming pool at Hotel Le Fontanelle

Where: Castelnuovo Berardenga, Siena

Located only 20 km from Siena nestled in the unique Chianti landscape, Hotel Le Fontanelle promises a holiday to remember for all times. After touring the vineyards, the hamlets and markets you can come home and indulge in a treatment at the Wellness Center after using the heated indoor pool, sauna, Turkish bath or Jacuzzi.

7. Villa Alba B&B

Villa Alba with Swimming poolVilla Alba within walking distance of San Giminano

Where: San Gimignano

If we were looking for something which catered to adults only, then we would definitely suggest a stay at Villa Alba B&B.  Within walking distance of perhaps one of the most visited towns in all of the Tuscan countryside, it is easy to imagine an evening stroll in the shade of the medieval towers of San Gimignano and a glass of wine at one of the many cafes.  

8. Borgo Argenina

Panoramo of Chianti from Borgo ArgeninaClassical Chianti landscape from Borgo Argenina

Where: Gaiole in Chianti

Without a doubt, Borgo Argenina is perfectly Tuscan. Positioned in the heart of Chianti with a classical country decor.  Surround yourself with fabulous views, good food and delicious wine and you have the recipe for romance. Cooking classes together and evenings watching the sunset are the perfect relaxing activity you need while create new memories.

9. Candida Bing Chianti House

Bedroom suite at Candida Bing Chianti HouseTuscan style bedroom suite at Candida Bing Chianti House

Where: San Casciano in Val di Pesa, Florence

We were charmed by the this exclusive three room B&B near San Casciano between Siena, Florence and Chianti where you can spend time getting to know each other or participate in cooking lessons, long walks and intimate meals. The quaint little Candida Bing Chianti House will spoil you with its familiar and casual atmosphere and enchanting green garden.

10. Palazzo Leopoldo

Indoor pool and spa at Palazzo LeopoldoIndoor pool and spa at Palazzo Leopoldo

Where: Radda in Chianti

In the lovely town of Radda in Chianti, surrounded by endless vineyards Palazzo Leopoldo creates an intimate setting for a romantic interlude. Plan on a couple of days exploring the local cantinas, small towns and rolling hills and then return here where you can pamper yourself with a wide range of extra services, massages and spa treatments.


Author: Donna Scharnagl

It has been over 24 years since I took my first steps in Italy and I still haven’t found a good reason to leave.  Between the food, the culture, the history, the art, the landscapes … did I mention the food? I have become a lifelong student. And I soon learned that Italians all have stories that long to be told; stories that paint a picture of how hard work produces character, how life is made of ups and downs and how good it feels to laugh.



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