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Our Top Romantic Lodgings in Chianti

Creating Fabulously Romantic Memories in Chianti

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

Our selection of the top 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-style 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 tub with the sun at your back.

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

1. Villa il Poggiale

Romantic bathroom at Villa PoggialeRomantic bathroom at Villa Poggiale

Where: San Casciano Val di Pesa

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

2. Villa Dianella

Wine Cellar at Villa DianellaA private wine tasting at Villa Dianella

Where: Vinci

Everyone knows that romance and good wine go together, and we couldn't think of anything more special than a wine tasting to make the evening sparkle. At Villa Dianella not only will they dazzle your taste buds with cooking classes and quality ingredients, but they will also surround you with a glamorous setting just perfect for an amorous getaway.

3. Palazzo Malaspina

Country styled decor at Palazzo MalaspinaCountry styled decor at Palazzo Malaspina

Where: San Donato in Poggio

Cozy 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 tranquil setting with lots of opportunities like the possibility to stroll hand in hand the cobbled stone streets of Tuscany.

4. Casolare Libbiano

Unique romantic decor with spacious bedrooms at Casolare LibbianoUnique romantic decor with spacious bedrooms at Casolare Libbiano

Where: San Gimignano

What makes the six-bedroom Casolare Libbiano B&B extraordinary is not its great position or the typical country style decor, or even the on-site restaurant with authentic and genuine recipes. The best part of this bed and breakfast is the warm hospitality and creative spirit of the owners, who go out of their way to find great ways to bring the romantic atmosphere into your vacation.

5. Romitorio di Serelle

Vineyards everywhere you look at Romitorio di SerelleVineyards everywhere you look at Romitorio di Serelle

Where: Barberino Val d'Elsa

The panoramic views from Romitorio di Serelle are incredible from every corner of this private oasis among the vineyards. What makes this place outstanding, besides the country decor and beautiful gardens, is the newest additions, a scenic covered gazebo, where you can sip an espresso or toast with a glass of prosecco. Hint: don't miss out on the restaurant which caters to a wide range of options from specialty meals, vegan and vegetarian to grilled Tuscan meats and tasty cheeses, not to mention candlelight romance.

6. Borgo di Pietrafitta Relais

Romantic vista from Pietrafitta RelaisRomantic vista from Borgo di Pietrafitta 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.

7. Taverna Bibbiano

Stupendous garden views towards San Gimignano: Taverna Bibbiano

Where: Colle di Val d'Elsa

Couples from all over the world come to celebrate their vows, honeymoon & anniversaries at Taverna Bibbiano There are ample secret corners where you can seek out some special private time to enjoy the tranquility, the perfumes of Tuscany and panoramic views of San Gimignano. Their trademarks are the bountiful lavender bushes that provide the basis for so many of their special holiday gifts and recipes. The roses in the gardens start blooming in late April & May and keep their lovely colors all the way into November.

8. Borgo Argenina

Panorama 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 creating new memories.

9. Il Cellese

Il CelleseA sunset dinner in Chianti with Il Cellese

Where: Castellina in Chianti

For those who dream of finding a secluded corner to read poetry and meditate in the tranquility provided by Mother Nature, you couldn’t choose better than Il Cellese. The country style decor, with its elegant signature, and its seemingly endless panoramic views will make this a romantic vacation for those falling in love, and those already in love. A true taste of Tuscany is hidden within the walls of their brand new wine cellar, where the owner Sergio, will be happy to give you a taste of (one of) his true loves: his wine.

10. Candida's Chianti House

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

Where: San Casciano in Val di Pesa

We were charmed by 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 Chianti House will spoil you with its familiar and casual atmosphere and enchanting green garden.

11. Art Rebus Tower

Incredible views from roof top terrace in the city centerIncredible views from the rooftop terrace

Where: Radda in Chianti

A new entry on our list of romantic charmers in the heart of Chianti Classico, the independent apartment rental Art Rebus Tower sits in a historic tower in the town center and combines the luxury of being within walking distance of shops, restaurants, and cafes as well as fabulous views from the private terrace overlooking the vineyards and lovely Chianti sunsets. The newly renovated apartment features all the comforts of home as well as many new modern accessories. Check it out and decide for yourself.

Even More Romantic Getaways in Tuscany

The above are just a few of the many places to stay in the Chianti area which promise to add a touch of romance during your vacation. However, if you are looking to make Florence your holiday base, and want a few of our best suggestions for a romantic accommodation in or around the city, you need to read our top choices for Florence.

Chianti is just one of the many exciting destinations in Tuscany, but if you prefer to look outside of the area, then you will want to check out this list of the best romantic lodgings in Tuscany which covers the entire region.

We also suggest browsing this link comprised of hand-picked B&B, rental villas and private apartments of romantic accommodations in Tuscany. This list invites you to book direct with the owner, and we at DiscoverTuscany always suggest going direct for the best price and sometimes, extra-special offers ;-)

Author: Donna Scharnagl

It has been more than 25 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. It didn't take long to learn 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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