Castello Di Casole in a Nutshell 
Had Travel + Leisure magazine published a millennium ago, it might have had high praise — casa bellisima! — for the 10th-century castle that once stood here, home to Italian nobility. Instead it took about a thousand years, the construction of a replacement castle in the 18th century, many changes in ownership, and a seven-year restoration (2005-2012) by Timbers Resorts for Castello di Casole to earn the rank No. 1 Resort in Europe 2013 by the magazine.

Surrounded by 4,200 acres of rolling hills and vineyards, Castello di Casole is certain to seduce honeymoon couples and other romantics. Not just because it’s right out of Under the Tuscan Sun. No, the allure of Castello di Casole is that in addition to the cypress-encircled exquisiteness of it all, everything at the hotel also works perfectly. Wi-fi is flawless, the staff is intelligent and easy to communicate with, the roomy suites are fancy and functional, and the crystal-blue infinity pool has a view to make the Mona Lisa swoon. 

Suites at Castello di Casole
The 41 suites surround a beautifully landscaped courtyard. Guest rooms are so silent that it’s almost scary…until you take the best afternoon nap of your life. They feel like big, dark, sleeping vaults furnished with an incredibly comfortable bed, medieval oil paintings on the walls, and a few pieces of antiques.

Draped on the bed and covering the floor-to-ceiling windows are rich Italian fabrics in deep rust-orange and royal blue custom-designed for Castello di Casole.

Sweep them aside to gaze out over lush vineyards and lemon and olive trees. 

Wi-fi, flat panel HDTVs with Sky TV, and a complimentary minibar (taste the amazing chocolate-covered ginger) are a few of the in-room perks. The just-big-enough-for-two bathtub and separate sleek shower are primped with lemon-scented soaps and dewy creams. Both heat and AC work as they should throughout.  

Fun fact: In the late 20th century, the Castello was owned by Italian film director Luchino Visconti. 

Dining at Castello di Casole
Like the suites, the hotel's three restaurants are concentrated around the scenic courtyard. Bar Visconti is a casual Italian bistro for a soup and salad lunch (order the minestrone); Pazzia is a pizzeria with a wood-burning oven, where creative off-the-menu pizza concoctions are possible. My friend asked for a ricotta, fig, and prosciutto pizza. No problem.

Tosca, the fine-dining restaurant designed with a red marble floor and silk-upholstered chairs, is upscale but not stuffy. The chef makes a memorable vegetable terrine and beef tenderloin. He also does a tasting menu with wine pairings.

The estate’s signature Sangiovese blend, Dodici, is only offered to guests, and it was the best wine I drank all weekend. The standout meal, however, is the breakfast buffet – a large, bountiful spread of Italian and continental options that includes homemade tortas, artisanal cheeses, and terrifically fresh kiwi, figs and melon. There are indoor and outdoor seating options for all of the restaurants, making meals glorious in the sun and/or comfy-and-cozy in the cold.

Destination Weddings at Castello di Casole
A complete Tuscan wedding can be customized on-site -- management does what it takes to make individual visions come true. Events can take place around the infinity pool, on a picturesque cliffside, or inside the elegant Tosca restaurant. The bride can even have her gown designed by a local Italian fashion designer provided by the hotel. Wedding officiants, flowers, photographers, and musical options are also available.

Honeymoons/Romance at Castello di Casole
For honeymoon duos and other couples in love, Castello has a luxurious 4-night package that includes a grand suite, a couples massage, a champagne breakfast in bed, a vintage Mercedes for the day, on-site cooking classes, and picnic baskets packed with estate wine and local specialties such as pecorino tuscano and Schiacciata con l’Uva  to feast on in the vineyards. Yet a stay as regular guests is just as romantic. On any given night, there might be a string quartet playing in the garden or a warm fireplace awaiting you. It is basically impossible not to feel like your most romantic selves here. 

Activities at  Castello di Casole
Painting classes with a resident artist is a unique pleasure; creating with watercolors in a Tuscan carriage house is art therapy at its finest. The hotel maintains light and sleek black bicycles available for long rides in the surrounding hills -- prepare for some serious cardio if you do this; those hills are intense! There are daily yoga and Pilates classes, as well as personal training if desired.

Nearby Castello di Casole
Guests are an hour or from Florence, Siena, and Pisa. Most visitors rent a car, but the hotel can provide a driver/tour guide for a fee. Just one mile away is the tiny historic village of Mensano, where foodies flock to the quaint and delicious Osteria del Borgo, a small restaurant with a big reputation.

Pros and Cons at Castello di Casole
The best thing about Castello is that it is 100% trouble-free. The food, wine, accommodations, staff, pool, even the weather (so it seemed to me) work perfectly, without one single, solitary glitch. Because of this profound attention to detail (and several smitten magazine articles), Americans are flocking there. This is a “pro” because it’s extra-tourist-friendly, but a “con” because almost all you hear is English; to some, this might diminish the hotel's authenticity but only slightly.

Castello di Casole Vibe 
Thanks to the dramatic countryside location, this hotel exudes romance. Add to that a violinist playing in the vineyards, a sachet of lavender in your lingerie drawer, the infinity pool overlooking the olive trees – and couples are in for some serious magic. More than once I found myself texting my sweetheart beggggging him to meet me here….

Castello di Casole Info and Reservations
Localita Querceto  53031|
Casole D'elsa, Italy
+39 0577 967557
Official Hotel Website

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As is common in the travel industry, the writer was provided with complimentary accommodation and  meals for the purpose of reviewing those services. While it has not influenced this review, About.com believes in full disclosure of all potential conflicts of interest. For more information, see our ethics policy.