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Best for VIP Treatment: Belmond Castello di Casole (Casole d'Elsa SI, Tuscany, Italy)
Tucked away on a sprawling 4,200-acre estate (one of the largest private landholdings in Italy), Belmond Castello di Casole is a historic hideaway tracing its noble roots back 5,000 years. Vestiges of its aristocratic past still remain. Elegant suites ornamented with wood-beamed ceilings and Etruscan farming artifacts recall the property’s rich agrarian heritage.
While heated floors, updated furnishings, and high thread count sheets tell a more modern tale. Needless to say, staying at Belmond Castello di Casole isn’t just about snoozing in a lovingly restored 10th-century castle.
Guests also receive the VIP treatment—gourmet meals, world-class wine, signature spa therapies showcasing local ingredients, and fairytale activities such as harvesting grapes. Not that we’d expect anything less from a storybook hotel that’s hosted crown-wearing royals, A-listers, international jetsetters, and diplomats.
Best for Romance: Villa Bordoni (Greve in Chianti, Tuscany, Italy)
There’s something so seductive about hauling up in a remodeled the 16th-century country house surrounded by olive groves and vineyards. Even better if it’s near some of the best wineries in the heart of Chianti. To that end, it’s impossible not to get swept up in the romance of Villa Bordoni, the ideal spot for couples dreaming of a refined Tuscan getaway with a genuine atmosphere and loads of rural charm.
Swathed in earthy hues, dwellings are individually decorated to reflect the character and quirks of each space. A favorite of love birds, the Montefioralle Double—affectionately referred to as the “honeymoon room”—features a clawfoot tub and walk-in tiled shower big enough for two people. All that’s left to do is run a warm bath, pop a bottle of spumante, and soak in the amour-inducing views.
Best Splurge: Rosewood Castiglion del Bosco (Montalcino, Tuscany, Italy)
Couples with deep pockets and a penchant for luxury flock to Rosewood Castiglion del Bosco in the renowned Brunello di Montalcino wine-making region. Sheltered within the majesty of Val d'Orcia Natural Park, it’s an exclusive honeymoon haven where a movie-set-worthy landscape, deeply magical ambiance, and priceless views coalesce.
Sure, staying at this historic estate turned five-star resort will set you back a pretty penny. In exchange for paying such a steep price tag? Total and utter flawlessness. The facilities are nothing short of spectacular and the level of service matches that—no request goes unanswered.
Accommodations range from sophisticated suites to grand private villas. The list of unforgettable adventures includes private wine tastings, truffle hunting, cycling excursions through the rolling hills, Tuscan cooking classes, and once-in-a-lifetime guided tours of the Ferrari headquarters.
Best (Almost) City Break: Il Salviatino (Florence, Tuscany, Italy)
Seeking something away from the urban excitement, but not ready to commit to full-on rural living? Occupying a restored 15th-century palazzo in the hills of Fiesole, overlooking the Tuscan capital, Il Salviatino is removed enough to register as a real respite—one with a polished yet unpretentious tenor and impeccable service—though not so far that it’s a pain to go into Florence for dinner or to visit one of the superb museums. (There’s even a free hourly shuttle to the city center.)
Gorgeous views of the Firenze rooftops and Duomo are a given. And we certainly don’t need to sell you on the appeal of manicured flower beds, luxuriously appointed suites, basil body scrubs, quiet afternoons lazing by the pool, or alfresco dinners. What you might not guess is just how quickly Il Salviatino will start to feel like home.
Best Agriturismo: Locanda Rossa (Pescia Fiorentina, Tuscany, Italy)
A laid-back hidden gem set amongst fragrant olive groves, Locanda Rossa, part of Preferred Hotels & Resorts, has all the requisites of an authentic and down-to-earth Tuscan farm stay.
Poised on a vast 21-hectare plot, it’s a remote setting to immerse yourself in the beauty of nature and connect as newlyweds. Forget mandatory manual labor. Locanda Rossa isn’t that kind of agriturismo. Instead, the vibe reads more rustic ranch with a dash of intimate, upmarket appeal. Every scrumptious meal at the osteria is a mouth-watering medley showcasing seasonal ingredients grown in the on-site garden. Hiking and biking trails bring guests even closer to the land.
In contrast to the bucolic backdrop, understated rooms and suites inside the classic red farmhouse are decidedly modern. Secluded villas provide complete privacy and far-reaching views.
Best for Sustainability: Il Borro (San Giustino Valdarno, Tuscany, Italy)
The very first European property to join the Kind Travel network and a member of Relais & Châteaux, Il Borro is a prime example of what happens when heritage, sustainability, hospitality, and luxury living in harmony. It’s the perfect place to honeymoon without worrying about the environmental or social impact of your post-wedding trip. A relic of old-world Tuscany nearly one thousand years in the making, this eco-friendly hotel preserves tradition—but not at the expense of progress.
Guests snooze in medieval villas outfitted with plenty of contemporary flourishes and solar panels. Electric vehicles further minimize the carbon footprint. Passion and purpose fuel Il Borro Relais & Chateaux. The result is a unique holiday that invites travelers to ride horses on unblemished pathways, participate in interactive workshops with local artisan instructors, and learn about organic wine production.
Best for Wellness: Relais La Corte Dei Papi (Cortona, Tuscany, Italy)
Endlessly charming and steeped in pastoral splendor, Relais La Corte Dei Papi is a peaceful retreat that puts a premium on wellness. Unwinding comes in many forms. For the ultimate in pampering, upgrade to a deluxe spa suite. Not only do these spacious 915-square-foot sanctuaries flaunt saunas, jacuzzis, Turkish baths, multi-sensory showers, relaxation areas, and private gardens, but guests can book in-room treatment to alleviate any lingering wedding-related stress.
We’d suggest opting for an aromatherapy massage and letting the soothing scent of lavender essential oil lull you into a state of serenity. Some of the most soul-satisfying moments are spent basking in the Tuscan sun and relishing pure, uninterrupted poolside bliss. If all else fails (which it won’t), tasty Tuscan recipes and terroir-driven reds always make everything that much better.
Best for Foodies: Borgo Santo Pietro (Chiusdino, Tuscany, Italy)
Nestled in a resplendent hillside location, Borgo Santo Pietro used to be a rest stop for weary wanders on the long pilgrimage from Canterbury to Rome. Though the clientele may be different (now, it’s a lot more honeymooners), the oasis-like sensibility and warm hospitality endure centuries later. Agrestic, viticulture, and culinary traditions continue to thrive, too. Today, the expansive estate comprises a working sheep farm, verdant vineyards, organic fruit and nut orchards, herb patches, vegetable gardens, and wild forests where pigs roam.
Driven by a field-to-fork philosophy, Michelin-starred Meo Modo lures diners with its seasonally inspired fishes. Every Monday, Trattoria Sull'Albero puts out a spread of fresh-picked produce, artisanal cheeses, and house-cured prosciutto. With a little advanced notice, Borgo Santo Pietro can put together a gourmet picnic basket to devour anywhere you heart, err stomach desires.
Best Value: Renaissance Tuscany Il Ciocco Resort & Spa (Castelvecchio Pascoli, Tuscany, Italy)
Sitting on 1,700 acres of parkland in the picturesque Serchio Valley, glancing down upon the beautiful medieval town Barga, the Renaissance Tuscany Il Ciocco Resort & Spa is a great launch point for journeying to tourist meccas such as Pisa and Lucca as well as the thermal springs of Bagni di Lucca.
Get the true Tuscan culinary experience by joining a chef on a market tour, followed by a hands-on cooking lesson where you'll acquire the skills to prepare gourmet dishes that will double as a romantic dinner for two. If you’d rather sit back and be served, head to La Veranda for delicious Italian fare.
End your evening with a nightcap at Nour Lounge. With so many irresistible attributes, the fact that the Renaissance Tuscany Il Ciocco Resort & Spa costs $150 per night is actually mind-blowing.
Best Amenities: Il Castelfalfi - Tui Blue Selection (Montaione, Tuscany, Italy)
Il Castelfalfi - Tui Blue Selection gives guests an authentic taste of Tuscany in an exclusive and scenic environment. What’s more, couples have access to all the top-notch facilities available at Toscana Resort Castelfalfi—notably red clay tennis courts and the largest golf course in the area.
Thanks to the temperate climate, it’s possible to play 27 holes or hit a few balls at the driving range year-round. And that’s just the beginning. There are tastings in the wine cellar and pizza making, too. While relaxation awaits at the top-of-the-line spa, which lists a bio sauna and sensory showers among its selling points.
In the late afternoon, snag a comfy bean bag by the pool and watch as the sky changes color. For a memorable date night, reserve an outdoor table under the stars at Michelin-rated La Rocca.