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Here’s How to do Fall and Winter in Tuscany

Castelfalfi's hilltop perch roughly an hour's drive from Florence and Pisa.


The newly remodeled Castelfalfi makes the case for off-season visits.

Tuscany’s summer tourism crush gives way to uncrowded olive oil pressing across the region in fall, making this the ideal time to visit one of Italy’s most popular regions. The pasta- and pizza-making classes, winetastings, and bike rides through cypress-tree-lined back roads remain in full swing, as does searching for truffles with curly-haired Lagotto Romagnolo dogs in the oak-studded hills.

Another reason to visit now: the medieval village-turned-resort of Castelfalfi, a 2,700-acre estate 43 miles southeast of Florence, where a recent multimillion-dollar renovation revealed a fresh new look. And for the first time this year, the property will stay open through January 7 to celebrate winter in Tuscany with live music, Christmas markets, and performances in the borgo (village); a Christmas lunch and a Casino Royale-themed New Year’s Eve party with a six-course dinner are also on the agenda. Castelfalfi’s refresh brings warm wood and earthy green, gray, and gold tones into its 146 rooms, five villas, restaurants, and bar, while antique brass accents, streamlined leather sofas, textured wallpaper, and sleek lighting lend contemporary flair.

Villa La Spina sleeps 16 and comes with a private pool.


When the resort reopens in April, guests will have their choice of two new villas, but those looking for more space now and during holiday gatherings can book one of four new suites introduced in July. These range up to more than 1,100 square feet, with private terraces, king bedrooms, pullout sofas in the separate living rooms, and walk-in closets that rival some entire European city hotel rooms for space. Decked in elegant textiles and custom furnishings chosen by studio Affine Design (past projects include Monaco’s Hôtel de Paris and the City of Light’s Hotel George V, Crillon, and Shangri-La), the new suites come with a bartender to shake up evening aperitivi and can be combined into one private floor.

The spa’s adults-only pool.


On the health and relaxation front, Castelfalfi partnered with Thailand’s RAKxa Wellness Spa – a European first for treatments that adds Thai stretching and massage as well as chakra-aligning therapies to the spa’s lineup.

Olivina serves up hearty, hyperlocal Tuscan fare.


At Castelfalfi’s new restaurant, Olivina, chef Davide de Simone leans on nearby farms and the property’s stash of olives, wine, herbs, and honey to create locavore Tuscan dishes, house-made pastas, cacciucco (an Italian fish stew of snapper, mussels, clams, octopus, and more), and his signature dish, the Virtuoso: seared Wagyu beef with caviar and butter sauce. Work up an appetite by booking one of more than 40 indoor and outdoor activities that take place on the resort’s grounds, from a fun yet challenging adventure course and pizza-making class for kids to falconry, archery, fishing, olive picking, and a golf academy for lessons on the estate’s links – the 18-hole Mountain Course or 9-hole Lake Course. Or spend an afternoon on the estate’s hiking trails before heading to Ecrù Lounge Bar, whose new menu of nonalcoholic drinks – including the house Castelfalfi Pomegranate Mocktail made with Tanqueray 0.0, a splash of pomegranate juice, and pink grapefruit soda – make for refreshing post-outing pick-me-ups.

The outdoor terrace at new Bar Ecrù.


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