Tuscany

Overview

From Andrew Harper

The only thing I don’t like about Tuscany is going there with a return ticket. There are few more agreeable ways to spend time than strolling through the great cities of Lucca, Pisa, Siena and Florence. But for me, the supreme pleasure is puttering along country roads through one of the most distinctive and civilized landscapes in the world. A patchwork of wine and olive estates dominates the Chianti district, a romantic 40-mile swath between Florence and Siena. Memorable sights include the historic picture-book wine villages of Castellina, Radda and Volpaia, plus the 13th-century fortress hamlet of Vertine; the ancient abbey/wine estate of Badia a Coltibuono (five miles east of Radda); and majestic Castello di Brolio (10 miles southeast of Radda near San Regolo). Outside the Chianti Classico area lie Monteriggioni (described in Dante’s “Inferno”) and the picturesque medieval city of San Gimignano. The Val d’Orcia wine region of southern Tuscany begins 45 minutes southeast of Siena, its vineyards producing celebrated reds such as the full-bodied Brunello di Montalcino and the refined Vino Nobile di Montepulciano. Generally, we choose September for our Tuscan rambles — when the summer crowds have gone home — but I also enjoy traveling in late spring, when mornings see the mist dissolve to reveal groves of silvery olives stirred by a gentle breeze, and pale green vineyards with newly unfolded leaves.

Hotels

All recommended hotels in Tuscany

Montalcino, Italy
Castello Banfi - Il Borgo
Castello Banfi - Il Borgo

Charming hotel within a hilltop castle of golden stone surrounded by vineyards and olive groves in the Tuscan countryside.

Castiglion del Bosco © Matteo Carassale
Castiglion del Bosco

Captivating stone hamlet straddling a hilltop restored and transformed into a sophisticated resort.

Siena, Italy
Hotel Borgo San Felice
Hotel Borgo San Felice

Enchanting resort enclave set within a restored medieval hamlet, 30 minutes northeast of Siena. Mellow stone dwellings contain 46 simple but comfortable lodgings.

Hotel Le Fontanelle
Hotel Le Fontanelle

Welcoming, understated 25-room hotel in handsome 13th-century brick-and-stone farmstead set on a hilltop overlooking miles of rolling countryside, eight miles east of Siena.

Torrita di Siena, Italy
La Chiusa
La Chiusa

Family-run manor that looks across to the hill town of Montepulciano. Fifteen lodgings are appointed with a mix of antique furnishings and modern amenities.

Tuscany, Italy
Castello del Nero Hotel & Spa
Castello del Nero Hotel & Spa

Fifty-room hilltop hotel constructed around an imposing 12th-century castle. Deluxe Rooms offer terra-cotta floors, vaulted ceilings, painted furniture and extra-spacious baths.

Hotel Certosa di Maggiano
Hotel Certosa di Maggiano

Romantic family-run hotel in a 14th-century monastery restored by the late architect and interior designer Renzo Mongiardino, amid serene gardens just outside of Siena.

Locanda dell'Amorosa
Locanda dell'Amorosa

Peaceful 27-room country inn fashioned from the remnants of a 14th-century stone hamlet amid vineyards and olive groves, 45 minutes east of Siena.

Borgo Santo Pietro
Relais Borgo Santo Pietro

Thirteenth-century stone manor house built as a resting place for pilgrims en route to Rome, converted to a lavish 15-room hotel (including six garden suites), 35 minutes southeast of Siena in a rural corner of Tuscany.

Relais Il Falconiere aerial
Relais Il Falconiere

Relaxing country house hotel on a scenic hillside. The 22 guest quarters are divided between a 17th-century villa and a nearby manor.

Villas

All recommended villas in Tuscany

Tuscany, Italy
Villa Il Sogno
Villa Il Sogno

A beautiful country road with pristine views leads up to the two-story villa situated on 3 acres of property.

Fiesole

Special Offers

Special Offers

Hotel Le Fontanelle - Complimentary Half-Day Winery Tour
Hotel Le Fontanelle - Complimentary Half-Day Winery Tour

Confirm a four-night stay in a suite and receive one complimentary self-driving winery tour for four hours at a nearby property. Guests must confirm day and time preference for the tour at time of booking the hotel stay.