Courtesy Castello Nero

Centered around Florence and encompassing such mystical towns as Siena, Montepulciano and Arrezzo, Tuscany is known for its gorgeous countryside, vineyards and old-world charm. One of the most challenging aspects of planning a trip to this large region is narrowing down the choices: do you prefer to be based close to Florence, in a remote country setting or right by the sea? There’s also myriad hotel options, ranging from very basic bed-and-breakfasts to high-luxury.

Cheat Sheet

  • Sleep…with a view of the sea at Il Pellicano
  • Experience…the best between Florence and Siena with a three-day itinerary
  • Splurge…on an incredible stay at the Ferragamo-owned Castiglion del Bosco
  • Eat…on the terrace overlooking the Val d’Orca at acclaimed restaurant La Porta
  • Drink…regional wines at Il Leccio, in Tuscany’s best Brunello-making vineyards
  • Savor…a cooking class at Villa San Michele
  • Visit…the lesser-known seaside region and stay at Il Pellicano
  • See…Tuscany from above during a hot air ballooning adventure
  • Shop…for discounted Valetino, Pucci and Feragamo at the Mall in Leccio
  • Know…that as an Indagare member you can contact our Bookings Team for customized recommendations and special tours, like hot air ballooning, behind-the-scenes vineyard visits and cooking classes

Lay of the Land

“Travel releases spontaneity. You become a godlike creature full of choice, free to visit the stately pleasure domes, make love in the morning, sketch a bell tower, read a history of Byzantium, stare for one hour at the face of Leonardo da Vinci’s Madonna dei fusi. You open as in childhood and – for a time – receive this world. ”
~Frances Mayes

Rolling hills and Cypress trees punctuate the Tuscan landscape, first settled by the Etruscans in 900 BC. Aesthetically similar to Provence with long drives leading to hilltop abodes, Tuscany is also home to a renowned wine region. Located in central Italy, Tuscany has a lengthy, storied history; the birthplace of the Italian Renaissance, the region also sports a long collection of notable residents (Michelangelo) and revered museums (like Florence’s Uffizi). Florence is the capital of the triangular region, but there are many smaller towns worth a visit.

Fiesole: Home to two exquisite hotel properties, this small town is located in the hillside north of Tuscany and offers a perfect combination of town and country. Note that you are not in wine country Chianti, since this begins south of Florence. See the Indagare-recommended hotels in this area.

Chianti & Siena: Starting just south of Florence and running to Siena, the Chianti region produces some of the finest red wine in the world. Wine tastings are the region’s main draw, but Chianti’s five regional towns offer cultural opportunities as well and the sweeping countryside is always stunning. Siena, meanwhile, is one of Tuscany’s most famous towns. Its historical center is one of Tuscany’s seven World Heritage Sites, and it sees a significant amount of tourism yearly thanks to its medieval architecture, ornate monuments and the biannual Palio, a horse race that draws crowds. A day or two is all that is needed to appreciate Siena, just an hour-and-a-half drive from Florence. See the Indagare-recommended hotels in this area.

Southern Tuscany: Just south of Siena lies the broader region of Southern Tuscany, which is dotted with such scenic and famous towns as Montepulciano, Montalcino, Pienza and Crete Senesi. With breathtaking vistas, succulent cuisine and old-world charm, a tour through Southern Tuscany makes for a great road trip or overnight excursion. Destinations in Southern Tuscany start at about a two-hour drive from Florence. See the Indagare-recommended hotels in this area.

Coastal Tuscany: Coastal Tuscany is part glam and part seaside haven; the restaurants are teeming with fresh seafood, chic Europeans frolic on the pristine beaches and there is a sprinkling of islands ideal for afternoon excursions. Monte Argentario, Ortobello, La Maremma, Elba and Porto Ercole (home to the legendary Il Pellicano) are popular beachside destinations that range between two- and three-hour drives from Florence. En route, don’t miss towns San Gimignano and Volterra. See the Indagare-recommended hotels in this area.

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Beyond… Tuscany

Consider combining your trip with one of these destinations.

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