Perhaps the most romanticized region in all of Italy, having featured in at least a dozen of Hollywood blockbusters, and considered the birthplace of The Renaissance, a cultural movement that continues to inspire awe to this day, Tuscany is never not teeming with tourists.
As diverse as this region of Italy is—it’s one of the largest in the country—most tourists will only briefly pass through, either for a scenic drive down a winding road lined by cypress trees, take pictures with the landmark Leaning Tower of Pisa, or stroll the narrow streets of Florence or Sienna.
Those are not overrated in any way, but as it turns out, there’s so much more to Tuscany than that, and if you’re a wine lover, you have a soft spot for medieval cities, and you’re looking for a quieter stretch of beach to relax after a long day of exploring, you’ve come to the right place:
Experience The Ancient Culture
Tuscany is best known for its historical towns that have remained virtually unchanged in over six centuries, and while a majority of tourists will spend most of their time in Florence, getting out of the the Tuscan capital is in fact your best chance at experiencing the culture.
San Gimignano is dubbed the Manhattan of the Middle Ages thanks to its numerous towers that might have been the precursor to the modern skyscraper, maze-like Old Town, cobblestone streets leading to beautifully frescoed churches, and hidden courtyards.
Not far from San Gimignano, Volterra is equally charming, and if you joined in on the Twilight frenzy of the late 2000s, you might recognize it as the fictional home of the Volturi, but if you’re expecting to spot actual vampires, perhaps you should try your luck instead in Transylvania.
Nestled in the Tuscan hills, Montepulciano is yet another gem awaiting discovery, with charming medieval piazze and wells, that continue to provide clean water in this current era, and magnificent Torre di Pulcinella, a clock tower looming over the otherwise-even, terracotta townscape.
Sample World-Renowned Wine
Tuscany is the leading destination in Italy for enotourism, which is just a fancy word travel publications love in reference to wine tourism, and it prides itself in being the birthplace of well-known exports like Chianti and Tignanello, but also countless more regional wines you won’t find easily on Tesco.
These are Brunello di Montalcino, one of the finest Italian reds, produced in the quaint ocher-colored town, Bolgheri, full-bodied offers originating from the dreamy Tuscan coast, and our personal favorite, Vernaccia di San Gimignano, made from native grapes grown around San Gimignano.
Tuscan Wine is an immaterial heritage, and it as representative of Tuscany as the Renaissance or its tower-dotted hilltop villages, and it’s fair to say no trip to the region is complete without a farmhouse stay coupled with wine tasting, and on Tripadvisor, there are at least 118 to pick from.
Three of the best-rated ‘agritourism’ experiences are in Fattoria Santa Vittoria in Pozzo, a traditional guesthouse attached to a thriving winery, Fattoria Lavacchio in Pontassieve, where you can sample wine, rise horses and enjoy homemade Italian food, and the exclusive, family-run Fattoria La Vialla.
Relax In The Tuscan Countryside
Tuscan hospitality is equally a big draw for tourists, particularly Americans crossing the pond this summer who may have reservations about coming to Italy considering its reputation for being blatantly anti-tourist (it’s not like Venice’s purging of day-trippers and Portofino’s selfie ban has gone unnoticed).
In the verdant hills of Italy’s wine region, however, they’re sure to be welcomed warmly, whether they’re staying in a luxurious farmhouse or a regular Airbnb: in fact, Tuscany boasts the highest concentration of five-star listings in the country, and (unsurprisingly) it ranks first in hospitality.
Wellness haven Castello Bonaria is a prime example of Tuscan excellence, with its friendly English-speaking staff, amazing food, modern spa facilities, lush gardens, and inviting aqua pool (this June, one-night stays start from as cheap as $161).
Elsewhere on the coast, in the trendy resort town of Livorno, GH Palazzo has nightly rates of $128 for a double room: their spa features an indoor pool, a sauna, and a jacuzzi, and the rooftop restaurant commands views of the azure Mediterranean.
Bask In The Tuscan Sun
Speaking of, we’ve saved the very best for last: many tourists are in fact not aware, but Tuscany is not a landlocked region. It has a Mediterranean coastline stretching for over 248 miles, interspersed with unspoiled beaches, nature reserves and lively beach towns.
They’re not exactly quaint and serene—Livorno is every Tuscan’s go-to sunny getaway in the warmer months—but the coast still feels less busy than the neighboring Italian Riviera, or worse even, Amalfi, as usually it’s only Italians coming here.
Other holiday towns include Viareggio, where a golden strip of sand seems to extend as far as the horizon, sprinkled with the classic blue-and-white parasols, Forte dei Marmi, where a long pier stretches out into the Med, and the more-recluse Elba.
Seeing it is an island lapped by Caribbean-like white sands and turquoise waters, Elba is deserving of a special nod: it is part of the multi-island Tuscan Archipelago National Park, and it’s most notorious former resident in exile is Napoleon, between 1814 and 1815.
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