We begin our tale in the Lucca Valley, northerly neighbor of a certain tilted tower. The Tyrrhenian Sea shimmers alluringly in the distance, succeeded as one moves inland by country estates and farmhouses in their natural habitat, a patchwork panorama of woodland and cultivated acreage. Here Albergo Villa Casanova presides from a hill over Lago di Messaciuccoli and seaside hamlet Torre del Lago, erstwhile stomping grounds of maestro Puccini. It’s your classic 18th-century villa, a sun-kissed vision in pale goldenrod with casement windows. The fourteen suites each boast regal corner views, skillfully balancing period furniture with an open, airy layout. That we encourage you to try the house olive oil and truffles should go without saying.
Take the A11 from Lucca to Florence, keeping your eye out for the telltale arches of the Neoclassical Aquedect of Nottolini — just the first taste of the astounding Old Mastery to be found in the regional capital, including a still-functional Roman aqueduct feeding Ammanati’s magnum opus, the 16th-century marble Fountain of Neptune. Far and away the most urban stop on your journey, Florence nonetheless sustains a rich old-world ambience: one part Medici, one part Gothic-Romanesque, one part walled medieval charm; stir gently and serve al fresco.
Just off the River Arno, a few blocks south from riotous Ponte Vecchio, Soprarno Suites adds modern style to its building’s vintage substance, deftly marrying contemporary Italian furniture design with captivating architectural filigree. The residentialist suites are spacious enough to avoid urban cramp, leaving plenty of room for a library and all manner of exquisite objets d’art.
A bit further south, Villa Cora offers a quieter, slightly removed atmosphere. Baron Oppenheim built it for his bride in the 19th century, and it shows in the opulent fittings, Persian rugs, and original artworks. Don’t be afraid to take your reprieve in the solarium or the year-round outdoor pool.
It’s a slightly longer trip to reach your next destination — thankfully, a savory pit stop of wide renown awaits in Panzano, Chianti: butcher-auteur Dario Cecchini’s shop and restaurant. Heading further east, look around while you digest and drink Arezzo in. You’ve reached the seat of the Etruscans and the birthplace of Petrarch and Michelangelo, a rarefied stretch of country marching inexorably up to the Apennines. The city of Arezzo itself is worth a visit, if you can spare the time, particularly in June or September when the Saracen Joust takes place in all its horseback glory.
The Ferragamo family — shoemakers, hoteliers, and much else — maintain their estate and family-run agriturismo at Il Borro, a prince’s residence built in 1848. In fact, they’ve taken it upon themselves to progressively restore the entire surrounding medieval village, comprising in total more than 100 acres of vineyard, a winery, olive and oak groves, three villas, three farmhouses, assorted town buildings, and the grand palazzo to rule them all. If any part of the province could be said to exemplify maximalism, here you have it.
The first of our cycling circuits, this 62-km stretch reaches from Arezzo in the north to Chiusi in the south, just east of Montalcino, largely running parallel to the master canal in Chiana. It’s a fine warm-up, perfect for families or those who prefer to take it slow and scenic, savoring the perfumed air and timeworn Etruscan landmarks along the way. Good thing there are plenty of spots along the way to picnic while you marvel at the ancient waterworks, as you’ll likely work up a killer appetite.
Now for one of the strongholds of global vintnery, Tuscany’s radiant agricultural heart. It’s a province of high notes — literally, Monte del Chianti and Monte Amiata are difficult climbs — and gustatory highlights: Chiana beef, dense tiers of grapes, and quantities of amber grain sufficient to rival the US Midwest. Farm to table, indeed. The anchor city itself, mythically founded by sons of Remus, preens in polychrome marble and crenellated stonework, a palazzo-dominated cityscape split since time immemorial into heraldic contrade. Catch them at their most competitive in July or August for the Palio, a thrilling bareback horse race wrapped in motley pageantry.
Roughly a millennium of accumulated history informs aptly named Castel Monastero, channeled architecturally by rough-hewn masonry, vaulted ceilings, and beams galore. One Gordon Ramsay serves as consulting chef — maybe you’ve heard of him? The hotel’s mushroom-foraging expeditions kill two birds with one stone, simultaneously putting you directly in touch with the land and awakening a ravenous palate just in time for lunch.
Hotel Borgo San Felice sticks with the converted-village formula, and we can’t blame them: in terms of aesthetics, utility, and leisure, the Tuscan equation comes as close to perfect as one can reasonably expect in this lifetime. The on-site winery helps, too, rounding out the ivy and oaks with with a resplendent array of vines.
This circuit from Gaiole in Chianti to Monalcino is as heroic as the name suggests, a full 209 km of mixed gravel and paved track well suited for the professional two-wheelers out there. You don’t have to tackle the whole thing, of course: several shorter routes, every bit as scenic, exist within the beast. At any length, this is a fine means of acquainting yourself with the region’s rural underpinnings, its farmhouses and livestock, its centuries-old villages and chestnut woods.
Many would lump this region in with Siena, but we feel that the residents and the view stand well enough on their own legs. The Crete Senesi in particular feels almost lunar, with characteristically grey, sedimentary clay. Here, too, the prestigious wines alone merit days of serious study; among many heavy hitters, the cellars here boast such luminaries as Brunello di Montalcino, Nobile di Montepucliano, and Rosso Orcia. The commune of Monalcino centers around its medieval walled fortress, with picturebook cobblestone streets radiating outward in no particular order. Poke around for more of those white truffles when you get a chance — they’d go great with the town’s famous archery contest, held twice a year in period dress.
La Bandita exemplifies a new breed of Tuscan hospitality, the sweet spot between grand-hotel excess and farmhouse authenticity. For a change, contemporary style rules the day at this smart little guesthouse — six bedrooms, a central kitchen, and open, breathable living space tie it all together.
Up the road in Pienza, the other half of this package deal occupies a Renaissance palazzo: La Bandita Townhouse. The building, once a convent, echoes its older sibling’s modernism with all-white furnishings and parquet floors; if it all gets a little recent, all you have to do is step outside to travel back in time a few centuries.
The last of our cycling circuits should test your mettle: 147 km of hilly terrain encompassing the Sovicille commune, best undertaken over the course of several days. Don’t let the prospect detract you, though, as the countryside in these parts more than justifies the effort. And you won’t have much distraction, either — this route is known for its gorgeous, lonely tranquility. Clear your mind, hydrate, stretch well, and get pedaling.
Back to the coast you go, but first another chow stop, this time in Rocca D’orcia for Podere Forte’s Osteria Perillà; doubtless these winemakers keep a few bottles of their personal favorites on hand. Better yet, bring some with you on your way as you finish your Tuscan tour in among the area’s wild, rugged natural splendor. The beaches, alternately sandy and rocky, host a surprising variety of wildlife, best seen around twilight when they emerge from the nearby pine groves. Rest your worn muscles like a buttero, the Tuscan cowboy of yore, born and raised in the Maremma.
A glorious Tuscan send-off calls for glorious accommodations, no? Enter Castello Banfi il Borgo, magisterially perched on a hill near the Ombrone river. Besides the lovingly restored architecture and fittings, there’s a museum of glass with artifacts dating back to ancient Rome, plus — incredibly — a recently unearthed complete whale skeleton.
Make it a castle double feature at Castello di Vicarello, a 12th-century structure somewhat closer to the coast. They’ve got la dolce vita down to a science here: twin swimming pools, a smattering of Indonesian antiques, and a merciful dearth of swarming tourists.