Located in the Tuscan province of Siena, Montepulciano is a small town encircled by walls dating back to 1511. The town is known for its steep streets, built upon a sloping and narrow limestone ridge. Famous for its wine production, notably red, don't leave town until you sip a glass in the outdoor terrace of a quaint café in the Piazza Grande, the town's main square.
Surrounded by a gray stone wall and outlying fields of flowers and vineyards, San Gimignano is a toy-like town in southern Tuscany. Statuesque, medieval-style towers define the cityscape, giving an air of a child's Barbie castle upon approach. Once a symbol of the town's wealth and power, the towers are now the city's biggest draw.
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To avoid San Gimignano's view-crushing crowds, come in winter or early spring, when you'll find that San Gimignano is an enchanting community, perfect for carrying out an ideal (and quiet) Tuscan holiday: writing poetry, reading books, and sipping tea. Pack a good camera and frame the near-perfect view of the hills of Tuscany from the top of one of the city's famous towers.
Florence is the capital city of Tuscany, and also the largest. Cutting the city into two parts is the River Arno. Several bridges connect the two sides, the most notable being the Ponte Vecchio, which dates back to 1345 and is the only bridge in Florence not destroyed by German troops during World War II. Shops still line the bridge, though the butchers of the past have been replaced with modern jewelers and art dealers. Nearly 150 miles long, the Arno flows into the Ligurian Sea seven miles below the Tuscan province of Pisa.
Florence is an effortlessly romantic destination. Art and history ooze from the city streetsthe same streets that Michelangelo, Leonardo, Donatello, and Giotto (among others) grew up on. Their art defines Florencefrom Michelangelo's naked statue of David to Boticelli's Birth of Venusand a main factor as to why Florence is one of the most visited cities in the world.
As you'd expect from a region with such artistic bonafides, street art is a big part of society and a norm of the day-to-day activity of locals. Here an artist in Pisa shades in a woman's face using sidewalk chalk.
Built to demonstrate the city of Pisa's power and wealth, construction on the iconic Tower of Pisa began in 1173 and didn't end until sometime between 1319 and 1350. Only three of its eight stories had been completed when it first started to lean, due to the soft riverbed soil on which it sits. The tower, located on Pisa's Piazza dei Miracoli, has undergone several reconstructions throughout the years to try to correct its lean. In 1990, the tower bells were taken out and cables were cinched around the third level to relieve some weight, setting the tower back 18 inches.
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Tuscany's annual grape harvest is in late September, early October. Many vineyards welcome visitors' help with the grape harvest. The stomping of the grapes tradition, while popular with the tourists, is today hugely out-of-date, with modern wine presses now being used to remove the juices more efficiently.
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Though fall is a dynamic time of year in Tuscany, spring is just as magical. With the sunshine (and rain) come fields of Tuscan wildflowers. The weather is moderate, with an average of 70 degrees from April to Juneperfect for flower-field walks during the day and chilly enough at night for an open fire stoked by last year's olive tree off-cuts, Italian-style.