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Things To Do and Activity Guide for Tuscany, Italy Vacations

A vacation spent under the Tuscan sun is to experience timeless beauty, soft-scented winds, and seemingly aimless roads that burst through forested glades to reveal historic hill towns rising out of a carpet of vineyards. Tuscany and its villages have many wonders and activites, from walking tours of Lucca to wine tastings in Multapulciano to touring art galleries in Sienna, and discoving simple trattorias in the countryside. Your WIMCO Villa Specialist can recommend things to do in Tuscany, then make the reservations for you.


A prosperous Tuscan city fueled by a vibrant jewelry industry, Arezzo features broad avenues and wide-open public squares such as the Piazza Grande. See Piero della Francesca's magnificent frescoes in the church of San Francesco, and visit the city's enormous Duomo and a host of high-end museums.


Known for its famous views from the book Under The Tuscan Sun, Cortona rises poignantly from a landscape of olive groves. Visit the Galleria d'Arte Nocchia and Il Pozzo, and see works by Fra Angelico and Signorelli at the Museo Diocesano.

Cupola del Brunelleschi

This cathedral is a famously historic feat of engineering and architecture. Climb the couple hundred stairs to enjoy 360 degree views of Florence. We recommend going early in the day to avoid the heat and crowds.


Literally and figuratively the cultural heart of Tuscany. View Renaissance master artwork at the Uffizi, or see firsthand Michelangelo's David at the Galleria dell'Accademia. Take the Ponte Vecchio across the Arno river to the Pitti Palace in Oltrarno, and shop bargains and boutiques at the San Lorenzo market.

Food Tours

The food tours in Florence are most popular throughout Tuscany and allow you to explore more local areas of the historic city in a unique way. Indulge in Tuscany's truffle shops, farmers markets, wineries, and more.


See why the city has become a mecca for classical music lovers. Experience the Festival of Sacred Music springing from every church in town from April to June; in September, enjoy the opera, including works created by hometown Luccan genius and celebrated composer Puccini.

Massa Carrara

The epicenter of some 300 marble quarries dating back to Roman times, Carrara is heralded around the world for the quality of its immaculate white stone, treasured by artisans and sculptors.


A wine connoisseur's dream come true, Montalcino is home to famous Brunello red wine and Rosso di Montalcino. A small village punctuated by one enoteca after another, it also is a source of extra-virgin olive oil.

Montefioralle Winery

Views from this winery are picture-book Tuscany: rolling hills and endless vineyards. Here, you'll find an array of classic Italian Chianti reds. Owners of the vineyard known for their hospitality. Be prepared to order a case of wine after your visit!

Piazza del Campo

The center of Siena is known to be one of the greatest medieval squares throughout Europe. Today, it hosts The Palio of Siena, a biannual festival celebrating the history of the square that occurs on July 2nd and August 16th. In addition, every summer the festival Il Palio delle Contrade is staged�a thrilling bareback horse race and urban festival.

Piazzale Michelangelo

A site famous for its 180 degree views over Florence. A bronze version of the statue of David stands here overlooking the plaza's guests.

Accademia Gallery

The museum gallery that holds the famous Statue of David by Michelangelo.


Head to the Campo dei Miracoli (field of miracles) to see the Leaning Tower that put this university city into popular lexicon, along with the great Duomo and Baptistry that flank it.


Located in the far southern reaches of Tuscany, Pitigliano is a visually spectacular town built into rocky cliffs that rise from a grassy gorge. There is a small Jewish ghetto here that came to be known as "Little Jerusalem" following its creation in the 17th century.

San Gimignano

Conspicuously well known for the thirteen dramatic towers that dominate its medieval skyline, the town is a magnet for local painters and craftsmen, and filled with works of art, good shops and great restaurants.

Siena Cathedral

This magnificent Roman Catholic church stands out among the city's outdoor cafés and eclectic high-end shopping. Step inside to experience to 11th century Italy.

Wine Tours and Vineyards

One of our favorite things to do in Tuscany is tour the exceptional Tuscan wineries. Some of our favorites include Antinori Chianti Classico, Castello di Ama, and Castella di Nipozzano. Enjoy a private tour of the vast valleys of vineyards, while tasting their specialty aged wine.

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