Tuscany Holidays

Drift above rolling vineyards, castles, and medieval villages at dawn, taking in sweeping views of Florence, Siena, and the Tyrrhenian coast from a peaceful, unforgettable vantage point.

Freefall from over 13,000 feet with tandem instructors, experiencing an intense adrenaline rush paired with breathtaking aerial views of Tuscany's patchwork hills and historic towns below.

Pedal winding country roads past 12th-century castles and family-run wineries, combining light exercise with scenic stops for wine tastings amid some of Italy's most photographed landscapes.

Explore the Tuscan countryside on horseback through olive groves and rolling farmland, with routes ranging from relaxed hour-long rides to full-day treks suited to beginners and experienced riders alike.

Ride a Land Rover deep into the legendary marble quarries once used by Michelangelo, uncovering dramatic rock formations and centuries of quarrying history within the mountain's core.

Navigate gentle rapids through forested valleys near Lucca, combining light whitewater thrills with immersive nature scenery, suitable for families and first-time rafters alike.

Rev through backcountry trails and rugged farmland on a guided quad tour, discovering hidden corners of the Tuscan countryside inaccessible by standard roads.

Trek through UNESCO-listed rolling hills, cypress-lined paths, and hilltop villages, rewarding hikers with sweeping panoramic views across one of Tuscany's most iconic landscapes.

Take the wheel of a Ferrari with a personal driving tutor beside you, cruising scenic routes around Florence for an exhilarating, high-performance twist on sightseeing.

Descend beneath the Tyrrhenian Sea near the Tuscan Archipelago to explore rocky reefs and marine life, offering certified divers a refreshing contrast to the region's inland hills.

Wander one of the world's oldest art museums, home to Renaissance masterpieces by Botticelli, Michelangelo, and Leonardo da Vinci, tracing the birthplace of Western artistic revolution.

Ascend the engineering marvel atop the Duomo, a Renaissance architectural triumph completed in 1436, for sweeping views over Florence's terracotta rooftops.

Marvel at this iconic bell tower, famous for its unintended tilt caused by unstable foundations, standing within Pisa's Piazza dei Miracoli since the 12th century.

Step into this shell-shaped medieval square, home to the historic Palio horse race, surrounded by Gothic palaces that once governed one of Tuscany's great rival republics.

Explore the elaborate tombs and chapels built for the powerful Medici family, whose patronage shaped Renaissance art, politics, and culture across Tuscany for centuries.

Stroll or cycle atop these remarkably intact 16th-century fortifications, which encircle the historic centre and offer a rare, elevated perspective on Tuscan urban history.

Wander this UNESCO-listed hill town, famous for its skyline of surviving stone towers built by rival medieval families competing for status and power.

Discover this UNESCO-listed town, rebuilt in the 15th century as a model of humanist urban planning under Pope Pius II's ambitious architectural vision.

Explore ancient burial sites and artefacts predating Roman rule, offering insight into the mysterious Etruscan civilisation that once flourished across this region of Tuscany.

Cross this medieval stone bridge lined with historic jewellery workshops, one of the few Florentine bridges to survive World War II bombing intact.

Run through the heart of the Renaissance city each November, passing landmarks like the Duomo and the Arno River, in one of Italy's most iconic urban marathon experiences.

Held in March or April, this flat, scenic 21km route winds through the historic centre and riverbanks, drawing competitive runners and casual participants alike during Florence's springtime bloom.

Ride vintage steel bikes along Chianti's gravel "strade bianche" each October, blending nostalgic cycling tradition with sweeping views of vineyards and rolling countryside.

Watch professional cyclists race through Tuscany's historic cities, coastal roads, and hillsides, as this legendary Italian cycling tour highlights the region's varied terrain.

Race past dramatic sea and mountain landscapes each February, with marathon, half-marathon, and 10km options catering to every fitness level and running ambition.

Run past the Leaning Tower and Pisa's historic streets each December, combining a Boston-qualifying course with the city's iconic architectural backdrop.

Watch competing contradas race horses each January, following a ceremonial blessing and parade, with the whole town joining in celebratory feasts beforehand.

Join runners circling Lucca's remarkably intact Renaissance walls each June 21st, marking the summer solstice with a scenic 5km loop through the historic centre.

Calcio Storico Fiorentino is a traditional Florentine game combining elements of football, wrestling and rugby. Matches take place in Piazza Santa Croce, with teams representing the city’s historic districts.

Tackle Tuscany's famous unpaved white roads on a gravel bike, riding through Chianti vineyards and Val d'Orcia's rolling countryside in this modern spin-off race.

The Palio di Siena is a traditional bareback horse race held in Piazza del Campo, usually on 2 July and 16 August. Siena’s historic districts, known as contrade, compete in the race, which is preceded by ceremonies and a procession in period costume. Check the official programme for event arrangements and access information.

On Easter Sunday, a dove-shaped rocket ignites a 17th-century firework-laden cart outside Florence's Duomo, a 350-year-old tradition believed to bring good fortune and a good harvest.

Held each June in Piazza Santa Croce, this Renaissance-era mix of football, rugby, and wrestling pits Florence's four historic districts against each other in a fierce spectacle.

Every Epiphany, a colourful costumed parade winds from Palazzo Pitti to the Duomo, recreating a 15th-century Florentine tradition where the Wise Men present gifts to baby Jesus.

On June 16th, Pisa's Arno riverbanks glow with 70,000 candles honouring the city's patron saint, followed by a historic boat race the next day.

Arezzo's knights joust in period costume, aiming lances at a wooden target in Piazza Grande, a tradition dating back centuries and referenced even in Dante's writing.

From late April through June, this internationally acclaimed festival fills the city with classical concerts, opera, and ballet performances across historic venues.

Each May, this hilltop town transforms into a flower-covered wonderland, with elaborate floral displays and parades celebrating spring and centuries-old local craftsmanship.

A lighthearted, chaotic twist on the traditional horse Palio, this donkey race brings comic unpredictability and community rivalry to the town's historic piazza.

Celebrating the iconic Fiorentina steak alongside seasonal porcini mushrooms, this autumn weekend festival blends food, tradition, and Tuscany's deep-rooted culinary identity.