Matthew & Vivian

Matthew and Vivian

September 1, 2026 • Sinalunga, Province of Siena, Italy
474 Days To Go!
Matthew & Vivian

Matthew and Vivian

September 1, 2026 • Sinalunga, Province of Siena, Italy
474 Days To Go!

The Surroundings

Visit nearby cities that are in driving distance and explore the wine country *** edit

San Gimignano (50 minutes)

Picture of San Gimignano (50 minutes)
Piazza Sant'Agostino, 53037 San Gimignano SI, Italy

Small walled medieval hill town in the province of Siena, Tuscany, north-central Italy. Known as the Town of Five Towers, San Gimignano is famous for its medieval architecture, unique in the preservation of about a dozen of its tower houses, which, with its hilltop setting and encircling walls, form an unforgettable skyline.

Website

Siena (30 minutes)

Picture of Siena (30 minutes)

Siena, a city in central Italy’s Tuscany region, is distinguished by its medieval brick buildings. The fan-shaped central square, Piazza del Campo, is the site of the Palazzo Pubblico, the Gothic town hall, and Torre del Mangia, a slender 14th-century tower with sweeping views from its distinctive white crown. The city’s 17 historic “contrade” (districts) extend outward from the piazza.

Montepulciano (20 minutes)

Picture of Montepulciano (20 minutes)
Via di Valardegna, 1, 53045 Montepulciano SI, Italy

Montepulciano is a medieval hilltop town in Tuscany, Italy. Surrounded by vineyards, it’s known for its vino nobile red wine. The Torre di Pulcinella is a clock tower topped by a figure of the Pulcinella, a commedia dell’arte character. On the Piazza Grande is the 14th-century Palazzo Comunale, with a tower offering views of the surrounding countryside. Also here is the Duomo, with a huge triptych above its altar.

Pienza (25 minutes)

Picture of Pienza (25 minutes)
Piazza Pio II, 2, 53026 Pienza SI, Italy

The little town of Pienza is today a listed UNESCO World Heritage site. The architecture, the views over the surrounding landscape, the atmosphere, and the wonderful Pecorino, sheep's milk cheese produced from the many flocks that wander over the surrounding.

Arezzo (30 minutes)

Picture of Arezzo (30 minutes)

Nestled in the heart of Tuscany, Arezzo is a hidden gem waiting to be discovered by avid travelers. Known for its rich history, captivating artistic heritage, and vibrant cultural scene, this enchanting town offers a unique blend of medieval architecture and charming streets. Famous for its renowned antiques markets.

Florence (1 hour)

Picture of Florence (1 hour)

Florence, often heralded as the cradle of the Renaissance, is a city overflowing with art, history, and culture. With its unique blend of historical landmarks, artistic masterpieces, and vibrant street life, Florence offers an unforgettable experience for every traveler.