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Things to do in San Gimignano

Itineraries for Your Trip to San Gimignano

San Gimignano locals share their perfect days.
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2 Days in San Gimignano for First Timers

Curated by Rebecca Winkewho's lived in Italy for almost 30 years.

Discover perfectly preserved medieval villages and captivating landscapes by taking two days to explore the historic center of San Gimignano and surrounding wine country plus the delightful town of Siena, Volterra, or Montalcino. Here are your best options for pairing striking cityscapes with scenic Tuscan countryside in two days.

Day 1: Morning

Begin first thing in the morning by getting to know San Gimignano’s delightful medieval center, a UNESCO World Heritage Site, on a walking tour. Learn about the history of its 14 towers, and visit highlights such as the Large Tower (Torre Grossa), Collegiate Church of Santa Maria Assunta, Cathedral Square (Piazza Duomo) and Cistern Square (Piazza della Cisterna), and ruins of the 16th-century fortress.

Day 1: Afternoon

San Gimignano is surrounded by some of the loveliest landscapes and most prestigious wine country in Tuscany. Tour the countryside by Fiat 500 car or Vespa scooter or with a more traditional wine tour stopping at nearby wineries. Foodies can join a truffle hunt and cooking class or a lesson in preparing pasta, pizza, or gelato followed by a convivial dinner.

Day 1: Night

In addition to excellent wine, traditional Tuscan food is at the heart of San Gimignano. Be sure to sample some of the most beloved local dishes over a romantic candlelight dinner in town or in a winery in the surrounding hills. Sample cheeses and charcuterie,ribollita (Tuscan bread soup), truffles, and area wines.

Day 2: Morning

Set your sights farther afield today and explore the hill town of Siena, home to a UNESCO-listed historic center, exquisite Gothic cathedral, and the rolicking Palio festival. Beat the crowds by booking skip-the-line tickets to the cathedral (duomo) complex so you have plenty of time to explore the cathedral, crypt, baptistry, museum, and Piccolomini Library.

Day 2: Afternoon

Ancient-history buffs can instead opt to tour Volterra, a former Etruscan stronghold with fascinating archaeological ruins and museum. Explore the historic center on foot to take in the medieval city hall and Via Porta all’Arco, known for its artisan book binderies, leather and bronze workshops, jewelers, and more.

Day 2: Night

True wine aficionados can cap off the day with a jaunt to Montalcino to sample its prestigious Brunello di Montalcino, one of the most popular Italian varietals. This area of Tuscany is known for its Fiorentina, an impressively thick steak cooked over wood coals and the perfect foil to the bold local red.

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