Romantic Revelry: 3 Days Lost in San Gimignano

Discover love amidst medieval charm in San Gimignano, Italy's romantic haven.

28 August 2023

Experience the epitome of romance in San Gimignano, Italy. Explore this enchanting medieval hilltop town adorned with iconic towers, stroll hand in hand through narrow cobblestone streets, and savor exquisite Tuscan cuisine in charming candlelit restaurants. Immerse yourself in the breathtaking Tuscan countryside, wine tasting at local vineyards, and create lifelong memories with your loved one in this idyllic and romantic setting.

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Travel plan

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Day 1

Lost in Medieval Marvels

  • Check into your romantic retreat at the charming Relais Santa Chiara Hotel, set within a restored medieval building with stunning views.
  • Take a whimsical stroll through the city's narrow streets, lined with ancient stone towers and picturesque vine-covered houses.
  • Marvel at the town's famous medieval towers, such as the Torre Grossa, that proudly defy gravity and provide panoramic views of the Tuscan countryside.
  • Visit the Piazza della Cisterna, where you'll feel as if you've stepped back in time. Grab a gelato and soak in the buzzing atmosphere.
  • Immerse yourself in history at the San Gimignano 1300 Museum, featuring detailed architectural models depicting the town as it stood in the Middle Ages.
Day 2

Fine Wine & Tuscan Delights

  • Embark on a delightful wine tour of San Gimignano's renowned vineyards. Sip on rich, velvety Vernaccia di San Gimignano, the region's prized white wine.
  • Indulge in a romantic picnic amidst the rolling vineyards, surrounded by lush greenery and the charming sounds of chirping birds.
  • Treat your taste buds to a culinary adventure at Ristorante Cum Quibus, where you can savor traditional Tuscan dishes with a modern twist.
  • Explore the enchanting Collegiate Church of San Gimignano, adorned with frescoes depicting religious stories and offering a tranquil atmosphere for reflection.
  • End the day with a spectacular sunset view from the panoramic terrace of Caffè Giardino, while sipping on a refreshing Aperol Spritz.
Day 3

Adventures on Two Wheels

  • Rent a couple of bicycles and pedal through the scenic Tuscan countryside, catching glimpses of vineyards, rolling hills, and charming farmhouses.
  • Stop by the world-class Gelateria Dondoli for an authentic taste of their award-winning gelato, tempting your taste buds with unique flavors like saffron and red wine.
  • Discover the hidden gems of San Gimignano's surrounding countryside with a guided horseback riding tour, trotting through olive groves and medieval villages.
  • Take a break and enjoy a leisurely lunch at Osteria del Carcere, indulging in local specialties like wild boar stew with a glass of rich Chianti Classico.
  • Bid farewell to San Gimignano with a romantic evening stroll, hand-in-hand, as the setting sun paints the town's ancient buildings in golden hues.

Length of stay

1 day 2 days 3 days 4 days 5 days

Type of trip

Standard trip Budget Family Friendly Romantic Stag do

How to get there

Plane

The best way to get to San Gimignano by plane is to fly into Florence Airport (FLR) and then take a bus or taxi to San Gimignano.

Car

To get to San Gimignano by car, you can drive on the A1 highway until Florence and then take the Siena-Firenze highway (SS2) towards Siena. From Siena, follow the signs to San Gimignano.

Train

There is no direct train to San Gimignano. The nearest train station is Poggibonsi-San Gimignano station. From there, you can take a bus or taxi to reach San Gimignano.

Boat

San Gimignano is an inland city and does not have direct access to the sea, so there are no boat options to reach it.

Bus

From Florence, you can take a direct bus to San Gimignano. The bus departs from Florence's SITA Bus Station in Via Santa Caterina da Siena.

Destination

San Gimignano

Welcome to a place where time seems to have stood still...unless you count the countless tourists trying to capture the perfect selfie with a medieval tower in the background. Get ready to step into the enchanting maze of San Gimignano, where gelato and gargoyles rule the roost!

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Number of days

1 2 3 4 5

Type of trip

Standard trip Budget Family Friendly Romantic Stag do

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