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

More travel plans

San Gimignano: A Tower-rific Adventure on a Budget!

San Gimignano, Italy offers an excellent opportunity for a budget-friendly trip without compromising on the charm and beauty of Tuscany. Explore the city's medieval architecture and iconic towers for free, and indulge in delicious, affordable local cuisine at the numerous trattorias dotted throughout the town. With budget-friendly accommodation options and easy access via public transportation, San Gimignano is the ideal destination for a wallet-friendly trip to Italy.

Unraveling the Charm of San Gimignano: A 3-Day Adventure

San Gimignano, Italy offers a captivating blend of medieval history and picturesque beauty. Known as the "Medieval Manhattan" for its collection of ancient towers, the town's skyline is truly enchanting. Explore its charming cobblestone streets, visit its well-preserved medieval architecture, and savor the local famed Vernaccia wine for an unforgettable trip.

San Gimignano: Unleash Your Medieval Magic in Tuscany!

San Gimignano, located in Tuscany, Italy, is a medieval hilltop town renowned for its stunning medieval architecture and encompassing panoramic views of the surrounding vineyards and rolling hills. Famous for its 14 remaining medieval towers, San Gimignano offers tourists the opportunity to immerse themselves in the rich history and charm of the past, while also indulging in the delicious local wines and authentic Tuscan cuisine found in its numerous trattorias and enotecas. Whether exploring the maze-like cobblestone streets, visiting the striking frescoes in the Collegiate Church, or simply enjoying a glass of Vernaccia wine in one of the picturesque squares, a trip to San Gimignano promises a memorable and enchanting experience for any history or culture lover.

Medieval Marvels: 3 Days of Family Fun in San Gimignano

San Gimignano, located in the heart of Tuscany, offers a family-friendly trip with its charming medieval atmosphere and rich history. Visitors can explore the city's famous medieval towers and admire the breathtaking views of the surrounding vineyards and countryside. With its delicious gelato, authentic Tuscan cuisine, and various outdoor activities, San Gimignano promises an unforgettable family adventure filled with culture, relaxation, and fun.