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

Experience the medieval charm and captivating skyline of San Gimignano in the heart of Tuscany.

28 August 2023

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.

Save and get deals

Travel plan

Getting latest place information
Day 1

Exploring the Tower-studded Beauty

  • Check in at Albergo Le Colline, a charming hotel in the heart of San Gimignano's medieval streets.
  • Start your day with a visit to the iconic Collegiate Church, adorned with stunning frescoes and Gothic architecture.
  • Marvel at the town's 14 remaining medieval towers, earning it the nickname "Medieval Manhattan."
  • Indulge in a delectable lunch at Osteria del Carcere, a cozy eatery serving mouthwatering Tuscan specialties.
  • Visit the Vernaccia Wine Museum to learn about the region's famous white wine and savor a glass or two.
  • Wind down the evening at Gelateria Dondoli, where the master gelato maker crafts inventive flavors like rosemary-infused gelato.
Day 2

Artisanal Delights and Hidden Gems

  • Start the day with a hearty breakfast at Pasticceria il Fornacino, a family-owned bakery known for its flaky pastries.
  • Explore the fascinating world of local artisans at the San Gimignano 1300 Museum, showcasing miniature reproductions of the town as it once was.
  • Discover hidden, picture-perfect corners of San Gimignano during a leisurely stroll through its charming streets.
  • Satisfy your taste buds with a traditional Tuscan lunch at Ristorante Cum Quibus, offering a farm-to-table culinary experience.
  • Embark on a wine tasting at Fattoria Poggio Alloro, a winery nestled in the rolling hills, offering organic wines bursting with flavor.
  • As the sun sets, enjoy a leisurely dinner at La Mandragola, where delicious food and live music come together in an intimate setting.
Day 3

Captivating Views and Culinary Adventures

  • Have a leisurely breakfast at Grotta di Santa Fina, a charming café famous for its homemade pastries and aromatic coffee.
  • Take a scenic drive to the nearby town of Volterra, known for its Etruscan origins and captivating views.
  • Marvel at the imposing Medici Fortress, which offers panoramic vistas of the surrounding Tuscan countryside.
  • Delight your taste buds with a delectable lunch at Ristorante Etrusco, serving dishes inspired by ancient Etruscan recipes.
  • Return to San Gimignano and explore the enchanting gardens of Rocca di Montestaffoli, a medieval fortress offering breathtaking views.
  • End your stay with a memorable dinner at Ristorante Cum Quibus, indulging in their renowned Chianina steak cooked to perfection.

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!

 Save and get deals

Number of days

1 2 3 4 5

Type of trip

Standard trip Budget Family Friendly Romantic Stag do

More travel plans

Step into the Medieval Magic of San Gimignano

San Gimignano is a charming medieval town located in the heart of Tuscany, Italy. Known for its iconic soaring towers that dot the skyline, the town offers a journey back in time with its well-preserved historic center. Visitors can explore the picturesque cobblestone streets, indulge in delicious local cuisine, and soak in enchanting views of the Tuscan countryside, making it a delightful destination for any tourist.

San Gimignano in 48: Time Travel and Tastes

San Gimignano, Italy offers a charming and budget-friendly experience for travelers. This medieval hill town is known for its intact medieval architecture and breathtaking views. Visitors can explore its cobbled streets, climb the town's towers for panoramic vistas, and enjoy delicious local delicacies at affordable prices in the trattorias and cafes scattered around the town.

Four Fun Days in Medieval San Gimignano

San Gimignano, located in the heart of Tuscany, is a picturesque medieval town that offers a great family-friendly vacation. The town is famous for its stunning skyline, with its 14 well-preserved towers, providing an enchanting and unique atmosphere. Families can explore the narrow streets, visit the fascinating museums, indulge in delicious local cuisine, and even enjoy outdoor activities such as hiking or cycling in the surrounding countryside.

Romancing San Gimignano: 5 Days of Love and Laughter

San Gimignano, located in the heart of Tuscany, Italy, is a picturesque and enchanting destination perfect for a romantic trip. With its well-preserved medieval architecture and breathtaking views of rolling vineyards and olive groves, the town offers a romantic atmosphere like no other. Couples can indulge in world-class wine and cuisine, stroll hand in hand through the narrow cobblestone streets, and admire the iconic 14 medieval towers that give San Gimignano its unique charm.