Siena, Italy: Your Ultimate 5-Day Medieval Adventure

Savor the essence of Tuscany in captivating Siena.

28 August 2023

Siena, Italy offers a captivating experience with its medieval charm and rich historical heritage. Visitors can explore the magnificent Piazza del Campo, famous for its unique shell-shaped layout and vibrant atmosphere. From its awe-inspiring Gothic architecture to the delicious local cuisine, a trip to Siena promises to be an unforgettable adventure for any curious traveler.

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Travel plan

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Day 1

Unleashing your Inner Medieval Knight:

  • Check into the charming Hotel Athena, where you'll feel as regal as a Medici.
  • Get lost in the maze of narrow streets in Siena's historic center, stumbling upon hidden gems at every turn.
  • Visit the awe-inspiring Siena Cathedral, where its stunning black and white façade will leave you breathless.
  • Climb to the top of the Torre del Mangia for panoramic views of the city, but watch out for vertigo-induced wobbles!
  • Indulge in traditional Tuscan cuisine at La Taverna di San Giuseppe, where the flavors will transport you to culinary heaven.
  • End your day savoring a gelato from Gelateria di Piazza, a local favorite with unique flavors like ricotta with figs.
Day 2

Conquering Tuscan Wine Country:

  • Embark on a vineyard adventure in the nearby Chianti region, stopping by the idyllic Castello di Brolio.
  • Become a sommelier for a day with a wine tasting at Fattoria dei Barbi, where the vino flows as smoothly as the Arbia River.
  • Savor a picturesque picnic among the vineyards, feasting on local cheeses, cured meats, and crusty, fresh bread.
  • Take a leisurely stroll through the vineyards, letting the Tuscan sun warm your soul and the views steal your breath away.
  • End your wine-soaked day with a glass (or two) of Brunello di Montalcino at Osteria le Logge, a cozy trattoria with timeless charm.
Day 3

Exploring Siena's Artistic Wonderland:

  • Marvel at the masterpieces in Pinacoteca Nazionale, from Duccio's ethereal Maestà to Simone Martini's lustrous Annunciation.
  • Wander through the halls of the Palazzo Pubblico, admiring its frescoed splendor and the legendary "Allegory of Good and Bad Government."
  • Immerse yourself in the enchanting Garden of the Horti Leonini, where meticulously clipped hedges and vibrant flowers create a living artwork.
  • Sip on a thoughtfully crafted cocktail at Byrd, a trendy bar mixing creativity with mixology to create liquid art.
  • Satisfy your artistic cravings with a plate of artfully presented pasta at La Taverna di San Giuseppe, where even your taste buds become artistic connoisseurs.
Day 4

A Truly Tuscan Adventure:

  • Head to San Gimignano, the "Medieval Manhattan," for a day trip from Siena. Marvel at its famous tower-studded skyline.
  • Sample the succulent Vernaccia di San Gimignano wine at Fattoria Poggio Alloro, a family-run winery amongst vineyard-dotted hills.
  • Take a leisurely bike ride through the countryside, passing by sunflower fields and olive groves, feeling like you're in a Tuscan dream.
  • Breathe in the charm of tiny hilltop villages like Monteriggioni, where medieval walls embrace cobblestone streets frozen in time.
  • Dine like a noble in Ristorante Malborghetto, indulging in their signature bistecca alla Fiorentina, a mouthwatering grilled T-bone steak.
Day 5

Siena's Hidden Treasures:

  • Unearth the secrets of Siena's Contrade Museum, where the intense rivalry between the city's historic neighborhoods comes to life.
  • Explore the underground wonders of the Crypt of San Miniato, a labyrinth of ancient chambers and sacred relics.
  • Find refuge from the city's hustle and bustle in the tranquil Orto de' Pecci garden, where fragrant roses entice you to stop and smell.
  • Taste the traditional panforte, a heavenly concoction of dried fruits, nuts, and spices, that has been a Sienese delight since the Middle Ages.
  • Bid farewell to Siena at La Taverna di San Giuseppe, enjoying one last heavenly meal before leaving this magical Tuscan city behind.

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 closest airport to Siena is Florence Airport (FLR). From there, you can take a taxi or a public bus to Florence Santa Maria Novella train station. From the train station, you can catch a train to Siena. The journey takes approximately 1 hour and offers beautiful views of the Tuscan countryside.

Car

To reach Siena by car, you can take the A1 highway from Rome or Florence. Follow the signs for Siena and take the Siena Ovest exit. From there, continue on the SS223 and follow the signs to the city center. The journey time can vary depending on traffic and your starting location.

Train

To reach Siena by train, you can take a train to Florence Santa Maria Novella train station. From there, you can catch a direct train to Siena. The train journey takes approximately 1.5 to 2 hours, depending on the type of train.

Boat

As Siena is located inland, there are no direct boat routes. However, if you would like to incorporate a boat journey into your trip, you can consider taking a boat to Livorno or Piombino on the coast of Tuscany. From there, you can rent a car or take a train or bus to reach Siena.

Bus

If you prefer to travel by bus, you can take a bus from Florence to Siena. Buses depart from Florence Santa Maria Novella bus station and arrive at Siena Piazza Gramsci. The journey takes around 1.5 to 2 hours, depending on traffic conditions.

Destination

Siena

Welcome to a city where time moves at the pace of leisurely strolls and gelato melts faster than your stress! Get ready to fall head over heels for Siena, a place so charming, it's practically a crime not to break into spontaneous laughter while exploring its cobbled streets.

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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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