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Siena & San Gimignano Day Tour with Discovery Guided Tours - Florence

Siena & San Gimignano Day Tour with Discovery Guided Tours

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Difficulty

easy

Duration

9 hours

Fitness Level

Suitable for all fitness levels; involves moderate walking with plenty of rest stops.

Overview

Spend a full day immersed in Tuscany’s rich history with Discovery Guided Tours. Visit Siena’s Gothic cathedral, sample local cuisine, and stroll San Gimignano’s iconic medieval streets.

Trevignano Romano, Lazio

Siena & San Gimignano tour

For all ages • 9 Hours • Price per group • Shore excursions with personal tour driver!

City Tour

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About This Adventure

Experience the enchanting Tuscan countryside on a 9-hour tour of Siena and San Gimignano. Explore Siena's Gothic architecture, including its stunning cathedral and historic streets, before savoring local cuisine. Then, wander through the medieval charm of San Gimignano, with its iconic towers and rich history, making for an unforgettable adventure.

Enjoy your day in the Tuscan countryside!

Duration

9 Hours

Description

Enjoy a tour of two of Tuscany’s most famous hill towns, Siena and San Gimignano. An English-speaking tour driver will be waiting for you at the Pier in Livorno Port, to start your shore excursion to Siena and San Gimignano

After driving through the idyllic countryside, you’ll arrive in Siena, the Gothic city, where your tour driver will introduce you to this fascinating city.

Wandering through the back-streets of Siena, you’ll soon be captivated by its history and culture. Next, you will visit the magnificent Cathedral of Siena, and its significant library, Piazza del Campo, where we’ll enjoy a stroll through the Jewish Ghetto and talk of the famous Paliohorse race that takes place here every year.

Discover Castellare degli Ugurgieri, a castle within a castle, and walk along some of Siena’s most elegant streets. For lunch, your English-speaking tour driver will be happy to suggest a few local restaurants where you can taste the local “Tuscan” cuisine, accompanied by local wines.

After a scenic drive, we’ll arrive at the hill town of San Gimignano, whose medieval walls and narrow streets are typical of Tuscan hill towns. Today, fourteen towers remain, reminding us of the Guelph and Ghibelline rivalry that caused a civil war between the families and citizens of San Gimignano. In the afternoon, you’ll return to your ship to complete your shore excursion from Livorno.

What's included

  • Cruising dock pick-up/drop off
  • A/C & bottled water on board
  • Luxury vehicle and private tour driver
  • Vehicle Expenses (fuel, toll, city pass etc.)

What to bring

  • Comfortable shoes
  • An appropriate attire is recommend to enter the religious sites
  • Pets are not allowed (If you have pets, please contact us before booking)
  • Baby seats available upon request

Adventure Tips

Wear comfortable shoes

Expect extensive walking on cobblestone streets and uneven surfaces in historic towns.

Dress respectfully for religious sites

Cathedrals and churches require covered shoulders and knees to enter.

Stay hydrated throughout the tour

The tour lasts about 9 hours; bring a reusable water bottle or use bottled water provided.

Prepare for variable weather

Tuscan weather can change rapidly, so pack a light rain jacket or sun protection accordingly.

Local Insights

Wildlife

  • European hoopoes occasionally seen in the countryside
  • Mediterranean tortoises in rural patches around San Gimignano

History

Siena’s Palio horse race dates back to the 17th century, reflecting the deep-rooted civic identity still celebrated today.

Conservation

Local efforts prioritize preserving medieval structures and limiting traffic in historic centers to protect the authenticity and environment of these towns.

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Adventure Hotspots in Florence

Frequently Asked Questions

Recommended Gear

Comfortable walking shoes

Essential

Necessary for navigating historic streets and uneven cobblestones.

Sunscreen

Essential

Protects skin during extended time outdoors in the Tuscan sun.

spring specific

Light rain jacket

Useful for unexpected showers common during transitional seasons.

fall specific

Refillable water bottle

Essential

Keeps you hydrated during long walks and warm weather.

summer specific