EXCLUSIVE PRIVATE TOUR OF SIENA & SAN GIMIGNANO

Timeless Tuscany, Tailored for You

Discover Tuscany’s iconic towns on this private day tour without crowds. Explore Siena’s Gothic architecture, San Gimignano's towers, and enjoy a Chianti winery for a taste of history and flavor.


Tour Type

Cultural, Historic & Wine Tour


Duration

Full Day (Approx. 8–9 Hours)


Reviews

5.0 ★ ★ ★ ★ ★ 


Price

From €700 per group (1–2 people)

Explore Siena & San Gimignano Your Way

Begin your day with a hotel pickup in Florence and a luxury vehicle with a private English-speaking driver. Explore Siena's medieval streets, visit Piazza del Campo and the stunning Siena Cathedral, and then head to San Gimignano to see ancient towers and artisan shops. End with an optional wine tasting at a Chianti boutique winery.

  • What makes this Siena & San Gimignano tour special and what will I experience?

    Our "Timeless Tuscany, Tailored for You" experience offers:

    • A private, full-day immersion in two of Tuscany's most enchanting towns
    • Flexible timetable and meeting location to suit your schedule
    • Luxury vehicle transportation with a knowledgeable English-speaking driver
    • In Siena, you'll wander medieval streets to the shell-shaped Piazza del Campo (home of the legendary Palio horse race) and marvel at the black-and-white marble of the Siena Cathedral with Gothic masterpieces by Pisano and Donatello
    • In San Gimignano, you'll explore this hilltop village famous for its skyline of ancient towers and saffron-colored stone, discover artisan shops, walk quiet lanes, and have the opportunity to taste award-winning wines in a locally owned boutique vineyard
    • Scenic stops for beautiful photo opportunities throughout the Tuscan countryside
    • Dedicated shopping time in each city
    • A truly personalized experience with all the attention focused on your interests
  • What are the practical details of the tour including timing, pickup, and group size?

    Our tour is designed with convenience and flexibility in mind:

    • Duration: Full-day experience lasting approximately 8-9 hours
    • Pick-up: Flexible departure from Florence or surrounding areas (pick-up from locations outside Florence available upon request)
    • Style: Completely private tour for 1-8 guests
    • Transportation: Private luxury vehicle throughout the day
    • Driver: Professional, knowledgeable English-speaking driver who remains with you for the entire experience
    • Itinerary: While we visit both Siena and San Gimignano, the exact schedule can be adjusted based on your preferences and interests
    • Photo opportunities: We'll make stops along the scenic route for memorable photos of the Tuscan landscape
    • Physical requirements: Moderate walking through historic town centers with some hills and uneven surfaces
  • What additional experiences can be added to enhance our tour?

    We offer several premium upgrades to personalise your experience:

    • Professional Local Guide: For a deeper understanding of Siena's history and architecture, we can arrange a professional local guide for a 3-hour walking tour at €190, which includes skip-the-line access to Siena Cathedral
    • Wine Tasting Experience: Enjoy a special tasting at a boutique winery in the heart of the Chianti area, starting from €50 per person (not included unless pre-arranged)
    • Lunch and Food Pairings: Enhance your wine tasting with traditional Tuscan delicacies (pricing varies based on selections)
    • Monument Entry: While not included in the base price, we can pre-arrange tickets to specific monuments or attractions you wish to visit
    • Extended Time: If you wish to spend more time in either location, we can adjust the itinerary accordingly (additional fees may apply)
    • Custom Stops: If there are specific places between the main destinations you'd like to visit, we can often accommodate these requests
  • What are the costs involved and what exactly is included in the price?

    Our transparent pricing structure is as follows:

    • €700 per group for 1-2 people
    • €800 per group for 3-4 people
    • €900 per group for 5-7 people
    • Custom pricing available for larger groups upon request

    The base price includes:

    • Private luxury vehicle transportation for the entire day
    • Professional English-speaking driver
    • Flexible pickup and drop-off in Florence area
    • Visits to both Siena and San Gimignano
    • Photo stops in the Tuscan countryside
    • Shopping time in each location
    • Expert recommendations throughout the day

    Not included unless pre-arranged:

    • Local guide services (€190 for up to 3 hours)
    • Wine tasting experiences (starting from €50 per person)
    • Entry fees to monuments and attractions
    • Meals and personal expenses
    • Gratuities (at your discretion)

    We can create a fully customized package including any additional services you desire with advance notice.

A Glimpse into Our Day Trips

GALLERY

What Makes Our Tours Special

With insider tips, luxury transport, and handpicked stops, this tour is built entirely around you. Let Florence Connection craft an unforgettable day in Tuscany’s most beloved towns.

Testimonials

TAGLINE

Charity Karimi

2 weeks ago

Very professional and knowledgeable. We enjoyed every bit of our tour.

Dan O'Connell

A year ago

Wonderful experience. Tour was tailored to my family’s needs with special attention to my older parents. Would highly recommend!

Luca Marilli

2 weeks ago

Professional team for the organisation, high quality wine tasting in an exclusive location. Relaxing stay and Tuscan emotions. Wonderful pool! Thank you.

Andre'a Lucca

2 weeks ago

Helena and The Florence Connection are truly the BEST guide, planner, and tour organizers I have ever experienced!

Book Now

READY TO EXPLORE

Contact Us

Call us

+39-339-7792426

Our office

Via del Proconsolo, 16 Florence, 50122

Explore our top services, from seamless airport transfers to exciting tours, safaris, and the best activities in Watamu. Let Claris African Experience guide your journey!

With Florence Connection we help you live an unforgettable experience

LUCCA & PISA

A DAY EXPERIENCE IN AN EXCLUSIVE PRIVATE TOUR

From €700 per group

(up to 7 people)

8-9 hours

Discover two of Tuscany’s most treasured cities in one unforgettable day. This private tour blends the elegance and quiet charm of Lucca’s medieval walls with the iconic sights of Pisa, including its world-famous Leaning Tower. Enjoy history, culture, and scenic beauty—all at your own pace.

SIENA & CHIANTI REGION

EXCLUSIVE TOUR THROUGH ART WINE & FOOD

From €700 per group (up to 7 people)

8-9 hours

Immerse yourself in the heart of Tuscany with a private, luxurious day discovering the historic splendor of Siena and the rolling vineyards of Chianti. This exclusive experience combines rich culture, stunning architecture, and world-class wine for an unforgettable journey.

AREZZO & TORRE A CONA

PRIVATE DAY TOUR OF ART, HISTORY & WINE

From €700 per group

(up to 7 people)

8-9 hours

Discover the timeless elegance of Tuscany with a perfect blend of art, history, and fine wine. This private tour takes you from the treasures of Arezzo—a medieval gem famous for its frescoes and antiques market—to the serene Torre a Cona estate, where you’ll enjoy a premium wine and olive oil experience.