Florence & Tuscany

Private Grand tour of Tuscany on a day trip from Florence to Pisa, Siena and San Gimignano

4.9/5

182 VERIFIED REVIEWS

Bestseller

Duration

12 hours

Group Size

Private

Languages

English

Italian

Cancellation

Free cancellation

Three hundred years ago, a tradition emerged among the European aristocracy and nobility – the Grand Tour. Young men, driven by a thirst for culture and an insatiable curiosity about the roots of Western civilization, embarked on a pilgrimage to Italy. Today, we invite you to embark on a journey that echoes the spirit of the Grand Tour, exploring the best of Tuscany with unparalleled exclusivity.

Included Description Meeting Point Important Info Faq Reviews

Included

Professional English speaking driver/tour leader

Round-trip transportation from Florence by luxury Mercedes Minivan or Minibus

Guided walking tour of Siena with professional English speaking guide

Surprise tasting in Siena or San Gimignano

San Gimignano visit with free time

Typical Tuscan lunch in a fascinating Chianti boutique winery

Winery guided tour and wine tasting learning about wine production

Pisa visit with focus on Miracle Square and Pisa Leaning Tower (tower tickets not included)

Highlights

Travel in comfort and style with a luxury Mercedes minibus or minivan equipped with air conditioning
Immerse yourself in the captivating history and charm of Siena with a guided walking tour
Explore the enchanting town of San Gimignano, known for its "medieval skyscrapers"
Discover the Tuscany culinary traditions during a delectable lunch in a Chianti boutique winery
Witness the dramatic elegance of the world-renowned Leaning Tower of Pisa in the iconic Piazza dei Miracoli

Description

This full-day excursion is designed to immerse you in the multifaceted essence of Tuscany, a land of diverse landscapes, ancient towns, timeless art, and rich food and wine traditions. As you step into the pages of history, you'll traverse the Middle Ages and the Renaissance, delving into the enchanting towns of Siena and San Gimignano, marveling at the world-famous Leaning Tower of Pisa, savoring the region's culinary delights during a sumptuous lunch, and indulging in the flavors of Chianti wines at a prestigious boutique winery.

From Florence to Siena: rival contrades and Palio revelations

In ancient times, Florence faced a formidable rival for power, wealth, and artistic splendor within Tuscany – the city of Siena. Your journey commences in Florence, where you will be greeted by an English-speaking driver and tour leader who will accompany you on your voyage to Siena. Once you arrive, you'll embark on a guided walking tour of the historic city, allowing you to immerse yourself in the charm of Siena. This tour will take you through iconic landmarks such as Piazza del Campo, the central square renowned for hosting the thrilling Palio horse race each year. Your exploration will extend to the quieter, labyrinthine backstreets, where you'll uncover the secrets of the Contrade – the 17 medieval city districts that fiercely compete in the Palio.

Discover San Gimignano medieval marvels and Chianti’s culinary delights

The journey carries on to San Gimignano, a town celebrated for its "medieval skyscrapers." Its high walls, narrow streets, and enchanting architecture are emblematic of the quintessential Tuscan hill town. San Gimignano stands out with its preservation of about a dozen tower houses, creating a skyline that is truly unforgettable.

Here, you will have the opportunity to enjoy some free time, allowing you to explore the town at your own pace, soaking in the historical ambiance and appreciating the town's unique character. As the day unfolds, your path will lead you to a prestigious Chianti boutique winery, offering a delightful respite. This picturesque setting will be the stage for a delicious Tuscan lunch that will tantalize your taste buds. You'll also have the chance to taste some exceptional Chianti wines, learning about the art of wine production and exploring the winery's cellars.

Discover Pisa’s architectural wonders and return to Florence

Relax and unwind while gazing out of the window during your journey to Pisa, where the magnificent Piazza dei Miracoli (Miracle Square) awaits. The square is graced by the breathtaking cathedral and baptistry, with all eyes drawn to the world-famous Leaning Tower. Its unique and dramatic elegance is a testament to architectural marvels of the past.

Please note that tickets to climb the Leaning Tower are not included due to typically long lines, but you will have the opportunity to purchase them directly in Pisa if you wish, provided that the lines are short.

As your adventure draws to a close, the final drive will transport you back to Florence, leaving you with memories to treasure.

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Meeting Point

Meet your tour leader in Via dei Vagellai, 22 red, corner with Piazza Mentana (opposite to the Arno River).

Important Information

Please inform us of any food intolerance or allergy in advance.

Please note that Italy's law doesn't permit selling alcoholic beverage to teens under 18 y.o. so clients under this age will be served non-alcoholic beverages.

We regret to inform that this tour is not suitable for guests with wheelchairs or with impaired mobility.

Please note that this tour might be run on Mercedes luxury 8-seater vans or Mercedes luxury minibuses according to the tour occupancy and always providing the highest possible quality.

Order of stops may change depeding on traffic (all stops and incluses are guaranteed anyway).

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Rain Policy

This tour runs on rain or shine.

Faq

What was the historical rivalry between Siena and Florence, and why does visiting both reveal so much more?

For centuries, Siena and Florence were fierce rivals competing for political power, trade supremacy, and artistic leadership across medieval Tuscany. Siena developed its own distinct Gothic artistic tradition - the Sienese School - and built one of the most extraordinary public squares in Europe: the shell-shaped Piazza del Campo. The rivalry shaped the art and architecture of both cities in profoundly different ways. Visiting Siena after Florence reveals a different vision of the Italian Middle Ages - more mystical, more decorative, and in many ways more intimate than the Renaissance grandeur of Florence.

What are the medieval towers of San Gimignano and why are they considered the skyscrapers of the Middle Ages?

San Gimignano is a small but extraordinary hilltop town in the heart of Tuscany, whose remarkable skyline of tall stone towers has made it one of the most photographed places in Italy. Of an original 72, fourteen towers still stand today - built between the 12th and 13th centuries by wealthy rival families as symbols of power, wealth, and prestige. The taller your tower, the greater your status. This competitive building culture produced what art historians call the medieval skyscrapers of Italy. The entire historic center is a UNESCO World Heritage Site.

What is the Palio di Siena and why has it captivated the world for centuries?

The Palio di Siena is one of the world's most emotionally charged events - a bareback horse race held twice a year in the extraordinary shell-shaped Piazza del Campo. Ten of Siena's 17 districts (contrade) compete in a frenzied race lasting barely 90 seconds, but preceded by days of pageantry, political alliances, espionage, and centuries-old rivalries. Each contrada has its own identity, colors, church, museum, and patron saint. The Palio is not a tourist spectacle - it is the living soul of Sienese identity. Your private guide will bring its history and drama to life during the walking tour of the city.

What makes Chianti wines among the most celebrated in the world?

Chianti is one of Italy's oldest and most prestigious wine regions, occupying the hills between Florence and Siena. Its wines - made principally from Sangiovese grapes - carry the prestigious DOCG certification, Italy's highest quality guarantee. The combination of warm Mediterranean climate, clay and limestone soils, and centuries of refined winemaking tradition produces wines of great personality: vibrant acidity, notes of red cherry, dried herbs, earthy tannins, and excellent aging potential. On this private tour, you will visit a boutique winery and taste the region's finest labels with an expert guide.

How does a private tour of Siena, San Gimignano and Chianti compare to a standard group excursion?

On a private tour, the vehicle, guide, and itinerary are yours alone. You travel in a comfortable, air-conditioned Mercedes minivan and you control the pace - more time in Piazza del Campo, a longer stop at the winery, or a detour through a hidden street in San Gimignano. Your private guide also adapts the narrative depth to what your group is most curious about, whether that is medieval history, the Palio, wine culture, or Tuscan landscape.

What is the cancellation policy?

For groups of 1 to 8 people, a full cancellation fee applies if you cancel within 7 days of your tour date or in case of no-show. For groups of 9 or more, availability and cancellation terms are available on request.