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Private Tuscany Day Trip from Rome

  • Group Size:
    Group Size: Private
  • Language:
    Language: English
  • Duration:
    Duration: 12 hrs
  • Start:
    Start: 07:00 AM
  • Price:
    Price: From 1049 €
  • Cancelation:
    Cancellation: Free Cancellation*

Tour Overview

From the iconic rolling hills and quaint medieval towns to ever-exquisite food, wine, and handicraft shopping, you’ll capture the very essence of Tuscany on this private full-day excursion to the heart of Italy. With one of our experienced drivers at the helm, your day will unforgettable – and completely stress-free.

Tour Highlights

  • Siena
  • San Gimignano

What's included

  • Expert English-speaking driver-guide
  • Private customizable tour
  • Wine tasting and farmhouse lunch
  • Time to shop and explore
  • Private luxury vehicle

What you’ll See Along the Way


Siena, today a medium-sized provincial city, was once one of the West's major powers that long fought against Florence for power over Tuscany. Siena lost this battle and, therefore, development almost stood still in the city – making this mini medieval metropolis a popular destination for visitors who want to soak up the historical atmosphere. Siena's main attractions are located around the fan-shaped Piazza del Campo, on which the "Palio” takes place every summer. This bareback horse race dates back to the 1600s and is still Italy’s most famous annual sporting event.

San Gimignano

San Gimignano is a small and delightfully picturesque town in the heart of Tuscany, boasting an intact urban design from the 1300s which is protected by a fantastically well-preserved city wall. The village is especially famous for its medieval towers, which completely dominate the city’s skyline and can be seen from miles away. The towers of most other Italian towns have been destroyed by wars, natural disasters or redevelopment – but in San Gimignano, 14 out of the original 72 towers still proudly stand guard over the UNESCO World Heritage listed city.

Tour Summary Get in the Know

Get the best of Tuscany – in one day

For most of us, Tuscany perfectly embodies our most romantic dreams of Italy. The region’s mouth-watering cuisine, stunning scenery, fascinating historical heritage, and wide range of cultural attractions make it a complete dreamland for any bon vivant – and a must-visit destination for every self-respecting Italophile. On this 12-hour outing, you’ll get to visit two of the province’s most spectacular medieval towns and a hidden gem winery, where we’ll treat you to a bounteous lunch and wine-tasting session.

As you travel north through the Tuscan countryside in a deluxe air-conditioned van, your cheerful driver will entertain you with intriguing stories of historical happenings that took place in this very region as well as interesting tidbits about the local culture. Tune in as you soak up the beautiful vistas sweeping past the car window; a rolling landscape of vineyards and sunflower fields, dotted with Renaissance villages enthroned on green hilltops. While your driver won’t be wandering into the cities with you, he will provide you with plenty of background information on each place visited so that you’ll be well-prepared to explore them independently.

Explore Siena – before wining and dining in Chianti

Our first destination is Siena. This medieval city had its heyday in the 1300 and 1400s and incredibly hasn’t changed much since. While brimming with architectural and artistic must-sees, this small town is easily manageable on foot. During the 2-hour stopover, you’ll have plenty of time to cover all the major architectural highlights, such as the main square, Piazza del Campo, and the striking cathedral with its dramatically decorated interior of black and white marble stripes. A climb to the top of the Mangia Tower just down the road offers a magnificent view of the brick-laden city below (a sight well worth the 400-step climb!).

In a rural area, just north of Siena, we’ll stop for lunch at our very favorite “fattoria”. Perched on a small hill in the very heart of the Chianti district, this family-run little winery is the perfect venue to get to know the Tuscan cuisine and wine tradition a little bit better. Your gracious hosts will show you how the wine is made – from grape to glass – through a thorough tour of the grounds. Should you wish, you’ll also get to try the farm’s own delicious produce (at your own expense).

Revel in the beauty of San Gimignano

We’ll cap our Tuscan day off with a stop in beautiful San Gimignano. This small hilltop village is especially famous for its many imposing towers, which create the unusual skyline that has earned the city its nickname – “the Medieval Manhattan”. During the Renaissance, dozens of towers were built by aristocratic families who wanted to show off their economic and political success, but today only 14 of the original structures from the city’s golden age remain. Admiring the imposing monuments and meandering through the picturesque alleys, one can easily get a sense of what it was like to walk the very streets some 500 years ago.

No visit to San Gimignano would be complete without a refreshing visit to Gelateria Dondoli – voted “Gelato World Champion” for two consecutive years. Unsurprisingly, the lines to enter the tiny shop often stretch around the block, but the heavenly gelato is well worth the wait! Another top tip is to indulge in some shopping in the numerous shops selling typical Tuscan products such as handmade glasswork, wooden goods, fine pottery, local wine, wild boar sausages, cured hams, and cheeses. With so many quality products on offer, we’re sure you’ll find that perfect gift for your loved ones back home before embarking on your journey back to the Eternal City.

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Private Tuscany Day Trip from Rome

What our Customers say...

Care Free planning at it's BEST!

Do you want a tour group that takes care of everything so that your vacation is truly special? What a Life Tours is that group of special people that go above and beyond in every way. I have to send a big hug to Pips, our planner for our excursions. We travelled all throughout Italy with stops in Rome, Pompeii, and Florence. In Rome, Pips set up the early morning Vatican trip which was phenomenal. Not only did we have our own guide in a group of 10 (we accounted for 4), we beat the crowds. The Sistine Chapel and St. Peter's Basilica took on a whole new meaning and truly came to life as the tour leader took us back in time. We also had a personalized one on one tour with Martina of historic Rome from the Pantheon to the Trevi Fountain to the catacombs with multiple other stops along the way to enjoy the culture and nightlife that is exclusively Italian. Martina loves her country and it definitely showed with her in-depth description of each site and it's importance to the people of Italy. The tour of the Coliseum was also amazing. Each and every one of the excursions was so thoughtfully planned and carried out in a small or personalized atmosphere. While in Florence, Pips, found us a personal guide of "The David". Angelo was amazing. His knowledge and the way he told the story of the creation of The David and it's importance to Florence and Italy brought the statue to life right before our eyes. He was truly an artist and historian. His enthusiasm to share Italy with people is unsurpassed. The next day, Pips also set up a tour with Giovanni, our own personal driver and guide to the Tuscan countryside complete with wine tasting at two family wineries (we shipped home multiple cases of wine from both). Giovanni is well spoken and did not disappoint as he painted a picture of life in this beautiful and picturesque setting. We took our oldest daughter to Pompeii and Herculaneum for her 16th birthday and was again greeted by our own personal guide of these incredible historic sites. His name was Andrea. You could tell that he was passionate about telling the story and history of the life and times of the people of these two doomed cities. It was incredible and I could feel myself being taken back to just before Vesuvius blew. All told, we experienced 7 excursions through What a Life Tours and I couldn't imagine doing it any other way. Everything was perfect down to the smallest detail and we have Pips and her team to thank. We didn't worry about a single thing and that is what a true vacation is about right? If you want a professional handling your vacation tour needs in Italy just call Joseph (owner) and his group at What a Life Tours. You won't be disappointed.”

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