Sightseeing on a Small Group Tour through Tuscany

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Tuscany is more than just the world-renowned picturesque region of Italy. Matching its otherworldly beauty and amazing culinary talents, the area is full of history. Today’s guest contributor, Shelli Elledge from Written FYI, recently took a small group tour through Tuscany, uncovering its profound character along the way.

Small Tour Tuscany
Without a doubt, Tuscany is one of the world’s most beautiful sites.

Learning about secret tunnels in the heart of Florence . . . exploring medieval hillside towns, amazing Etruscan ruins, and extraordinary cathedrals . . . sampling local fare, including Chianti wines, salamis, burrata and pecorino cheeses, hearty pastas, smooth gelatos, and rich panfortes . . .

If this sounds like an immersion into Italian history and culinary arts, it is.  But these are just a few of the highlights of taking a guided tour in some of the world’s most beautiful and famous cities.

My husband and I have found that sightseeing with a small group tour has many advantages, some that we hadn’t even expected.  Small group tours help us make the most of our limited sightseeing time because, instead of wasting time in long lines, or looking for a parking place, or purchasing tickets for each venue, we gain insightful information and have easier access.

First Stop: Scenic overview of Florence

Our Tuscany tour started in Florence at the Piazza della Repubblica located near the iconic Duomo.  After greetings and introductions, our tour guide, Claudia, tour driver, Francesco, and our group boarded the eight-person van and headed across the Arno River.

Small Tour Tuscany
The views of Florence are just spectacular.
Small Tour Tuscany
The more rural side of the city is just as gorgeous!

Within minutes, our first stop was one of the most scenic places to view Florence we’ve ever seen – from the Piazzale Michelangelo. From this vantage point, we could see the densely-foliaged hillsides, remnants of Etruscan ruins, stately Italian Cypress, the meandering Arno River, and traditional amber-colored homes.

Small Tour Tuscany

Claudia told us about the historical significance of the Etruscan civilization and how it impacted the country and the world.  She described the “secret” tunnel called the Vasari Corridor, originally built for the Medici family in 1565 and used in more current times for evacuation purposes. She showed us the tower located on the banks of the Arno where Italy’s first gold coins, or fiorinas, were made during the 12th and 13th centuries, later becoming a dominant currency in medieval Western Europe. Before heading to our next stop, Claudia pointed out the ornate San Miniato Church where prayer services still include Gregorian chants.

These nuggets of information brought the city of Florence to life and made our tour experience more memorable!

Second Stop:  Siena

The ultimate “hill town,” Siena is a favorite tourist destination and UNESCO World Heritage Site in Tuscany. Three reasons for its popularity is that it’s only 35 miles from Florence, it is the location for the famous Palio horse race, and it has a strikingly beautiful 13th-century Gothic cathedral filled with treasures.

However, Siena is also a place where it’s an advantage to be on a small group tour!

Because the town is built on hilltops, sightseeing in Siena is exhausting! Although many visitors rent cars for the convenience, parking spaces are limited and found along the winding roadway. That means visitors have to hike uphill to get to the city center. However, on a small group tour, there are no parking problems. Our driver delivered us at the top of the hill in front of the cathedral, saving time and energy. Plus, we had entrance tickets to the cathedral which saved us from standing in the ticket line.

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Siena’s Cathedral

Small Tour Tuscany
The Duomo in Siena is an amazing cathedral built as a tribute to the Virgin Mary. The richly ornamented interior has black and white striped walls and pillars, arched ceilings, gleaming inlaid marble floors, and spectacular stained glass.

Small Tour Tuscany
Ornate details cover the interior.

It is a masterpiece that houses hundreds of other masterpieces. Statues of popes look down from above, but one statute seemed out of place in its niche in the wall. Often overlooked by visitors, Claudia explained that this is a “selfie” that Michelangelo created of himself.

Another interesting detailed gleaned during our tour!

The Il Campo

Small Tour Tuscany
The Il Campo is a busy shell-shaped town square in the heart of Siena. Dozens of shops line the edges of this bustling outdoor people center, many selling leather products, ceramics, or regional culinary treats. Claudia lead us to one of these little shops where we sampled different types of panforte, an Italian dessert made with cocoa, almonds, and fruits.  Delicious!

But the Il Campo is more importantly known as being the setting for the world-famous horse race, the Palio, that takes place in July and August. On race days, the Il Campo is packed with locals and visitors, all straining to see the action. Although the race lasts only a little more than a minute, it is a wildly popular and dangerous event that attracts tens of thousands of people every year to this town.

Getting inspired to plan a trip to beautiful Italy? Make sure to check out our Italy Travel Planning Guide!

Third Stop:  Lunch and Wine Tasting in Chianti

As we set off from Siena, we headed for the Chianti Region where we enjoyed lunch and wine tasting at one of the most unique agriturismos, or rural B&Bs, in the area. The Sant’ Appiano, with its history dating back to the 14th century, is a place that should not be overlooked.

Small Tour Tuscany
The Cappelli family of Fattoria Sant’Appiano.

Delicious aromas wafting from the cucina, grape-inspired furnishings, and meticulously-shelved bottles of chiantis on handsome wall displays. And then we noticed the adjacent wine cellar. A large carved-out cave with rounded walls and high earthen ceiling, it was the setting for our leisurely four-course lunch and authentic chianti wine tasting.

Small Tour Tuscany
Old barrels = amazing wine.

From the generous servings of homemade antipasto to the cocoa-dusted tiramisu, all expertly paired with locally grown chianti, our delectable meal was a culinary delight and a memorable and authentic Tuscan experience!

Fourth Stop:  San Gimignano

Small Tour Tuscany
San Gimignano is known as the Town of Fine Towers.

San Gimignano is another Tuscan hill town rich in medieval history. As in Siena, our group appreciated that our driver drove us to the top of the hill just steps away from the amazingly well-preserved stone walls surrounding the village. And, as if still thinking about our wonderful lunch, this is where we learned from Claudia that the plants growing between the rocks produce capers, an ingredient often used in Italian cuisine.

Small Tour Tuscany
A quintessential shot of Italian street life.

Besides being a picturesque Italian hill town, San Gimignano is eye-catching with its fourteen medieval towers, fountains, and large piazza. Here, we were treated to fruity gelatos, climbed one of the towers for a bird-eye view of the Italian countryside, and did some shopping.


This was a Walks of Italy tour which incorporated both walking and driving. The schedule was flexible, so we had some discretionary time to shop, explore, or enjoy the ambiance at a sidewalk café at each stop during the day. Walking shoes are advised because most walking surfaces are cobblestones, marbled tiles, or hardened dirt.

My husband and I have taken several tours with this company and we agree that each one has been an exceptional experience. Although this tour was sponsored, all opinions in this article are my own.

Photography by Ron Elledge

Have you explored Tuscany on a small group tour? Come join the conversation at the My Itchy Travel Feet page on Facebook. Or send us an email with your thoughts.

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