This tour opens up an array of wonderful sights in Tuscany – from the well known towns, through to producer visits and lesser known spots.
This allows you to visit the charming small towns of Tuscany, and to immerse yourself in the classic Tuscan countryside. Only by getting into these harder to reach areas do you really get a feel for the heartland of this region.
The tour features a combination of cuisine, history and culture, as well as leaving time for you to soak up the atmosphere in these unmissable destinations.
Some of our visits are missed by many visitors to Tuscany, as they are hard to find or not in the normal highlights list.
Tuscany Villages Tour Highlights
- Visits include San Gimignano (with its medieval towers), Siena, Volterra and Monteriggioni.
- See places that many people miss, such as ancient Etruscan structures and natural springs used by the Romans
- Indulge in the Tuscan cuisine. As well as our meals together, we enjoy many items from the pasticceria such as ricciarelli and panforte.
- Winetasting of Brunello di Montalcino
- Dine in a 14th century abbey
- Visit a private formal garden near Montepulciano
- Visit the ancient Roman baths of Bagno Vignoni
Tuscany Villages Tour Itinerary
DAY 1 - From Florence to Chianti
We meet in Florence and head into the hinterland. The Tuscan countryside is one of the quintessential images of Italy, and the hill-top towns make for excellent visits for either dining or exploring. This is our plan for the week.
Our first stop is the town of Castellina in Chianti, which features a small piazza alongside the 15th century castle. We enjoy the village atmosphere, and make time for a gelato or a coffee.
Next we view an Etruscan burial site nearby, the Tomb of Montecalvario. Etruscans were one of the early populations in Tuscany, in pre-Roman times. This tomb has four chambers partially underground in a burial mound, and was constructed in the 6th century BC.
We reach our accommodation, a boutique hotel called Tenuta di Mensanello. You will be staying in a 500 year old rural estate, a special experience in which you can feel echoes of the past traditional life all around you. This estate was really a type of farm village, and alongside the rooms you can see the chapel and the farm buildings.
In the evening we have dinner together in their restaurant right here on the estate. This is our first introduction to the Tuscan cuisine, much of which is grown on the farm right outside our door. This is farm to table at its best. During the week we will continue our exploration of Tuscan cuisine, with a progressive discovery of the local cuisine.
Amanda from Australia writes: “Italy with Pleasure deserves more than 5 stars. The comprehensive tour was very carefully & thoughtfully arranged with a well paced ratio of sightseeing activities and long lunches. I was impressed with the Italian with Pleasure brochure full of everything you need to know and the maps given out at each town. Riccardo our guide is the most affable, caring, energised, knowledgeable guide you could wish for. He has a lovely personable nature and spent time with each of us. He clearly genuinely loves his work. Italy with Pleasure all make a good team with emphasis on attention to every detail for a safe comprehensive experience – congratulations!” (from Google Reviews)
MEALS: DINNER (3 COURSES INCLUDING WINE)
DAY 2 – Bagno Vignoni - Montalcino
We depart for our first stop, a place called Bagno Vignoni. These are thermal pools that have been used since ancient Roman times. Back then they were prized for their therapeutic properties, and are still well patronised today.
We move on to the town of Montalcino. After a walk through the town centre together, we also leave you some free time to browse the shops and to wander around.
In this part of Tuscany the highly regarded Brunello di Montalcino is produced. We sample this and a range of other wines to accompany our lunch.
After lunch we visit an elegant formal garden. This garden was established in the early twentieth century and has a fascinating history – and it’s not just the botanical history that we find out about.
Our small group tour advantage: Your tour leader is your ‘safety net’. Many people appreciate having their tour leader to be able to turn to, whether it be for help getting something from a pharmacy / drugstore, or simply where to find the best gelato! While you are far from home, you can count on your tour leader and their support team for anything that you need to deal with.
MEALS: BREAKFAST, LUNCH (3 COURSES INCLUDING WINE)
DAY 3 – Siena - Volterra
We spend the day exploring the town of Siena. On a guided visit we look around various parts of town you’ll see how loyal the locals are to their zone – the area that they represent in the palio, the bareback horse race around the central Piazza del Campo. We continue on to see the cathedral, where you discover some interesting quirks of its construction and history. Once the capital of a republic, and arch rival of Florence, Siena has a rich and varied history.
We also leave the afternoon for you to see Siena independently. Most people head to a café for some of Siena’s renowned biscuits such as ricciarelli and cantucci. A great idea is to visit one of the historic cafes of the town centre, such as Caffe Poliziano, which started in the 1800s.
After a break back at our countryside lodgings – a good time for a swim – we venture out for an evening in Volterra. As well as the Etruscan and Roman features here, this is a classic Tuscan hill town. After we see some of the town together, you have time to look around yourself – wandering cobblestone lanes inside the ancient town walls, finding that perfect trattoria for dinner, or just an aperol spritz on the piazza if you prefer.
Sandra from USA writes: “We were looking for a small group tour that offered learning about the local culture of Italy, the cuisine and free time. Italy with Pleasure did just that and more! If you are looking for a small group tour to explore various regions of Italy, I would highly recommend Italy with Pleasure!” (from Google Reviews)
MEALS: BREAKFAST
DAY 4 – San Gimignano
This morning we travel to the town of San Gimignano. From a distance we start to see the medieval towers of San Gimignano, erected by the noble families in a bid to out do each other.
San Gimignano is one of Italy’s most well-preserved medieval towns. Perched on a hilltop, it is a commanding presence dominating the patchwork of olives and vineyards in the valley below. San Gimignano’s narrow streets boast many artisan workshops. And there’s a particularly good gelateria in the piazza. While busy in the summer months, our visit is off peak and a great time to be here. You have free time to explore the town independently.
We stop in to the Tenuta di Mensanello to recharge in the afternoon, then head out again for an evening on a lovely property where we spend some time looking around and enjoy a meal of classic Tuscan dishes.
Our small group tour advantage: We give the tours a personal feel. With a maximum of 14 in our groups, the feel of our tours is like travelling with a group of friends. We make our tour the style that you want, for example our focus on good restaurants – the sort of places you’d choose yourself. And not cramming too much into one day. All this gives your time with us a less commercial feel and ensures that we maintain a relaxed atmosphere.
MEALS: BREAKFAST, DINNER (4 COURSES INCLUDING WINE)
DAY 5 - MONTERIGGIONI
Our first stop is the village of Monteriggioni, a rare example of a town still contained within the original 3th century walls, just as it was centuries ago. The small piazza and old stone buildings are simply charming, this village has a medieval feel. We allow time for you enjoy being in Monteriggioni, and to look around the central village. You can do a circular walk along the top of the town walls to enjoy the fantastic views, or simply relax in the piazza with a coffee or gelato
Lunch is in a restaurant contained within a 12th century monastery complex, the Monastery of San Salvatore. Originally this would house pilgrims en route to Rome, so we dine in a courtyard that has seen many centuries of monks walk its paving stones.
After lunch we return to Florence, where our tour ends in the afternoon.
Our small group tour advantage: Our local insights help you to maximise your time. When you are in a country or region only for a week or two you want to make the most of your time. On our tours, we give you the local insights, the understanding of what you are seeing. Without this, you might recognise that a particular feature or building seems interesting, but not ever know the full story behind it. Guidebooks will detail the main monuments or museums but tend to be quite limited when you start to see the smaller (and often more interesting) sights.
MEALS: BREAKFAST, LUNCH (4 COURSES INCLUDING WINE)
Tuscany Villages Tour Cost and Inclusions
TOUR PRICE: €2350
Price is denominated in Euros. Price listed is based on twin share/double occupancy
Single supplement of €300 for solo travellers
- All accommodation is included
- Meals as listed in the itinerary: breakfast every morning, plus a main meal each day including wine
- All costs/entry fees for activities listed in the itinerary are included
- All transport during the tour is included. Travel is in our minibus with a professional driver
- 'Italy With Pleasure' provides a tour leader who will be with you for the duration of the tour, on hand to provide any support that you need
Tuscany Villages Tour Accommodation
We stay at the Tenuta di Mensanello. Different to a hotel, this is a farmstay (agriturismo). It is a collection of stone buildings that developed initially around a chapel in the 11th century, gradually expanding over the centuries. Originally the farm workers lived in these buildings.
Today, as well as the accommodation, this estate still operates as a farm. The farm and accommodation are family run. They produce a range of crops, wine and olive oil.
Staying here is part of the experience of being in the Tuscan heartland. This is where you can get in touch with the people who work the land and produce some of the things that make this region special. You can enjoy their homegrown food at their restaurant.
When the Tenuta di Mensanello is not available we stay at the San Lorenzo Hotel in the town of Colle di Val d’Elsa.
Tour Reviews
L Z 
Italy With Pleasure curated an amazing itinerary and ultimately, experience in Puglia for our group of 7. Mark, our incredible tour guide, shared the history, highlights, and hidden gems in each glorious location. Daily, we shared delicious meals, all local recipes, made with fresh ingredients from the region…a true highlight of the entire experience. Each day had the right balance of group and free time and while I may be biased, I think our group was the best…a shared experience with amazing people from around the world!
This was the first time I joined a tour and it will not be the last. I have my eye on Sicily next! My entire experience with Italy With Pleasure was superb and I highly recommend them for anyone who wants to immerse themselves in the beauty and culture of Italy.
P B
I can't thank the small tour group, Italy With Pleasure, enough for a fantastic trip to Puglia. The group size was perfect and our guide, Anita, was amazing, knowledgeable and so caring of everyone. This area of Italy for non-Italian speaking guests was the absolute best way to visit. I was amazed at the beautiful cultural sites in all the towns AND the fabulous late luncheons featuring the local specialties.Spectacular! I have never had such great food on a tour or anywhere.
Thanks again and I have already shared our great experience with a number of my friends and family.
J I
The tour was first class, excellent in every way. An amazing way to see & learn about Puglia. The accomodation, sightseeing, superb food & mini van with great driver and Anita leading the group was sensational.
We highly recommend this is the best way to see and learn about Puglia.
John & Anita
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