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.
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.
Tuscany Villages Tour Highlights
- Visits include San Gimignano (with its medieval towers), Siena, Volterra and Monteriggioni.
- Stay on a historic farm estate, enjoying the Chianti wine they produce and their homegrown produce.
- See places that many people miss, such as a private formal garden near Montepulciano, the ancient thermal baths Bagno Vignoni, ancient Etruscan structures, and the Diborrato falls.
- Indulge in the Tuscan cuisine. As well as our meals together, we enjoy many items from the pasticceria such as ricciarelli and panforte, and do a winetasting with a quality producer of Brunello di Montalcino.
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.
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 beautifully renovated rooms you can see the chapel and the farm buildings.
We spend the afternoon exploring the estate with the owners, seeing their horticultural activities, their rare breeds of livestock, and their vineyard that produces the chianti wine that we enjoy with our dinner together in the evening. We delve into their production philosophies, which are focused on compatibility with their land and the use of heritage varieties.
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.
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.
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.
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.
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.
MEALS: BREAKFAST, LUNCH (4 COURSES INCLUDING WINE)
Tuscany Villages Tour Cost and Inclusions
TOUR PRICE: €2500
* Price is denominated in Euros. Price listed is based on twin share
* 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, a collection of historic stone buildings that developed initially around a chapel in the 11th century, gradually expanding over the centuries. Today this estate is run as a boutique hotel, with the agricultural activities still carrying on too.
Around the grounds you will see numerous aspects of times gone by, giving an insight into the lifestyle here in centuries past – you are immersed in history. For this week, you live amongst it.
But we don’t forget the needs of the present! The Tenuta di Mensanello offers all you would expect during your time here, such as wifi, air conditioned rooms, and a swimming pool.
The farm and accommodation are family run. They produce a range of crops and olive oil. You can enjoy their homegrown food at their excellent restaurant.
And a glass of Chianti at the end of the day sourced from the vineyard right outside your door is also not to be missed.
Tuscany Villages 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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