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The Secret Places of Tuscany Tour


A summer sunset dinner table outside in Tuscany with a view
Dinner in the Maremma hills

If your idea of Tuscany is ancient towns and villages, each with their own story to tell, nestled in gently rolling hills carpeted with vines and olive trees under azure blue skies, that’s our idea of Tuscany too. 

You don’t have to travel back in time to experience this dream of Tuscany and nor do you have to share it with crowds of tourists because on this tour you’ll stay in two places you’ve probably never heard of but in fact are perfect little towns that compete for the best scenery in Tuscany. 


maremma view of Scarlino and coastline
Coastal Maremma has something for everyone and we fell in love at first sight

Suvereto will be the first destination, located in the heart of the Maremma close to the most beautiful stretch of the Tuscan coastline. And then on to Seggiano for the final 4 nights; think of it as the back door into the nearby Val d’Orcia and Brunello wine country. Both of our chosen towns lie on opposite sides of the Province of Grosseto, the largest and by far the least visited of the nine provinces of Tuscany, located half way between Florence and Rome.


Massa Marittima
Massa Marittima, one of the Maremma highlights of the tour, and as always there's a glimpse of the sea

This tour will not be visiting any of the major Tuscan cities because so many people have already seen Florence, Siena and our home town of Lucca but there will still be a few famous names on the itinerary like Montepulciano, Montalcino and Pienza. Though many of the other towns will likely be unfamiliar to you, these are the places that Elena and her fellow Tuscans love and the places they flee to when tourists take over their cities in the summer.


Magliano in Toscana
A typical Maremma view of an ancient walled town totally unspoiled by modern development or ugly suburbs

We’d be ecstatic if this Secret Places of Tuscany Tour turned out to be our only tour and we’d gladly repeat it ten times every spring, summer and autumn if we could because we love these locations so much. In fact Suvereto and Seggiano are our top two choices in Tuscany to move to permanently when our time in Lucca is over.

We’ve chosen to base the tour in these two towns because it means that everywhere on the daily itinerary is only a short drive away from one or the other so the time spent in transit every day will be kept to an absolute minimum. Furthermore, and just as important, is that the accommodation in both these places is simply first class. 



The first hotel just outside Suvereto called Boschi di Montecalvi (above) is an authentic Maremma agriturismo. A collection of 19th century casali (farmhouses) that have been renovated with traditional materials to a luxury standard to faithfully reproduce the classic Tuscan farmhouse. The stone buildings include terracotta tiled roofs, exposed wooden beams and travertine floors, all tastefully divided into very comfortable apartments.

These very attractive buildings sit alone in a natural environment, completely surrounded by wildflower meadows and forested hills with no other structures in sight apart from an infinity pool perched on the ridge line with spectacular views of the Maremma countryside. It's such a perfect setting that we might have to drag you away every morning but we’ll make sure to allocate plenty of afternoon time to relax and enjoy the atmosphere before dinner.


Breakfasts and dinners in the agriturismo’s restaurant with its panoramic views are included in the tour price and everything is sourced locally including wine and olive oil from their own estate which extends to over 50 acres and also includes many trails for walking or cycling.



The second property near Seggiano is even more remarkable in that it is an ancient castle completely restored with such attention to detail that every room is unique. The restoration was so long and comprehensive that the owner wrote a book about the entire process (above photo).


Castello di Potentino is truly a one-of-a-kind-place where no effort has been spared to include all modern comforts, including ensuite bathrooms and a lovely pool, while retaining the special atmosphere of a 1,000 year old building. The owners, who live here and have also become award winning winemakers, have been researching the history of Potentino for the last 20 years and continue to discover new interesting facts about the incredibly long line of previous owners.


Breakfast and dinners at the castle are also included in the price as well as an afternoon cooking class.


Needless to say both these properties are quite popular among those like us who know Tuscany well and as both have a limited number of rooms early booking for this tour is advised.


Tour Dates, Itinerary and Cost:

This is a small group tour for 6-12 people. You can book as an individual or couple or as a group.

If booking as a group you will have the freedom to suggest some changes to our proposed itinerary and then together we can come up with a schedule that exactly matches your requirements.

If booking as an individual or couple please note that a total of 6 people is a realistic minimum for the tour to proceed.


2025 Proposed Tour Dates: May 21-31, June 4-14, June 25-July 5, September 3-13, September 24-October 4. A group booking can also request a different tour start date.


Cost for 10 days based on double room occupancy, transportation and all meals, including lunches6,100 euros per person for a party of 8. Single room occupancy will require a supplement of 975 euros. (The cost per person will be less for 9-12 people and more for 6-7 people). See below for the main inclusions and exclusions.



DAY 1: Florence or Rome pick-up at a pre-agreed time with transport (2 or 3 hours) to Suvereto by mid afternoon. We will be present at the hotel check-in to assist if necessary and once you’re settled in we’ll get together over pre-dinner drinks to welcome you to Tuscany and answer any questions. Dinner at the hotel.


DAY 2: Morning visit to the towns of Suvereto and nearby Campiglia Marittima followed by a comprehensive wine tasting, vineyard and cellar tour plus lunch at either Tua Rita or Petra (photo right).


These are the two most prestigious wineries in Suvereto and the final choice will be made when the composition of the group is known because Petra makes only red wines whereas Tua Rita produces both red and white. Petra however has an architecturally very impressive winery building (photo right).


With very little travel today there will be time to relax at the hotel in the afternoon prior to an early evening Olive Oil tutorial by Elena where she will present a small selection of some of the best Tuscan and Umbrian olive oils and educate you on how to properly evaluate olive oil prior to tomorrow's visit to Fonte di Foiano.


DAY 3: Morning visit to the fascinating Etruscan settlement of Populonia just 30 minutes away. The Populonia archeological park contains the most impressive acropolis and necropolis combination in Tuscany and demonstrating the importance of this coastal town through subsequent ages there are also the remains of a Roman domus adjacent to the acropolis and a medieval village and fortress that overlook the gorgeous Gulf of Baratti. By now all of you will begin to understand our affection for the Maremma but there is a lot more to come.


Gulf of Baratti, Tuscany
The Gulf of Baratti

After Populonia we'll drive north for barely another 30 minutes to Fonte di Foiano just outside the wine town of Castagneto Carducci for a tasting of their wonderful selection of award winning olive oils, followed by lunch on their Farmhouse Restaurant terrace where the chef's simple dishes are designed to showcase their oils. Elena will be on hand to provide further olive oil tuition at lunch.

Castagneto Carducci

After lunch there will be time for a stroll around the delightful wine town of Castagneto Carducci high up on the hill with great sea views. Late afternoon return to the hotel followed by dinner.



DAY 4: We'll head to the seaside after breakfast this morning, starting with a walk along the beach near Principina a Mare which is only a couple of miles away from our morning visit to the cheese emporium of Guido Pallini called La Maremmana where he raises water buffalo to make exquisite mozzarella and other fresh and aged cheeses.


Principina a Mare beach, Tuscany
The wild beach of Principina a Mare not far from Castiglione della Pescaia

After learning all the secrets of mozzarella from the person at La Maremmana who actually hails from Battipaglia, the most famous mozzarella town in Italy, we'll travel a very short distance to the lovely seaside town of Castiglione della Pescaia for a relaxing lunch and stroll through town.


The sea front at Castiglione della Pescaia
The sea front at Castiglione della Pescaia

The afternoon will include a few hours in the single most impressive town in the Maremma in our opinion - Massa Marittima - which lies conveniently on the return journey to Suvereto. Late afternoon return to the hotel followed by dinner.


DAY 5: Today we're following in the footsteps of James Bond or rather in his wake to the historically important town of Talamone, an hour's drive from the hotel.



Lunch will be in nearby Porto Santo Stefano on Monte Argentario and after a walk around this delightful port we'll get you back to the hotel for some relaxation time.

We’ll make this evening a Tuscan white wine celebration so Elena will conduct a wine tasting of some of our favorite Vermentino white wines from coastal Tuscany and also a couple of our preferred Vernaccia white wines from San Gimignano, followed by dinner in the hotel.


DAY 6: Today is the transfer to the castle at Seggiano for the remaining 4 nights. After 2 hours we'll stop to see the remarkable town of Pitigliano. A forbidding looking place carved out of volcanic rock and once inhabited by Etruscans. It became an important place of refuge for people of the Jewish faith as long ago as the 14th century, acquiring the nickname 'little Jerusalem'. Certainly a very different looking town to the Maremma of the last 5 days.

Reaching Seggiano and the Castello di Potentino will take less than an hour after lunch leaving plenty of afternoon relaxation time at the hotel before dinner.


DAY 7: We'll stay very close to the hotel today with visits to Seggiano and nearby Abbadia San Salvatore as well as Bagni San Filippo for a dip in the remarkable hot springs there. There will be a late afternoon cooking class at the hotel followed by dinner.


DAY 8: Today is when you realize why I previously described Seggiano as being the back door to the Val d'Orcia because it's only 30 minutes from the hotel to the famous Brunello winery of Col d'Orcia where a five course lunch awaits as part of their VIP tour and tasting experience.


But before lunch the first visit will be to Montalcino, which is also a very short drive away. A medieval town that has barely changed for centuries and whose name is synonymous with one of the world's greatest red wines. We might also try to squeeze in a visit to the 12th century Romanesque Abbey of Sant’Antimo to listen to the  Gregorian chants at 12.45 p.m. before lunch.

After a leisurely lunch we'll arrive back at the hotel for plenty of quality relaxation time that can include taking advantage of some of the many activities that the hotel offers.


DAY 9: The last full day of the tour can easily include 3 towns that are all situated in a direct line from Seggiano, thereby minimizing travel time. After breakfast we'll head first to the fascinating medieval town of Montepulciano, followed by lunch in the astonishingly perfect Renaissance town of Pienza and take in the pretty village of San Quirico d'Orcia afterwards, all the while enjoying the gorgeous scenery of the Val d'Orcia as we travel through this iconic landscape on our journey.


The 16th century Horti Leonini gardens in San Quirico d'Orcia
The 16th century Horti Leonini gardens in San Quirico d'Orcia designed by Diomede Leoni, most likely with help from his close friend Michelangelo

NOTES:

1. Included in the price are 9 nights in superb accommodation, including ensuite bathrooms, 9 breakfasts and dinners at these hotels and 9 lunches at the various places we have mentioned in the above itinerary. Wine at lunch and dinner is also included.

2. Also included are all of the activities mentioned - wine tastings, olive oil tastings, cooking class, the cheese producer visit and any entrance fees.

3. All transportation is included, starting from the pick-up in Florence or Rome (to be decided) to the drop-off in Florence or Rome (to be decided).

4. This is a fully escorted tour so also included in the price is as much time and assistance from Mike & Elena as you require, which will include at no extra charge informal Italian lessons from Elena if required by anyone (see also the Language section of this website) and Mike is always happy to accompany you on a bike ride, whether on electric bikes or regular bikes.

5. Not included are additional and optional hotel provided activities, drinks (other than mealtime water and wine) and incidental expenses of any kind.

6. Detailed terms and conditions will be submitted later to interested parties. Meanwhile for further information, discussions about changes to the itinerary or to express interest in booking this tour please email us at Mike@mykindofitaly.com or use the contact form in the About Us section of this website.


Additional background information written by us on this website:

Tuscany Wines - overview of the entire Tuscany wine region

Caveat Emptor - examples of unscrupulous labelling practices to be aware of when buying Italian olive oil, especially outside Italy



Why choose to tour with us?

Having guided British and American family and friends around Tuscany for several years there are few people better qualified than Elena and I to personally escort you on a tour of Tuscany, especially one with an emphasis on wine and olive oil


Born and raised in Florence, Elena has lived in Tuscany her entire life, the last 15 years of which have been in Lucca where I joined her from America 11 years ago after a cycling trip through the Tuscan Apennines across the entire width of Italy from sea to sea.


Elena is a qualified Italian Sommelier and Maestro d’Olio (the olive oil equivalent of a wine sommelier) and conducts tutored tastings on both subjects as well as guiding her language students through all aspects of Italian life in Lucca (left photo).

Together on this website we have written extensively about Italian wine, food and olive oil, documenting our visits to numerous producers of some of Italy's finest gastronomic products like Culatello di Zibello.


Our Mission Statement:

Our goal is simple. We want you to experience for ten days some of the highlights of our trips through Tuscany over the last decade that we have written about and photographed for this website. Reading about our travels may be interesting but experiencing them for yourself will be much more rewarding.

Our goal is never to become a typical tour operator and we view ourselves as providing a personal service rather than trying to create a business burdened with employees. We want to stay firmly within our Italian areas of expertise and we will accompany every tour ourselves because our knowledge and experience acquired over the years cannot be outsourced without compromising the fun and enjoyment that we promise to our guests.


Overview of Tuscany

Tuscany covers a large and very diverse area, extending from Michelangelo’s marble mountains in the Apuan Alps (above Carrara) in the extreme north-west to the small town tucked away in Tuscany’s north-east corner (Stia) that is famous for being the home of Audrey Hepburn’s coat in the iconic movie ‘Breakfast at Tiffany’s’.


Porto Ercole (left) and Porto Santo Stefano (right)


From the little known rocky promontory (Monte Argentario) in the south-west where Caravaggio died (Porto Ercole) and where Richard Burton and Elizabeth Taylor fled from the paparazzi while filming Cleopatra in 1963 (Porto Santo Stefano), Tuscany extends 100 miles east to the Umbrian border where you find the small town  (Castiglion Fiorentino) that gave us Italy’s most revered comedic actor (Roberto Benigni) as well as a celebrated sculptor (Andrea Roggi) whose work seems to follow us on our travels around Italy.

In fact as close to the Umbrian border as you can get is a place that should be familiar to devotees of Piero della Francesca because the museum in the tiny but lovely village of Monterchi contains just one item - the fresco known as Madonna del Parto.


Montemassi, Tuscany
Montemassi, deep in the Maremma and barely changed from the 1330 painting by Simone Martini depicting the town under siege

There is nowhere that Elena and I haven’t been in Tuscany, including all across the island of Elba, and though many people are familiar with some of the more famous places in this region of Italy, very few know much about all the little towns and villages that Tuscans themselves love. Who reading this has ever heard of Montemassi (above) or Magliano in Toscana for example.

Only a native of Tuscany truly understands the culture, history and traditions of this most famous of all Italian regions and that is what makes Elena an indispensable part of your tour and why she will accompany you every step of the way to ensure that this will be a learning experience as well as a unique vacation.


Vongole veraci
This tour will also be a learning experience and perhaps our lunches in Porto Santo Stefano or Castiglione della Pescaia will send you home an expert on Vongole Veraci versus Lupini

When are the best times to visit Tuscany?

Our thoughts regarding the ideal months to tour Tuscany are as follows: (see also our article on When to Visit Italy)


February & March: Very underrated months for visiting central Italy with moderate daytime temperatures and generally clear skies but some seasonal hotels will still be closed during this period. Some of our recent articles on towns in Veneto were written after a trip through that region in the first week of February and it turned out to be a fabulous time in which to experience Italy as only Italians do.


the coastal Via dei Cavalleggeri path in Tuscany
Clear skies and pleasant early February temperatures make for perfect walking conditions along the coastal Via dei Cavalleggeri near Populonia

April & May: Spring has been wetter and cooler than usual in recent years but these are perfect touring months for people that find the summer heat oppressive.

June, September & October: Our favorite months of the year, always warm and sunny and rarely too hot.


Field of Tuscan sunflowers in late June
Anywhere around the longest day of the year is the perfect time to enjoy the Tuscan countryside

July & August: Despite the sometimes intense heat we still enjoy peak summer in Italy but Tuscany can get very crowded and Italians tend to escape to the mountains or to the seaside leaving their cities to the tourists. You need to adjust your daily routine to stay comfortable when temperatures get close to 40°C. Prices for accommodation are much higher in these months and there are weeks when many good restaurants close for the August holidays.


late autumn view of Lucca from the hills
Late autumn isn't always miserable as this November 30 photo from the hills above Lucca demonstrates

November, December & January: November is the wettest month of the year everywhere in Italy so I would not recommend a November trip. Sometimes the rain persists until Christmas and though January normally sees clearer skies, the February weather is less cold and more reliable with more daylight hours. These three months are best for visiting Florence, Lucca, Siena, Arezzo and other Tuscan towns and cities rather than the Italian countryside and we can tailor an off-season tour for those interested because we live year-round in Lucca.







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