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Best of Tuscany 10 Day Tour


A rare unobstructed view through the Ponte Vecchio in Florence
A rare unobstructed view through the Ponte Vecchio in Florence but you'll have to visit in February to enjoy this privilege

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.


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.


A wild Tuscan beach in the Maremma
Our smallest group tour of just one American couple enjoying the wild Tuscan beach on the way to Cala di Forno

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.


Vongole veraci
This tour will also be a learning experience and we'll try to send you home an expert on Vongole Veraci versus Lupini

Proposed Itinerary for Best of Tuscany 10 Day Tour:

The following itinerary is for a small group of 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 changes to our proposed itinerary and then together we can come up with a schedule that exactly matches your requirements. Changes could include reducing or increasing the overall length of the tour, reducing the number of wine tastings, increasing the hotel relaxation time etc etc.

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


This tour was originally designed for some of our personal friends who were looking for an itinerary that was a little more interesting than the typical tour of Tuscany. Splitting the 9 hotel nights among 3 different locations has the intended result of significantly reducing the amount of daily travel which would otherwise be both tedious and a waste of precious vacation time.


Mercato Centrale Florence
The Mercato Centrale in Florence

The Best of Tuscany 10 Day Tour  will utilize approved and vetted high quality hotels and equivalent agriturismo lodgings, always with private bathroom facilities and for the final 3 nights in the Maremma also with kitchenettes. This is exactly the sort of accommodation that we stay in ourselves when traveling around Italy. Mike & Elena will travel alongside you and stay nearby throughout the 10 days and a professional driver will provide all the transportation once the tour starts.


Cost for 10 days based on double room occupancy4,850 euros per person for a party of 8. Single room occupancy will require a supplement of 750 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.

There will be several tour start dates from mid May to early June and again from early September to early October.


Contact us at mike@mykindofitaly.com


DAY 1: Arrive at the agriturismo/hotel just outside Montepulciano. If you need some assistance with travel arrangements to reach Montepulciano we can help with bookings or advice.

We will be available at the hotel check-in to assist if necessary and once you’re settled in we’ll have a quick meeting over pre-dinner drinks to welcome you to Tuscany and answer any questions.


Madrevite's owner Nicola Chiucchiurlotto with Montepulciano and the Tuscan hills in the distance
Madrevite's owner Nicola Chiucchiurlotto with Montepulciano and the Tuscan hills in the distance

DAY 2: Morning visit to the Etruscan Tomba delle Scimmie and catacombs in Chiusi, a wine tasting at Madrevite and lunch and sightseeing in Cortona. Cortona is perhaps now more famous for the quality of its Syrah wine than as the setting for the book 'Under the Tuscan Sun'.

This will be a relaxing day with very little time spent in transit as all three places are less than 20 miles away from the hotel. There will be time for a dip in the pool before a late afternoon cooking class at the residence that will continue through to dinner.


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
Montalcino

DAY 3: A trip through the classic Val d’Orcia to include the astonishingly perfect Renaissance town of Pienza and the equally fascinating medieval town of Montalcino. 


You can choose to visit the 12th century Romanesque Abbey of Sant’Antimo to listen to the  Gregorian chants at 12.45pm prior to a five course lunch nearby at the Col d’Orcia Brunello winery as part of their VIP tour and tasting experience.


Today is also a short driving day with less than an hour’s journey from Montepulciano to the furthest point at Col d’Orcia, stopping at Pienza and Montalcino on the way there and back.


DAY 4: Visit Panzano, our favorite town in the heart of Chianti Classico with a wine tasting at Monte Bernardi or Fontodi followed by lunch at Dario Cecchini’s famous Officina della Bistecca or if that is too much meat at lunchtime there is always the Cecchini Panini Truck (below) which we personally love and it leaves room for dinner.


Dario Cecchini Panini Truck, Panzano

Early evening Olive Oil tutorial by Elena where we will present some of the best Tuscan and Umbrian olive oils. 

Trip time from the hotel to Panzano will be about 90 minutes. Dinner at the hotel or in Montepulciano.


A summer sunset dinner table outside in Tuscany with a view

DAY 5: Florence all day. Check out of the hotel and travel 90 minutes to Florence for a private guided tour and lunch (perhaps a Lampredotto panino in the Mercato Centrale if you want to  eat like a Florentine) and time to stroll around and shop in the afternoon. 


A Florence wine window serving wine
One of the few original buchette now functioning again

Some of the highlights, many of which are to be found in our article Florence in Winter Part 2, include the Oltrarno, Piazza Santo Spirito, the Mona Lisa house, Ponte Santa Trinita and the story of the missing head of the Primavera statue (that Spike Lee mangled unforgivably in his movie Miracle at St. Anna).


Also the Duomo, Piazza Santa Croce, the Boboli Gardens and of course Ponte Vecchio, the Accademia Gallery and Piazza della Signoria with its many iconic statues and the spot where Savonarola was burned. See how many wine windows or buchette you can find on your walk.

Early evening transfer to the hotel in the centro storico of Lucca less than an hour away. Dinner recommendations to follow.


Lucca viewed from the Guinigi Tower
Lucca viewed from the Guinigi Tower

DAY 6: Private guided tour of Lucca in the morning to show you where everything is located and then in the afternoon you can walk or bike on the famous Lucca walls, visit Duomo San Martino, relax in Piazza San Michele, shop in Via Fillungo, climb to the top of the Guinigi Tower or seek out the Roman ruins in town. There’s also the small Puccini museum and the lovely garden of Palazzo Pfanner. We’ve written detailed articles on most of the interesting places in Lucca so you’ll have expert knowledge at your fingertips. Dinner suggestion tonight is Osteria da Pasquale, a favorite of ours with the most reasonably priced wine list in Lucca.


The Cathedral in Massa Marittima
This photo of Massa Marittima in June without crowds shows why we love the Maremma so much

DAY 7: After two hectic days in the bustling centers of Florence and Lucca it’s time to transfer 90 minutes south to the peaceful open spaces of the Maremma. On the way to the hotel you’ll stop at Massa Marittima and visit Podere La Pace winery nearby for a tour and wine tasting.


Zuccherini farmhouse below Suvereto

Accommodation for the next 3 nights will depend on how many are in the group. Zuccherini farmhouse near Vetulonia has a 4 bed/4 bath apartment for a group of 8 or the other choice is the Gualdo del Rey winery property just outside Suvereto. Both choices come with kitchen facilities.

Tonight or tomorrow night will be a seafood cooking class with Andrea at Il Baciarino in the Etruscan hilltop town of Vetulonia overlooking the sea. 


We’ll make the cooking class evening a Tuscan white wine celebration to accompany dinner 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.


The Maremma hills above Castiglione della Pescaia give way to the alluvial plains of the Ombrone river with Grosseto in the distance
The Maremma hills above Castiglione della Pescaia give way to the alluvial plains of the Ombrone river with Grosseto in the distance

DAY 8: Exploring the Maremma. A relaxing day awaits with a tour of the charming unspoiled towns of the Maremma like Campiglia Marittima, Suvereto and Castiglione della Pescaia including a visit to Fonte di Foiano in Castagneto Carducci to taste their award winning range of olive oils followed by a light lunch on their farmhouse terrace.

And we would also suggest making time for a walk along the wild beach towards Cala di Forno in the Maremma Regional Park.



DAY 9: The final full day of the tour begins with a 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. Also close by is the tiny but historic town of Talamone where Nelson and Garibaldi passed through on their way to great victories 62 years apart and James Bond visited more recently. Today would also present another opportunity to visit the seaside resort of Castiglione della Pescaia if there was not enough time yesterday.


DAY 10: The southern Maremma is handy for both Pisa and Rome airports, being about half way between, and Florence also not too far away so transport to the departure airport should not be too problematic.



NOTES:

1. Included in the price are 9 nights in 3 star hotels based on double occupancy. All hotel bookings will be agreed with you first before being finalized.


2. This is an 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.


3. Other inclusions are all transportation during the tour from the arrival hotel to the departure hotel and 5 scheduled wine tastings, 2 olive oil tastings, 2 cooking classes and other guided day tours, visits and entrance fees as described.


4. Breakfasts are included but lunches and dinners not specifically mentioned as part of wine or olive oil tastings or cooking classes are not included in the price, nor are hotel activities, drinks and incidental expenses.


5. 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


Inside the Lucca walls
There's always something going on inside the massively thick Lucca walls

What dates in 2025 are available?

We are only planning to do Tuscany tours in 2025, with Umbria and Abruzzo potentially being added in 2026 or successive years. Which means that in 2025 we can be extremely flexible with dates and the timing can accommodate your needs assuming that you book early enough.

That being said, our suggestions regarding the ideal months for this tour 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 opposite Elba

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.


late December view of Florence from the Ponte Vecchio
5.00 pm on the last day of December is a perfect time to be in Florence taking advantage of a lovely winter light

Having said all of the above, you pick the dates and we will try our best to make ourselves available.


Finally, if you're still hungry for more photographs of places on the itinerary or along the route then the following short video contains some additional photographs of Tuscany alongside a soundtrack of 'Mediterraneo' by Giuni Russo, sadly no longer with us but who possessed a superb singing voice with incredible range.





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