Vespa tour in Maremma

The vespa experience offers an original opportunity on touring around Tuscany. While we take care of each and every detail, leave chaos behind you, enjoy the best of Tuscany’s landscapes from your stylish vespa, perfect not just to skip traffic but to have a feeling of what being Italian really means.
We will stop as many times as we like during the day, discovering the Chianti area that features medieval villages, marvelous views and some of the best producers of wine in the world. The itinerary involves the ‘via Francigena’ once pilgrimage route that nowadays has become an iconic road for modern travelers that today can set off on a surprising and enchanting route on their colorful Vespa.
It’s only at the end of our ride that we will stop there and visit the organic farm as well as the cellar, relaxing on the terrace overviewing rolling hills covered by vines. Lunch will be served, typical Tuscan meal, traditional fresh ingredients, paired with a specific wine selection.

per adult from




5 hours


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  • What's included :
    • Lunch
    • Wine tasting
    • All activities
    • Tour escort/host
    • Use of helmet
    • Alcoholic Beverages
    • Entry/Admission - Castello di Montemassi
    • Entry/Admission - Rocca di Montemassi
    What's excluded :
    • Gratuities
    • Hotel pickup
  • This is a typical itinerary for this product

    Pass By: Castiglione Della Pescaia, Castiglione Della Pescaia, Province of Grosseto, Tuscany

    The area in which the municipal territory of Castiglione della Pescaia extends has brought to light some prehistoric evidence of the upper Paleolithic, which were found in the western hilly area (Val Berretta) and on the eastern hilly offshoots included between the Badiola farm, Ampio and the area south of the hamlet of Buriano.

    The greatest splendor of the Etruscan period was found in the hamlet of Vetulonia, while other findings came to light in the western part of the municipal area between the Val Beretta and Pian di Rocca, an area that was already inhabited in prehistoric times. The area where the built-up area of ​​Castiglione della Pescaia stands was instead an important Roman settlement, given the archaeological remains found on the right bank of the Bruna river near the port-canal and the modern built-up area, among which the remains stand out of the Roman villa of the Paduline. Furthermore, the presence of a consular road and a cobblestones, the remains of which were lost during the nineteenth century, which from the Roman settlement headed towards the pine forest of Tombolo and towards Giuncarico, are also ascertained.

    After a period of abandonment between the fifth and eighth centuries, there was a gradual rebirth of Castiglione della Pescaia, which took particular force during the tenth century thanks to the Republic of Pisa: in this period the primitive medieval village was built in the lower part, which was enclosed by the Pisan walls. The Pisan domination began from 962, although there were discontinuities of power which, at the end of the same century, initially benefited the Aldobrandeschi, then the monks of the abbey of San Salvatore al Monte Amiata. In the twelfth century, the castle settlement passed to the Lambardi family who controlled the hamlet of Buriano at the time, whose influence became significant in the thirteenth century. The center began a phase of prosperity until it became a free municipality in the thirteenth century. In 1274 the Pisans resumed the active exercise of power that lasted until the end of the fourteenth century, a period in which the free Municipality of Castiglione della Pescaia was established, which with an act of submission to Florence managed to secure protection. During the following century the long phase of free Commune ended, following the conquest of the castle by the troops of King Alfonso V of Aragon; previously there was a temporary Sienese occupation during 1432. In 1449 the militias of the Principality of Piombino managed to free the entire village, except for the castle which remained an Aragonese garrison. In 1460 the castle was ceded to the Piccolomini family of Siena, who sold it almost a century later (1559) to the Medici, in whose grand duchy the remaining village had joined a few years earlier. The marquisate of Castiglione della Pescaja with the islands of Giglio and Giannutri was purchased by Cosimo I on 20 January 1559 for his wife Eleonora of Toledo by the Piccolomini d'Aragona de 'duchi di Amalfi with the consent of Philip II of Spain. It also extended to the Rocchette without however having ownership on the "Formiche della Troja" rocks in possession of the princes of Piombino who authorized the grand duke, however, the sale of an area on the Punta di Troja for the construction of a coastal tower. It was administered independently until 1737, depending on the Pisan province, until it was suppressed in 1765 by Pietro Leopoldo and annexed to the rest of the Sienese state.

    From the eighteenth century onwards, the center experienced a strong revival thanks to the reclamation and canalization works of the ancient Prile Lake and to the large commercial exchanges favored by the leading role that the port of Castiglione della Pescaia had assumed in that period. However, the opening of the Maremma Railway after the mid-nineteenth century, which passing through the hinterland was not connected to the center or the port, caused a sudden decline in trade and during the period of great prosperity, which however were overcome between the end of the same century and the beginning of the twentieth century with the development of the first bathing establishments which in fact constituted the dawn of the modern tourist structures that characterize the center.

    Stop At: Castello di Montemassi, 58027 Montemassi Italy

    The castle was built shortly after the year 1000 as a possession of the Aldobrandeschi family. Their control over the fortification ended in the second half of the thirteenth century following a violent siege by the Sienese.

    After a few decades under the control of Siena, the castle passed under the control of the Pannocchieschi and Cappucciani di Sticciano at the beginning of the 14th century.

    Subsequently, the entire town was again besieged and conquered by the Sienese, thanks to the siege conducted by Guidoriccio da Fogliano in 1328, an event depicted in a famous fresco by Simone Martini in the Palazzo Pubblico of Siena. In the following decades, the castle was once again at the center of disputes that also fomented various local revolts; in 1374 the Salimbeni took possession of it, while a few years later it passed to the Verdelli di Montalcino family.

    At the beginning of the fifteenth century the Sienese managed to regain control of the fortification, which was incorporated into the territory of the Republic of Siena. The control was, however, maintained very laboriously for the continuous revolts of the inhabitants who claimed wide margins of autonomy and the recognition of the free municipality of Montemassi, which never happened.

    In the mid-sixteenth century, following the definitive fall of the Sienese Republic, Montemassi and its castle became part of the Grand Duchy of Tuscany. The Medici ceded the fortified complex to the Marquis Malaspina in the first half of the seventeenth century and, in subsequent periods, there were other changes of ownership until the abandonment occurred around 1840.

    Since then, a long period of degradation began, ending only with the restorations that took place between the end of the 20th century and the beginning of the new millennium.

    Duration: 30 minutes

    Stop At: Rocca di Montemassi, Strada Provinciale 91 Loc. Pian del Bichi, 58027 Montemassi Italy

    The Etruscans were the first to plant vines in the Maremma. From as early as the sixth century B.C., they had one of their most important vineyard areas in the fields that pan out from the Castle of Montemassi along the gentle slopes of the hills towards the lapis lazuli-like blue of the Tyrrhenian Sea.

    It was the wine of the Maremma that sailed on the Etruscans’ fast wooden ships along the trading routes of the then-known world. Then the Romans called the area Ager Cosanus, the land promised to Bacchus, where they produced the wine that was served at the Emperor’s tables in Rome.

    And it was again that wine that Columella, Pliny and later Redi described as the “blood of the land”, an enchanted and rugged land full of the scents of forests and brine. You only have to consider that Pian dei Bichi covered six thousand hectares, all of them cultivated. Here Siena grew wheat and the Medici began to plant vineyards. In more recent times certain pioneers wagered on the Maremma as a wine region, such as Trecci or Bettino Ricasoli and his brother Vincenzo, or the Princes Corsini.

    It was certainly the cause of some wonder when – as one can read in a report of the “Accademia dei Georgofili” from the early 19th century – there was the presentation at a symposium of these professors of agriculture of a “three year-old vine whose branch stretched no less than 10 arms’ length from the earth”, which correspond to about 5 and a half metres in today’s terms.

    The writings of Imbrecciadori remain memorable. He speaks about the Maremma as “the other Tuscany” where the countryside and especially vines (and olive trees) are the linchpins for the possible redemption of this area that was once considered sickly: a land made up of sweat and toil, whether the work involved was above ground or indeed below, in the mines, but which, with its sometimes harsh nature - of sharp contrasts and particularly bewitching colours – displays great potential for development.

    Duration: 2 hours

  • Departure Point :
    58043 Castiglione della Pescaia, Province of Grosseto, Italy
    Return Detail :
    Returns to original departure point
    Hotel Pickup :
    • Confirmation will be received at time of booking
    • Not wheelchair accessible
    • Children must be accompanied by an adult
    • Minimum drinking age is 18 years
    • Dress code is smart casual
    • A minimum of 4 people per booking is required
    • Driving license
    • Not recommended for pregnant travelers
    • Most travelers can participate
    • This tour/activity will have a maximum of 20 travelers
    • Face masks required for travelers in public areas
    • Face masks required for guides in public areas
    • Hand sanitizer available to travelers and staff
    • Social distancing enforced throughout experience
    • Regularly sanitized high-traffic areas
    • Gear/equipment sanitized between use
    • Transportation vehicles regularly sanitized
    • Guides required to regularly wash hands
  • You can present either a paper or an electronic voucher for this activity.
  • For a full refund, cancel at least 24 hours in advance of the start date of the experience.


English - Guide

Age Req.


Fitness Req.


Group Size


Organised by Tuscany Private Tour

Activity ID: V-30491P28

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