Things to do in Pienza, Tuscany: The 10 best experiences

A wine tasting with a visit to the Tenuta degli Dei in Chianti is the perfect opportunity to spend a relaxing time surrounded by the picturesque Tuscan vineyards.

The meeting begins in front of the Church of San Leolino, a three-nave basilica that preserves valuable works of art from the Tuscan artistic tradition.

The tour continues with a visit to the vat cellar, where the vats in which the fermentation of the wines takes place, and the barrique cellar, which houses the fine French oak barrels in which the wine rests until it reaches perfect maturity.

Next, you will reach the Estate, where the tasting will take place. In the dedicated room, you will have the opportunity to taste five wines: a white wine, a rosé, a Chianti Classico and two IGTs, accompanied by a small sampling of local cured meats and cheeses.

You can choose between the tour in Italian and in English.

Minors and those not participating in the tasting do not pay and will receive a tasting of local products.

In case of food allergies or intolerances, you can contact the estate after booking.

Finally, the estate is pet friendly, welcoming your four-legged friends as well.

Explore the Sienese countryside on horseback and experience the authentic beauty of Tuscany through this relaxing ride.

You will ride through hillsides embellished with vineyards, olive groves and cypress trees following scenic trails and immersing yourself in the vibrant colors and scents of unspoiled nature.

Accompanied by an experienced guide, you will learn about the local flora and fauna, discovering fascinating details about the plants and animals that inhabit this extraordinary land. Your guide will also share some stories about the region's history and traditions, transporting you back in time among medieval villages and historic rural estates.

These horseback rides are suitable for everyone from beginners to experienced riders. The well-trained and docile horses ensure a safe and enjoyable experience for all participants.

Comfortable and sporty clothing with closed shoes and long pants is required to participate in this experience.

To make your adventure even more special, you can choose to stop for lunch or indulge in a wine tour with tasting at a local winery, savoring the exquisite flavors of the best Tuscan wines and traditional delicacies (not included in the price).

Lunch with wine tasting at Cantina Brogioni is a perfect experience to spend a relaxing moment surrounded by the Chianti hills.

After a short walk during which you will be given a description of the winery and the process of extracting extra virgin olive oil, you will visit the winery, where you will learn more about the winemaking process.

Following this, you will be served a three-course lunch paired with 4 local wines:

•    1 first course of pasta al pesto (pine nuts, fresh basil, EVO oil and parmesan cheese), paired with an IGT white wine and a vintage Chianti classico
•    1 second course consisting of bruschetta with local EVO oil, selection of typical Tuscan salumi, 36 month Parmigiano Reggiano and Tuscan pecorino cheese, paired with a Chianti classico riserva and a Supertuscan
•    2 samples of Tuscan pecorino, one with local EVO oil with San Miniato white truffle and the other with cooked must
•    1 dessert consisting of a Greek yogurt mousse sprinkled with a dark cocoa cream with 12% EVO oil

In case of food allergies and intolerances it is possible to contact the facility after booking.

Picnic in Radda, in classic Chianti, allows you to spend a relaxing moment surrounded by the Tuscan hills.

You can enjoy unique moments in the company of your loved ones while enjoying locally produced wine accompanied by local schiacciate (flat bread).

The picnic takes place in the garden a you will be provided with towel, pillows and a basket that includes:

•    2 traditional gourmet schiacciate per person (one with Tuscan prosciutto, sun-dried tomato cream and arugula; one with fresh pecorino, acacia honey and Tuscan salami)
•    Cantuccini
•    1 bottle of IGT Toscana red organic wine Granbruno
•    Water
•    Dishware, recyclable cutlery and napkins

At the end of the experience you can also taste the local Vermouth Rosato.

In case of allergies, intolerances or food preferences you can contact the facility after booking.

The Chianti e-bike tour departing from Castellina allows you to experience a full day of fun cycling in the Tuscan hills.

This experience allows you to rent an e-bike for the whole day (9 hours) and admire hills, vineyards and historic villages in the company of friends or family.

Be enchanted by the Tuscan landscapes and panoramas while discovering evocative views.

This experience is suitable for everyone and e-bike rental does not require special physical training. Remember, however, that Chianti is an area with no flat roads.

Wine tasting in Radda, Chianti, allows you to enjoy a unique experience in the heart of Tuscany, in one of the most important wine production areas in the world.

You will be welcomed by a winery entirely surrounded by Sangiovese vineyards and overlooking the medieval village of Radda in Chianti.

You can choose from 2 tasting routes.

Wine tasting with winery tour

This tour will allow you to learn all the secrets of the winemaking process: from the fermentation cellar to the aging cellar in wood and bottle.

Following the guided tour of the winery (fermentation area, barrique cellar and aging area), you will taste 3 wines and a Vermouth:

•    Tuscan I.G.T. Granbruno
•    Chianti Classico D.O.C.G.
•    Chianti Classico D.O.C.G. Riserva
•    Vermouth Rosé

Wine tasting with cutting board

This food and wine tour combines local wines with a tasting of typical Tuscan cold cuts and cheeses. You can enjoy it in the Florentine porch or in the turret, surrounded by the Tuscan countryside.

This experience includes a tasting of 3 different types of Tuscan cheeses and 3 types of cured meats. In combination you will be able to taste:

•    Tuscan I.G.T. Rosato
•    Tuscan I.G.T. Granbruno
•    Chianti Classico D.O.C.G.
•    Chianti Classico D.O.C.G. Riserva
•    Chianti Classico D.O.C.G. Gran Selezione Vigna Il Corno
•    SuperTuscan Guss IGT
•    Vermouth Rosé

If you choose this option, the winery tour is not included.

In case of food allergies and intolerances you can contact the facility after booking.

A vintage gozzo excursion along the coast of the Argentario promontory departing from Porto Santo Stefano.

During the navigation, you will skirt the coast and visit some of the Argentario's most beautiful coves, where you can stop for a swim and snorkel in the crystal clear waters.

The boat is made entirely of wood, and is equipped with a large sundeck and awning. A small snack will be offered on board.

The activity can be booked for a morning or afternoon ride. It is also possible to book the boat in private mode.

Maximum capacity: 7 people.

The Argentario e-bike tour from Porto Santo Stefano, in the province of Grosseto, begins at 10:00 am. There you will meet the guide, who will hand over the mountain bikes and help you get ready for departure (rental is included in the price!).

Once you leave the center of town, you will start climbing the promontory of Monte Argentario, facing hairpin bend after hairpin bend until you reach a paved alley road that will lead you to the Capo d'Uomo tower, located 350 m above sea level.

The last part of the climb will require considerable effort, but the spectacular views of the coast below will repay the effort.

The route will continue through hairpin bends and dirt roads in the direction of Porto Ercole, a town that has been part of Italy's most beautiful villages since 2014. During the lunch break you will stop near Forte Stella, a 16th-century defensive fortification characterized by its distinctive shape.

In the afternoon you will cross the Orbetello Lagoon, which is a WWF oasis and an important habitat for many species of waterfowl, including the wonderful pink flamingos. You will return to Porto Santo Stefano at 3 p.m., having completed a 41-km route that includes quite challenging uphill and downhill sections.

Don't miss a unique opportunity to sail Argentario, Giannutri Island or Giglio Island aboard a boat, enjoying lunch on board and snorkeling in excellent company.

Departing from Porto Santo Stefano, the destination will be chosen according to weather and sea conditions, and during the trip, you will be accompanied by the crew who will guide you through corals, volcanic rocks and gorgonians, telling the story of these picturesque places.

You will enjoy the sunshine and an onboard lunch of pasta, fruit, wine, soft drinks and coffee.

The itinerary will be determined by marine weather conditions, with at least 4 stops for swimming and snorkeling activities. Return is scheduled in the afternoon between 4:30 and 5:30 p.m., with a total excursion duration of about 8 hours.

Two boats are available. The Negis boat carries up to 18 people, while the Gigliola boat carries up to 28 people.

The Argentario catamaran and snorkeling day will begin at 9 a.m. in Porto Santo Stefano, in the province of Grosseto, where you will meet the crew who will accompany you on the catamaran excursion.

The boat ride will take you along the coast of the Monte Argentario promontory, past sandy bays, inlets, cliffs and coves of great natural beauty.

During the trip you will make several stops to snorkel in the most beautiful places, including Cala del Gesso, Cala dell'Olio and Cala Mar Morto. The crew will provide you with all the necessary equipment. You can also relax in the sun and enjoy the open bar with water, soft drinks, red and white wine.

During the first stop you will be offered a selection of local mixed flatbreads prepared with Tuscan olive oil, Taggiasca olives, and the local super with anchovies.

At lunch, the delicious Captain's mixed bruschetta will be offered, which may vary from day to day following the freshness of the products. At the end of the meal, a basket of fresh fruit and coffee will be offered, and in the afternoon there will be a Nutella party for everyone to recharge their energy and keep diving and swimming.

The day will end with the return to Porto Santo Stefano scheduled for 6 p.m. The excursion is confirmed with a minimum of 15 participants.

The quad bike excursion in the countryside between Volterra and San Gimignano è a unique experience that combines adventure, nature and Tuscan culture.

This tour traverses hills, woods and country roads with panoramic views and breathtaking scenery. You will begin the l'excursion with a brief introduction to ATV riding and safety measures.

Following that, the adventure can begin! This type of experience è the ideal for nature lovers looking for an adventure off the beaten path, to discover an authentic and adventurous side of Tuscany that goes beyond the classic tourist routes.

The tours can be one hour or one and a half hours and are suitable for all levels of experience and families even with children, as long as they are over 5 years old.

Unforgettable stay in the heart of Tuscany with overnight stay in a standard room for two, with picnic or wine tasting included.

You will stay at a farmhouse surrounded by nature in San Gimigano, the package includes:

•    One night in a standard room for two people
•    Breakfast

Choice of:

•    Tasting of locally produced wines
•    Picnic

A perfect experience for those who wish to immerse themselves in the food and wine culture of one of Tuscany's most fascinating medieval towns.

The horseback riding tour among the vineyards and tasting in San Gimignano will take place among the unforgettable panoramic views among rustic farmhouses and vineyards in the area.

It is a horseback tour of the estate, nearby vineyards and the forest around San Gimignano (1 hour).

Afterwards there will be a short lecture on wine and vineyards, after which there will be a full wine tasting and then, if selected, lunch outdoors in the garden.

The picnic in the vineyard in San Gimignano offers you the opportunity to enjoy a unique and relaxing experience, surrounded by the rows of Vernaccia grapes.

You can taste typical Tuscan products, accompanied by a bottle of local wine, your choice of Vernaccia, Chianti and Rosato.

This experience is ideal for couples and will allow you to indulge in a relaxing break with a splendid view of the Towers of San Gimignano.

A wine tasting with a visit to the Tenuta degli Dei in Chianti is the perfect opportunity to spend a relaxing time surrounded by the picturesque Tuscan vineyards.

The meeting begins in front of the Church of San Leolino, a three-nave basilica that preserves valuable works of art from the Tuscan artistic tradition.

The tour continues with a visit to the vat cellar, where the vats in which the fermentation of the wines takes place, and the barrique cellar, which houses the fine French oak barrels in which the wine rests until it reaches perfect maturity.

Next, you will reach the Estate, where the tasting will take place. In the dedicated room, you will have the opportunity to taste five wines: a white wine, a rosé, a Chianti Classico and two IGTs, accompanied by a small sampling of local cured meats and cheeses.

You can choose between the tour in Italian and in English.

Minors and those not participating in the tasting do not pay and will receive a tasting of local products.

In case of food allergies or intolerances, you can contact the estate after booking.

Finally, the estate is pet friendly, welcoming your four-legged friends as well.

Cooking course in the heart of Tuscany, with wine tasting and full lunch.

Under the guidance of the chef you will learn how to make bruschetta with seasonal ingredients, a type of fresh handmade pasta with typical Tuscan sauces and a traditional dessert.

At the end you will enjoy the lunch you cooked in a typical setting, accompanied by locally produced wines.

The course è hands-on and engaging, designed to let you participate firsthand in the preparation of the dishes.

Horseback riding by the sea in Maremma departing from Marina di Grosseto, perfect for an alternative day out as a couple or with friends.

The experience begins at the stables where you will be assigned horses and provided with the equipment to ride a horse.

Once you leave, the hike lasts about 2 hours through the Tombolo Pine Forest, San Leopoldo Canal, backdune area, dunes and beach. 

The quad bike excursion in the Tuscan Maremma and aperitif will allow you to visit picturesque landscapes, admire breathtaking views, learn about local scents and guster Maremma snacks.

For this quad bike tour you have the possibility to choose the route of 1 hour or 2 1/2 hours.

The 2-hour one also includes a barbecue in the woods with grilled sausages, cheese and local wine.

Alternatively è you can choose a visit to the "La Pierotta" winery, where participants can taste some of the fine wines produced by the winery, accompanied by an aperitif of local products.

Remember to bring with you:

.

•    Trekking shoes
•    Bandana or scarf in summer (can be purchased locally)
•    Gloves in winter
•    K-way in winter and mid-season (can be purchased locally)

The ATV rental è is suitable for people of all skill levels and guarantees a fun and adventurous experience. It takes place in the Bandite di Scarlino area, where participants will have the opportunity to admire beautiful landscapes and discover unusual places.

During the hike, there will be some technical parts, fords and fun climbs, but nothing too challenging. In addition, participants will have the opportunity to enjoy the local scents.

This experience è an excellent opportunity to discover the culture and traditions of Maremma and to taste some of the best wines and products of the area.

For all Fridays in the fall and winter months, è a minimum of two quads is required for reservations.

Wine tasting in Maremma, outside Grosseto, allows you to taste local wines in a Tuscan winery.

You will be welcomed by an estate that produces natural wines from native Tuscan grape varieties and aged in terracotta jars and barriques used to enhance the flavors of biodynamic grapes.

The winery, which you will have the opportunity to visit, is mainly underground so as not to distort the gentle curves of the land and it is the result of geological architecture, which is based on the characteristics of the landscape.

You can choose between two options.

The Colors of Sequerciani

This experience begins with a visit to the winery. You'll descend into the depths of the hillside to discover where the wines are born, and then look out again over the panorama, where your gaze sweeps from the countryside to the sea.

The visit will continue with a tasting of three wines that embody the spirit of the estate, three fresh and versatile labels. All of this will be accompanied by a board of your choice of local specialties.

Anfora Experience

During a visit to the winery, you will descend into the depths of the hillside to discover where the wines are born, and then take in the view again, where your gaze sweeps from the countryside to the sea.

The visit will continue with a tasting of three wines aged in amphora, accompanied by a board of your choice.

The cutting board can be classic, vegetarian or vegan. You can communicate your preference (and any food allergies and intolerances) to the facility following the reservation.

Bark in a comfortable motorboat and visit Giglio Island, Giannutri and the most hidden coves and islets of the Tyrrhenian Sea.

Leaving from Castiglione della Pescaia, the tour will last about 8 hours and 30 minutes and will be structured as it follows:

Giglio and Giannutri

•    Embarkation starting at 8 a.m.; at 8:30 a.m. we set sail! (check in by 8.10 am)
•    Sailing along the coast of Maremma and Parco dell’Uccellina to Talamone and afterwards along the north coast dell’Argentario.
•    Just before 11 a.m. disembarking at Giglio. You will be able to visit at liberty or with Toscana Trekking guides, booking visits with them during navigation
•    At approximately 2 p.m. we set sail for Giannutri.
•    At about 2.45 pm arrival in Giannutri, where it will be possible to take more guided tours or engage in bathing.
•    At 4 p.m. we set sail from Giannutri to return to Castiglione (7:30 p.m.), after a brief technical stop at Giglio.

The tour stops may vary depending on weather conditions and skipper's decisions.

It is required to pay in cash, before departure, the Municipal Disembarkation Fee for Giglio Island of 3.00€ per person and the Giannutri Island Access Fee of 2.50€ per person.

The alpaca walk in the Tuscan Maremma, Val d'Orcia, is designed to give an unforgettable experience of contact with nature and animals.

The walk with alpacas is about 2.5 km long and takes place between a very short stretch of country road and then enters paths through fields, vineyards, grove until you reach the bank of the Ombrone River.

The route of the alpaca walk may vary depending on weather conditions (so as to avoid excessive mud), hunting season or excessive heat preferring shadier stretches.

The approximate duration of the walk is about 1.5 hours but obviously depends on how the animals are prepared on that day, the ability of the participants to "lead" them, and other variables such as the state of the trails.

During the alpaca walk there are stops for a total of about 10 minutes during which you can interact with the alpacas, feed them, take photos and videos.

The private boat excursion to Cala Violina is an experience suitable for both those who want to relax and the more adventurous.

As the first destination of the tour you can choose the beach of Cala Violina or the one you prefer from Scarlino to the Sparviero islet. In any case, the skipper will be ready to advise you on the best destination also depending on the day.

Once you have chosen your destination, you will depart from the port and move along the coast, taking a short tour of the rocky beaches and coves, including Cala Terre Rosse, Cala Martina, and Cala Civette.

When you arrive at your destination, you will drop anchor as close to shore as possible, so you can see the seabed and give the more athletic people a chance to swim to the beach. A ring life jacket will be provided to make the crossing safely (or a pink flamingo!).

On board you will have masks to do some snorkeling, beautiful experience especially at the Sparrowhawk and the rocky little beaches. You can choose from 2 tours:

Tour with lunch

With the morning tour, an onboard lunch of rice or cold pasta, Tuscan crush, fruit, water, beer and wine is included.

Tour with aperitif

With the afternoon tour an aperitif of white wine, beer or prosecco accompanied with some pizza, schiaccia Toscana and fruit is included. If you prefer something more sophisticated, however, you will have the option of choosing wine and champagne from a menu provided by a renowned local winery, which you can even accompany with oysters.