Things to do in Pienza, Tuscany: The 7 best experiences

Horseback riding in the Chiana Valley will give you a unique experience in the nature outside of Arezzo.

Excursions of 1 or 2 hours are available to best meet your needs.

At the stables, the instructor will teach you the basics of horseback riding and then you will go out for the hike. During the ride, you will be immersed in the Tuscan countryside by crossing the trails amidst vineyards, woods and meadows.

During the summer season there is an opportunity to do the walk even at sunset making the activity even more unique.

To participate you must be at least 14 years old and sportswear with long pants and closed shoes is required. Maximum weight 85/90 kg. 

Wine tasting with a visit to Tenuta degli Dei in Chianti is a 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 the Tuscan artistic tradition.

The tour continues with a visit to the vat cellar, where the vats in which wine fermentation 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 six wines: a sparkling wine, a white wine, a rosé, a Chianti Classico and two IGTs, accompanied by a small sampling of local cured meats and cheeses.

The wine tasting will be held in the tasting room.

You can choose between the tour in Italian and English.

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

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

Finally, the Estate is pet friendly, welcoming even your four-legged friends.

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.

Horseback riding in Siena is a unique opportunity for prinipianti to get closer to horseback riding while enjoying a wonderful view of Siena and the Sienese hills.

After cleaning the horse together with the equestrian guide, you will be taught how to mount the horse and how to walk in total peace. You will then have the opportunity to stop at the organic farm for a tasting of typical Tuscan products.

The walk takes about 1 1/2 hours and can be organized as a group or exclusively.

You can walk in the morning or at sunset and the minimum age required to participate is 14 years old.

Horseback riding in the hills of the Sienese Chianti is a unique experience that allows you to admire the striking views of Tuscany.

On arrival at the stables you will be greeted by experienced equestrian guides who will hand you the’equipment and safety devices to be able to ride a horse.

Before leaving for the ride you will go to the sand rectangle where the guides will explain the basics of horseback riding.

At this point you will be ready to set off and reach the hills of the Sienese Chianti region, where you can admire unique landscapes and discover more about local products: wine and oil.

There will be no lack of little pearls of history and anecdotes that will make the walk even more enjoyable.

Comfortable clothing with long pants and closed shoes is recommended.

The walk with alpacas in the Florentine Hills is a pleasant experience in the midst of woods and fields on the outskirts of Florence, accompanied by the sweetest alpacas. During the loop trail, about 3 km long, you will learn about all the alpacas you will walk with.

After the walk you can stop on the meadow and enjoy the spectacle of the alpacas in the wild.

We recommend that you wear comfortable clothes and sports or hiking shoes.

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.

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 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 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.

Wine tasting with a visit to Tenuta degli Dei in Chianti is a 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 the Tuscan artistic tradition.

The tour continues with a visit to the vat cellar, where the vats in which wine fermentation 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 six wines: a sparkling wine, a white wine, a rosé, a Chianti Classico and two IGTs, accompanied by a small sampling of local cured meats and cheeses.

The wine tasting will be held in the tasting room.

You can choose between the tour in Italian and English.

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

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

Finally, the Estate is pet friendly, welcoming even your four-legged friends.

Horseback riding in San Gimignano is a pleasant experience among the beautiful views of San Gimignano, in the hills just outside the town.

The walk starts in the morning or afternoon. During the trek you will have the opportunity to love getting to know the horse thanks to the guides who will accompany you during the tour.

The horseback ride lasts 1h. You will take a pleasant horseback ride among the beautiful views of San Gimignano, where you will have the opportunity to love getting to know the horse thanks to the guides who will accompany you during the tour.

You will be provided with all horse riding equipment, including helmet (mandatory). Recommended clothing includes long pants and closed shoes.

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.

Horseback riding in the hills of the Sienese Chianti is a unique experience that allows you to admire the striking views of Tuscany.

On arrival at the stables you will be greeted by experienced equestrian guides who will hand you the’equipment and safety devices to be able to ride a horse.

Before leaving for the ride you will go to the sand rectangle where the guides will explain the basics of horseback riding.

At this point you will be ready to set off and reach the hills of the Sienese Chianti region, where you can admire unique landscapes and discover more about local products: wine and oil.

There will be no lack of little pearls of history and anecdotes that will make the walk even more enjoyable.

Comfortable clothing with long pants and closed shoes is recommended.

The walk with alpacas in the Florentine Hills is a pleasant experience in the midst of woods and fields on the outskirts of Florence, accompanied by the sweetest alpacas. During the loop trail, about 3 km long, you will learn about all the alpacas you will walk with.

After the walk you can stop on the meadow and enjoy the spectacle of the alpacas in the wild.

We recommend that you wear comfortable clothes and sports or hiking shoes.

Lunch among the vineyards and wine tasting in San Gimignano is a very romantic experience in Tuscany. It is also available for dinner and includes a walk through the vineyards, during which you will be shown the technique of harvesting grapes. Afterwards you will be given a lesson on wine, from winemaking techniques to how to preserve a vineyard.

This will be followed by a tasting of wines and typical Tuscan products among the rows of the estate vineyard, with lunch or dinner served. The experience consists of a vertical tasting of 15 Tuscan products.

Lunch or dinner will be accompanied by the tasting and the following courses:

•    Aperitivo with typical Tuscan cold cuts and cheeses and bruschetta.
•    Tuscan Ribollita or Lasagna with truffles
•    Roasted meat with side dish
•    Cantuccini with Dessert Wine or Vanilla Ice Cream with Balsamic.

Available upon request are vegetarian, vegan and gluten-free menu.

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.

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.

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.

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 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:

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•    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.

The Giglio Island Tour by boat from Giglio Porto offers a choice of 4 different tours. 

Tour Classic 

The Classic tour starts from the port of Giglio Island. Along the way, you will make 3 or 4 bathroom stops. During the tour you will be offered a delicious aperitif on board.

Tour Luxury 

The Luxury tour starts from the port of Giglio Island. This mini-cruise takes place aboard one of the luxury boats that offer maximum comfort. During the tour, you will make 3 or 4 bathroom stops and enjoy the crystal clear sea. The most exclusive part of this tour will be the arrival at the Caldane Beach, which è can only be reached by sea. Here you will find umbrellas and sunbeds reserved just for you and you can refresh yourself with delicious drinks. At the end of the tour, you can return to Giglio Porto with our Shuttle Boat, choosing the time you prefer.

Half Day - Private

The half-day private tour starts from Giglio Island port at the agreed time. During the tour you can make 3 or 4 bathroom stops. Along the way, you will enjoy a delicious aperitif on board. Finally, you will arrive at the Caldane Beach, the most exclusive beach on the island, reachable only by sea. Here umbrellas, reserved sunbeds and refreshments await you. At the end of the tour you can return to Giglio Porto with our Shuttle Boat, choosing your return time.

Full Day - Private

The full-day private tour starts from Giglio Island port at the agreed time. During the tour you will have the opportunity to choose your stops, explore the island's most fascinating coves and swim. During the day, you will be delighted with an aperitif on board and have the opportunity to enjoy a lunch selected from the menu. Finally, you will return to Giglio Porto, with a maximum return time of 6:30 p.m.

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All boats are equipped with sundecks and awnings. Snorkeling equipment will be available on the boat, so you can explore the wonderful underwater world.