The 10 best experiences to have in the Tuscan Maremma on vacation in 2025

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 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 property after booking.

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

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.

Tasting of four locally produced wines accompanied by typical Tuscan products in San Gimignano.

Program

The experience will begin with guests gathering at the winery, where dedicated staff will welcome you.

After a brief introduction about the family history and presentation of the winery, you will begin the tasting of 4 wines that will be accompanied by typical Tuscan pecorino cheese and bruschetta.

Tasting wines and local products at the Brogioni Winery in Chianti provides you with a relaxing experience on a Tuscan estate.

This experience will begin with a short walk where you will be given a description of the winery and the process of extracting extra virgin olive oil will be explained.

Following that, you will visit the winery, where the winemaking process will be described.

Finally, you will taste 4 wines accompanied by typical products:

•    1 White IGT or Rosé IGT, paired with samples of bread and typical cold cuts
•    1 Chianti classico d’vintage, paired with bruschetta with local extra virgin olive oil
•    1 Chianti classico riserva, paired with a 36 month parmigiano reggiano
•    1 Supertuscan, paired with Tuscan pecorino cheese

In addition to the wines, it will be possible to taste Tuscan pecorino cheese with EVO oil with white truffle from San Miniato and with cooked must, dark cocoa cream containing 12% of EVO oil, and face, hand and body creams produced on site.

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

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.

Wine tasting and winery tour in the Crete Senesi in Tuscany can be done with 4 different tours to choose from:

Classic tour

This tour includes a visit to the historic Fèlsina winery, where you will be taken on a journey to discover the wines produced by this winery. During the tasting, you will have the opportunity to taste four of their most representative wines, selected to offer you a true sensory experience:

•    Classic Method Brut Sparkling Wine: a sparkling wine produced with the classic method, characterized by a refined effervescence and a dry and harmonious flavor.
•    I Sistri Igt Toscana (100% Chardonnay): a dry white wine produced with the Chardonnay grape variety, with an elegant and complex character.
•    Chianti Classico Docg Berardenga (100% Sangiovese): a red wine produced with the Sangiovese grape variety, typical of the Tuscan region, with an intense and tannic flavor.
•    Chianti Classico Riserva Docg Berardenga (100% Sangiovese): a high quality red wine produced with selected Sangiovese grapes, aged in oak barrels for at least 24 months, which gives it an intense and complex character.

Jeep Tour

This private tour offers an experience that will lead you to discover the vineyards of Fèlsina through a jeep tour on the dirt road. Along the way, you will be accompanied by a specialized guide who will explain the methods of vine cultivation and wine production, while you admire the magnificent Tuscan hills.

The visit will continue at the Rancia estate and vineyard, where you will have the opportunity to learn first-hand about wine production processes and observe the vineyards and winery. Here, you will be offered a tasting of four of Fèlsina's representative wines.

Classic tour and lunch

The classic tour with lunch takes place exactly like the classic tour, but allows you to combine the tasting of 4 wines with a 3-course lunch consisting of farm and local products.

Jeep tour and lunch

The Jeep tour with lunch takes place exactly like the Jeep Tour, but allows you to combine a three-course lunch of farm and local products. In addition, you will also be offered a tasting of four mono-cultivar oils, produced by Fèlsina and selected to offer you a true sensory experience of the Tuscan territory.

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 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 property after booking.

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

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.

Enjoy a horseback ride through the typical Tuscan countryside, along the scenic trails that connect Volterra and San Gimignano.

This experience is suitable for everyone, even those who are approaching the world of horseback riding for the first time. As far as horseback riding is concerned, children, from 14 years of age, can also participate.

You will be accompanied by experienced instructors and docile, trained horses. Suitable sportswear with long pants and closed shoes is required.

When booking, you can choose from several options.

1-hour ride in the hills (from 14 years of age)

This horseback ride in the hills between Volterra and San Gimignano allows you to admire unique views. It is suitable for all levels of experience in the saddle, for experts and novices.

1½-hour ride in the hills (from 14 years of age)

The 1½-hour walk will take you discovering the hills between Volterra and San Gimignano. This activity is suitable for all levels of experience in the saddle, for the more experienced and for novices.

Sunset ride with aperitif (from 14 years of age)

From May to October, there è the possibility of a horseback ride at sunset: a unique way to admire the Tuscan countryside in one of the most fascinating moments of the day.

As the sun sets, the hills are tinged with a warm golden light, creating an evocative and unforgettable atmosphere.

At the end of the hike, you can enjoy a refreshing drink surrounded by nature.

For children

An activity tailored for little ones, offering a gentle and guided first approach to the world of horseback riding.

Accompanied by a qualified instructor, children will participate in a small, hand-led ride that will help them become familiar with the horse in a safe and welcoming environment.

The experience also includes a grooming session, during which young participants will learn the basics of horse care, developing trust, respect and an authentic bond with the animal.

Tasting of four locally produced wines accompanied by typical Tuscan products in San Gimignano.

Program

The experience will begin with guests gathering at the winery, where dedicated staff will welcome you.

After a brief introduction about the family history and presentation of the winery, you will begin the tasting of 4 wines that will be accompanied by typical Tuscan pecorino cheese and bruschetta.

Tasting wines and local products at the Brogioni Winery in Chianti provides you with a relaxing experience on a Tuscan estate.

This experience will begin with a short walk where you will be given a description of the winery and the process of extracting extra virgin olive oil will be explained.

Following that, you will visit the winery, where the winemaking process will be described.

Finally, you will taste 4 wines accompanied by typical products:

•    1 White IGT or Rosé IGT, paired with samples of bread and typical cold cuts
•    1 Chianti classico d’vintage, paired with bruschetta with local extra virgin olive oil
•    1 Chianti classico riserva, paired with a 36 month parmigiano reggiano
•    1 Supertuscan, paired with Tuscan pecorino cheese

In addition to the wines, it will be possible to taste Tuscan pecorino cheese with EVO oil with white truffle from San Miniato and with cooked must, dark cocoa cream containing 12% of EVO oil, and face, hand and body creams produced on site.

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

Tasting of artisanal chocolate and liqueurs with a guided tour of the workshop, outside Prato and less than an hour from Florence.

After a brief introduction to the Roberto Catinari chocolate factory and its artisanal tradition, you will be guided on a journey to discover the raw ingredients, the production techniques, and the various cocoa varieties.

During the experience, you will taste chocolates from different origins, exploring aromas, intensities and pairings with Tuscan wines and liqueurs such as Vin Santo or Rum.

Finally, you will have the opportunity to create your own personalized chocolate bar, with handmade decorations or lettering, to enjoy on the spot or take with you as a sweet souvenir.

Tasting of four locally produced wines accompanied by typical Tuscan products in San Gimignano.

Program

The experience will begin with guests gathering at the winery, where dedicated staff will welcome you.

After a brief introduction about the family history and presentation of the winery, you will begin the tasting of 4 wines that will be accompanied by typical Tuscan pecorino cheese and bruschetta.

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.

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.

Tasting of four locally produced wines accompanied by a board with typical Tuscan products in San Gimignano.

Program

The experience will begin with a meeting at the winery, where dedicated staff will welcome you.

After a brief introduction about the family history and presentation of the winery, you will begin the tasting of 4 wines accompanied by a rich platter of typical Tuscan cold cuts, mixed bruschetta and selection of Tuscan pecorino cheeses.

Truffle hunting with wine tasting in San Gimignano offers you the opportunity to discover the secrets of searching techniques for this precious ingredient.

You will be accompanied by a professional guide and his faithful dog. Walking through the surrounding woods, you will search for truffles together.

At the end of the hunt, you can relax with a tasting of truffle products and typical local wines, inside an atmospheric barrique cellar.

Lunch based on Tuscan products and specialties with tasting of 4 wines in San Gimignano.

Program

The experience will begin with guests meeting at the winery, where dedicated staff will welcome you.

After a brief introduction to the history of the family and a presentation of the winery, a tasting of the local production of Rosso DOC di San Gimignano will begin, accompanied by a rich dish consisting of Cinta Senese cured meats, crostino with lard, and a selection of aged Tuscan pecorino cheeses.

Next you will be served pasta with Cinta Senese ragù and, in closing, dark chocolate paired with San Gimignano Rosso DOC Sottobosco.

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.

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 half-day boat trip to Cala Violina departing from Scarlino is a perfect tour to explore the famous Maremma cove.

You can choose from 3 different tours.

Morning

The morning tour starts at the port of Scarlino at 9:30 am. The first stop will be Cala Violina. Here it will be possible to have a breakfast consisting of typical Tuscan products. It will then continue to Cala Martina and Cala Civetta. This tour is suitable for people of all ages, especially children, thanks to the always calm waters that offer maximum serenity and safety.

Afternoon

The afternoon tour starts at the port of Scarlino at 4 pm. The first stop will be Cala Violina, where you will anchor for a swim stop. Next, you will visit the other coves along the park's stretch of coastline, including Cala Martina and Cala Civetta. You will be offered an aperitif composed exclusively of Tuscan products: a quality white wine, excellent cold cuts, focaccia and fresh fruit. Especially in the afternoon, the itinerary may change depending on sea weather conditions.

Sunset

The sunset tour starts at the port of Scarlino at 6 pm. The first stop will be Cala Violina, where you will anchor around 18:00 for a swim stop. You will then proceed to the other coves, including Cala Martina and Cala Civetta. Finally, you will be offered an aperitif consisting of typical Tuscan products to enjoy during the sunset.

The sunset tour lasts three hours, while the morning tour and the afternoon tour last four hours.

Horseback riding in the countryside of the Maremma Grossetana will allow you to discover the nature of the Tuscan hills.

The activity begins at the riding stables in Castiglione della Pescantia where the instructor will teach you the basics of riding and then you will go out for the horseback ride.

Two-hour rides are available in which you will discover the picturesque views of the Maremma.

At the end of the hikes, you can also enjoy an aperitif while enjoying the surrounding picturesque landscapes.

To participate in the excursions è required sportswear with long pants and closed shoes.

2 walks per day, from 09:00 to 11:00 or 17:00 to 19:00 between June 15 and September 15. Outside these dates, subject to availability.

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.