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

Horseback riding in the Sienese Hills in Tuscany can last one or two hours, and has the riding stables as its starting point. Nearby there are many woods through which you will be led.

Favorite destinations to reach are several hermitages, such as churches and monasteries, including Eremo di Lecceto or San Leonardo al Lago (2h). The latter is located on the Via Francigena, a beautiful scenic road with views of the Sienese hills.

Little curiosity: the Via Francigena is a pilgrimage route that in the Middle Ages joined Canterbury to Rome, site of St. Peter's tomb, and this to the ports of Puglia, where it was possible to embark to the Holy Land.

Wine tasting in San Gimignano at a family-run estate surrounded by Tuscan nature.

You can choose from 4 types of tastings:

As you want them

This tasting begins with a short walk through one of the vineyards where the guide will give you information about the estate along with several trivia about the vine. Once back you can then choose 4 wines to taste from the 7 types produced.

4 wines for a few

This tasting will allow you to taste 4 "special" wines since less than 1,000 bottles of each are produced per year. The wines are: "Ximon” Toscana Bianco IGT, “Donna Lucia” Vernaccia di San Gimignano DOCG, “Centodue” Toscana Rosso IGT, Chianti Riserva DOCG.

4 DOCG wines

In this tasting you will taste the most classic wines of the Tuscan tradition, including Vernaccia di San Gimignano DOCG, “Donna Lucia” Vernaccia di San Gimignano DOCG, Chianti Colli Senesi DOCG, Chianti Riserva DOCG.

The Fantastic 7

During this tasting you will taste all 7 wines that are produced by the estate, specifically: Vernaccia di San Gimignano DOCG, “Donna Lucia” Vernaccia di San Gimignano DOCG, “Ximon” Toscana Bianco IGT, “Il Rosato della via vecchia”, Chianti Colli Senesi DOCG, Chianti Riserva DOCG, “Centodue” Toscana Rosso IGT.

During the vespa tour of Chianti from Castellina, you will have the opportunity to rent vespas for an entire day, as a couple or with friends to explore the Chianti hills.

The experience is unique, one of the most beautiful in the area, and you will spend a day immersed in green fields, or among vines ripe in autumn.

The wasps are easy to ride so even beginners can use them, only a B-type license required.

If you decide to participate in this Vespa ride, you will be immersed in the beauty of Tuscany and experience an adventure you will remember forever.

Gasoline is not included and will have to be paid on site.

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.

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.

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.

Wine tasting in San Gimignano at a family-run estate surrounded by Tuscan nature.

You can choose from 4 types of tastings:

As you want them

This tasting begins with a short walk through one of the vineyards where the guide will give you information about the estate along with several trivia about the vine. Once back you can then choose 4 wines to taste from the 7 types produced.

4 wines for a few

This tasting will allow you to taste 4 "special" wines since less than 1,000 bottles of each are produced per year. The wines are: "Ximon” Toscana Bianco IGT, “Donna Lucia” Vernaccia di San Gimignano DOCG, “Centodue” Toscana Rosso IGT, Chianti Riserva DOCG.

4 DOCG wines

In this tasting you will taste the most classic wines of the Tuscan tradition, including Vernaccia di San Gimignano DOCG, “Donna Lucia” Vernaccia di San Gimignano DOCG, Chianti Colli Senesi DOCG, Chianti Riserva DOCG.

The Fantastic 7

During this tasting you will taste all 7 wines that are produced by the estate, specifically: Vernaccia di San Gimignano DOCG, “Donna Lucia” Vernaccia di San Gimignano DOCG, “Ximon” Toscana Bianco IGT, “Il Rosato della via vecchia”, Chianti Colli Senesi DOCG, Chianti Riserva DOCG, “Centodue” Toscana Rosso IGT.

During the vespa tour of Chianti from Castellina, you will have the opportunity to rent vespas for an entire day, as a couple or with friends to explore the Chianti hills.

The experience is unique, one of the most beautiful in the area, and you will spend a day immersed in green fields, or among vines ripe in autumn.

The wasps are easy to ride so even beginners can use them, only a B-type license required.

If you decide to participate in this Vespa ride, you will be immersed in the beauty of Tuscany and experience an adventure you will remember forever.

Gasoline is not included and will have to be paid on site.

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.

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.

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.

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.

Wine tasting in San Gimignano at a family-run estate surrounded by Tuscan nature.

You can choose from 4 types of tastings:

As you want them

This tasting begins with a short walk through one of the vineyards where the guide will give you information about the estate along with several trivia about the vine. Once back you can then choose 4 wines to taste from the 7 types produced.

4 wines for a few

This tasting will allow you to taste 4 "special" wines since less than 1,000 bottles of each are produced per year. The wines are: "Ximon” Toscana Bianco IGT, “Donna Lucia” Vernaccia di San Gimignano DOCG, “Centodue” Toscana Rosso IGT, Chianti Riserva DOCG.

4 DOCG wines

In this tasting you will taste the most classic wines of the Tuscan tradition, including Vernaccia di San Gimignano DOCG, “Donna Lucia” Vernaccia di San Gimignano DOCG, Chianti Colli Senesi DOCG, Chianti Riserva DOCG.

The Fantastic 7

During this tasting you will taste all 7 wines that are produced by the estate, specifically: Vernaccia di San Gimignano DOCG, “Donna Lucia” Vernaccia di San Gimignano DOCG, “Ximon” Toscana Bianco IGT, “Il Rosato della via vecchia”, Chianti Colli Senesi DOCG, Chianti Riserva DOCG, “Centodue” Toscana Rosso IGT.

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.

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.

Wine and oil tasting with a visit to the winery offers you the opportunity to enjoy an authentic experience in the heart of Chianti.

You will be welcomed by a winery nestled among rolling hills, cypress trees, vineyards and olive groves.

The experience includes a guided tour of the winery, during which you will discover firsthand the winemaking techniques adopted by the estate.

Afterwards, you will have the opportunity to taste 2 or 3 wines together with locally produced Extra Virgin Olive Oil, accompanied by olives in oil, freshly baked Tuscan bread, salami and Tuscan pecorino cheese.

For any food allergies or intolerances you can contact the property after booking.

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.

Rafting from Colle Val d'Elsa in Tuscany, perfect for an adventure within nature suitable for adults and children.

Two tours can be distinguished within the experience:

Rafting

The duration of the route è of 1 hour where the river offers gentle and accessible navigation away from adrenaline rapids. This experience è designed for those approaching this type of activity for the first time. The minimum age for children is 6 years old. At the meeting point, the necessary equipment will be handed over and a briefing will be given to explain safety rules. The arrival è point is different from the departure point, about 15 minutes walk.

Packrafting

The duration of the trail è is 1 hour and 30 minutes and è perfect for those who wish to explore the river on their own, but in complete safety. The minimum age for children è is 12 years old. At the meeting point, the necessary equipment will be handed over and a briefing will be given to explain safety rules. The arrival è point is different from the departure point, about 15 minutes walk.

Tours are subject to weather conditions, so the activity may be subject to change.

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.

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. 

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 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.

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.