The 10 best experiences to have in the Tuscan Maremma on vacation in 2026

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).

Tuscan winery lunch in San Gimignano, with guided tasting of 5 wines and local dishes.

During the experience you will meet in the winery for a brief introduction to the history of the family and the winery. Following this, you will participate in a tasting of five wines, paired with a lunch of Tuscan specialties including typical salumi, mixed bruschetta, selection of pecorino cheese, a traditional first course and, for dessert, chocolate and Sottobosco.

The experience will take place in San Gimignano and is designed for those who wish to discover local flavors in an authentic setting. The tasting will be guided and the menù is fixed.

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.

This Truffle Hunt is ideal for spending an alternative day in the woods of Tuscany.

You can choose between two available options:

Truffle Hunt with Tasting

At the meeting point you will meet the guide, who also speaks English, with his truffle dogs who will accompany you during your experience. As soon as the hunt is over, which will last about 2 hours, you will have the opportunity to move on to a tasting of fresh truffle crostini and other local products. Finally, you will also have the opportunity to taste a glass of the Chianti Colli Senese wine produced by the facility.

Truffle hunt with tasting and lunch

At the meeting point you will meet the guide with his truffle dogs, who will accompany you during your experience. As soon as the hunt is over, which will last about 2 hours, you will have the opportunity to participate and learn a cooking lesson offered by the facility's chefs. During this class you will try to prepare a complete typical menu through the use of fresh truffles. At the end of the course you will taste your menu accompanied by Chianti Colli Senese wine produced by the facility.

In case of bad weather the activity may be subject to change or cancellation.

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.

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.

Horseback riding in the Tuscan hills outside Florence.

This horseback ride will offer you the opportunity to explore the beautiful Pelago countryside on horseback, enjoying an experience in contact with nature.

The rides are led by experienced instructors to whom you can ask questions to learn about the area and discover curiosities about horses and their lives. The horses that will accompany you are docile and well-trained making the experience suitable even for beginners and children from 10 years old.

You will explore scenic trails, cross green hills and admire typical landscapes of the area, immersed in the beauty of Tuscan nature. 

You can choose from several tours:

•    1-hour walk
•    1-hour walk and aperitif on the way back
•    1-hour and 30-minute walk
•    2-hour walk
•    4-hour walk with lunch at a farmhouse

The equipment for horseback riding will be provided to you by the facility, but the appropriate sportswear (long pants and closed shoes) should be your own.

Tuscan winery lunch in San Gimignano, with guided tasting of 5 wines and local dishes.

During the experience you will meet in the winery for a brief introduction to the history of the family and the winery. Following this, you will participate in a tasting of five wines, paired with a lunch of Tuscan specialties including typical salumi, mixed bruschetta, selection of pecorino cheese, a traditional first course and, for dessert, chocolate and Sottobosco.

The experience will take place in San Gimignano and is designed for those who wish to discover local flavors in an authentic setting. The tasting will be guided and the menù is fixed.

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 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.

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.

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.

Tuscan winery lunch in San Gimignano, with guided tasting of 5 wines and local dishes.

During the experience you will meet in the winery for a brief introduction to the history of the family and the winery. Following this, you will participate in a tasting of five wines, paired with a lunch of Tuscan specialties including typical salumi, mixed bruschetta, selection of pecorino cheese, a traditional first course and, for dessert, chocolate and Sottobosco.

The experience will take place in San Gimignano and is designed for those who wish to discover local flavors in an authentic setting. The tasting will be guided and the menù is fixed.

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.

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.

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.

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.

Explore the magnificent Maremma Natural Park on horseback, accompanied by an experienced environmental equestrian guide. Ride through unspoiled wilderness landscapes, immersing yourself in the historic lands of the Maremma cowboys.

The 2-hour ride is suitable for both beginner and experienced riders, offering an authentic experience in contact with nature and the equestrian tradition of the Maremma.

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 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.