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

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.

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.

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.

Enjoy a horseback ride through the hills of the Crete Senesi, in the heart of Tuscany, accompanied by expert guides. You will have the opportunity to choose whether to enrich the experience with a swim in the pool and/or dinner.

When you arrive, you can enjoy a refreshing break at the reception bar before heading to the riding stables, just a few minutes' walk away, where guides Clara and Marco will introduce you to the horse that will accompany you on the excursion. After a brief introduction to the basics of riding and proper interaction with the horse, you will receive your helmet and be ready to go.

The horseback ride takes about two hours and will take you through authentic landscapes on the Val d’Arbia, Val d’Orcia, Montalcino and Monte Amiata. You will ride along scenic ridges from which you can admire unique views and enjoy a relaxing experience in close contact with nature.

The experience è perfect even for beginners thanks to the docile horses and the presence of experienced guides, while dedicated rides for more experienced riders can be arranged upon request.

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 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.

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.

Rafting on the Arno River at Sant'Ellero in Tuscany ideal for those seeking an adventurous yet accessible experience, among natural rapids, calmer stretches and still unspoiled landscapes.

As soon as you arrive at the meeting point you will be handed the necessary equipment and then an initial briefing will be given where safety rules and descent techniques will be explained. Along the way there will be informative stops and the possibility of swimming. The route è also suitable for beginners sinceè you è always followed by an experienced guide. The age limit è for children è is 8 years old.

Because è the experience è subject to weather conditions the activity will be moved, rescheduled or refunded, depending on the situation.

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.

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 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.

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

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

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

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.

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 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 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.

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 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 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. 

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.

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.