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

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.

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).

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.

Horseback rides in the Crete Senesi, Buonconvento, can be an hour or an hour and a half, and have the riding stables as their starting point.

The horseback rides follow routes through the countryside that will allow you to pass by some ancient villas and cypress avenues.

What are you waiting for? Book this experience that will leave you with unforgettable memories!

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 5 wines accompanied by a rich platter of typical Tuscan cold cuts, mixed bruschetta and selection of Tuscan pecorino cheeses.

Horseback riding and wine tasting in the surroundings of Florence.

You will leave from the stables in Pelago together with an equestrian guide and, after about an hour of riding through the hills, you will reach a historic winery nestled in the countryside.

Here you will visit the estate and learn about the winemaking processes, and then taste 4 glasses of local wine. You can also choose the "with chopping board" tour to taste local cured meats and cheeses.

When the tasting is over, you will get back on horseback to return to the stables accompanied by your guide.

The equipment for horseback riding will be provided to you by the facility, but appropriate sportswear (long pants and closed shoes) should be your own. We also recommend the'use of a sweatshirt for the winery visit.

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 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.

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.

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.

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.

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 5 wines accompanied by a rich platter of typical Tuscan cold cuts, mixed bruschetta and selection of Tuscan pecorino cheeses.

Cooking course in the heart of Tuscany, with wine tasting and full lunch.

Under the guidance of the chef you will learn how to make bruschetta with seasonal ingredients, a type of fresh handmade pasta with typical Tuscan sauces and a traditional dessert.

At the end you will enjoy the lunch you cooked in a typical setting, accompanied by locally produced wines.

The course è hands-on and engaging, designed to let you participate firsthand in the preparation of the dishes.

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 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.

Board a comfortable motorboat and visit Giglio Island, Giannutri, and the most secluded coves and islets of the Tyrrhenian Sea.

Departing from Castiglione della Pescaia, the tour will last approximately 8 hours and 30 minutes and will be structured as follows:

Giglio and Giannutri

•    Boarding begins at 8:00 a.m.; at 8:30 a.m. we set sail! (Check-in by 8:10 a.m.)
•    Cruise along the Maremma coast and the Uccellina Nature Reserve to Talamone, then along the northern coast of the Argentario.
•    Shortly before 11:00 a.m., disembarkation at Giglio. You can explore on your own or with Toscana Trekking guides; book tours with them during the cruise
•    At approximately 2:00 p.m., we set sail for Giannutri.
•    Around 2:45 p.m., we arrive at Giannutri, where you can take part in other guided tours or enjoy swimming.
•    At 4:00 PM, we’ll set sail from Giannutri to return to Castiglione (7:30 PM), after a brief technical stop at Giglio.

The tour itinerary may vary depending on weather conditions and the skipper’s decisions.

Cash payment is required for the municipal landing fee for theIsland of Giglio of 3.00€ per person and the access ticket to the island of Giannutri of 2.50€ per person before departure.

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.

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.