People visiting Maremma for the first time often discover something: it is far more diverse than they expected.
Within just a few kilometres, the landscape shifts from the coast to rolling hills, from medieval villages to woodland, from scenic roads to vineyards. This is not a place that asks you to rush from one attraction to the next. Instead, it invites you to slow down, pause, and build a day made up of different experiences that are all close together.
If you are planning a day trip or a weekend in Maremma, Tuscany, here are a few ideas for exploring the Alta Maremma and including a visit to Ampeleia along the way.
The villages you should not miss in Alta Maremma.
One of the best ways to discover Maremma is through its villages.
Massa Marittima is often the first stop, and for good reason. It is one of the most charming towns in Maremma, and it fits naturally into a day spent exploring the hills of Alta Maremma before heading to Ampeleia. At its heart lies Piazza Garibaldi, widely considered one of the most beautiful medieval squares in Tuscany, dominated by the Cathedral of San Cerbone. Built between the 12th and 13th centuries, the cathedral is known for its travertine façade, rich in sculpted details and remarkable for its harmonious proportions. As you wander through the historic centre, you will come across narrow streets, stairways and unexpected viewpoints that encourage you to slow down. One of the town’s most famous curiosities is the Tree of Fertility, a fresco preserved inside the Palazzo dell’Abbondanza, depicting a tree bearing rather unusual fruit.
The village of Montemassi rises above the surrounding hills and offers one of the most iconic views in the area. Even more intimate is Roccatederighi, a hilltop village built directly on the rock, where winding alleys, panoramic terraces and hidden corners unfold without any fixed route.
Roccastrada is also worth a visit. One of the most important historic centres in Alta Maremma, it sits on a ridge overlooking the countryside and retains a calm, authentic atmosphere. Cobbled streets, historic buildings and sweeping views make it an ideal stop for anyone wanting to experience a less touristy and more everyday side of Maremma.
Closer to Grosseto lies Montepescali, often called the “Balcony of Maremma” thanks to its panoramic position overlooking the plain and stretching all the way to the sea. Its well-preserved medieval structure makes it perfect for a leisurely walk through narrow streets, small squares and viewpoints that tell the story of the connection between inland Tuscany and the coast.
Nature, woodland and landscapes to explore.
Maremma is best known for its coastline, but the inland areas offer some of the region’s most rewarding experiences.
The hills of Alta Maremma are crossed by scenic roads winding through woodland, vineyards and small villages. Every season brings a different landscape: the vivid greens of spring, the golden tones of summer and the warm colours of autumn.
Even without planning a demanding hike, simply driving these roads reveals a lesser-known side of Tuscany. One where the relationship between human activity and the natural environment is still clearly visible.
For those who enjoy walking, Alta Maremma also offers a wide range of hiking trails of varying lengths and difficulty levels. Some routes are perfect for a short walk of a few hours, while others cross forests, hills and panoramic viewpoints, allowing you to explore the territory at a slower pace.
Where to enjoy a wine tasting in Maremma.
Among the most popular activities in the area is, of course, wine tasting. In recent years, Maremma has become one of Tuscany’s most exciting wine regions, thanks to a wide variety of wineries with different histories, scales and approaches.
If you are looking for a wine tasting in Maremma, it is worth choosing a winery that offers more than a tasting alone. Visiting the vineyards, understanding the landscape and learning about the work behind each bottle makes the experience far richer.
In Ampeleia, the visit begins with the landscape and the farm before moving on to the wines themselves. It is a way of understanding the territory through everything that surrounds it: the woodland, the vineyards, the hills and the daily work that shapes its character.
A one-day itinerary: Massa Marittima, Roccatederighi and Ampeleia.
If you only have one day available, it is easy to create a rewarding itinerary without covering long distances.
Start your morning with a walk through Massa Marittima and a coffee in one of the cafés in the historic centre. Visit the cathedral and look for the famous Tree of Fertility before continuing into the hills of Alta Maremma, through a landscape that gradually becomes more wooded and rural.
Roccatederighi is an ideal stop for a quiet stroll and for taking in the views from above. From here, you can see the Tyrrhenian Sea, the Island of Giglio and the Argentario peninsula. Looking in the opposite direction, you will also enjoy a beautiful view over our vineyards.
From the village, it takes only a few minutes to reach Ampeleia. Here you can spend a few hours touring the estate and tasting the wines while discovering a working farm deeply connected to the landscape you have just travelled through.
If you are planning a day in Alta Maremma, book a visit to Ampeleia and include it in your itinerary. It fits naturally into the journey, without requiring long detours or complicated planning.
Why include a winery visit in your trip?
When travelling, it is easy to admire beautiful places without really understanding how people live and work within them.
A winery visit offers a different perspective. It allows you to connect with the territory through agriculture, to see how wine is made and to better understand the landscape around you. In a region like Maremma, this becomes even more meaningful because wine, woodland, villages and countryside are all part of the same story.
Some destinations stay in your memory because of what you saw. Others because of what you came to understand.
And very often, it is the latter that stay with you the longest.
