Italy Road Trip: The Best Stops and Sights in Tuscany

Planning an Italy road trip and looking for route inspiration, tips, and sights along the way? You've come to the right place! Simeon Baker traveled through Tuscany in a campervan and shares his favorite spots.

Rolling hills, vineyards, cypress-lined avenues, picturesque mountain villages, and charming old towns – Tuscany is definitely one of the most beautiful regions for an unforgettable road trip. It wonderfully combines the Italian way of life with a perfect holiday vibe.

With a campervan, you can easily reach Tuscany's most beautiful sights and even explore more secluded places.

But where's the ideal starting point for a Tuscany road trip, and what's the best route? We've put together all the highlights for you and hope reading this sparks your wanderlust.

By the way: You'll find a video of the Italy road trip at the very bottom of this post.

Italy Road Trip: Route and Tips

• San Gimignano
• Wild camping near Monteriggioni
• Monteriggioni
• Tuscan Hills & Podere Belvedere
• Assisi
• Sibillini Mountains
• Gargano Coast
• San Marino
• Dolomites

San Gimignano

Simeon and his friend Yelte started their Italy road trip in San Gimignano with a California Beach.

San Gimignano is one of Tuscany's most beautiful towns, also known as "medieval Manhattan" or the "City of Towers." Once you enter San Gimignano, you'll understand why: 15 medieval towers pierce the sky, giving the town its distinctive appearance.

A highlight is the view from one of the towers over San Gimignano. The most famous view is from the Torre Grosso.

Wild Camping Near Monteriggioni

The next day, they continued to a beautiful pitch not far from Monteriggioni. Once there, they grilled delicious steaks with vegetables and enjoyed a relaxed evening.

The next morning, after a cup of coffee, the journey continued.

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Monteriggioni

The charming village of Monteriggioni is a must-see on any Italy road trip. Located in the province of Siena, the municipality is home to a historic castle perched on Monte Ala hill, offering breathtaking views of the Tuscan landscape.

The old town is delightful, full of charm and coziness. Key attractions include the medieval city walls and the well-preserved defensive towers.

The area around Monteriggioni, with its green vineyards and numerous excursion destinations, is also well worth seeing.

Simeon opted for a campsite near the town. Electricity and sanitary facilities were available. However, he parked among countless cars, and it was paid parking.

If you come to this pitch, you should definitely avoid parking in this overcrowded spot.

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Podere Belvedere

Podere Belvedere is probably the most beautiful viewpoint in all of Tuscany and is, for many, the highlight of any Italy road trip.

And for good reason: it's the perfect spot for anyone who loves taking photos. This is where those famous postcard-perfect images come from, the ones that make every visitor swoon.

It's an old farmhouse situated on a hill, surrounded by majestic cypress trees, olive groves, and vineyards. The atmosphere here is indescribably magical, especially in the early morning or late evening.

You should know that many photographers gather here, so you definitely won't be alone trying to capture the impressive landscape.

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Assisi

The Italy road trip continued to Assisi.

Here, Simeon camped at Camping Fontemaggio. A nice pitch with a beautiful view, surrounded by nature, and not as crowded as other places.

It feels more like wild camping, but with the luxury of all necessary services. Highly recommended! Plus, the campsite is only fifteen minutes from the town of Assisi.

Assisi promises rich culture and history. The town is famous for its world-renowned ring wall, designated a UNESCO World Heritage site, as well as the Basilica of San Francesco.

But the Mediterranean charm of narrow alleys and stairs, picturesque small squares, and new and surprising insights also beckon.

Simeon was definitely impressed by the small town. He ended the day in a restaurant with wine and pasta.

Sibillini Mountains

Twenty minutes from Assisi, you'll find the Sibillini Mountains. The core area of the Sibilline Mountains is protected as a national park.

Simeon was absolutely captivated when he reached the breathtaking landscape. Wild horses, wild donkeys, secluded places, and a beautiful mountain backdrop.

Simeon set out to find a suitable spot for camping and spent the night there. Early in the morning, he set off to photograph the wild horses and the landscape.

On the way to their next stop, he and his friend Yelte found another beautiful location in the mountains. They stayed overnight and spent the entire next day there.

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Gargano Coast

Clear water, steep cliffs, beautiful sandy beaches, authentic villages, the Tremiti Islands, and more – the Gargano Coast is one of the most beautiful spots in southern Italy.

Simeon spent the first night at Camping "Lido Azzurro Sosta Camper". Here you'll find a pitch right by the sea. Perfect for grilling, swimming, and enjoying the sunset.

They continued to a small town to get some cash and end the day with a pizza.

Simeon spent another night on the cliffs of the Gargano Coast. Here he found a very quiet pitch with an incredible sea view.

Caution: It quickly became clear that camping here is not allowed, even though a gentleman initially claimed it was private property and camping was permitted for a fee. The police, however, explained that it was a national park.

The journey continued to Vieste. This small town was once a fishing village and is a worthwhile destination for everyone. The town has a lot to offer, both scenically and historically.

Narrow streets, temples, olive groves, beautiful beaches, crystal-clear water, and cliffs with breathtaking views.

To take advantage of the beautiful view and get some drone shots, Simeon explored Arco di San Felice.

They stayed overnight at a wild camping spot.

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San Marino

After a long drive, Simeon reached his next destination: Guaita, San Marino. Early in the morning, he made his way to Guaita Castle. Not only to see the landmark but also to admire the beautiful panorama over San Marino.

Dolomites

The Italy road trip ended with a drive through the Dolomites. A visit to the Three Peaks was planned, but some roads were still closed, and the weather wasn't very good.

What's the ideal season for an Italy road trip through Tuscany?

Tuscany is best visited in spring or autumn, with May and June, as well as September and October, being the ideal months. During this period, temperatures are usually pleasantly warm but not yet too hot, and there are fewer tourists than in the peak summer season.

High summer, especially July and August, should be avoided. Some parts of Tuscany are very crowded at this time. This applies particularly to historic city centers like San Gimignano.

If you want to combine your Tuscany trip with a beach holiday, then summer is, of course, preferable.

How much time should I plan for an Italy road trip?

This is entirely individual and depends on which places you want to visit and how long you want to stay there. If you want to travel through Tuscany but prefer to take it slower, we recommend planning two weeks.

This will give you enough time to explore some places off the beaten tourist path.

Also, don't underestimate the distances. Tuscany is very spread out. There are nine provinces. To cross them by campervan, you'll need several hours.

Tip: If you want to experience Tuscany and its flair to the fullest, you should definitely rent a campervan. Otherwise, you won't be able to explore many landscapes.

Conclusion: Italy Road Trip

"Tuscany is a scenic highlight in Italy. Combined with the beautiful beaches, delicious food, excellent wines, and olives, the trip becomes unforgettable for everyone. The country has so much to offer and is great to explore by campervan." – Simeon Baker