3 of the best self-guided tours in Italy

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1. Veneto and Trentino with FunActive

Best for a gentle, scenic ride from the Dolomites to Venice with minimal climbing.

Descending the Cortina d’Ampezzo road in the Italian Dolomites (photo credit: ©wisthaler.com via FunActive Tours)

Key information

Route: Point-to-point ride from the Dolomites (Dobbiaco/Villabassa) to Venice, via Cortina d’Ampezzo, Belluno, Bassano del Grappa and Treviso.

Terrain: Mostly paved, with a mix of dedicated cycle paths (including old railway lines), gentle descents, rolling hills and flat sections approaching Venice.

Difficulty: Easy overall. Gradients are generally gentle, making it suitable for leisure riders and families with older children.

Highlights: Riding beneath the Tre Cime di Lavaredo, Cortina d’Ampezzo, Prosecco hills, Bassano del Grappa, Treviso and a memorable finish in Venice.

Logistics: Start in the Dolomites (Dobbiaco or Villabassa) and finish in Venice; luggage transfer, navigation app and route notes included.

Best time to visit: Late spring to early autumn; summer can be busier, especially in popular Dolomite spots.

The riding

This is a classic, gently descending journey from the dramatic peaks of the Dolomites down to the Venetian plains, designed to be accessible rather than challenging. The early stages are the standout, following quiet cycle paths and old railway lines beneath iconic Dolomite scenery, including views of the Tre Cime di Lavaredo and the climb to Cortina d’Ampezzo.

From there, the route gradually softens as you roll through the foothills and into the green Venetian hills, where vineyards, small towns and quieter backroads take over. As the days progress, the terrain becomes flatter and more relaxed, especially from Bassano del Grappa onwards.

The final stretch along the River Sile into Venice is almost entirely flat, offering an easy and scenic finish. With short daily distances, modest elevation and well-planned routing, this is more about enjoying the journey than testing your limits.

What we love

This trip from FunActive is all about the sense of progression. Starting in the mountains and finishing in Venice gives it a real journey feel, with each day bringing a noticeable shift in landscape, from high Dolomite peaks to vineyard-covered hills and finally the wide-open plains.

We also love how accessible it is, combining iconic scenery with riding that feels relaxed and manageable throughout.

What else they offer

FunActive offers a wide range of self-guided cycling holidays across Europe, particularly in Italy, Austria and Germany, with routes that often follow scenic cycle paths and classic long-distance trails. Their trips are designed to be accessible and well-supported, with luggage transfers, detailed navigation and flexible itineraries suited to a broad range of riders.

More information

• 4 best cycling routes in the Dolomites, including more information on what FunActive Tours has to offer.
• FunActive Tours’ own website, for information on dates and prices if you wish to book this tour.

2. Tuscany with Girolibero (Pisa to Florence)

Best for a relaxed cultural ride linking Tuscany’s iconic cities and countryside.

Tuscan countryside with vineyards (photo credit: Adriano Ongaro via Girolibero)

Key information

Route: Circular route from Pisa to Florence and back, via Lucca, Montecatini Terme, Vinci and Empoli.

Terrain: Mostly flat to gently rolling, with some short hills inland and optional hillier sections; mainly quiet secondary roads with occasional gravel paths.

Difficulty: Easy to moderate. Accessible for most riders, with options to shorten stages using trains and take rest days.

Highlights: Pisa’s Leaning Tower, Lucca’s Renaissance walls, Vinci (Leonardo’s birthplace), Florence’s historic centre and classic Tuscan countryside.

Logistics: Start and finish in Pisa; luggage transfers, route notes and navigation app included, with flexible daily options.

Best time to visit: Spring and autumn are ideal; summer can be hot but remains manageable due to shorter distances and flexible routing.

The riding

This is a relaxed, accessible route that links some of Tuscany’s most famous cities via quiet countryside and smaller towns that give the journey its character. The riding is mostly flat or gently rolling, particularly on the opening stretch from Pisa to Lucca along the Serchio River, before gradually introducing more undulating terrain as you head inland towards Montecatini and Vinci.

There are a few slightly more demanding sections, such as the optional climb out of Montecatini, but nothing sustained, and train options make it easy to shorten the tougher days. Much of the riding takes place on low-traffic backroads, with occasional gravel sections adding variety without difficulty.

The final approach into Florence follows the Arno River, offering a smooth and scenic run into the city. Overall, it is less about physical challenge and more about linking together landscapes, towns and cultural highlights at an enjoyable pace.

What we love

What makes Girolibero’s route special is how naturally it connects Tuscany’s big-name highlights with lesser-known places in between.

You move from Pisa to Florence not in a rush, but through a series of characterful stops, from Lucca’s elegant streets to Vinci’s quiet hilltop setting. It also strikes a great balance between flexibility and structure, with options to rest, shorten stages or explore more, depending on how you feel each day.

What else they offer

Girolibero runs a wide range of self-guided cycling holidays across Italy, with a strong focus on Tuscany, including routes linking Pisa, Florence and Siena, as well as shorter loops and point-to-point trips. They also offer tours in regions such as Puglia, Piedmont, Umbria, South Tyrol, the Dolomites and Veneto, along with selected routes beyond Italy, including France’s Loire Valley.

More information

• Cycling Tuscany, giving an overview of the region.
• Pisa to Florence bike tours, with more tips from the Girolibero experts.
• Our pick of the best Tuscany bike tours
• Girolibero’s website with details on how to book this tour.

3. Puglia with Puglia Cycle Tours (Alberobello to Lecce)

Best for easy-going coastal and countryside riding with strong food and cultural appeal.

Gravel cycling tours in Puglia (photo credit: Puglia Cycle Tours)

Key information

Route: Point-to-point from Alberobello to Lecce, via Monopoli, Ostuni, Martano and Otranto, with a loop ride in the Itria Valley.

Terrain: Mostly flat to gently rolling, with short climbs through the Apulian hills and flatter coastal sections.

Difficulty: Easy to moderate. Daily distances of around 40–55 kilometres make it accessible for regular riders.

Highlights: Trulli in Alberobello, Polignano a Mare cliffs, Ostuni’s whitewashed old town, Salento coastline and Lecce’s Baroque architecture.

Logistics: Start in Alberobello (accessible from Bari or Brindisi) and finish in Lecce; luggage transfer, navigation and full support included.

Best time to visit: Spring and autumn are ideal; summer can be very hot, especially inland.

The riding

This is relaxed, point-to-point riding that showcases Puglia’s changing landscapes as you travel south from the Itria Valley to the Salento peninsula. The early stages roll through countryside dotted with trulli, olive groves and quiet villages, with gentle climbs and descents that keep things interesting without ever becoming demanding.

As you reach the coast, the riding becomes more open and scenic, with stretches along the Adriatic and visits to towns like Polignano a Mare and Monopoli. Further south, the terrain flattens slightly, especially around Salento, where long, quiet lanes and coastal sections make for easy kilometres.

Daily distances are manageable, and the surfaces are mostly smooth, with a mix of country roads and coastal riding. Overall, it is a steady, enjoyable ride that focuses on exploration rather than effort.

What we love

This route from Puglia Cycle Tours captures the essence of Puglia in a single journey. You move from the unique trulli landscapes of Alberobello to the dramatic coastline and on to the Baroque beauty of Lecce, with each day offering something distinct.

We also love how food, culture and scenery are woven into the ride, making it feel less like a cycling challenge and more like a deep dive into southern Italy.

What else they offer

Puglia Cycle Tours specialises in cycling holidays across Puglia, offering both guided and self-guided trips, as well as tailor-made itineraries built around individual preferences. Their range also includes flexible options such as “bike and trulli” stays for a more relaxed experience, along with shorter daily tours led by local guides.

More information

• Cycling tours in Puglia, with nine different tour options to explore.
• Puglia Cycle Tours’ website, including information on this and other Puglia tours they offer.

What’s next?

• The best bike tours in Italy, if you’d prefer guided options.
• Cycling Italy, our hub page with destination guides and more.
• 9 of the best places to cycle in Italy, looking at the major regions and tips for riding in the country.
• 12 best Italy bike hotels, should you wish to plan your own cycling trip independently.
• 10 iconic Giro d’Italia cycling climbs, so you can follow in the tread marks of cycling legends.

Clare Dewey is a cyclist with a passion for travel. She set up epicroadrides.com in 2018 to help make it easy for cyclists to explore the world by bike. Today her mission is still inspiring cyclists to discover new places on two wheels - and doing what she can to make sure they have the best possible time while they're there. Clare has visited 50+ destinations around the world, many of them by bike.

Want to connect with Clare? Find her over on LinkedIn.