10 best historical bike tours

1. New Zealand

Best for: Exploring gold rush history on the country’s most famous rail trail

New Zealand might be best known for its jaw-dropping scenery, but its history is woven into the landscapes, and the Otago Central Rail Trail is a perfect way to uncover it. This converted railway line cuts through the heart of Otago’s gold rush country, offering a gentle multi-day ride past old mining settlements, preserved station buildings, and stone viaducts built by early railway engineers.

Places like Ophir, Oturehua and Hyde offer glimpses into a rugged frontier past, where gold once lured hopeful settlers inland. Many towns still proudly showcase their heritage, from restored general stores to heritage engineering works.

You’ll also learn about the broader story of European settlement, rail expansion, and local Māori history that shaped this part of New Zealand. The combination of scenery and storytelling makes this one of the more unique cycling journeys for those who want more than just a ride.

More information

• Our Otago Rail Trail guide includes full route tips and history highlights.

Old rail bridge, Otago Central Rail Trail

2. Japan

Best for: Tracing samurai routes and spiritual traditions through timeless landscapes

In Japan, history isn’t something kept hidden in a museum – it’s woven into the roads, forests and mountain paths you ride through. Many cycling routes follow the footprints of samurai and traders, passing wooden post towns, weathered shrines and quiet rural landscapes that have changed little over the centuries.

On the Noto Peninsula or inland along the Nakasendō, you’ll find echoes of feudal Japan in castle towns and ancient inns. Some tours link together sacred places, such as the UNESCO-listed Kumano Kodo pilgrimage trails or Shikoku’s 88-temple circuit.

Others reveal the quieter rhythms of daily life that preserve tradition, from calligraphy workshops to centuries-old farming techniques. Whether you’re sleeping in a ryokan or stopping for soba noodles in a village shop, cycling here becomes a way to step into the country’s layered, living history.

More information

• Get tips on Japan cycling tours from Ride and Seek and learn more about the tours they can organise for you.
• Our wider guide to cycling in Japan covers lots more practical tips and information about the country.
• Don’t miss our guide to the Shimanami Kaido cycling route – Japan’s most famous trail.

An ornate fountain at a rural temple in Japan (photo credit: Ride and Seek)

3. Rajasthan, India

Best for: Desert forts and royal palaces

If you’re a history lover, Rajasthan is the crown jewel of Indian cycling. This region was once the land of Rajput kings and warrior clans, and it shows! Nowhere else in India offers such a dense concentration of preserved forts, palaces and historic cities, all set against the dramatic backdrop of the Thar Desert and Aravalli Hills.

You’ll ride into cities like Jodhpur and Udaipur, where towering forts rise above tangled streets and royal palaces overlook shimmering lakes. Along the way, quiet backroads lead to centuries-old temples, traditional villages and crumbling stepwells that whisper stories from the past.

Rajasthan’s blend of majestic architecture, living traditions and evocative desert landscapes makes it one of the most rewarding places in India to explore on two wheels.

More information

• Considering a cycling tour in India? Check out these useful tips to get started
• Don’t miss this in-depth guide to cycling in India, for more detailed information about cycling in Rajasthan, as well as other regions in India

Jodhpur at sunset with a view of the Mehrangarh Fort a UNESCO World Heritage Site with Jaswant Thada in the foreground.

4. Cuba

Best for: Colonial cities and revolutionary history

Cycling in Cuba feels like riding through a time warp. With limited Wi-Fi and a refreshing lack of modernisation, this is a place where digital distractions melt away and the past feels strikingly present.

Grand colonial cities like Havana and Trinidad reveal layers of Spanish rule, Afro-Caribbean influence and revolutionary heritage. Vintage American cars are also ever-present in these cities, adding a unique charm to these colourful urban spaces.

On the bike, you’ll pass horse-drawn carts, tobacco fields, and vibrant plazas where locals still gather to chat, dance or make music. In Viñales, you ride through dramatic limestone hills where cigar-making traditions continue unchanged. Along the southern coast, you can cycle the quiet road that traces the Bay of Pigs, the site of one of the Cold War’s most infamous invasions.

More information

We’re working on a new in-depth guide to cycling in Cuba with Intrepid. Stay tuned for further details!

Convertible cars driving on the street in front of El Capitolio building in Cuba, Havana

5. Turkey

Best for: Ancient ruins and layered civilisations across continents

Few places rival Turkey when it comes to cycling through the remnants of multiple empires. The country’s landscapes are stitched with the legacies of the Hittites, Romans, Byzantines and Ottomans, and its position between Europe and Asia gives it a unique cultural depth.

In Cappadocia, riders weave through surreal rock formations and past early Christian cave dwellings carved into the soft volcanic stone. Further west, the roads skirt ancient sites like Ephesus, one of the best-preserved Roman cities in the Mediterranean, and Pergamon, once a powerful Greek and Roman cultural centre.

For those following the Black Sea coast or cycling inland into the Taurus Mountains, small villages and remote monasteries give an ongoing sense of the past still being part of the landscape. From amphitheatres to abandoned caravanserais, cycling in Turkey often feels like a rolling history lesson played out across striking terrain.

More information

• Find out more about planning your own Turkey cycling tour with tips from tour operator Islandhopping.
• Encounter even more history on one epic journey with our guide to cycling the Balkans.

The Amphitheatre of Kaunos (photo credit: Islandhopping, photographer: Kleomenis Koufalioti)

6. Greece

Best for: Island ruins and ancient myths mixed with Mediterranean flavours

Cycling through the Greek islands is about more than just sea views and sunshine; it’s a journey through thousands of years of layered history. From the crumbling columns of ancient temples to the winding alleyways of Venetian-era towns, the past is ever-present as you ride.

On bike and boat tours, each day delivers something new: the Aphaia Temple on Aegina, the Asklepion on Kos, the old town of Corfu, or quiet monasteries perched above the sea. The rides may be hilly, but they’re also rich with stories – from gods and philosophers to resistance fighters and sponge divers.

These tours offer far more than a scenic cruise. They thread together scattered islands that once held strategic and spiritual importance, revealing Greece not just as a postcard-perfect destination, but as a crossroads of civilisations – best explored slowly, and with salty wind in your hair.

More information

• Plan your own bike and boat tour with Islandhopping and their tips on the best way to cycle the Greek Isles.
• Our 12 practical tips for Greece cycling holidays will also come in handy for your own tour planning.

Temple of Aphaia on the island of Aegina (photo credit: Islandhopping)

7. Puglia, Italy

Best for: Impressive cave dwellings and ancient olive groves

If you’re drawn to places where every pedal stroke reveals a new layer of the past, Puglia is for you. This sun-drenched region in southern Italy is a cultural melting pot, shaped by Greeks, Romans, Normans and beyond. The result? A cycling experience rich in history, architecture and atmosphere.

Highlights include the fairytale trulli houses of Alberobello, the dramatic UNESCO-listed Castel del Monte, and the honey-hued Baroque city of Lecce, often called the “Florence of the South”. Many riders also tack on a visit to the ancient city of Matera. Although technically in nearby Basilicata, it’s a must-visit for history-loving cyclists! Home to stone-carved cave dwellings and labyrinthine alleys, it’s the oldest continuously inhabited city in the world, and a UNESCO World Heritage Site.

Beyond its wealth of historical treasures, Puglia is also a foodie’s paradise. This sun-soaked corner of Italy produces the majority of Italy’s olive oil, a staple of Italian cooking. Cyclists will notice countless olive groves which are an iconic part of the landscape in Puglia. Olive trees have grown here for centuries, and there are also many underground oil mills in the region.

More information

• Don’t miss this in-depth guide to discover the best Puglia cycle tours
• Read practical tips for cycling in Puglia

The ancient city of Matera (photo credit: Puglia Cycle Tours)

8. Portugal

Best for: Exploring historic towns and the Roman roads linking them

Cycling through Portugal offers a captivating glimpse into a country shaped by exploration, trade, and deep-rooted traditions. Between Portugal and Spain (next on the list), there are some incredible options for Christian cycling holidays if you want to trace the history of the religion.

From tiled towns with age-worn cathedrals to quiet fishing villages and medieval hilltop fortresses, the landscape reflects centuries of history layered along the Atlantic coast. The Portuguese Coastal Route, starting from Porto, delivers a mix of sea air, local flavour and cultural landmarks – without the crowds or intensity of the more famous Spanish roads. It’s one of the more iconic coastal cycle routes you can enjo,y and many cycling holidays in Portugal are based around this trail.

The route north to Santiago follows in the footsteps of pilgrims, but also traces Portugal’s own story, from Roman milestones and Moorish influences to baroque churches and cobbled lanes.

All of it unfolds against a backdrop of windswept beaches, eucalyptus forests and warm, understated hospitality. In between the historical sights, there’s always time to linger over grilled fish and vinho verde in the sun.

More information

• Read tips on cycling the Portuguese Camino from Top Bike Tours Portugal.
• Or learn about cycling the northern Vía do Castelo region with tips from our own experiences there.

Cycling the historic Portuguese Camino (photo credit: Top Biketours Portugal)

9. Spain

Best for: Cycling ancient pilgrimage trails through historic towns and varied Spanish landscapes

Spain is a country layered with history, and Spain cycling holidays are one of the best ways to travel through its past. Across the country, ancient Roman trade routes, Moorish fortresses, medieval paths, and Renaissance cities reveal themselves at handlebar height. You might find yourself riding past crumbling aqueducts in the wilds of Extremadura, weaving through whitewashed towns in Andalucía, or rolling along coastal roads once patrolled by medieval navies.

Each region tells a different story – from the Roman amphitheatres of Mérida to the Gothic cathedrals of León and Burgos, or the twisting lanes of Jewish quarters in towns like Córdoba and Girona. And it’s not just architecture: Spain’s food, language, and traditions shift dramatically as you cross regions, echoing the complex history of the peninsula. A cycling holiday here is more than just a journey through the landscape, it’s a ride through time.

More information

• Get expert advice on cycling the Camino de Santiago with help from tour experts Saddle Skedaddle.
• Read our guide on picking the best cycling holiday in Spain to suit you.
• Check out our unbiased comparison of 10 bike tour companies in Spain for helping planning your next adventure.

The impressive Roman amphitheatre in Merida

10. UK

Best for: Exploring a melting pot of industrial heritage and ancient landmarks

Cycle through history on Britain’s ancient byways and Roman roads, where each bend reveals another chapter – a medieval castle, a Norman church, or a Victorian viaduct. The landscape carries the marks of thousands of years of movement and trade, from drovers’ tracks to old coaching inns.

Whether riding along Hadrian’s Wall, tracing the coast of Cornwall, or pedalling across Yorkshire moors, the scenery shifts quickly, but the sense of connection with the past endures. Expect hilltop forts, cobbled villages and timeworn lanes where hedgerows crowd the verge and skylarks fill the air.

Classic long-distance routes like the Sea to Sea (C2C) and Land’s End to John O’Groats offer a deeper dive into Britain’s story – from coalfields and cathedral cities to Neolithic standing stones and remote Highland glens.

More information

• The Coast to Coast (C2C) cycling route offers a ton of options for exploring British heritage – read tips on planning your own tour with UK Bike Tours.
• Prefer the more comprehensive Land’s End to John O’Groats cycling route? We spoke with Pedal Britain about their tips and experiences.

Castlerigg stone circle in the Lake District in morning light

What’s next

Looking for more inspiration for your next cycling tour, beyond historic bike rides?

• Our guide to the best river cycling routes offers some of the most beautiful inland scenery anywhere in the world.
• Discover the best bike and wine tours if you like to combine scenic vineyard views with tasting sessions.
• See the destinations that make the cut for our guide to the best cycling islands, and tour an entire island in one epic holiday.
• Read our take on the best coastal cycling routes for those fresh sea-air tours and incredible views out to sea.
• Check out our review of the best bike tours across Europe, including some long-distance epics for the ultimate getaway.

Fran Wilson is a cyclist based in the Northeast of the UK and has a particular passion for cycle touring. Her love for cycling has seen her take on some of the UK and Europe's best-known multi-day cycle routes, including the Hebridean Way, Camino de Santiago and the Via Francigena. Beyond exploring on two wheels, Fran is a key member of the Epic Road Rides team and is usually found writing travel guides for other cyclists who also want to explore the world by bike.