Prague to Vienna: The Grand Greenway

Day 1: Arrival in Prague
Welcome to Prague, the City of a Hundred Spires. Check in to your hotel and let the magic of the Czech capital unfold before you. Wander through the cobblestone streets of the Old Town, admire the Gothic silhouette of Prague Castle from across the Vltava, or simply settle into a riverside café as the city glows in the evening light. Tomorrow, the open road awaits.

Day 2: Prague – Benešov (68 km)
Your cycling adventure begins with a relaxed ride along the Vltava River, following smooth bike trails upstream through gentle countryside. After the first flat stretch, the landscape opens into the romantic Posázaví highlands, where every climb is rewarded with sweeping views of wooded valleys. At Zborný Kostelec, a short hike leads to atmospheric castle ruins. You will pass through Týnec nad Sázavou with its Gothic stronghold and Romanesque rotunda before arriving at your day’s crowning highlight: Konopiště Castle, the summer palace of Archduke Franz Ferdinand, whose assassination in Sarajevo in 1914 ignited World War I.

Day 3: Benešov – Tábor (60 km)
The second cycling day carries you along quiet side roads through a part of Central Bohemia sometimes called Czech Meran for its gentle ups and downs — or Czech Siberia for the crisp morning air in the valleys. The landscape unfolds in a rhythm of fantastic views and satisfying descents, with an equal measure of climbs to keep your legs engaged. At the end of this invigorating ride, the mighty fortress town of Tábor awaits. Headquarters of the Czech Reformation during the 15th-century Hussite wars, never conquered, it offers a wealth of history and a deeply atmospheric evening.

Day 4: Tábor – Jindřichův Hradec (52 km)
In the morning, walk the ramparts of Tábor, where the landscape was ingeniously woven into the town’s defences during the Religious Wars. Then you will pedal into the heart of South Bohemia, where green fields, fishponds, and quiet forests unfold in every direction. The romantic water castle of Červená Lhota appears like a painting, rising from a lake surrounded by woodland. Your destination is Jindřichův Hradec, one of the largest medieval centres in Bohemia, with a beautifully preserved castle and town centre. Legend has it that the famous White Lady ghost still walks these halls.

Day 5: Jindřichův Hradec – Telč (45 km)
You will leave South Bohemia and enter the Bohemian-Moravian highlands, a landscape of rolling hills, meadows, and countless fishponds. Try counting them as you pedal through this peaceful countryside. In Střímilov, you may visit an artistic weaving factory, a craft that has been part of this region for centuries. Your reward at the end of the day is Telč — inscribed on the UNESCO World Heritage List and widely considered the most beautiful Renaissance town in Europe. Its arcaded main square, painted in soft pastels, will take your breath away.

Day 6: Telč – Podyjí area (67 km)
From Telč, you will cycle towards Dačice, the town where the first sugar cube was ever produced. The route takes you through a highland area with fantastic views and very few other cyclists — a sense of splendid solitude. Near the Austrian border, you will pass a well-preserved system of WWII fortifications that were never used. The fairy-tale castle of Uhěřčice and the Renaissance castle of Písečná punctuate the rolling landscape. Before reaching your destination, a descent to the Vranov water dam rewards you with stunning views of Bítov Castle perched above the valley.

Day 7: Podyjí area – Znojmo (67 km)
This day explores Podyjí National Park, a pristine wilderness where the Dyje River carves unforgettable meanders through untouched forest. From the ruins of Nový Hrádek and the viewpoint above medieval Hardegg Castle, you will gaze across the Czech-Austrian border at landscapes that seem frozen in time. An Iron Curtain memorial stands as a quiet witness to recent history. The trail leads along the park’s edges — no cars, only birdsong and the rustle of leaves. Descending through the Šobes vineyard, ranked among the world’s ten finest, you may pause for a glass of crisp white wine. The day concludes in Znojmo, the ancient seat of the Moravian Přemyslid dynasty, with its atmospheric wine cellars and medieval streets.

Day 8: Znojmo – Mikulov (68 km)
In the morning, you will follow the river out of Znojmo, then cycle through sun-drenched fields and vineyards towards the Austrian border. At Jaroslavice, a Renaissance château marks the gateway south. You will cross briefly into Austria, cycling through the picturesque wine-growing area of Galgenberg before following a brand-new bike trail through peaceful countryside to Mikulov. This hidden gem will captivate you with its Baroque castle, historic synagogue, and an extraordinary curiosity — a gigantic wine cask large enough to hold a chamber orchestra.

Day 9: Mikulov – Poysdorf (37–54 km)
Your penultimate cycling day follows the Iron Curtain trail, framed by storyboards of those who attempted to escape the Eastern Bloc. You will also have the opportunity to explore the world-famous Lednice-Valtice UNESCO heritage area — a former Liechtenstein estate lovingly shaped to blend natural beauty with architectural splendour, most of it blissfully car-free. After crossing into Austria, you will pass through Herrnbaumgarten, famous for its poetic Museum of Nonsense, before reaching Poysdorf, the wine capital of the Weinviertel.

Day 10: Poysdorf – Vienna (76 km)
The final cycling day carries you through the poetic landscape of the Weinviertel, past Mistelbach and Wolkersdorf, where vineyards give way to gentle farmland. The route mixes open countryside with charming technical sections, including a romantic stretch along a dismantled railway path. Gradually, the capital approaches — and you will ride directly into the heart of Vienna on the banks of the blue Danube. The city of waltzes, the Spanish Riding School, and centuries of Habsburg history welcomes you.

Day 11: Departure from Vienna
Enjoy your final morning in Vienna, or extend your stay to explore the city’s world-class museums, palatial gardens, and legendary coffee houses. Your cycling journey from Prague to Vienna is complete — a mosaic of castles, vineyards, UNESCO treasures, and two magnificent capitals.