

Peaks, lakes and legends
Northern Greece & North Macedonia
Follow In the Footsteps of Alexander the Great:
The Northern Greece & North Macedonia Cycling Odyssey
Follow the legendary path of Alexander the Great on a 14-day cycling odyssey through the heart of Northern Greece and North Macedonia. This epic journey combines the thrill of conquering challenging routes with the discovery of ancient lands that once shaped history.
Starting in the vibrant city of Thessaloniki, the cultural capital of Alexander’s empire, you’ll ride through the lush vineyards of Tikveš, trace the shores of tranquil lakes, and ascend to the mythical heights of Mount Olympus, home of the Greek gods. Along the way, explore the timeless charm of historic villages, marvel at the gravity-defying monasteries of Meteora, and experience the unique traditions of this storied region.
This tour celebrates not only the legendary conqueror but also the enduring spirit of the lands he called home. Every pedal stroke takes you deeper into the landscapes that inspired one of the world’s greatest leaders.
Highlights of the Tour:
-
Cycle through the ancient Macedonian lands where Alexander the Great was born and raised.
-
Visit iconic landmarks like Mount Olympus and the awe-inspiring Meteora.
-
Immerse yourself in local culture, from the vineyards of Tikveš to the cobblestone streets of Nymphaio.
-
Tackle the climb to Prionia Refuge, reaching alpine heights on Mount Olympus.
-
Enjoy the serene beauty of Lake Kastoria and Lake Dojran, surrounded by picturesque scenery.
-
Relish local cuisine and wines that have been enjoyed for millennia.
Whether you're inspired by history, adventure, or the sheer beauty of the region, this tour offers a unique opportunity to ride through lands steeped in myth and legend.
Embark on an adventure where history meets endurance and Alexander’s legacy becomes your road.
​
WHEN ?
Custom Dates:
We run tours fully inclusive throughout the year For private groups groups of 6 or more aswell as self supported tours
Contact us for availabiliy
ITINERARY:

Day 1: Thessaloniki to Dojran "From the Heart of Macedonia to the Tranquil Lake"
-
Distance: 80 km | Elevation Gain: ~450 m
-
Route Narration: Your journey begins in Thessaloniki, cycling out of the city along flat roads that lead to the peaceful surroundings of Lake Dojran at the Greece-North Macedonia border.
-
Cultural Stops: Visit Thessaloniki’s White Tower and Ano Poli (Old Town) before riding out. Enjoy Lake Dojran’s tranquil lakeside promenade.
-
Accommodation: Lakeside guesthouse with serene views.
-
Challenge Level: Easy to Moderate.
Day 2: Dojran to Negotino "Through the Vineyards of the Ancient Kingdom"
-
Distance: 75 km | Elevation Gain: ~540 m
-
Route Narration: Cycle through rolling hills and green farmland as you enter the Tikveš wine region, renowned for its vineyards and relaxed rural charm.
-
Cultural Stops: Stop at a local winery to sample North Macedonia’s famous Vranec wine and learn about ancient winemaking traditions.
-
Accommodation: Boutique guesthouse or winery stay with tastings.
-
Challenge Level: easy to Moderate.
Day 3: Negotino to Bitola "On the Road to the City of Consuls"
-
Distance: 110 km | Elevation Gain: ~1100m
-
Route Narration: Pedal through open plains, passing small villages before tackling gradual climbs toward Bitola, a historic city with Ottoman influences and vibrant culture.
-
Cultural Stops: Explore Heraclea Lyncestis, an ancient Macedonian city with exquisite mosaics, and stroll Širok Sokak, Bitola’s lively pedestrian boulevard.
-
Accommodation: Centrally located hotel in Bitola.
-
Challenge Level: Moderate to Hard
Day 4: Bitola to Nymphaio "Crossing Borders and Climbing into the Clouds"
-
Distance: 58 km | Elevation Gain: ~1,000 m
-
Route Narration: Begin with a flat ride to the Niki border crossing, where you’ll re-enter Greece. The road then ascends steadily into the mountains, rewarding you with dramatic vistas as you approach Nymphaio.
-
Cultural Stops: Visit the Arcturos Bear Sanctuary, which protects brown bears in their natural habitat, and explore Nymphaio’s charming cobblestone streets.
-
Accommodation: Traditional mountain lodge.
-
Challenge Level: Hard.
Day 5: Nymphaio to Kastoria "Descending into Lakeside Elegance"
-
Distance: 61 km | Elevation Gain: ~570 m
-
Route Narration: Start with a scenic descent from Nymphaio, winding through forests and open valleys before reaching the beautiful lakeside town of Kastoria. Ride along the lakefront to complete the day.
-
Cultural Stops: Discover Kastoria’s Byzantine churches and learn about the town’s historical connection to fur trading.
-
Accommodation: Lakeside hotel with panoramic views of the lake.
-
Challenge Level: easy.
Day 6: Rest Day in Kastoria "Reflections by the Lake"
-
Activities: Spend the day exploring the tranquil surroundings of Kastoria. Walk along the lake’s edge, visit the Byzantine Museum, or take a boat ride to experience the serene beauty of the water. Alternatively, explore the Dragon’s Cave, a lakeside cavern steeped in myth.
-
Cultural Stops: Visit Panagia Mavriotissa Monastery and enjoy traditional Kastorian cuisine, including freshwater fish dishes.
-
Accommodation: Same as Day 5.
-
Challenge Level: Easy.
Day 7: Kastoria to Grevena "Stone Bridges and Mountain Passes"
-
Distance: 67 km | Elevation Gain: ~800 m
-
Route Narration: Cycle through rugged terrain and quiet mountain passes. The ride takes you through picturesque valleys dotted with ancient stone bridges before reaching Grevena.
-
Cultural Stops: Pause to admire the Portitsa Bridge, nestled in a dramatic gorge.
-
Accommodation: Quaint guesthouse with a cozy atmosphere.
-
Challenge Level: moderate.
Day 8: Grevena to Kastraki (Meteora) "Pedaling Toward the Pinnacles of Faith"
-
Distance: 65 km | Elevation Gain: ~740 m
-
Route Narration: Start with a steady climb through lush forests and rolling hills. As you approach Kastraki, the surreal rock formations of Meteora rise dramatically on the horizon.
-
Cultural Stops: Take in the awe-inspiring views of Meteora’s monasteries perched atop towering cliffs.
-
Accommodation: Charming guesthouse at the foot of Meteora.
-
Challenge Level: moderate.
Day 9: Rest and Exploration Day in Meteora "The Monasteries of Heaven"
-
Activities: Spend the day exploring Meteora’s UNESCO-listed monasteries. Walk the trails connecting these spiritual marvels or relax while taking in the surreal rock landscapes.
-
Cultural Stops: Visit Great Meteoron Monastery and Varlaam Monastery, learning about their history and significance.
-
Accommodation: Same as Day 8.
-
Challenge Level: na.
Day 10: Kastraki to Elassona "Rolling Toward the Shadow of Olympus"
-
Distance: 110 km | Elevation Gain: ~600 m
-
Route Narration: Pedal through the fertile plains of Thessaly, passing villages surrounded by golden fields. Mount Olympus grows larger as you approach Elassona.
-
Cultural Stops: Visit the historic Monastery of Olympiotissa.
-
Accommodation: Comfortable guesthouse.
-
Challenge Level: Moderate.
Day 11: Elassona to Palaios Panteleimonas "To the Village Above the Sea"
-
Distance: 65 km | Elevation Gain: ~1,400 m
-
Route Narration: Ride through rolling hills and climb toward the slopes of Mount Olympus. The ascent to Palaios Panteleimonas rewards you with stunning views of the Thermaic Gulf and a charming mountain setting.
-
Cultural Stops: Explore the cobblestone streets of Palaios Panteleimonas and enjoy local delicacies in its tavernas.
-
Accommodation: Stone-built guesthouse.
-
Challenge Level: Hard.
Day 12: Palaios Panteleimonas to Prionia and Litochoro "Ascending to the Throne of Zeus"
-
Distance: ~57 km | Elevation Gain: ~1400m
-
Route Narration: Begin with a descent toward Litochoro before tackling the iconic climb to Prionia Refuge on Mount Olympus. This challenging ascent is matched only by the thrill of descending back to Litochoro.
-
Cultural Stops: Stop at Prionia Refuge to marvel at the surrounding alpine beauty and Olympus National Park.
-
Accommodation: Hotel or guesthouse in Litochoro.
-
Challenge Level: Hard.
Day 13: Rest Day in Litochoro
"Olympus Unwind: Sea, Sky, and Serenity"
-
Activities: Relax by the sea, hike to the Orlias waterfalls, or explore Litochoro’s quaint streets. Reflect on your journey under the shadow of the gods.
-
Cultural Stops: Visit the Olympus National Park Information Center.
-
Accommodation: Same as Day 12.
-
Challenge Level: Easy.
Day 14: Departure from Thessaloniki
"Farewell to Alexander’s Homeland"
-
Activities: Transfer to Thessaloniki or take a final morning stroll in Litochoro before concluding your journey.


















​
BREVET
2 Riders €1180
3-6 Riders €1080
6 + Riders €980
​
GRAND TOUR
MINIMUM 6
€3500
​
​
SPORTIVE
2 Riders €1480
3-6 Riders €1380
6 + Riders €1280
optional extras:
€550 single person supplement
€250–bike rental
E-BIKE - upon request
Custom Tour:
If you would like this, or any of our tours customising to your specific needs and request please dont hestitate to contact us
What's Included
Extra Info
-
Exact itinerary and activities may be subject to change depending on availability
-
Distances and elevation are Approx. and may vary slightly depending on exact location of destination accommodation and starting points
-
Difficulty: The tour is a medium to high challenging tour designed for people who are experienced cyclists comfortable with cycling 6 hours a day with some challenging hills
-
Flight info: You Will have to fly to Athens international airport and aim to arrive at least one day prior to the tour start and at least one day after.
-
Hotels in Athens before and after the tour are not included