Sail and cycle along the best-preserved coastline of the Aegean Sea aboard a handcrafted traditional gulet. Discover the Dodecanese archipelago – whitewashed villages, secluded beaches, active volcanoes, and ancient ruins – while pedaling quiet island roads with a full support team. A unique combination of luxury cruising and guided cycling in the heart of Greek civilization.
As Homer described it in the Iliad, the Aegean Sea played a crucial role in the emergence of Greek civilization and mythology. The Dodecanese archipelago represents the pinnacle of rugged Mediterranean beauty: whitewashed villages, secluded beaches, and a surprising food and wine scene await you at every anchorage.
From ancient settlements and temples to medieval castles, stylish Italian architecture, and submerged wartime wrecks, the past comes alive in the Dodecanese. Each island — large and small — reveals its own individual character and story.
This incredibly rich program combines the ancient Greek history with the natural beauty of the Aegean, the finest Greek cuisine, and the pampering service of our diligent onboard crew.
◉ Meet our guides at Milas-Bodrum Airport (BJV) and take the private transfer to the boat for a bit of free time before your tour begins.
◉ We clear the customs paperwork and cruise to Aquarium Bay while toasting to adventure with a welcome drink served by our crew.
◉ After anchoring in the bay, we enjoy a sunset dinner aboard the gulet and our first magical night on deck.
Meals: Dinner | Accommodation: Luxury private gulet
◉ We weigh anchor before breakfast and cruise to Kalymnos Island (21 NM – 2h30min). We drop anchor in Kalymnos port and clear Greek customs over breakfast.
◉ After getting fitted to our bikes we explore the port town and learn about Kalymnos' famous sponge-diving tradition.
◉ We ride to Vathys Bay with its dramatic sheer cliffs. After a refuel of Greek coffee and nutritious snacks, challenge yourself with a gradual climb to the island's highest pass and soak in impressive Aegean vistas before descending to the western shores.
◉ After lunch onboard, cruise to Leros Island (10 NM – 1h30min) with an afternoon siesta on deck. Enjoy a swim and an evening stroll in the port town before dinner onboard.
Meals: Breakfast / Lunch / Dinner | Distance: 33 km, +815 m | Long Route: 47 km, +1172 m | Accommodation: Luxury private gulet
◉ After breakfast onboard, cycle around the charming island of Leros discovering fascinating chapels scattered across different bays — starting from Agios Isodoros on its picturesque islet, then pedaling to Panagia Kavouradena at the south end of the island.
◉ Taste local flavors and wines at a family-run winery during lunch. A 10-min downhill brings us back to the boat for a refreshing swim in Alinda Bay.
◉ Cruise to Kos Island (28 NM – 3h) enjoying the views of the Turkish coastline and the Greek islands of Kalymnos and Pserimos.
◉ Discover Kos town around the harbor before a free dinner ashore.
Meals: Breakfast / Lunch | Distance: 33 km, +600 m | Long Route: 45 km, +903 m | Accommodation: Luxury private gulet
◉ After a Mediterranean breakfast onboard, cycle the island from northeast to southwest through central hills dotted with picturesque villages.
◉ Pause at the ancient healing temple of Asclepion — where the Hippocratic Oath was formulated — then climb to the mountain village of Zia for a panoramic view of Kalymnos Island.
◉ After free time for shopping and lunch, cycle from Zia to Kardamena along the southern coastline. Cruise to Nisiros Island (10 NM – 1h20min) in the late afternoon.
◉ Visit the well-preserved 4th-century acropolis, stroll through back streets greeting locals before sunset, and watch the sun dip from the volcanic black beach before dinner onboard.
Meals: Breakfast / Dinner | Distance: 27 km, +490 m | Long Route: 45.5 km, +846 m | Accommodation: Luxury private gulet
◉ Enjoy breakfast with freshly baked island bread and start pedaling early. A climb to the top of Nisiros reveals infinite views of the Aegean Sea, Greek islands, and Turkey's imposing coastline.
◉ Arrive in Nikia, the island's highest village, and walk through the best-preserved Greek village overlooking the volcanic crater. After homemade snacks, peer into the mouth of the volcano from the rim before descending back to the boat.
◉ Enjoy a well-deserved lunch onboard and cruise toward Simi (35 NM – 4h), the most charming harbor of the Dodecanese. Anchor in a secluded bay for an afternoon swim, then explore the port's unique neoclassical architectural treasures.
◉ Dinner is on your own at a restaurant tucked among 19th-century houses and Orthodox churches.
Meals: Breakfast / Lunch | Distance: 36 km, +729 m | Long Route: 48 km, +899 m | Accommodation: Luxury private gulet
◉ We return to our bikes in the morning and ascend to a scenic ridge perched above the sea with the whole charming Dodecanese port spread below us.
◉ Our epic ride ends with a visit to the remote monastery of Panormitis for an illuminating glimpse of Greek Orthodox monastic life. A short final ride brings us back to our boat at Marathounta Bay.
◉ Enjoy a swim from the beach or take the dinghy back to the boat before lunch. Then cruise to the Turkish town of Datça (16 NM – 2h) where our local guide shows us the traditional bazaar and artisan shops.
◉ Free time to shop for local products before a festive dinner onboard.
Meals: Breakfast / Lunch / Dinner | Distance: 30 km, +713 m | Accommodation: Luxury private gulet
◉ After breakfast, warm up riding through Datça — famous for organic produce and its prized almonds — then tackle a 5.5 km climb to the peninsula's highest pass.
◉ Descend to Mesudiye Village and roll along the southern edge of the peninsula with breathtaking views of the Aegean and Simi Island. Pass through the welcoming villages of Palamut and Yazi for a tea-house break.
◉ Continue the final descent to Knidos along the ancient road. The spectacular ruins of Knidos welcome you at the tip of the peninsula: explore the theater, the ancient harbor monuments, and hear the myths of Aphrodite — patron goddess of the city.
◉ After lunch and a swim in the ancient harbor, cruise to Bodrum (22 NM – 2h45min). A festive farewell dinner marks our last unforgettable memory.
Meals: Breakfast / Lunch / Dinner | Distance: 32 km, +450 m | Long Route: 47 km, +905 m | Accommodation: Luxury private gulet
◉ After breakfast onboard, say goodbye to our crew and guides, and take the private transfer to Milas-Bodrum Airport (BJV).
◉ Fly back home — until next time!
Meals: Breakfast | Transfer: Milas-Bodrum Airport (BJV)
A non-refundable deposit of €1,200 per person is required to reserve your spot. Balance payment is due 150 days before departure.
Minimum group size: 6 people. Prices based on a group of 6. Lower rates may apply for larger groups — enquire for details. Maximum group size: 14 people.
Upon request: travel insurance, private transfers. Contact our team for details.
For speed and efficiency enthusiasts on the road.
Adventure on varied terrain with the perfect electric assistance.
Ideal for those seeking to explore mixed terrain with versatility.
For adventurers wanting to tackle trails with electric technology.
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Congratulations! You are one step away from confirming your unforgettable adventure in Italy. Thank you for trusting our team.
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Specialized service in Belo Horizonte to facilitate your booking.
Own local team and support in Portuguese throughout the journey.
