Greece Bike & Yacht

Bodrum

Welcome to the Greek Isles – Arrive in Bodrum and transfer to the harbour where you will meet your guides and we’ll embark at 5 pm. You’ll have time to get settled aboard your private yacht, or gulet, a wooden sailing vessel originating from southwestern Turkey. Toast to adventure with a welcome drink served by the five-person sailing crew as we enjoy a sunset dinner aboard the gulet and our first night on deck.

Kalymnos

Enjoy a relaxed breakfast on board before we clear customs and set sail for Kalymnos. After dropping anchor in the harbour, we’ll get fitted to our bikes and begin today’s ride toward Emporios Bay. Take on a steady climb to the island’s highest pass, where sweeping views of the Aegean Sea reward your efforts, then enjoy an exhilarating descent to the eastern coast.

Pause at a local taverna to refuel with a traditional Greek coffee before pedaling back to rejoin the boat. A refreshing swim in the Aegean sets the stage for a leisurely lunch served on board. This evening, gather on deck for dinner beneath a canopy of stars.

Distance: 33 km; 683 m gain

Leros and Kos

Enjoy breakfast aboard the gulet as we cruise from Emporios Bay to Leros. Today we set out to bike the length of the island, discovering charming chapels tucked into quiet bays along the way. Our ride begins in the seaside village of Agios Isidoros and continues to the iconic church of Panagia Kavouradena, perched dramatically above the sea.

Midday, we’ll pause at a local micro-winery where the owners welcome us for a tasting paired with a home-cooked lunch. Afterward, enjoy a scenic pedal back to the boat and time to relax before another beautifully prepared dinner on board. As the evening unfolds, the captain sets a course for Kos.

Distance: 29 km; 415 m gain

Kos and Nisyros

This morning, set out to bike Kos from north to south, riding through rolling central hills dotted with picturesque villages. Pause at the ancient ruins of the Asclepeion of Kos—the revered healing sanctuary where the Hippocratic Oath is believed to have originated—before continuing your climb to the mountain village of Zia. From here, savour a coffee with sweeping views toward Kalymnos.

This afternoon, choose to cycle along Kos’s southern coastline or return directly to the boat for some well-earned relaxation. Take a refreshing swim off the sandy beaches of Kardamaina before we cruise onward to Nisyros. As evening falls, stroll through the charming port town and settle in to watch a spectacular sunset from a volcanic black-sand beach, followed by dinner at a welcoming local taverna.

Distance: 21 km; 448 m gain

Nisyros and Symi

Greet the morning with breakfast in the charming port of Nisyros, framed by an amphitheater of whitewashed, flat-roofed homes cascading toward the sea. From here, climb toward the island’s summit for sweeping views across the Aegean Sea, neighbouring Greek isles, and the dramatic coastline of Turkey. Reach Nikia, the island’s highest village, where you’ll peer into the crater of an active volcano far below. Enjoy a breezy descent back to the boat in time for a well-deserved lunch. Later, relax with a siesta or cocktails on deck as we sail toward Symi, chasing the glow of sunset. This evening, dinner is on your own at a local restaurant tucked among elegant neoclassical mansions and late 19th-century churches lining Symi’s picturesque harbor.

Distance: 26 km; 495 m gain

Symi to Datça

We’re on our bikes early this morning, climbing toward a scenic ridge high above the sea. The sweeping views over Symi are well worth the effort—you may even spot our own gulet cruising below, bound for a secluded bay where it will meet us. Continue pedaling to the waterfront monastery of Panormitis Monastery, where we pause for a glimpse into Greek Orthodox monastic life.

Back on board, the afternoon is yours to enjoy: savour a leisurely lunch, swim in brilliant turquoise waters, or stretch out for a siesta as we sail toward Datça, Turkey—our berth for the night. After clearing customs, you’re free to explore this laid-back seaside town and choose from one of its many inviting seafood restaurants for dinner on your own.

Distance: 29 km; 686 m gain

Knidos to Bodrum

After breakfast on board, set out for a ride along the southern shores of the Datça Peninsula. It’s a quintessential Mediterranean day, with azure bays, rugged coastline, and sun-drenched villages along the way. Our route concludes at Temple of Aphrodite at Knidos, dedicated to the Greek goddess of love in the ancient city of Knidos. This afternoon, unwind with a leisurely lunch, snorkel in the storied ancient harbour, or relax on the bow with a cold beer in hand. Later, we sail back to Bodrum for one final evening aboard, celebrating the journey with a farewell dinner prepared by the boat’s private chef.

Distance: 25 km; 400 m gain

Depart

A final breakfast on our gulet is followed by goodbyes with your guides before they see you off.