Bike and Boat: Cycling Greece’s Dodecanese Islands Plus! Samos

Highlights: Neratzia Castle and the old town of Kos, test ride – Board the Yacht

Welcome to the island of Kos! We’ll meet this afternoon to fit and test bikes before boarding our private yacht and home for the next seven days. Dinner together on board.

Highlights: Kalymnos

This morning we cruise to Kalymnos for our ride. The views are spectacular – it’s no wonder Kalymnos is rated a must-visit Greek island – so stop often to admire the scenery. Our lunch stop after a short but stout hill climb is worth the effort. Find time to visit the wonderful Archaeological and Nautical museums this afternoon. Dinner together on board.

Highlights: Visit to the island’s Volcano, Paleokastro Castle, the picture-perfect village of Nikia

The island of Nisyros is one of Greece’s more active but less known volcanoes. The last eruption of Nisyros in 1887 left a moonscape with colorful craters and very active fumaroles. Later this morning, enjoy a refreshment in one of the most photogenic squares on the Dodecanese before sitting down to an authentic lunch on the island’s most famous balcony. Dinner together in the village square of Mandraki tonight.

Highlights: Leisurely lunch and swim in a secluded bay, exploration ride on Halki, pastel -colored neoclassical architecture

Whatever Halki lacks in size, it makes up for in landscapes and colors. Brightly colored 19th Century houses – many of them lovingly restored – line the port of Emporios. Their ceramic-tiled roofs and wooden windows will charm you before you even step off the boat. Our ride today is short enough to allow you to enjoy the afternoon in this colorful town.

Highlights: Rhodes’ natural beauty, Ancient and Medieval monuments, afternoon walking tour

Traveling from Halki to Rhodes will feel like leaping between two different worlds. Our ride will lead us away from the coast, providing the opportunity to explore authentic villages and the island’s natural beauty. This afternoon we’ll take a walking tour to learn about the island’s complex, multi-faceted history. Rhodes’ ancient and medieval monuments, the legacy of the Colossus of Rhodes and the Crusades will tell the story of an island prized by all.

Highlights: The Monastery of Archangel Michael, the pictureque settlements of Gialos and Chorio

The magic of the small island of Symi is revealed from the moment we enter the elegant harbor in Yialos. We will pedal to Panormitis Bay, on the island’s southern tip, where Symi’s most visited attraction is located. We will return in time to witness the afternoon light that highlights the beauty of Chora’s pastel-colored neoclassical houses dating back to the island’s glorious past. 

Highlights: Sanctuary of the God of Medicine, cypress forest, the tree of Hippocrates

Today we head back to Kos and will enjoy exploring the island on our bikes. Our route will allow you to connect several attractions including the famous ancient site of Asklepieion, the attractive villages of Lagoudi, Pyli, and Mastichari and the tree under which Hippocrates is said to have taught his pupils! Dinner together on board.

Highlights: Italian rationalist architecture, War Museum, the Medieval Castle of Pandeli

You’ll be intrigued when we arrive at the port town of Lakki on Leros, thinking you’ve traveled back in time to 1930’s Italy. During the Italian occupation this entire town was built in typically Italian rationalist style, which resembles art deco. After a week on board our yacht, we are on land tonight for a good night’s rest in an elegant hotel.

Highlights: Monastery of St. John, the Cave of the Apocalypse, explore the alleys of Chora

The small island of Patmos is most renowned for being where St. John’s vision and writing of the Bible’s Book of Revelations took place. Today, along with its spiritual significance, the island boasts unique beauty with its sheer cliffs, volcanic soil and beautifully preserved villages, including the island’s capital, Chora, a UNESCO World Heritage site. We will have a day full of scenic cycling and memorable cultural visits.

Highlights: The Heraion, Samos Wine Museum and our seaside retreat

Famous for its sweet wine, Samos is also historically significant. It was the legendary birthplace of Hera, and the sprawling ruins of her ancient sanctuary, the Heraion — which we will visit on our ride today, are impressive. Don’t miss the opportunity to visit the spectacular Archaeological Museum, with its colossal statue of a Kouros dating to the 6th Century BC.

Highlights: Spectacular coastal views, authentic villages of Samos and the town of Karlovasi

Our last ride might be the most impressive of the whole tour. We will ride through lush forests and beautifully kept villages with breathtaking panoramic views of the turquoise water below. Our destination is Karlovasi, a flourishing tannery and tobacco manufacturing center in the early 1900s. We will have time to explore the many magnificent neoclassical mansions from that period as well as the remains of the large stone-built factories at the “Ormos” seaside. Dinner tonight will be a special conclusion to our island hopping adventure.

Highlights: Say goodbye

Depart this morning after breakfast. Explore more of the Dodecanese Islands, jump over to Turkey, or fly to Athens.