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

Bike and Boat Cycling Greece Plus
  • Length 12 days
  • From USD$6695
  • Style/Level Bike and Boat 3.5
  • Countries Greece
  • Begin/End Kos/Samos
See related tours

The Dodecanese islands, almost within hailing distance of Anatolia, are the furthest island group from the Greek mainland. Each island has its own charm and characteristic landmarks, ranging historically from the times of Byzantine and Ottoman rule to the Italian era and contemporary Greece. Our 12-day cycling tour of the Dodecanese features seven days on a privately chartered yacht, which will not only provide us with comfortable accommodations and freshly prepared meals, but will also allow us to explore the beautifully carved coastlines of the islands we visit, and enjoy leisurely stops in impressive bays with crystal-clear water. Cycle along quiet roads on hilly terrain and explore 9 different islands. Attractions include the wonderful medieval enclave of Rhodes Old Town; the gorgeous ensemble of Neoclassical mansions that surrounds the harbor on Sými; the grandiose temple-sanatorium of Asklepion on Kos; the rugged landscapes of Kálymnos; the cave and monastery on Pátmos, where St John had his vision of the Apocalypse…and many more.

***If this sounds great but you prefer a shorter trip, check out our 7 night, 8 day Bike and Boat the Dodecanese Islands tour. ***


  • Sail on a private yacht, swim in the cool water after a ride, enjoy exploring the Dodecanese islands including Kos, Rhodes, Patmos, Samos and ancient temples and monasteries.


  • 12 days, 11 nights (7 nights aboard our gulet-style yacht)

  • meals as noted in itinerary

  • 1 wine tasting

  • guided walking tour on Rhodes

  • admission to all the sites visited together (The Palace of the Grand Master on Rhodes, the Archaeological Museum of Rhodes, the Asclypeion on Kos, the Monastery of St. John on Patmos and the Heraion of Samos) and the usual.

  • All Bike and Boat tour inclusions

Keep in mind

We work hard to maintain consistency across all of our tours, but some trips have unique differences. Here are some things to keep in mind about this tour.

Itineraries can change depending on weather conditions, coast guard restrictions, tour logistics and our captain’s discretion. Limited to one private room.

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.

Meals : Dinner
Lodging : Private Greek Yacht

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.

Meals : Breakfast, Dinner
Lodging : Private Greek Yacht

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.

Meals : Breakfast, Dinner
Lodging : Private Greek Yacht

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.

Meals : Breakfast, Lunch
Lodging : Private Greek Yacht

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.

Meals : Breakfast
Lodging : Private Greek Yacht

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. 

Meals : Breakfast, Dinner
Lodging : Private Greek Yacht

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.

Meals : Breakfast, Dinner
Lodging : Private Greek Yacht

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.

Meals : Breakfast, Dinner
Lodging : Skala Hotel Patmos

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.

Meals : Breakfast
Lodging : Casa Cook Samos

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.

Meals : Breakfast
Lodging : Casa Cook Samos

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.

Meals : Breakfast, Dinner
Lodging : Casa Cook Samos

Highlights: Say goodbye

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

Meals : Breakfast

Visit our Tour Level page to learn more about terrain levels and how we dermine day and tour levels.

Date Price Private room fee Note
Oct 7-18, 2023 USD$6195 USD$1200 Just 1 space available for a woman willing to share a room.
Jun 1-12, 2024 USD$6695 USD$1200 Book by November 1 and save $200 per person. Will-shares not available. 1 private room available.
Oct 5-16, 2024 USD$6695 USD$1200 Sold out! Waitlist available.
DateOct 7-18, 2023
Private room feeUSD$1200
NoteJust 1 space available for a woman willing to share a room.
DateJun 1-12, 2024
Private room feeUSD$1200
NoteBook by November 1 and save $200 per person. Will-shares not available. 1 private room available.
DateOct 5-16, 2024
Private room feeUSD$1200
NoteSold out! Waitlist available.

Download Itinerary

We’ll send you a link to a full day by day tour itinerary that can be downloaded and printed so you can review all the details online and offline. This packet also includes details about what to expect on tour and arrival and departure details.
Tour date(Required)
Have you traveled with us before?(Required)

Pre-trip planning checklist

  • It was a great way to explore some lesser known Greek islands. Loved the comaraderie of being with leaders and participants on the boat and off.

    Becky P., Napa, CA – May 2023
  • If you like being on the water and biking some remote Greek islands this is tour for you. It is well run and it is great you can stay on the boat the whole time and not pack each day. The cycling is not very hard except for one day and very easy if you are on a e-bike.

    Michael P., Napa, CA – May 2023
  • The rides were challenging and rewarding and the scenery was beautiful. The wildflowers were in full bloom and beautiful. The meals and wines were a delight. We also had a great group to be with.

    Cliff M., Knockville, TN – May 2023