Bike and Boat: Cycling Greece’s Dodecanese Islands

Bike and Boat Cycling Greece's Dodecanese Islands
  • Length 8 days
  • From USD$5095
  • Style/Level Bike and Boat 3.5
  • Countries Greece
  • Begin/End Kos/Kos
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. This 8 day trip includes 7 nights on our private gulet so you never have to re-pack. We’ll cycle quiet roads and hop islands as we explore Rhodes, Symi, and end back in Kos where we embarked.

***If this sounds great and you prefer a longer tour, check out our 12 day, 11 night tour Bike and Boat the Dodecanese Islands Plus Samos tour. ***


  • Stay on a private gulet, swim in the cool water after a ride, enjoy exploring the Dodecanese islands including Kos, and Rhodes and Symi. Medieval castles and ancient temples.


  • 8 days, 7 nights (all 7 nights aboard our gulet-style motorized sailing boat)

  • meals as noted in itinerary

  • 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, and the Asclypeion on Kos) 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. 
  • Our boat is a traditional wooden sailing gulet that has been equipped with a motor. Although the boat has masts and sails, we depend on the engine to improve speed and assure the itinerary can be met. Motor-less sailing will be determined at the captain's discretion. 
  • The boat is limited to one private room.

Date Price Private room fee Note
Sep 28-Oct 5, 2024 USD$5095 1000  Private departure. Not available to the public.
Oct 5-12, 2024 USD$5095 USD$1000 Sold out! Waitlist available.
DateSep 28-Oct 5, 2024
Private room feeUSD$1000
Note Private departure. Not available to the public.
DateOct 5-12, 2024
Private room feeUSD$1000
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.
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  • Total distance 290km (180 miles)
  • Average daily distance 25-63km (16-39 miles)
  • Tour style Bike and Boat
  • Tour level 3.5

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

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

The June 1, 2024 group will gather at our luxurious seafront hotel for the first night.

Meals : Dinner
Lodging : Private Greek Gulet , Kos Aktis

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 Gulet

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 Gulet

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 Gulet

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 Gulet

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 Gulet

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 Gulet

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 determine day and tour levels.

Pre-trip planning checklist

Greece travel planning page

  • 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
  • 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