Bike and Boat: Cycling Greece’s Dodecanese Islands

  • Length 8 days
  • From USD$6095
  • Style/Level Bike and Boat 3.0
  • Countries Greece
  • Begin/End Bodrum, Turkey
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. Starting in Bodrum, Turkey, this unforgettable 8-day tour sails to the islands of Kalymnos, Kos, Nisyros, Tilos, and Symi. Daily rides will have your heart pumping as you explore scenic coastlines and rugged interior landscapes. You’ll visit the ancient site of Asklepieion on Kos, explore the volcanic landscape of Nisyros, plunge into crystal clear waters, and marvel at the diverse cultural footprints left by those who came before. What’s more, you’ll sleep comfortably each night on a newly revamped (2023) gulet.

Highlights

  • Explore the Asklepieion on Kos and nearby villages where Hippocrates taught

  • Discover Nisyros’s volcanic landscape with colorful craters and active fumaroles

  • See the medieval Mesaria Castle on Tilos

  • Marvel at the neoclassical architecture of Symi in the afternoon light from Chora

  • Ride from Datça to the ancient city of Knidos, with views of the Aegean Sea and historic ruins 

Includes

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. 
  • For tours beginning in 2025, we will sail on the Aegean Clipper.
  • Greece Bike and Boat tours will include 2 tour leaders, even with 18 maximum passengers.

Date Price Private room fee Note
Sep 28-Oct 5, 2025 USD$5850 USD$1250 Departure confirmed to go! One private cabin available. Re-Cycle discounts no longer available.
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May 10-17, 2026 USD$6095 USD$1300 Book Now and Save $300 per person. 1 private cabin available. 
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Sep 27-Oct 4, 2026 USD$6095 USD$1300 Book Now and Save $200 per person.
Book it
DateSep 28-Oct 5, 2025
PriceUSD$5850
Private room feeUSD$1250
NoteDeparture confirmed to go! One private cabin available. Re-Cycle discounts no longer available.
Book it
DateMay 10-17, 2026
PriceUSD$6095
Private room feeUSD$1300
NoteBook Now and Save $300 per person. 1 private cabin available. 
Book it
DateSep 27-Oct 4, 2026
PriceUSD$6095
Private room feeUSD$1300
NoteBook Now and Save $200 per person.
Book it

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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Open all days
  • Total distance 210 km (130 mi)
  • Average daily distance 35 km (22 mi)
  • Tour style Bike and Boat
  • Tour level 3.0

Highlights: Bodrum

This afternoon we’ll board our gulet and fit bikes. After a quick warm-up ride, we’ll enjoy our first delicious dinner together. Plan to arrive early to visit the Castle of St. Peter and the best underwater archeology museum in the world. The Mausoleum at Halicarnassus is one of the Seven Wonders of the Ancient World.

Meals : Dinner
 Lodging : Aegean Clipper

Highlights: Kalymnos

This morning we’ll sail to Kalymnos for your first island ride. The island’s rugged limestone cliffs, craggy mountains, and turquoise waters create striking scenery – it’s no wonder Kalymnos is rated a must-visit Greek island – so stop often to admire the views. Enjoy lunch in the seaside town of Panormos. This afternoon we’ll sail to our next destination: Kos, where we’ll enjoy dinner together.

Meals : Breakfast, Dinner
 Lodging : Aegean Clipper

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

Today you’ll explore the island of Kos. Our route allows you to connect several attractions from one of the most important archaeological sites in Greece, Asklepieion, built in the 4th century as a healing center and sanctuary, to the picturesque mountain villages of Lagoudi and Pyli, and the site of the tree under which Hippocrates is said to have taught his pupils. Dinner together tonight.

Meals : Breakfast, Dinner
 Lodging : Aegean Clipper

Highlights: Nisyros volcano and crater, 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 for an authentic lunch on the island’s most famous balcony.

Meals : Breakfast, Lunch
 Lodging : Aegean Clipper

Highlights: Tilos island, Museum of Elephants, Mesaria medieval castle

Today, depart from the tranquil village of Livadia to explore the island of Tilos. Begin with a short climb to the island’s interior, passing by the ruins of Mesaria Castle which was built by the Knights of Rhodes in 1366. Continue to Megalo Chorio village, where you can enjoy a coffee break and visit the local archaeological museum before stopping by the Paleontological Museum of Elephants, which displays fossils of the pygmy elephants that once roamed southern Europe.

Meals : Breakfast
 Lodging : Aegean Clipper

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 Panormitis. We will pedal from Panormitis Bay, on the island’s southern tip, where Symi’s most visited attraction is located. We will be in Symi 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. Dinner together tonight.

Meals : Breakfast, Dinner
 Lodging : Aegean Clipper

Highlights: Datça, biking on the Turkish coast, Ancient Greek city of Knidos

Set out from the charming coastal town of Datça, pedaling through rugged terrain with sweeping views of the Aegean Sea. This scenic route to Knidos combines challenging climbs and gentle descents, winding through aromatic pine forests, olive groves, and hidden coves. Arrive at Knidos, the ancient city at the tip of the peninsula, where sea and history meet. We’ll celebrate the end our journey with dinner together this evening.

Meals : Breakfast, Dinner
 Lodging : Aegean Clipper

Highlights: Say goodbye

We’ll motor back to Bodrum after enjoying a last lunch at sea together. You may want to spend a few days exploring Turkey.

Meals : Breakfast, Lunch

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

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