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

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

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. ***

Tour Dates & Prices

Private Room Fee
Oct 7-18, 2023
Just 1 space available for a woman willing to share a room.
Jun 1-12, 2024
Book now and save $200 per person. Will-shares not available. 1 private room available.
Oct 5-16, 2024
Sold Out - Wait List Available

* We are happy to match solo travelers who would like to share a room with someone of the same gender. If no match exists, due to hotel pricing, we will charge 50% of the private room charge. This charge will be collected at the time of the final payment. If a roommate assignment is available it will be refunded at the conclusion of the tour.

** For information about what your tour status means please see our FAQ page.

Tour Style: Bike and Boat Hold A Space Request Private Departure Download Itinerary Tour Map
  • Trip At-A-Glance
  • Tour Summary
  • Daily Itinerary
  • Travel Information
  • Map
  • Reviews
  • Similar Tours
Trip At-A-Glance

Trip At-A-Glance

  • Length / 12 Days
  • Total Distance / 450km (280 miles)
  • Avg. Distance / 25-63km (16-39 miles) per riding day
  • Tour Level & Tour Style / 3.5 Bike and Boat
  • Countries / Greece
  • Begin/End / Kos/Samos
  • Price / From USD$6195
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Tour Summary

Tour Summary

  • Highlights
    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.

    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.
  • Includes
    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.

    Learn more about what is included and what to expect on your Bike and Boat tour at the Bike and Boat Tour Style page.
  • Arrive / Depart
    Kos Ippokratis Airport (KGS)/Samos Aristarchos Intl Airport (SMI)
  • Overall Tour Level
    3.5 difficulty level 3.5

    All of the rides, with the exception of two, are loops or out-and-back's, which means various riding distances available.

  • Daily Ride Summary




    Day Level


    Test ride
    43km / 1017m
    Very hilly
    difficulty level 3.5
    38km / 995m
    difficulty level 3.5
    16km / 624m
    difficulty level 3.0
    56km / 650m
    Rolling hills
    difficulty level 2.5
    49km / 1436m
    Very hilly
    difficulty level 4.5
    62km / 1076m
    difficulty level 4.0
    44km / 776m
    difficulty level 3.0
    27km / 612m
    difficulty level 2.5
    49km / 840m
    difficulty level 3.5
    45km / 981m
    Very hilly
    difficulty level 4.0
    Last day

Terrain Legend

Gentle Gentle

Rolling hills Rolling hills

Hilly Hilly

Very hilly Very hilly

Mountainous Mountainous

Daily Itinerary
Download Itinerary

DAY 1: Welcome to Greece!

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.

DAY 2: Kalymnos Loop Ride

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.

  • Distance: 43km (27mi)
  • Gain: 1017m (3336ft)
  • Terrain: Very hilly
  • Day Level: difficulty level 3.5
  • Meals: Breakfast, Dinner
  • Lodging:

DAY 3: Cycling on Nisyros

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.

  • Distance: 38km (24mi)
  • Gain: 995m (3264ft)
  • Terrain: Hilly
  • Day Level: difficulty level 3.5
  • Meals: Breakfast, Dinner
  • Lodging:

DAY 4: Swim off the boat and ride on Halki

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.

  • Distance: 16km (10mi)
  • Gain: 624m (2047ft)
  • Terrain: Mountainous
  • Day Level: difficulty level 3.0
  • Meals: Breakfast, Lunch
  • Lodging:

DAY 5: Cycle on the island of Rhodes

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.

  • Distance: 56km (35mi)
  • Gain: 650m (2132ft)
  • Terrain: Rolling hills
  • Day Level: difficulty level 2.5
  • Meals: Breakfast
  • Lodging:

DAY 6: Cycling on the island of Symi

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. 

  • Distance: 49km (31mi)
  • Gain: 1436m (4710ft)
  • Terrain: Very hilly
  • Day Level: difficulty level 4.5
  • Meals: Breakfast, Dinner
  • Lodging:

DAY 7: Kos Loop Ride

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.

  • Distance: 62km (39mi)
  • Gain: 1076m (3529ft)
  • Terrain: Hilly
  • Day Level: difficulty level 4.0
  • Meals: Breakfast, Dinner
  • Lodging:

DAY 8: Explore Leros on bike

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.

  • Distance: 44km (28mi)
  • Gain: 776m (2545ft)
  • Terrain: Hilly
  • Day Level: difficulty level 3.0
  • Meals: Breakfast, Dinner
  • Lodging:

DAY 9: Patmos Loop Ride

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.

DAY 10: Ride from Pythagorio to Samos Town

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.

DAY 11: Cycling from Pythagorio to Karlovasi

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.

DAY 12: Farewell!

Highlights: Say goodbye

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

  • Meals: Breakfast
Travel Information

Travel Information

Day 1: Arrival Information

Welcome to Greece!

Meeting time 2 p.m. - on Day 1, meet your fellow cyclists and Tour Leaders at the boat dock at Limenas Ko Harbor (click here for map). You won't miss the bikes and our boat. 

Note: As you are planning, remember that the hotels listed in our itineraries are our primary hotels and are - in rare cases - subject to change. Before you make arrangements, check with us if your tour departure is guaranteed. If your tour departure is out further than 6 months, please also check with us as there might be slight changes to the itinerary.

We recommend flying into the Kos Ippokratis Airport (KGS)

  • Bus, see schedule here (40 min/EUR 5)


  • Taxi (20 min/EUR 37)

Hotel recommendations: If you are planning to arrive a day or two early, you are free to book any hotel and arrangement of your choice. You can find hotel recommendations in walking distance to the boat dock on our website. You may wish to ask for a late check-out by 2 PM.

Day 12: Departure Information


Your trip ends on the final day after breakfast. 

The below information will help you plan your departure. For more tips or other routes, you might like Rome2Rio

We recommend flying out of the Samos Aristarchos Intl Airport (SMI)

Getting from the ending hotel to the Samos Airport:

  • Taxi (5 min/EUR 12)

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.

Pre-Trip Planning Checklist

To do right after you booked!

6 to 3 Months Prior to Tour Start Date

  • Refer to your Tour Packet/Itinerary to see step-by-step arrival and departure information for your tour, meeting place and time, if a reservation on a complimentary ExperiencePlus! Shuttle (if applicable) is required, and other important information to help you plan your arrival and departure.
  • Reserve your flights after you know you have a confirmed tour departure. Please check with our office if you do not know if your trip is confirmed.
  • Book your pre and post-tour hotel nights.
  • Begin your chosen training program.
  • Final payment is due 90 days (120 days for Bike &Barge/Boat tours) prior to the tour start. Please refer to your Invoice and the Final Payment Reminder e-mail we send 10 days prior to the due date for detailed instructions.

6 to 2 Weeks Prior to Tour Start Date

  • Start reading one of the books or watching one of the movies from our Reading and Movie Lists:
  • Plan what you are going to pack and start packing! Refer to the Packing Lists on our website at
  • We'll email you your access code to Digital Daysheets, Hotel Itinerary, Participant Roster, names and contact information of your Tour Leaders, emergency phone numbers, and other important departure information about 2 weeks prior to your tour start date. All this will be provided to you via a feature called Experiences via the RideWithGPS App (tracks available but not necessary for navigation on Classic, Expedition and Bike & Boat tours).

Day of Your Flight

Get as much sleep on the plane as you can. Pack your one day of cycling gear in your carry-on. See you soon!

What to Expect on Tour

Bike and Boat Tour Style

Learn more about what is included and what to expect on your Bike and Boat tour at the Bike and Boat page.





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