The Odyssey – Istanbul to Ithaca

THE ODYSSEY - ISTANBUL TO ITHACA CYCLING TOUR OVERVIEW

What is in a name? Our Odyssey, the original Odyssey.

From the soaring Byzantine dome of the Aya Sofya in Istanbul, across the glittering island studded Mediterranean, to Odysseus´ home, Ithaca in the Ionian Islands. 'The Odyssey' is true to its origins (besides its 10 year duration!) and the modern day definition of the word. Stage 1 starts in-continent spanning Istanbul. From this city of cities, we depart via the Bosphorus south towards Troy, the historic and legendary starting point for Odysseus' famed journey home. Turkey is heralded for its beautiful coastlines and rugged interior, the The Cycling Tour of Turkey (the rider's favourite UCI World event) is known for the same spectacular scenery. Taking in Gallipoli and Ephesus, castles and ancient temples, our historical journey spans the ages. We finish our Turkish adventure on the stunning Bodrum Peninsula which shows this country off at its most staggeringly beautiful - sweeping sandy beaches hugging a steep rocky coastline, gently caressed by jade waters, backed by forest-blanketed slopes dotted with ancient settlements. Scenery doesn't get much better!

As we step onto our luxury gulets, our homes for the coming week, you will be amazed at their beauty - and their ability to support us on an island hopping adventure taking in the very best of Greek Island living! We finish Stage 1 cruising the Dodecanese islands, Leros, Kalymnos, Kos, Symi and Nisiros rolling on our bikes along ancient pathways, never for long without a view of the azure Mediterranean waters, feasting on deck in between swims in the Mediterranean!

Stage 2 begins in the modern and ancient capital of Greece, Athens. After a day of touring and exploring where democracy was born we head deep inland, but don't worry, we will board a boat again as we finish with the irresistible Ionian Islands - famous for their cycling pedigree, history and beauty! Although one of our favourite cities for its amazing history, we are glad to mount our bikes and depart Athens heading west across the Corinthian Canal onto the Peloponnese, with magnificent archaeology at Epidaurus, Mycenae - home of Agamemnon - and Nemea the vine and olive clad hills make for amazing riding as we ride Gulf to Gulf, Argos to Corinth. Crossing the latter by speedboat we pause under the genuinely epic Delphi...but not for long as we continue our Odyssey west via Venetian harbour towns and five star hotels. Then to the Ionian Islands we ride - first Kefalonia, which has its very own Mont Ventoux called Mount Einos! This island is hard to beat for cycling, even considering where we have come from. After circumnavigating our penultimate isle we then head to Odysseus' 3000 year old home, Ithaca, where we celebrate completing our modern day Odyssey.

THE ODYSSEY

ISTANBUL TO ITHACA

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Tour Leader - Aydin Aygun

Aydin is an absolute gem. Knowledgeable, attentive and super organised he is a class tour leader who knows Turkey and Greece genuinely like the back of his hand. Aydin has been leading tours here for 15 years his enthusiasm for this part of the world is infective and captivating.

THE ODYSSEY BIKE TOUR HIGHLIGHTS
Stage 1- Istanbul to Athens

The Odyssey Bike Tour

  • Istanbul - built on two continents, divided by the Bosphorus, a melting pot of many civilisations both Eastern and Western and certainly one of the greatest cities in the world
  • UNESCO World Heritage Ruins. From Troy where it all began both with its physical remains and for its Homeric literary links to Ephesus, one of the greatest classical cities of the ancient world. Beyond these well-known sites we also roll through ruins of once great cities at every turn from Pergamon to Euromos, Assos to Alexander Troas.
  • Turkey - a succession of historical figures and empires – including the Romans, Byzantines and Ottomans have all left their indelible mark on this ancient country
  • Delightful people - from picnics made by local villagers, ready for us as we roll in to our local crew. The Turkish people are amazing hosts
  • The Turkish delights of the Turquoise Coast. The water is a surreal electric blue, teal and green, the beaches white and underpopulated. It will be hard to board the ferry for Kos (not really!)
  • Bodrum is a lively and friendly city and also the site of the ancient city of Halicarnassus which houses one of the Seven Wonders of the Ancient World, the Mausoleum of Halicarnassus (built circa 353 BCE)
  • Island hopping on our very own luxury yacht through the Dodecanese Islands. For 6 nights we will call the yacht home. We will sail from port to port, riding on and off and exploring one of the most beautiful archipelagos in the world
  • Spectacular Kos, rolling through pine forests with idyllic views and brilliant local tavernas to enjoy before reboarding our gulet to sail on.
  • Leros, Kalymnos, Nisiros and Symi, beautiful lesser known Greek islands with Venetian influences, volcanoes and stunning harbours. Beyond these challenging rides is some of the most beautiful scenery anywhere in the world - this is cycling and exploring genuinely at its very best.
  • One final epic ride in Turkey to finish....cruise from Datcha to beautiful ancient Knidos with its double harbour, along the ReÅŸadiye Peninsula. Our gulets will await us there (as in the pic above!), ready to whisk us off to our final island destination!
Stage 2 - Athens to Ithaca

  • My personal favourite city in the world - Athens! Hectic, noisy and sometimes maddening, Athens is where democracy was born. The history here, with the Acropolis dominating the city, is entwined in everything of our society today and Athenians are hugely proud of their ancestry. A magic place to explore and experience
  • The Peloponnese...mountain ranges which fall dramatically into the Gulf of Corinth, where olive groves, fruit trees and deep forests line the roads and frame the never ending views of the ocean and mountains beyond.
  • Mycenae, Argos and Nemea! Not just where Agamemnon called the Greek forces to invade Troy but also Herakles' stomping grounds! The riding between these is remote and rugged with challenging climbing and a surprising array of quality vineyards!
  • Of all Greece's archaeological sites, Ancient Delphi stands out both for archaeological remains and the museum, and for its presence of place - a close second is Epidaurus, the ancient theatre to dominate all ancient theatres and our lunch spot on day 2!
  • A mid stage dash - after some of the best rugged cycling of the tour we wind our way back to the Gulf of Corinth, where we swap bikes for speed boats and dash across the sea to pretty Galaxidi where the best of hostesses Chrisoula waits, ready to teach and feed us Spanakopita and other local delights.
  • An enduring theme of this Odyssey is spectacular island riding - views, villages, quiet roads and quintessential Greek life - Kefalonia is our last and maybe best taste of this! Our honest opinion is even after all the amazing places you have ridden a bike, this two-wheel island paradise will still blow you away. Be prepared for Alpe d'Huez esc switchbacks overlooking vivid white rocked beaches and ridgeline riding with roads to yourself and views across the perfect azure Ionian Sea!
  • A dream come true for some (well me anyway!) but an Odyssean return to Ithaca where we ride to the Palace where Argos, Odysseus´ loyal wolfhound waited. (please note our logo and this fantastic story of THIS wolfhound!) Our return will certainly not be so violent (you'll have to read The Odyssey!) but it will be dramatic as we celebrate the culmination of our epic adventure.
2025 Tour Dates and Prices
2026 Tour Dates and Prices
Tour Essentials
  • *For 6 nights through the Dodecanese Islands we will be accommodated on a Gulet (Yacht) This accommodation along with Greek Island Entry Taxes are why Stage 1 is significantly more expensive than Stage 2.
  • Rates are based on twin share. Single supplement for Stage 1 is €1950 EUR total (high cost due to cabins on boats). For Stage 2 €900.
  • The fall dates are €300 euros more expensive to cover the boat docking costs which are higher in September.
  • There are master cabins available on all departures, enquire for cost and availability.
  • For bike rental options please click here
Read our guest's personal blog written on 'The Odyssey'

Guest Charles Morgan is pictured here riding along the shores of Symi Island in the Dodecanese, Greece. Charles wrote another fantastic blog on The Odyssey in 2023. You can read Following the Big O right here.

Tour Accommodation

Fittingly on this historic Odyssey, we stay in Ottoman Palaces, Traditional Greek abodes, luxury island resorts and of course our very own luxury Yacht! Here are some places you will stay at on the tour:

Bengodi Hotel, Eceabat Turkey
A beautiful hotel on our second night on tour, next to the eminent Sulva winery where we, of course, dine!
Luxury Yacht, Dodecanese Islands
Our very own luxury Turkish Gulets. For 5 nights our home as we island-hop through the exceptional Dodecanese Islands.
Elecktra Palace, Athens
A neoclassical gem in the heart of Athens. Beautiful rooms, amazing Acropolis views from the pool, what else do you need?
Emelisse Nature Resort, Kefalonia
Our final 3 nights - where else would you stay besides overlooking the Ionian Sea looking towards Ithaka? A class hotel and a magic last abode.
Food and Wine

Nestled between Asia and Europe, Turkish food is diverse and unique. It is an exotic rich fusion of flavours. Greek food is integral to their way of life - it is so much more than sustenance – it’s about culture, comfort, family and life itself.

Suvla Wine Factory, Eceabat Turkey
Sulva Winery is Turkey's leading wine producer and their cellar door is spectacular with food to match!
Marco Polo Mansion, Rhodes
Location, quiet leafy rooftop, superb traditional and modern Greek food make this a favourite tour night out.
Acropolis Museum, Athens
The Acropolis Museum restaurant, has a spectacular reputation and amazing views of the Acropolis. It serves creative dishes based on traditional Greek recipes.
Do you fancy a massage?
Our amazing soigneurs join our tours when our numbers of riders reach 19. What could be better than a massage every few days on tour!
The History

This tour is inextricably linked to Odysseus and his intrepid journey. However, it also takes in so many great Classical and Mythological Greek sites. Odysseus' journey began after the end of the Trojan War with his famous ruse with the Trojan Horse tricking the Trojans when 10 years of vicious battle had failed. Troy fell and archaeological remains (now a UNESCO World Heritage site) tell a story of the raising of a great city around the 13th century B.C.E. which matches nicely with Homer's Iliad and Odyssey tales. Odysseus' journey does not plot with great confidence onto modern geography - Homer certainly doesn't specify locations which are easily identifiable. However, this has not stopped Homer's readers throughout the ages from trying to match his travels with real world landmarks in the Mediterranean. From modern day Tunisia to Sardinia, Mallorca, Sicily and Malta, Odysseus´10 year journey potentially covered much of the known classical Greek world. Luckily his journey by boat leaves us with a lot of flexibility to create our own Odyssey through Classical Turkey and Greece! Our Odyssey takes in this magic part of the Mediterranean's best locations for beauty, cycling and history. Our tour history will journey both through and beyond Odysseus' world, from towering temples and classical ruins dedicated to Odyssean Gods to exceptional historic towns layered for 1000s of years with epoch upon epoch of archaeology. This region of Europe is where our modern western society was born.

Testimonials

Loved all parts of this trip! It’s only when you do some in-depth chatting to the guides that you realise the enormity and critical aspects of the logistics. Accommodation and food was superb (I would really like to kidnap Ali, the cook on our Gulet and have him as my private chef)!!
So happy I was on the Fall trip – the weather was superb. I swam at every possible opportunity!

Nikki Baker, The Odyssey Fall 2024

What an amazing trip. I am still in awe of the ability for you to come up with this concept, develop the itinerary, and think ‘outside the box’ to arrange the highly complex and detailed logistics that it entailed. It is an absolute testament to the team’s attention to detail and the ‘behind the scenes’ operations in moving people/bikes/provisions/border controls from place to place via shuttles, ferries.. it all appears so seamless to us, the clients.

Nikki Baker, The Odyssey Fall 2024
The guides were amazing.  Enrico is calm, organized and gets things done.  We appreciated his relationships with the hotels and restaurants in the smaller villages.  It was so lovely to be welcomed warmly and fed so well.  His knowledge of history was great! Aris is absolutely lovely and kind.  He is a competent mechanic and always there for any bike maintenance.
We have done trips with various cycling tour companies but Bike Odyssey surpassed our previous experiences. We can’t wait for the next trip.  In fact we would like to reserve spots for Hannibal in 2026 please!
Caroline and Danny, The Odyssey Fall 2024

As I look at the Parthenon this evening from the rooftop restaurant… A fantastic historical tour with all and more than I had hoped for in knowledgeable historians of Yasir and our guides.  Marjolein – fantastic rider and physio.  James – the consummate professional guide.  Special appreciation to Moritz for his diligence on the bike, enthusiasm, competence and engaging wit.

Bernie Ritznik, The Odyssey 2023
Oh wow!!!!
That makes the ending of this trip the beginning of another!!!!!
Yes yes yes!!! Book me 🙂
Moyra Deans, The Odyssey 2024

I’ve ridden with Sam’s tours before. He’s a first rate guy running a fantastic operation. If you’re looking to mix culture, great saddle time, good food and wine and stellar company – look no further!

Top 5 Rides South America Bike Odyssey Tours
Alex Berg, The Odyssey 2017

What a magnificent itinerary! The trip was very well organised; all I had to do was turn up in my lycra, rearing to go. Accommodation top notch. Cruising the Greek islands on a gulet – unforgettable.

Sarah Gillis, The Odyssey 2024

Having gone on Othello, the Morocco tour, we signed up for Odyssey, the Turkey/Greece trip. Again, we were not disappointed – Sam and Isabel put on a good show. We will continue to patronize Bike Odyssey for all our international trips as they can’t be matched by other outfits. Highly recommend.

Marina Marra, The Odyssey 2024
See all our testimonials
Some Light Reading
Stone
Funny, insightful and a great read, a perfect book to read as we wind our way down the Turkish coast.
Wilson
The best version to read. Wilson's 2017 translation is the most readable and modern. When sifting through the various translations, this is the one to go for.
Atwood
Reowned author Margaret Atwood has reworked the The Odyssey and tells it from the different perspective of Penelope and the hanged maids.
Mendelsohn
An Odyssey: A Father, a Son, and an Epic
A great story and insight into The Odyssey told through Mendelsohn's relationship with his own father. Great read recommended by Enrico!
Miller
This story of the Trojan War is both very moving and beautifully told. It's an excellent dramatic interpretation.
Cahill
An excellent readable introduction to classical Greek culture - Plato, Homer, Socrates, Aristotle, Athenians and Spartans - essential background!