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.
Turkey and Greece
27 Days / 26 Nights
Watch The Odyssey grading video below
1683km | 1046mi
Istanbul
Athens (Kefalonia)
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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.
Turkey 9 days | Greek Islands 7 days | Greece 12 days
- 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 7 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.
- Beautiful lesser-known Kalymnos with epic island views over the azure oceans.
- Volcanic Nisiros, where we climb to one of the most beautiful Greek villages, Nikia.
- Symi - with its Venetian heritage, this is truly one of the most spectacular harbours to sail into, and ride from! 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!
- 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.
Odyssey
Istanbul to Ithaca
Istanbul to Ithaca
Date
New dates TBC in May, 2027
05 May to 01 June, 2028
Days/Nights
27/26
27/26
Distance
1683km | 1046mi
1683km | 1046mi
Price
€19,800
€19,800
Athens
The Odyssey rides from Istanbul to Ithaka. Prefer a shorter ride? Join or leave us in Athens - get in touch for details.
€140 per night
The single supplement is payable for guests travelling alone who want a room to themselves.
Our new Odyssey What to Expect videos cover everything practical on tour.
From why this is a 3 banana Odyssey to all the essential details - average kms and elevation, terrain, road quality, logistics and weather on this epic Odyssey.
...and don't worry, Sam's 'tattoos' are just arm warmers, a gift from a guest on Che - Thanks Pat!
Enrico, who else!
Enrico is the ultimate man of the world! With over 15 years of guiding experience and speaking more than 7 languages, Enrico is organised, knowledgeable, empathetic and capable. Enrico has also studied in Italy, Spain, Morocco and Australia -he is simply the perfect leader for The Odyssey!
"Enrico was a total professional with a huge heart and impressive knowledge." - Bill
"Enrico’s knowledge and passion for the actual Odyssey story blew my mind! This was clearly not only about cycling, but a great way to follow the history." - Kristi
"The guides were amazing.  Enrico is calm, organised 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!" - Caroline
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:
Luxury Turkish gulets are the epitome of elegance and comfort on the open sea, blending traditional craftsmanship with modern luxury. These handcrafted wooden yachts, often made from mahogany or teak, boast spacious decks, stylish interiors, and first-class amenities, including en-suite cabins, gourmet dining, and attentive crew service. Designed for both relaxation and adventure, gulets offer an intimate sailing experience. Whether riding directly off the boats, basking in the sun, enjoying alfresco dining, or diving into crystal-clear waters, our journeys aboard Turkish gulets are unforgettable. We spend seven nights on our gulets, riding every day, either point to point, with our gulets sailing ahead, or loops to sites or destinations.
Food across Turkey and Greece is best understood as a shared Eastern Mediterranean tradition, split and reshaped over centuries by empire, geography, and the sea itself. Turkish cuisine draws on a vast Ottoman legacy, blending Central Asian, Persian, Arab, and Balkan influences into dishes like kebabs, mezze, and pide, with regional specialities ranging from the rich, butter-laden cooking of the southeast to the olive-oil-based dishes of the Aegean coast. Istanbul alone reflects centuries as an imperial capital, its street food and grand restaurant traditions sitting side by side.
Greece, meanwhile, is defined by its islands and coastline as much as its mainland, with olive oil, fresh vegetables, cheese, and seafood forming the backbone of a cuisine built for a hot, dry climate and a life lived close to the water. Dishes like moussaka, souvlaki, and horiatiki salad reflect simple, ingredient-led cooking, while regional specialities - from Cretan dakos to Macedonian pites - show just how much variation exists within a single national cuisine. Across both countries, the legacy of the Ottoman Empire has left a shared culinary vocabulary - baklava, yoghurt, stuffed vegetables, strong coffee - even as each nation insists, often fiercely, on its own version being the original (of course!).
Bike Odyssey, as always, leans into this regional distinctiveness. Expect a proper Aegean meze spread on a taverna terrace somewhere on the Turkish coast, a plate of freshly grilled octopus and a glass of local wine on a harbourside terrace in the Peloponnese and on the Ionian islands, a slow-cooked kleftiko pulled straight from a wood-fired oven the old way. We'll certainly test a glass of ouzo watching the sun go down over the Aegean, and there'll be no shortage of strong Turkish coffee and honey-soaked baklava to fuel the climbs the next morning!
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. Standing among the excavated walls and trenches today, it takes surprisingly little imagination to picture Agamemnon's fleet massed offshore, or the wooden horse being dragged through the very gates archaeologists have uncovered.
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. Scholars, poets and obsessives have argued for centuries over whether the Cyclops' cave sits in Sicily, whether Scylla and Charybdis guard the Strait of Messina, or whether Calypso's island is Malta, Gozo, or somewhere else entirely lost to time. 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. Every day in the saddle brings another layer of this story to life - a ruined theatre here, a half-submerged harbour wall there, a temple whose columns have watched over this coastline since long before Rome ever rose to prominence. This region of Europe is where our modern Western society was born, and cycling through it remains one of the few ways left to experience its scale, its beauty and its sheer age at the pace it was actually built to be seen.
This is where it all began - before novels, cinema and podcasts, there was just a voice around a fire telling you about a man trying to find his way home. Homer invented the cliffhanger, the flashback, the unreliable narrator, three thousand years before anyone had a word for them. Wilson gets you as close to that original voice as English will allow, rhythm and all. Fry picks up the same story and can't resist adding his own jokes. Miller proves the oldest trick in the book is still the best: make the audience fall in love before you break their heart. Atwood shows what happens when you finally let the silent characters pick up the microphone. Mendelsohn turns the act of teaching this ancient poem into a story every bit as layered as the one Homer told. Cahill traces the line from that fireside voice to pretty much every idea we've had since. Jeff Wright puts it where it belongs, spoken aloud into your ears on a long, long drive and Nolan gives the oldest story ever told the newest technology ever built to tell it on. Storytelling began here. Everything since has just been finding new ways to say it again.
Legendary guest Charlie Morgan is pictured here enjoying a Turkish coffee with fellow Odyssean John.
Charlie wrote this fantastic blog on The Odyssey in 2023. You can read Following the Big O right here.



Sam, Isi, and co. are the real deal. Cyclists can count on this Australia- and Europe-based operator, from picking the most interesting routes to handling logistics to supporting every rider, even not very experienced ones like me. I’ve been on three of their tours, Venetians, The Odyssey, and Tasmania. Their guides are excellent. And you’ll learn some history and eat good food along the way.
Very well planned and amazing. I will be taking another trip with Bike Odyssey!
We have been on 3 tours and have 3 more booked. Bike Odyssey is an EXCELLENT touring company with first-rate guides, fabulous itineraries and attention to detail that is beyond belief. Importantly, this is a small company which means you interact with the owners, who are the decision-makers, not a sales rep or underling who has no authority to make decisions or changes based on your input. Truly, a valuable enterprise!!! I have no hesitation recommending these tours to friends.
My wife and I did The Odyssey tour last year and thoroughly enjoyed it.
We visited amazing places and learnt a lot about the history. The support and tour guides were excellent. We had great companionship from fellow travellers. I fully recommend and trust this company if biking is one of your favourite activities.
My wife and I are both in our seventies and we have thoroughly enjoyed every adventure. There are certainly some challenging days, but Bike Odyssey does an excellent job of balancing the harder rides with easier days and well-timed rest days.
These trips have provided us with some truly wonderful experiences and memories. We would not hesitate to recommend Bike Odyssey to anyone looking for a well-run cycling holiday with a rich cultural dimension
My wife and I have now completed three tours with Bike Odyssey – Morocco, Japan, and most recently Turkey and Greece – and every trip has been outstanding. The tours are exceptionally well organised, with excellent guides, high-quality accommodation, reliable transport, and great attention to detail throughout.
What sets Bike Odyssey apart is that their tours are not just about cycling. Each trip has a strong historical and cultural theme, giving you a real understanding of the places you visit and the people who live there.
The bike tour was incredible and memorable and gave us extra extra extraordinary experiences which Rob and I have never had the opportunity to experience before.
The team leaders were awesome – always thinking ahead. They are the best.
Thank you for all the hard work behind the scenes. Huge credit to the trip designer (Sam) who did a magnificent job.
What a great trip we had!
The team was just excellent and trying to get Sue and I off the boats was nearly impossible.
Our fingernail marks are still etched into the deck as they dragged us off….
The guides did an incredible job which surpassed all my expectations!
Congratulations and thanks to all of them!
The trip was rewarding for me: I would not want to miss it!
Over the past 25 years, I’ve done many tours, and I can honestly say that it’s the best tour I’ve ever done. The planning, support and accommodation were excellent. And the guides – the friendliest, most enthusiastic and well-informed, and keen to share their knowledge. I enjoyed every day. Some of the best riding I’ve done. I’d do it again; the route was wonderful!
I’m really looking forward to doing Venetians in 2026!
If anyone is on the lookout for an adventurous way to see foreign lands, we highly recommend joining a cycling tour with Bike Odyssey! Cycling from Istanbul to Athens was so experiential and lots of fun. We will always remember the friendships and quips shared with fellow cyclists (adventurers). And we will never forget the humour, support and organisation from our guides.
Wow, what a trip. Had high expectations and everyone of them was surpassed!
Where do I start? The tour – phenomenal!
I cannot speak highly enough of our guide team! Organising a group of people of such a range in ages, personalities, demographics etc. can be like herding cats, but we were well informed, prepared for each day and I felt completely safe, supported and incredibly well looked after both on and off the bike. Enrico’s knowledge and passion for the actual Odyssey story blew my mind! This was clearly not only about cycling, but a great way to follow the history.
The accommodation and meals were fabulous. I have told so many people how incredible Bike Odyssey has been to travel with!
A massive well done for the quality of tour you guys have created from the itinerary; the accommodation, the food and without doubt the most professional, personable and caring guides we have encountered. They are really your point of difference. Never ‘flustered’ but always accommodating and tolerant . This also includes the day guides we had particularly at the Acropolis and Delphi
Thank you again and we look forward to our next Bike Odyssey ride!
I really enjoyed The Odyssey Part 1. A little easier riding as expected, and the gulets made packing (or lack thereof!) a non-issue. The Greek Islands are magical and the Anzac coast was quite an emotional experience with so many Aussies on the trip.
It has been the BEST first day. Everyone is lovely, the riding was stunning and Enrico, Moris and Alex are a great support crew. I’ve been on a number of cycling tours as a rider and also as a charity rep for work and the team can make or break it…you guys have nailed it.
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!
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.
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!
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.
Oh wow!!!!That makes the ending of this trip the beginning of another!!!!!Yes yes yes!!! Book me 🙂
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!
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.
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.






