Greek Islands cycling and sailing holiday

“Cycle and sail amongst the stunning scenery of the Cyclades as you experience ancient sites, untouched villages, beautiful beaches and 160kms spent in the saddle.”


Kythnos Island | Merichas | Seriphos Island | Siphnos Island | Syros Island | Ermoupolis - capital of the Cyclades | Coastal cycle rides | Mykonos Island | Delos Island - birthplace of Apollo | Tinos Island | Kea Island | Time to visit monasteries, tavernas, Aegean beaches, churches, mountain villages and towns

Description of Greek Islands cycling and sailing holiday

This Greek Islands cycling and sailing holiday takes you to the South Aegean to a group of islands called the Cyclades. It’s a beautiful part of the world, full of white sandy beaches, bright blue waters and narrow cobbled streets lined with whitewashed houses. Unsurprisingly, the islands attract plenty of tourists, but as well as taking in the most popular sights, this small group tour will take you to quiet coves, little-visited rock formations and villages well off the tourist trail.

Starting from the yacht harbour of Piraeus, near Athens, you’ll spend your days cruising from island to island and exploring historic sites, towns and villages by bike, at a relaxed and enjoyable pace. You’ll visit six islands in total, and as well as spending time in the saddle, there will be plenty of opportunity to chill out on beaches, take leisurely swims and spend evenings out in cosy tavernas.

Travel Team

If you would like some help or advice, or just want to discuss your ideas for your next trip, do give us a call.


Check dates, prices & availability

31 Aug 2019
excluding flights
07 Sep 2019
excluding flights
14 Sep 2019
excluding flights
21 Sep 2019
excluding flights
Our top tip:
Although there are a limited number of helmets available it's well worth bringing your own from home to ensure maximum safety.
Trip type:
Small group. Avg size 14-20.
Activity level:
Moderate. Avg 25km daily cycle.
Sailing boat with double berth cabins. Deck level cabins available at a supplement.
21 speed trekking bike, fully crewed sailing boat, 6 guided cycle tours, entrance fees.
7 breakfasts, 6 lunches, 2 dinners.
Single cabin supplement applies.
Holiday type
Small group holidays
Small group travel is not large group travel scaled down. It is modelled on independent travel – but with the advantage of a group leader to take care of the itinerary, accommodation and tickets, and dealing with the language. It’s easy to tick off the big sights independently – but finding those one-off experiences, local festivals, travelling markets and secret viewpoints is almost impossible for someone without the insider knowledge gained from years in the field. If you’re heading off on a gap year your, perhaps – but for those with a two-week holiday, a small group tour will save valuable planning time.

The leaders are not guides – they’re not there to shepherd you around. Instead, they’ll let you know which local restaurant serves great value food – without running the risk of travellers’ tummy. They’ll allow you to avoid hour-long queues at train stations and attractions.

We like to think of small group travel as the Goldilocks option. It is independent travel without the fuss, worry and bunk beds – and organised travel without the coaches. And it’s cheaper than a tailor made tour. It’s sits somewhere in the middle – and we think it’s just about right.
What are the main benefits?
Big experiences
Have big, life-enriching experiences that would be impossible to organise without lots of time and insider knowledge.

Make the most of your holiday time by letting someone else do the hard work and boring logistics!

Peace of mind
Small group tours take care of the security aspects – and provide a safety net should anything unexpected happen.
Who is it ideal for?
Travellers who are short of time
If you don’t have three months to spend exploring, small groups trips let you cover more ground in less time. Your days are not spent queuing for tickets or finding hotels – so you can squeeze more into your holiday.

Solo travellers who’d like company
Likeminded travel companions plus peace of mind for those travelling alone. Single supplements are usually available – providing privacy if you want it.

Less confident travellers
Stray from the tourist trail without worrying about getting lost, and meet local people without dealing with the language barrier.
“I won’t get any privacy!”
Couples and friends have private rooms, and you can choose to eat alone or not. Single supplements give solo travellers their own room.

“There won’t be any free time”
Free mornings or afternoons let you explore on your own, or just relax.

“The accommodation will be basic”
Trips are as high or low end as you like. Though off the beaten track destinations won’t have luxury hotels, this is all part of the adventure.

“I won’t like the other travellers!”
Tour operators try to create groups with a similar demographic – age, families, activity levels... Chances are, you’ll even make new friends.

“Will we be following an umbrella?”
Meet a group leader
As well as taking care of all the day-to-day practicalities, your group leader is the one who will turn your trip into an adventure. Leaders are extraordinary characters – the kind of person who has spent 14 Christmas days on the slopes of Mount Everest, runs marathons wearing tiger suits to raise funds for their conservation and thinks nothing of leading an overland trip in Sudan or Afghanistan. Fearless and inspiring, group leaders are as important as the destination itself.

Meet a local guide
No matter how experienced your group leader, they can never make up for the knowledge gained from a lifetime in the destination. That’s why many of our trips work with local guides around the world – who invite you into their homeland with pleasure. As well as doing crazy things like climbing Kilimanjaro 100 times, they also donate their time to local projects supported by travellers – such as rebuilding Sri Lankan villages following the 2004 tsunami.

Responsible tourism

Responsible tourism: Greek Islands cycling and sailing holiday


This exceptional ship based experience is heightened by the fact that we are not using a massive cruise liner, rather, a small boat which uses much less fuel, creates fewer emissions and creates much less visual and noise pollution for the local people who encounter it during your travels.

Travelling by bicycle is one of the lowest impact forms of travel. In the company of a local guide you will travel, by bike, to some of the more remote sections of Greece’s Cyclades Islands and travel through its landscapes and villages and your guide will ensure that we leave no visible trace behind. By travelling in a small group we further minimise our impact on the landscapes and communities we visit.

Our environmental sustainable principles
True sustainability is a guiding aspect in all aspects of our business planning and operations. Specifically our tour operations should be managed in a way where the natural and cultural values of the host region are undiminished in the long-term.

Where possible, we engage in partnerships with local environmental groups and/or land managers to actively campaign for conservation or promote environmental protection and/or rehabilitation.

Our Responsible Travel Guidebook
Our philosophy since 1975 has been to leave only footprints and take only photographs. To reiterate this, every customer who travels with us receives a copy of our award-winning Responsible Travel guidebook. This detailed book outlines our environmentally sustainable principles, and outlines how each customer can minimize their impact while travelling.

Global Warming and Carbon Balancing
The root cause of Global Warming is society's dependence on emission creating fossil fuel. Planting trees is not going to reverse this trend or cancel our carbon emissions very quickly or effectively. We believe the way to reduce these dependencies is to create clean energy production. Therefore, we support renewable energy projects like wind and solar power, and we are aligned with Climate Friendly, the gold standard setter in effective, meaningful action addressing climate change. So, while we believe that tree planting can play a small role in greenhouse gas abatement, we have gone the extra mile in promoting a longer term solution. Is this cheap? No. Is it responsible? Absolutely!


Your guide and crew are all local. They are people who know and love Greece and are passionate about sharing it with you in a responsible manner. They will help you maximise the encounters you have with local people allowing for a more fulfilling cultural experience. You will also assist many communities on islands that are not on the mainstream tourism trails. Since we travel by bike and yacht we are able to access places most travellers never visit hence allowing you to spread the benefits of your tourism dollars further. Unlike larger cruise style holidays, each evening you will be able to discuss your day at length with local crew and learn more about the region you are travelling through which will ultimately provide a more enriching cultural experience.

Our local partner donates €5 from each travellers tour cost to a clinic taking care of families whose children have been receiving cancer treatment. With the monies raised these families are invited to experience this trip for free, to allow them to forget about their troubles for a short time. It is an experience most of these families would not have a budget for after paying for medical expenses.

Our responsible travel principles
Our company aims to maximise the positive benefits of tourism for host communities. This includes training and employment of local staff, using local suppliers and assisting in the development of sustainable local businesses. We actively minimise the negative effects that tourism can have by ensuring that tourism does not divert resources away from local communities or drive up prices on local resources.

We provide opportunities for real cultural exchange, where locals and visitors alike can share and learn from each other in an environment of mutual respect. We contribute to the welfare of the host community. This is epitomised in our Community Project Travel program where we organise for our travellers to spend time in disadvantaged villages upgrading basic facilities such as health, education and water access.

We strive to educate our travellers about the destination and its local cultures as well as providing guidelines on appropriate behaviour to minimise impact.

No local payments policy
Local cash payments are becoming increasingly popular with many operators in the adventure travel industry. This policy seems to benefit the tour operators more than the local economies or the travellers, as it avoids local taxes and transfers the costs and risks of cash handling onto the travellers. In accordance with our Responsible Travel practices, we have chosen a policy of not asking for such payments.

2 Reviews of Greek Islands cycling and sailing holiday

4.5 out of 5 stars

Reviewed on 03 Jul 2016 by

1. What was the most memorable or exciting part of your holiday?

Start to finish this was the BEST vacation I've ever taken. Everything about the cycling and sailing was planned so well and I just got to cycle, enjoy the company and the great views and food!!This was a cycling trip to Ionian Islands in Greece; not the Umbria trip.

2. What tips would you give other travellers booking this holiday?

If you aren't fit for cycling and especially some steep and long hill climbs, then take the e-bike option. All who did the trip were thrilled with the vistas but if you aren't in shape you won't e able to tackle those hills!

3. Did you feel that your holiday benefited local people, reduced environmental impacts or supported conservation?

Definitely, we followed philosophy of Leave No Trace.

4. Finally, how would you rate your holiday overall?

10 out of 10. If you want to see the real Greece and not just hot tourist spots which are crowded and expensive, then hit the side roads with a cycle and sail tour.

Reviewed on 21 Sep 2016 by

1. What was the most memorable or exciting part of your holiday?

Good company - both crew and holidaymakers

2. What tips would you give other travellers booking this holiday?

Take chewy bars/energy gels for the longer rides

3. Did you feel that your holiday benefited local people, reduced environmental impacts or supported conservation?

Not really

4. Finally, how would you rate your holiday overall?

Great fun

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