Another World Adventures

Greece Sailing Adventure: Cyclades Islands

Duration: 10 days
View Dates

Fulfil your dreams of sailing the Greek Islands on a ten-day seafaring adventure around the renowned Cyclades.

Setting off from Santorini, cruise the Aegean Sea in search of ancient towns, secluded coves and holiday hotspots like Mykonos and Paxos. Throw in some freshly caught seafood, local wines and a laidback way of life, and you’re set to drift and roll to the patterns of the ocean. Cool off with regular swims in the Aegean’s turquoise seas and get the lay of the land from a local leader who’s got all the people in the right places. Trust us – it’s all smooth sailing from here.

Why you'll love this adventure

  • A Santorini sunset around the caldera is a sight to behold. Walk along the volcanic rim of the island past white villages that cling to plunging cliffs and watch as day turns to night in the most stunning of ways.
  • Sail the Aegean Sea on your small group yacht and island-hop through the Cyclades, taking regular stops to swim off the side of your boat and letting the pitch and roll of the ocean help you sleep at night.
  • Feast on fresh seafood at a sleepy waterfront taverna in the Small Cyclades islands – far away from tourist crowds and deep in the local way of life. This is island living, Greek style.
  • Step back in time among the Venetian architecture of Naxos and consider learning about rural life with a daytrip to a country village – a couple of the many experiences to be had around the Cyclades.
  • No Greek island adventure is complete without a stop in Mykonos. Embrace your hedonistic side with its boutique culture and nightlife or relax on one of the many beaches dotted along the coast.
Start
Santorini
Finish
Santorini
Trip Duration
10 Days
Group Size
Min 1, Max 11
Activity
Sailing
Style of Travel
Guided Group, Private Departure, Solo Traveller

Dates

From

Saturday

13 July 2024

To

Monday

22 July 2024

From

Wednesday

17 July 2024

To

Friday

26 July 2024

From

Tuesday

23 July 2024

To

Thursday

1 August 2024

From

Saturday

27 July 2024

To

Monday

5 August 2024

From

Friday

2 August 2024

To

Sunday

11 August 2024

From

Tuesday

6 August 2024

To

Thursday

15 August 2024

From

Monday

12 August 2024

To

Wednesday

21 August 2024

From

Friday

16 August 2024

To

Sunday

25 August 2024

From

Thursday

22 August 2024

To

Saturday

31 August 2024

From

Monday

26 August 2024

To

Wednesday

4 September 2024

From

Sunday

1 September 2024

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Tuesday

10 September 2024

From

Thursday

5 September 2024

To

Saturday

14 September 2024

From

Wednesday

11 September 2024

To

Friday

20 September 2024

From

Sunday

15 September 2024

To

Tuesday

24 September 2024

From

Saturday

21 September 2024

To

Monday

30 September 2024

From

Tuesday

1 October 2024

To

Thursday

10 October 2024

From

Friday

11 October 2024

To

Sunday

20 October 2024

From

Saturday

3 May 2025

To

Monday

12 May 2025

From

Tuesday

13 May 2025

To

Thursday

22 May 2025

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Friday

23 May 2025

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Sunday

1 June 2025

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Tuesday

27 May 2025

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Thursday

5 June 2025

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2 June 2025

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Wednesday

11 June 2025

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Friday

6 June 2025

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Sunday

15 June 2025

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Thursday

12 June 2025

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Saturday

21 June 2025

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Monday

16 June 2025

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Wednesday

25 June 2025

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Sunday

22 June 2025

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Tuesday

1 July 2025

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Thursday

26 June 2025

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5 July 2025

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2 July 2025

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11 July 2025

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6 July 2025

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15 July 2025

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Saturday

12 July 2025

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Monday

21 July 2025

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Wednesday

16 July 2025

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25 July 2025

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Tuesday

22 July 2025

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Thursday

31 July 2025

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Saturday

26 July 2025

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4 August 2025

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Friday

1 August 2025

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Sunday

10 August 2025

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Tuesday

5 August 2025

To

Thursday

14 August 2025

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Monday

11 August 2025

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Wednesday

20 August 2025

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Friday

15 August 2025

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Sunday

24 August 2025

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Thursday

21 August 2025

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Saturday

30 August 2025

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Monday

25 August 2025

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Wednesday

3 September 2025

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Sunday

31 August 2025

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Tuesday

9 September 2025

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Thursday

4 September 2025

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Saturday

13 September 2025

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Wednesday

10 September 2025

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Friday

19 September 2025

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Sunday

14 September 2025

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23 September 2025

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Saturday

20 September 2025

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Monday

29 September 2025

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Wednesday

24 September 2025

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Friday

3 October 2025

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Tuesday

30 September 2025

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Thursday

9 October 2025

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Saturday

2 May 2026

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Monday

11 May 2026

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Tuesday

12 May 2026

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Thursday

21 May 2026

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Friday

22 May 2026

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Sunday

31 May 2026

From

Tuesday

26 May 2026

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Thursday

4 June 2026

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Monday

1 June 2026

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Wednesday

10 June 2026

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Friday

5 June 2026

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Sunday

14 June 2026

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Thursday

11 June 2026

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Saturday

20 June 2026

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Monday

15 June 2026

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Wednesday

24 June 2026

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Sunday

21 June 2026

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Tuesday

30 June 2026

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Thursday

25 June 2026

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Saturday

4 July 2026

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Wednesday

1 July 2026

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Friday

10 July 2026

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Sunday

5 July 2026

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Tuesday

14 July 2026

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Saturday

11 July 2026

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Monday

20 July 2026

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Wednesday

15 July 2026

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Friday

24 July 2026

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Tuesday

21 July 2026

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Thursday

30 July 2026

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Saturday

25 July 2026

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Monday

3 August 2026

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Friday

31 July 2026

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Sunday

9 August 2026

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Tuesday

4 August 2026

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Thursday

13 August 2026

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Monday

10 August 2026

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Wednesday

19 August 2026

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Friday

14 August 2026

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Sunday

23 August 2026

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Thursday

20 August 2026

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Saturday

29 August 2026

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Monday

24 August 2026

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Wednesday

2 September 2026

From

Sunday

30 August 2026

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Tuesday

8 September 2026

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Thursday

3 September 2026

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Saturday

12 September 2026

From

Wednesday

9 September 2026

To

Friday

18 September 2026

From

Sunday

13 September 2026

To

Tuesday

22 September 2026

From

Saturday

19 September 2026

To

Monday

28 September 2026

From

Wednesday

23 September 2026

To

Friday

2 October 2026

From

Tuesday

29 September 2026

To

Thursday

8 October 2026

This trip can be tailor made for your perfect travel dates. Please make a booking enquiry for more information.

Itinerary

This trip includes an action packed itinerary! Please make an enquiry and we'll send you the full itinerary for each day including meals, activities, travel and accommodation.

Enquire Today
Greece Sailing Adventure: Cyclades Islands

What's included

  • 0 breakfasts, 0 dinners and 0 lunches
  • Overnight boat (9 nights)
  • Boat

Trip notes

Price

From £1386 land only (flight option package available from some countries on request)

Min age

15

Accommodation

Overnight boat (9 nights)

Accommodation notes

This trip is accommodated entirely on board a yacht of between 54ft to 56ft. A typical yacht for 11 travellers is equipped with a mixture of 2 x double cabins, 2 x twin cabins and 1 x triple cabin. There are 5 shared bathrooms. Our boats are real yachts and this is a real sailing trip. Yachts are designed to keep sleeping areas to the absolute minimum of space, while maximising common areas as much as possible. 

Rooms are allocated on arrival by our skipper according to group composition, which means it is not possible to reserve or guarantee any specific berth or cabin. Single passengers will be paired up with another passenger of the same gender, this may mean sharing a double cabin with a double mattress. Everyone including the skipper shares the bathrooms on board.

While not everyone may feel entirely comfortable living in such close quarters, those who are looking to revel in the adventure and exhilaration of an authentic sailing trip usually find any discomfort from cramped living conditions is more than made up for by the whole experience.

ADDITIONAL ACCOMMODATION:
Please note that the majority of our sailing trips start and/or finish at a marina or port. For most of our destinations, we can provide transfers between the airport/hotel and the port/marina. Please check the joining and finish point information in the trip notes for details.

ELECTRICITY:
While there should be electricity on board throughout your trip the voltage is likely to vary widely, from 12V to 220V, and when in port or moored we are dependent on the supply available. Please be aware that the supply may not be sufficient to power some electronic devices all the time and that you may need a voltage adapter or similar (such as portable inverter used in cars). On some trips it may be possible to charge devices ashore at restaurants or resorts, however this is not guaranteed.

WI-FI:
Please note that our sailing boats do not have Wi-Fi. You will be getting off the boat and visiting towns regularly so you will be able to connect with the outside world then.

Meals

0 breakfasts, 0 dinners and 0 lunches

Food and dietary requirements

The amazing food on offer is one of the highlights of any trip in Europe. To make the most of this we’ve structured our meal arrangements to provide both flexibility and variety.

For most dinners and some lunches we will moored in a port or marina near meaning that the group will have a choice of on-land eating options available. We find our group often eat together however you have the freedom to go off and do your own thing. Our skippers can recommend options for restaurants and on many occasions will dine with the group.

While your skipper will co-ordinate the shopping for and preparation of these meals we’ve found that the best trips are those where everyone pitches in together to help with the meal preparation.

If you have dietary requirements and/or food allergies please notify us at the time of booking so we can determine the extent to which your dietary requirements can be met. There are many vegetarian options available in Greece, Croatia, Italy and France though vegans might find their choice less varied especially away from the bigger cities. Travellers that require a gluten free diet may also find their choices limited. Most of our trips start in a larger towns where you will find greater choice of supermarkets and markets however they do not stock the range of gluten free products that you may be used to at home.

Who is this trip for?

Is this trip right for you

As the majority of this trip takes place on a sailing boat, you’ll need to feel comfortable with moving about the vessel, including the use of stairs. With that said, sea legs come naturally to some but not so much for others. Most of our departures run in peak season, when the seas are calmer. The ship will experience some roll and pitch in choppy conditions, however all of our ships come equipped with stabilisers to minimise movement. There will be seasickness tablets on board and your crew will do all they can to minimise any discomfort.

A Zodiac is used to transport passengers from the boat to the mainland, with landings taking place at piers (dry landings) as well as on beaches (wet landings). Zodiacs can sometimes be awkward to climb in and out of, but a sense of humour and can-do attitude is all you need.

This is an adventure on board a real yacht, which means living spaces, cabins, bathrooms and showers need to be shared with other passengers. Sleeping quarters can be quite compact, but you will be spending the majority of your time above board in the open air.

Time on the water also means time in the sun. Remember to pack sun protection, such as sunscreen and a hat, and drink plenty of water to keep hydrated. See the Essential Trip Information below for a full packing list.

Please note that smooth sailing is dependent on the weather, so itinerary changes may occur at the last minute if the weather becomes unfavourable. If any changes are made, you can trust in your knowledgeable skipper to choose an alternative route or activity.

Due to the size of the yachts, sound carries easily from one side to the other and can wake your fellow travellers. If you’re planning to have a late night, it’s a good idea to head into town and experience the local nightlife.

Transport notes

This is a sailing adventure so our time is spent on board a monohull yacht. You may be asked to assist on-deck, particularly when coming into or leaving port. No experience is necessary, but getting to know some ‘sailing language’ might help to get you into the spirit of the adventure.

Bow – front of the boat
Stern – rear of the boat
Port – left
Starboard – right
Deck – outside, upper area of the boat
Hull – the main part or body of the boat
Keel – part of the boat under water that keeps the boat stable and stops it capsizing
Mainsail – the large sail attached to the mast and boom
Mast – the big vertical pole that supports the mainsail
Boom – the big horizontal pole attached to the mainsail, coming off the rear of the mast (swing from side to side)
Jib, headsail, genoa, foresail – smaller sail near the front of the boat
Sheet – ropes used to control the sails
Booty – another word for pirate treasure
Lines – other ropes on the boat (ropes are never called ropes on yachts)
Spinnaker – large extra sail
Trim the sails – adjust the position of the sails when the wind changes strength or direction
Tiller or wheel or helm – used to steer the boat
Helmsman – person steering the boat
Running – sailing with the wind
Tack – turning the bow of the boat when sailing through the wind
Jibe – turning the stern of the boat when sailing through the wind
Figure-eight knot – the stopper: often used at the end of lines to stop them getting away.
Bowline (knot) – strong and dependable knot that is commonly used
Clove Hitch (knot) – not as secure it is often used to attach an object to a line

Additional notes

Covid-19

Health related to Covid-19. This operator has a policy in place for COVID-19 and their adventures. Please request full details so we can share the most up to date information with you and be aware that the note below was relevant at the time of writing but may have changed. Thanks!

Is this trip right for you

As the majority of this trip takes place on a sailing boat, you’ll need to feel comfortable with moving about the vessel, including the use of stairs. With that said, sea legs come naturally to some but not so much for others. Most of our departures run in peak season, when the seas are calmer. The ship will experience some roll and pitch in choppy conditions, however all of our ships come equipped with stabilisers to minimise movement. There will be seasickness tablets on board and your crew will do all they can to minimise any discomfort.

A Zodiac is used to transport passengers from the boat to the mainland, with landings taking place at piers (dry landings) as well as on beaches (wet landings). Zodiacs can sometimes be awkward to climb in and out of, but a sense of humour and can-do attitude is all you need.

This is an adventure on board a real yacht, which means living spaces, cabins, bathrooms and showers need to be shared with other passengers. Sleeping quarters can be quite compact, but you will be spending the majority of your time above board in the open air.

Time on the water also means time in the sun. Remember to pack sun protection, such as sunscreen and a hat, and drink plenty of water to keep hydrated. See the Essential Trip Information below for a full packing list.

Please note that smooth sailing is dependent on the weather, so itinerary changes may occur at the last minute if the weather becomes unfavourable. If any changes are made, you can trust in your knowledgeable skipper to choose an alternative route or activity.

Due to the size of the yachts, sound carries easily from one side to the other and can wake your fellow travellers. If you’re planning to have a late night, it’s a good idea to head into town and experience the local nightlife.

Health

GENERAL HEALTH
All travellers need to be in good physical health in order to participate fully on this trip. For the safety and wellbeing of yourself and others, if you are unwell prior to travelling, please stay at home and contact us to make alternative arrangements.

When selecting your trip please make sure you have read through the itinerary carefully and assess your ability to manage and enjoy our style of travel. Please note that if in the assessment of our group leader or local representative a traveller is unable to complete the itinerary without undue risk to themselves and/or the rest of the group, we reserve the right to exclude them from all or part of a trip without refund.

You should consult your doctor for up-to-date medical travel information or for any necessary vaccinations before departure. We recommend that you carry a first aid kit as well as any personal medical requirements in their original packaging as they may not easily be obtained while travelling. If you are carrying medication, ensure you check your government’s foreign travel advice for any local restrictions or requirements. 

CPAP Machines:
If you are travelling with a CPAP machine on our Europe sailing trips, please note that there is a 220V socket in each cabin on most boats. These sockets only work when we are connected to shore power and is only available at some of the ports that we visit. Sometimes shore power sockets are interrupted causing a trip of the supply or is not available at all. We cannot guarantee power for the whole trip so we recommend that you bring a back-up battery (or two). If you are travelling by yourself, you will need to pay a single supplement to limit disruption to other passengers.

Your fellow travellers

As you travel on a group trip you will be exposed to all the pleasures and maybe some of the frustrations of travelling in a group. Your fellow travellers will probably come from all corners of the world and likely a range of age groups too. We ask you to be understanding of the various needs and preferences of your group – patience with your fellow travellers is sometimes required for the benefit of everyone’s travel experience. Remember too that you have responsibilities to the group. If you are requested to be at a place at a certain time, ensure that you don’t keep the rest of the group waiting. We have found time and time again that the very best trips we operate are those where the dynamics within the group work well – this takes just a little effort on your part. Due to privacy reasons, we are unable to provide you with contact details and any personal information about your fellow travellers booked on your trip prior to departure.

The bonus of our sailing adventures are that they are small groups, a maximum of 8 – 11 travellers (with the average number of travellers 7). However when you add in a Skipper and the fact you will be eating, sleeping and lounging about together for up to 9 days in the confines of a monohull you may need to call on some patience, maybe some headphones but above all a sense of humour.
Most travellers come away from our sailing adventures saying it was a the trip of a lifetime and that they have made lifelong friends…………..we’re sure you will too!

If you wish to have a single cabin on our sailing trips, please advise at the time of booking. You will be required to pay double to guarantee a cabin to yourself.

PARTICIPATION:
You don’t need to hold a recreational skippers ticket or any sailing experience at all to join this trip however you may be called on to help around the boat, help keep the bathrooms and galley clean by emptying the bins and overall keeping the communal areas free and available for your fellow travellers. You will also be asked to chip in at meal time, either helping with food preparation, cooking, setting or clearing the table and washing up dishes.

Covid-19

This operator has a policy in place for COVID-19 and their adventures. Please request full details so we can share the most up to date information with you. Thanks!

Tour operator

We love this operator for the freedom and flexibility they give travellers to get off the tourist trails and really experience local cultures. Their style of small group travel is perfect for solo travellers, couples or small groups of friends and their grassroots style of travel seeks to have a positive impact on the communities they visit.

They use local leaders, local accommodation & transport and support local community projects, ensuring sustainability is at the centre of everything they do.

In addition, they expect their staff and travellers to demonstrate the principles of responsible travel – respecting people, cultures and local environments; in the distribution of wealth; in good will and cross-cultural sharing; and in contributing to sustainable development.

 

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Greece Sailing Adventure: Cyclades Islands

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A most helpful, friendly and knowledgeable travel company!

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