Another World Adventures

Greece Sailing Adventure: Cyclades Islands

Duration: 10 days
View Dates

Sail through the gorgeous Greek Islands on a ten-day seafaring adventure around the Cyclades.

Setting off from Santorini, you’ll 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 turquoise seas and get the lay of the land from a local leader who’s got all the people in the right places.

Why you'll love this adventure

  • 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.
  • Walk along the volcanic rim of Santorini, past white villages that cling to cliffs and watch as day turns to night during sunset at the caldera – this is a memory you’ll bring home!
  • 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.
  • Step back in time among the Venetian architecture of Naxos and consider learning about rural life with a daytrip to a country village.
  • Visit Mykonos for the quintessential Greek Islands experience. Embrace your hedonistic side with the 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

3 May 2025

To

Monday

12 May 2025

From

Tuesday

13 May 2025

To

Thursday

22 May 2025

From

Friday

23 May 2025

To

Sunday

1 June 2025

From

Tuesday

27 May 2025

To

Thursday

5 June 2025

From

Monday

2 June 2025

To

Wednesday

11 June 2025

From

Friday

6 June 2025

To

Sunday

15 June 2025

From

Thursday

12 June 2025

To

Saturday

21 June 2025

From

Monday

16 June 2025

To

Wednesday

25 June 2025

From

Sunday

22 June 2025

To

Tuesday

1 July 2025

From

Thursday

26 June 2025

To

Saturday

5 July 2025

From

Wednesday

2 July 2025

To

Friday

11 July 2025

From

Sunday

6 July 2025

To

Tuesday

15 July 2025

From

Saturday

12 July 2025

To

Monday

21 July 2025

From

Wednesday

16 July 2025

To

Friday

25 July 2025

From

Tuesday

22 July 2025

To

Thursday

31 July 2025

From

Saturday

26 July 2025

To

Monday

4 August 2025

From

Friday

1 August 2025

To

Sunday

10 August 2025

From

Tuesday

5 August 2025

To

Thursday

14 August 2025

From

Monday

11 August 2025

To

Wednesday

20 August 2025

From

Friday

15 August 2025

To

Sunday

24 August 2025

From

Thursday

21 August 2025

To

Saturday

30 August 2025

From

Monday

25 August 2025

To

Wednesday

3 September 2025

From

Sunday

31 August 2025

To

Tuesday

9 September 2025

From

Thursday

4 September 2025

To

Saturday

13 September 2025

From

Wednesday

10 September 2025

To

Friday

19 September 2025

From

Sunday

14 September 2025

To

Tuesday

23 September 2025

From

Saturday

20 September 2025

To

Monday

29 September 2025

From

Wednesday

24 September 2025

To

Friday

3 October 2025

From

Tuesday

30 September 2025

To

Thursday

9 October 2025

From

Friday

10 October 2025

To

Sunday

19 October 2025

From

Wednesday

15 October 2025

To

Friday

24 October 2025

From

Saturday

2 May 2026

To

Monday

11 May 2026

From

Tuesday

12 May 2026

To

Thursday

21 May 2026

From

Friday

22 May 2026

To

Sunday

31 May 2026

From

Tuesday

26 May 2026

To

Thursday

4 June 2026

From

Monday

1 June 2026

To

Wednesday

10 June 2026

From

Friday

5 June 2026

To

Sunday

14 June 2026

From

Thursday

11 June 2026

To

Saturday

20 June 2026

From

Monday

15 June 2026

To

Wednesday

24 June 2026

From

Sunday

21 June 2026

To

Tuesday

30 June 2026

From

Thursday

25 June 2026

To

Saturday

4 July 2026

From

Wednesday

1 July 2026

To

Friday

10 July 2026

From

Sunday

5 July 2026

To

Tuesday

14 July 2026

From

Saturday

11 July 2026

To

Monday

20 July 2026

From

Wednesday

15 July 2026

To

Friday

24 July 2026

From

Tuesday

21 July 2026

To

Thursday

30 July 2026

From

Saturday

25 July 2026

To

Monday

3 August 2026

From

Friday

31 July 2026

To

Sunday

9 August 2026

From

Tuesday

4 August 2026

To

Thursday

13 August 2026

From

Monday

10 August 2026

To

Wednesday

19 August 2026

From

Friday

14 August 2026

To

Sunday

23 August 2026

From

Thursday

20 August 2026

To

Saturday

29 August 2026

From

Monday

24 August 2026

To

Wednesday

2 September 2026

From

Sunday

30 August 2026

To

Tuesday

8 September 2026

From

Thursday

3 September 2026

To

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 £1450 land only (flight option package available from some countries on request)

Min age

Accommodation

Meals

Who is this trip for?

Additional notes

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.

 

Enquire today

Greece Sailing Adventure: Cyclades Islands

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Please complete the enquiry form above with as much detail as you can and we will send you all the trip information and connect you with the operator so you can make a booking directly.

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A most helpful, friendly and knowledgeable travel company!

Very helpful and provided lots of research material and excellent personal perspectives on the tall ship sailing trip I was interested in taking.

— Martin

Excellent thoughtful service.

They were prompt and friendly, and so thorough and helpful in connecting me with my adventure.

— Tina

One of a Kind Service!

From the very beginning of reaching out to AWA, they were super helpful, enthusiastic and informative.

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