Greece Sailing Adventure: Cyclades Islands




















From AUD $2880
Group Tour
Average
Rating
(20 reviews)

Greece Sailing Adventure: Cyclades Islands
10 days
Group Tour
Moderate
Average
English
Experience Overview
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.
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.
Highlights
- 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.
Trip Details
10 days
Boat
Group Tour
English
Santorini – Ios, Greece
Santorini, Greece
Moderate
SailVentures
Average
Itinerary
Accommodation:
- Overnight boat (Number of Nights: 1)
Accommodation:
- Overnight boat (Number of Nights: 1)
Accommodation:
- Overnight boat (Number of Nights: 1)
Accommodation:
- Overnight boat (Number of Nights: 1)
Accommodation:
- Overnight boat (Number of Nights: 2)
Accommodation:
- Overnight boat (Number of Nights: 1)
Accommodation:
- Overnight boat (Number of Nights: 1)
Accommodation:
- Overnight boat (Number of Nights: 1)
- Flights to and from origin and destinations
- Airport transfers (arrival and departure)
- Anything else not explicitly listed in tour inclusions
- Recommended gratuities/tipping
- Optional activities/tours
- Personal expenses
- Travel insurance
- Visas, meals and beverages not stated in the list of inclusions.
When meals are not included, your tour leader (where available) will be happy to help with restaurant recommendations, bookings, and directions. Please let us know if you have any dietary needs or preferences. We willdo our best to accommodate these, though we cannot guarantee that every request can be met.
You are responsible for your personal belongings throughout the tour. You will need to carry your own bags between the vehicle and your hotel room. Drivers will assist with loading and unloading luggage from the vehicle.
Travellers requiring wheelchair access should contact our sales and service team, who can make enquiries on your behalf.
This tour requires an Average level of fitness. Activities are paced gently and include leisure time. You may be expected to join guided walks of up to one hour, navigate short stairways and mild inclines, and manage your own luggage. You should also be able to board and exit all transport without assistance.
Travellers are expected to be self-sufficient and capable of handling all aspects of their journey. Please discuss your circumstances and support needs with your booking agent to confirm this trip is suitable.
If you are unsure, we recommend consulting your doctor before booking or travelling. (Note: I assume each tour has a different description depending on level of fitness required).
If a planned site visit is unavailable due to changes in operating hours or holiday closures, the itinerary may be altered, or a comparable activity will be substituted where possible and subject to availability.
Visa conditions can change. Once you receive your travel documents, check with the relevant embassy, consulate, or immigration office of your destination for the latest information.
- It is your responsibility to ensure you have the correct and valid travel documents and to comply with all entry requirements.
- Non-Australian citizens must also confirm visa and identification requirements with the appropriate consulate or visa agency.
- Certain occupations (for example, journalists, government officials, or those working in charities) may face additional restrictions when applying for visas, which could affect the type of application required.
Duration: 10 days
Trip Type: Group Tour
Activity Level: Average
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.
Price based on per person in Double Room for departure 02 May 2026
Customer Reviews
10/01/2023
Our skipper, George was great! He was highly experienced and knowledgeable. He gave us briefings at every port so we would have local insight and history of the area. We had lots of opportunities to swim in crystal clear water and explore the islands. Great trip!
09/26/2023
This was a great experience sailing around the Cyclades Islands. It's good to get a taste of each island (you don't get to stay at each one for long) and get a taste for boat life. Our itinerary had to change due to poor weather but we got to spend a night on anchor instead which was fun. The swim spots we went to were fantastic. The accommodation on the boat is basic and tight when at full capacity. Definitely pack light if you can. Best for the group when everyone pitches in to help with cleaning, shopping or food prep so be prepared to help out and don't be lazy as your group will notice!
Tour Operator

Intrepid Travel is a global adventure travel company, dedicated to providing sustainable, experience-rich travel opportunities. They’ve been the leader in ethical, small-group travel since 1989 - taking people around the world for more than 30 years. They’re the world’s largest travel B Corporation - dedicated to being the best travel company for the world. In 2002, they established The Intrepid Foundation so their travellers could make a lasting impact on the communities they had visited. Although Intrepid Travel absorbs all administrative costs of The Intrepid Foundation, they are separate legal entities, allowing The Intrepid Foundation to grow independently. Intrepid Travel is made up of a collection of tour operator brands and 28 destination management companies all united by one vision: To change the way we all see the world.
In Business Since 1989
10/01/2023
Our skipper, George was great! He was highly experienced and knowledgeable. He gave us briefings at every port so we would have local insight and history of the area. We had lots of opportunities to swim in crystal clear water and explore the islands. Great trip!
09/26/2023
This was a great experience sailing around the Cyclades Islands. It's good to get a taste of each island (you don't get to stay at each one for long) and get a taste for boat life. Our itinerary had to change due to poor weather but we got to spend a night on anchor instead which was fun. The swim spots we went to were fantastic. The accommodation on the boat is basic and tight when at full capacity. Definitely pack light if you can. Best for the group when everyone pitches in to help with cleaning, shopping or food prep so be prepared to help out and don't be lazy as your group will notice!
08/24/2023
My partner and I went on this trip together and had a wonderful time! The boat was lovely, we really enjoyed sailing time (it was very relaxing haha) and all of the beautiful swimming spots we got to stop at. Make sure you listen to the pre-warning that the itinerary is just a guide and your destinations are dependent on the wind & the availability of the marinas - just go with the flow and you’ll have a great time! Our skipper was Fotis and he did an all round fantastic job - but a particular highlight for us was that our group asked him to organise family style dinners for us almost every night (I think all but two nights), where Fotis chose the restaurant and ordered a selection of traditional Greek dishes for us all to share. It really added to our experience and got us to try things we normally wouldn’t have chosen ourselves. We really appreciated the extra effort he put in for us - thank you Fotis!
08/03/2023
The Cyclades are amazing and I loved the sailing. Fotis is the best and I always felt safe and taken care of. While the boat has close quarters you get to know everyone so well and had an amazing time! I loved sailing every day and then getting to explore the islands in the late afternoon/evening. Highly recommend this trip!
08/03/2023
A true once and a life time trip. Be prepared to “rough it” on a boat for 10 days, but it is the perfect way to sail the islands of Greece on a budget and with less tourist spot.
10/17/2023
This was such a unique and incredible experience. I would definitely say the a trip of a lifetime! What I'd like to pass onto anyone considering this trip is that you should pack an open mindset for adventure, cooperation and a can-do attitude. You are greatly rewarded with an incredibly rich experience of the Greek Islands. Our itinerary changed slightly due to weather, but we made the most of it with our knowledgeable skippers help. Georgie gave us so many great recommendations for every destination. He also organised many group dinners that were a total success. Not only did we see so much of Greece, we also made lifelong friends too! Highly recommend this trip. Hot tip: Pack an inflatable mattress if you can!
09/27/2023
Thoroughly recommend this trip. The boat was excellent, the sailing fantastic and we were under sail most of the time. Overnight destinations were lovely, with lovely restaurants/tavernas. Swimming opportunities most days. We found ourselves in a great group of like-minded people and came home with amazing memories and new friends.
09/03/2023
Sailing the Greek Isles far exceeded my expectations. All of the places visited were stunning and it was a great way to tick off some of the smaller Greek Islands. George and Oreistis were amazing hosts and looked after the group very well.
09/04/2023
A fantastic trip sailing around some of the many Greek islands, most days included a swim stop in the pristine waters, the skipper offers information at each stopover to further enhance the island experience.
09/04/2023
I’m amazed by how wonderful this trip has been. The captain, the guests, the Cyclades isles themselves made this sailing trip wonderful and unforgettable!
07/09/2023
This trip was the perfect blend of work, relaxation, and culture. I could not give it higher praises.
07/09/2023
Excellent tour for people who love the water. It is all about the experience of being on the boat and enjoying the amazing scenery. It's a good sampler of the Cyclades islands so you can decide which you want to revisit. Just go with the flow and don't get attached to the itinerary!
06/02/2023
I’ve just stepped back on land after the best trip ever. Fun, cultural, and the best time meeting new friends. Would highly recommend!
06/25/2023
This was an amazing and very educational trip, made extraordinary by our skipper George and our fellow travellers.
06/24/2023
Had a great time on board and on land. This is a great length of time as you really get to do a decent amount of sailing, see the islands, and enjoy the company of other travellers and your skipper. Fotis ‘the Italian’ was fantastic and if you have him as your skipper you know you are in safe hands!
06/24/2023
A great way to explore the Greek Islands especially if you have a love of boats, sailing and swimming
06/24/2023
Sailing in the Greek Isles with Intrepid and Fotis as our captain was such an amazing experience. I could just do it all again. Favourite spots …. Naxos, Syros, and Small Cyclades. But generally just a great trip.
06/24/2023
This is a SAILING holiday. And there were many and varied Greek islands as well. Read Intrepid's notes and come prepared. The air is dry and we drank more water than expected. Swimming on most days. The yacht felt safe and sailed well. The engine was a touch too loud and restricted conversation when under power which was about 20% of the time. There is shade over the cockpit. But sitting on the cabin roof is a delight We had 4 couples on our trip and we had a great time together. Our Skipper , Fotis K. was pofessional, warm and helpful - just what we needed for a trip like this. 10/10 Intrepid.
06/17/2023
The tour was very well planned and adjusted to suit the daily weather conditions and it offered a great variety of experiences and islands with an extremely knowledgeable and enthusiastic skipper. We not just saw and experienced a lot but also learned many new skills and facts - an amazing experience!
06/30/2023
This is an excellent experience for those wanting to let go of time, experience local food, learn history about the Greek Islands and enjoy small group interactions. It is not a trip for those who cannot share and become one of team. Cannot recommend Fotis highly enough for his sailing experience, historical knowledge and friendliness.

Family trips cannot be booked online.
Please contact webjet customer service to book the trip.
Email: [email protected]