From CAD 2,945
Guarantee
Small Group
Average
Rating
(20 reviews)
Experience Overview
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.
Highlights
- 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.
Trip Details
Product Code: 3309
Tour Type: Small Group
Accommodation: Moderate
Transport: Boat
Guide Language: English
Supplier Code: ZSRV
Starts: Santorini – Ios, Greece
Finishes: Santorini, Greece
Duration: 10 days
Departures: Guaranteed
Physical rating:
Average
Includes
Accommodation: Overnight boat (9 nights)
Price
Price per person: (Double Occupancy) CAD 2945 (CAD 294 /day)
Itinerary
Welcome to Greece! Meet your skipper and shipmates at Cafe Spartakos at 1pm at Athinios Port, Santorini and take a ferry to Ios where you will board your yacht. If you’ve got time, why not consider arriving a couple of days early to enjoy Santorini. Check out the range of restaurants, shops and bars in the island's capital, Thira. An absolute, must is to take a walk along the caldera's rim to Firostefani, Imerovigli and Oia. This is a particularly memorable experience at sunset, but make sure you leave plenty of time, so you aren't walking in darkness. Santorini's volcanic beaches are another must-see.
After your welcome meeting, unpack and get settled into your new home away from home a real sailing yacht. You will have some free time today to enjoy everything that Ios as to offer, including the beautiful nearby sandy beaches or check out Hora's shops, restaurants and bars – it’s all accessible within a short walk from the harbour in Ios – which all come alive in the evenings.
Accommodation:
- Overnight boat (Number of Nights: 1)
Sail to the rugged island of Amorgos (approximately 4 hours). This is the stunning location of Luc Bresson's film, 'The Big Blue'. Stop for a swim at Paradisi Beach before continuing along the coast to the port of Katapola. The restaurants, cafes and bars along the waterfront are an excellent place to relax and enjoy views of classic Cycladic windmills and an old Venetian castle. You might like to explore the ancient Minoan Settlement or drive up to the spectacular 11th-century monastery, Moni Hozoviotissis, for beautiful views of the Aegean Sea. Also worth a visit is the village of Hora, sitting high up in the rocky mountainside. Stroll through the labyrinth of stone laneways and Byzantine churches surrounding the town square. The Amorgos Archaeological Collection is housed nearby in Gavros Tower.
Accommodation:
- Overnight boat (Number of Nights: 1)
Cast off and sail to the Small Cyclades this morning (approximately 4 hours). This group of islands boast quaint fishing villages, clear waters and beautiful beaches. While all of these islands once harboured communities in ancient times, the middle ages saw this reduced to just pirates and goats. Today, only Koufonisia, Iraklia, Schinoussa and Donousa have permanent residents, with the largest population said to be around 300. In the evening, perhaps sample fresh seafood in a waterfront taverna and sit back to enjoy the peace of the Mediterranean.
Accommodation:
- Overnight boat (Number of Nights: 1)
Today you'll make your way to the largest Cycladic island of Naxos. There’s the option of taking a day trip around the island, but you can always stay behind and relax. The island’s best beaches are to the south, where water sports are also on offer. Perhaps hike up to the old Roman Catholic neighbourhood of Kastro, where winding laneways, mansions and churches all retain a medieval feel. While here, stop by the Roman Catholic Cathedral in the square, and the nearby Archaeological Museum which is housed in the former Jesuit School of Commerce. Take an optional trip to the countryside to observe rural life, see one of the oldest temples in Greece and enjoy lunch in the hills at a family tavern. Get a taste of the local brew with a shot of Kitron (best described as a lemon liquor). In the evenings, indulge in the vibrant nightlife of Hora.
Accommodation:
- Overnight boat (Number of Nights: 1)
Sail to the island of Syros (approximately 4 hours), dropping by the Bay of Gaidharos along the way for a swim. Known for its relaxed atmosphere and neo-classical architecture, Syros’ neutral role during the Greek revolution made it a safe haven for the persecuted. Perhaps catch a bus up the hill to the fortress-like village of Ano Syros and explore the town’s stone archways and narrow alleyways (the views of the Aegean are stunning from up here). Sample authentic Greek food and culture in the capital of Syros and the Cyclades, Ermoupoli, and check out the magnificent town hall in the main square.
Accommodation:
- Overnight boat (Number of Nights: 2)
In the morning, raise anchor and set off on a short cruise (approximately 3 hours) to an island packed with beauty and glamour, Mykonos. With a history of around 5000 years, the island is said to be named after Apollo's grandson. It was also the mythological base for a deadly battle between Zeus and the Titans, their giant petrified bodies forming the rocks of the island. Browse the chic galleries and boutiques in town, examine the unique architecture of the Church of Panagia Paraportiani or relax on one of the island’s white beaches. In the evening, perhaps wander down to Little Venice, where colourful wooden balconies hang precariously over the sea – the ideal spot to sit back with a cocktail and enjoy an Aegean sunset. Afterwards, join in the fun of Mykonos’ notorious nightlife.
Accommodation:
- Overnight boat (Number of Nights: 1)
Set sail for the island of Sifnos, known for its production of high quality ceramics. The island's bare hills belie fertile valleys of wild juniper, terraced olive groves and almond trees. The beach in the main port of Kamares is one of the best on the island and the ideal place to swim. Wander among the whitewashed houses, churches and chapels of the village of Apollonia, which is the capital of Sifnos. The Museum of Popular Art displays old photographs, textiles, costumes and pots. Climb up the headland to enjoy panoramic ocean views and see the medieval architecture of the fortress of Kastro.
Accommodation:
- Overnight boat (Number of Nights: 1)
Sail towards the tranquil island of Folegandros this morning. Named after the son of a former King of Crete, Folegandros has suffered a long history of colonisation and occupation like many of the surrounding islands. In the port of Karavostasis, the pebbly beach or a waterfront taverna are nice places to relax. Take a stroll through the island’s capital of Hora, one of the oldest villages in the Cyclades. The area in and around the Kastro is the most striking. In the evening wander up the hill to the pretty Church of the Panagia, an excellent vantage point to view the sunset.
Accommodation:
- Overnight boat (Number of Nights: 1)
Bid farewell to the open water as you catch the ferry back from Ios to Santorini arriving back at Athinios port just before 12pm midday. With no other activities planned for today, your adventure ends on arrival in Santorini. Your skipper can assist with organising a taxi to drop you off at your hotel or Santorini International Airport.
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Tour Operator
Intrepid Travel
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
Reviews
Mallory - Traveled, September 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!
Source: Tour operator Submitted: 10/01/2023
Katie - Traveled, September 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!
Source: Tour operator Submitted: 09/26/2023
Pahnia - Traveled, August 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!
Source: Tour operator Submitted: 08/24/2023
Lisa - Traveled, July 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!
Source: Tour operator Submitted: 08/03/2023
Monica - Traveled, July 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.
Source: Tour operator Submitted: 08/03/2023
Mara - Traveled, September 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!
Source: Tour operator Submitted: 10/17/2023
David - Traveled, September 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.
Source: Tour operator Submitted: 09/27/2023
Julie - Traveled, August 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.
Source: Tour operator Submitted: 09/03/2023
Paul - Traveled, August 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.
Source: Tour operator Submitted: 09/04/2023
David - Traveled, August 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!
Source: Tour operator Submitted: 09/04/2023
Sharon - Traveled, June 2023
This trip was the perfect blend of work, relaxation, and culture. I could not give it higher praises.
Source: Tour operator Submitted: 07/09/2023
Alicia - Traveled, June 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!
Source: Tour operator Submitted: 07/09/2023
Beth - Traveled, June 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!
Source: Tour operator Submitted: 06/02/2023
Chris - Traveled, June 2023
This was an amazing and very educational trip, made extraordinary by our skipper George and our fellow travellers.
Source: Tour operator Submitted: 06/25/2023
Gerrit - Traveled, June 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!
Source: Tour operator Submitted: 06/24/2023
Robert - Traveled, June 2023
A great way to explore the Greek Islands especially if you have a love of boats, sailing and swimming
Source: Tour operator Submitted: 06/24/2023
Alex - Traveled, June 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.
Source: Tour operator Submitted: 06/24/2023
Martin - Traveled, June 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.
Source: Tour operator Submitted: 06/24/2023
Bernhard - Traveled, June 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!
Source: Tour operator Submitted: 06/17/2023
Mary - Traveled, June 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.
Source: Tour operator Submitted: 06/30/2023
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