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Greece Sail Cruises and Charters

Greece sailboat

The authentic way to sail the Greek islands with our comfortable traditional wooden sailing yachts on the Aegean and the Ionian Seas. Rent a cabin or the entire boat for you and your family and friends

Our Sailing Itineraries

Mykonos harbor

The Cyclades
We do the Cyclades in May, June, September or October because these are the times when the weather is the best, not too windy, and not too many people. Leaving from Mykonos we visit the islands of Delos - Naoussa (Paros) - Kato Koufonissi - Koufonissi - Schinoussa - Piso Livadi (Paros) - Naxos - Rineia (next to Delos) - Mykonos. We do not go to Santorini because of the distance and there is no good harbor for boats our side. But many people get off on the last island and take the highspeed to Santorini instead of returning to Mykonos. And of course if you charter the whole boat we can go to Santorini or anywhere you like!
Contact us for more info

Milos, Greece

Western Cyclades
For the Western Cyclades we leave from Syros and visit Sifnos, Serifos, Kimolos, Milos and the beautiful uninhabited island of Polyaigos. Those who want to go to Santorini also have the option of getting off at the last island and taking the highspeed to spend a night or two there.
Contact us for more info

Skiathos

Sporades Islands
A One Week Cruise in July & August aboard the yacht Syrolana to the Sporades to avoid the meltemi winds. We pick you up at the airport in Athens and take you to the small port of Oreous on the island of Evia where we get on the boat and visit not only the well known islands of the Sporades, Skiathos, Skopelos and Alonissos, but we also the Pelion Peninsula.
Contact us for more info

Lefkada

Sailing In The calm Ionian islands
One Week Cruise in July & August on board the yacht ANATOLIE or KAPETAN-KOSMAS. Our private or cabin cruises are from Saturday to Saturday and we pick you up and take you back to Athens Airport.. We start in Messolongi or Asrakis and visit the larger islands of Ithaki, Kefalonia, Lefkada and the small islands between Lefkada and the mainland. Our itinerary focuses mainly on coves, small ports away from the big tourist places. If you choose a private cruise the Captain adapts the route to your wishes taking into consideration various factors such as ports, weather forecast and the date you need to return.
Contact us for more info

Corinth Canal

The 7 Wonders Cruise
We do this once or twice a summer, going west and another going east passing through the famous Corinth Canal, one of the most incredible man made structures in the world!
Day 1: Boarding in Aegina island or Marina Zea Piraeus
Day 2: Epidavros
Day 3: Epidavros visit - Leaving after lunch - Evening and night in a cove close to Corinth
Day 4: Corinth canal - stop in a creek at noon - Galaxidi
Day 5: Galaxidi (visit of Delfous) - Trizonia island
Day 6: Trizonia - Nafpaktos - Messolongi
Day 7: Landing till 9:00am, transfer back to Athens Airport

Our boats and skippers are also available for private charters where you decide where we go. Contact us for more info

Santorini

Eating, fishing and passing the time
We leave after breakfast for one or two hours of travel, mostly along the coast, before landing in a beautiful cove. Swim, snorkel equipment, paddle or sunbathing are among the options available to you while the crew prepares a meal based on the Mediterranean diet (fresh produce, cooking with olive oil. Our meals include appetizer, main course and dessert. Drinks on board are in "open bar". After a nap on the comfortable sun beds or more swimming or fishing, we go to the port of the next island (one or two hours of navigation), where you can visit or simply stroll and test pubs and local taverns. The boat remains at night in port, so you can come back whenever you want, after, according to your taste, appetite and budget, dining on a souvlaki, Greek salad or a fresh lobster at the local tavernas. Sometimes we reverse in order to enjoy a night at anchor in a beautiful bay, under the stars (dinner on board then).

Greece sailboat charter

The Boats

Anatolie

Completely renovated from 2014 to 2018 (new Master cabins, new heavy duty engines, air-condition in all cabins, new soundless generator) ANATOLIE is a wooden gullet registered as professional tourist sailing boat by the Greek Authorities. The expression "professional sailing yacht" means that she passed stability tests and met with required technical specifications. For this reason she is allowed to sail with winds of 6 Beaufort and stronger whereas other professional tourist boats up to 83 feet are not (but we avoid this situation if possible!). And the sails are not here just for decoration ;-) ANATOLIE has 2 heavy-duty 190HP marine engines and around 200 square meters sails. There is a tender with Yamaha outboard engine, autopilot, 2 VHF, 2 GPS and the electronic standard equipment. There is always 220AC for charge any telephone or other items like cameras or MP3 players and a WIFI/3G connection free for email use (not to download movies ;-).

There is also a generator for any big AC power need. Of course there is an electric fridge, 1500 liters water tanks, hot water and all the equipment expected in such yacht.

There is a paddle on board, snorkeling equipment, some fishing lines, and the possibility to connect your MP3 player to the yacht stereo. The bar is open for basic beverages (refreshment or beers) and you can also bring and drink your bottles without extra-charge. There is a large sunbathing area with sun beds... Bed linen and hand towels provided - please bring your own beach towel.

Everything to enjoy a comfortable cruise with also very good food - breakfast and one lunch or dinner on board!

Anatolie, yacht

Kapetan Kosmas

Renovated in 2017/2018 (shower boxes, top marine toilets with selenoid, stern thruster, new soundless generator, saloon leather etc...) Kapetan Kosmas is a wooden gulet registered as professional sailing boat by the Greek Authorities. She is allowed to sail with winds of 6 Beaufort and stronger whereas other professional boats up to 83 feet are not (but we avoid this situation if possible!). And the sails are not here just for decoration ;-) Kapetan Kosmas has around 200 square meters sails. There is a tender with Yamaha outboard engine, autopilot, 2 VHF, 2 GPS and the electronic standard equipment. There is always 220AC for charge any telephone or other items like cameras or MP3 players and a WIFI/3G connection free for email use (not to download movies ;-). There is a paddle and kayak on board, snorkeling equipment, some fishing lines, and the possibility to connect your MP3 player to the yacht stereo. The bar is open for basic beverages (refreshment or beers) and you can also bring and drink your bottles without extra-charge. There is a large sunbathing area with sun beds... Bed linen and hand towels provided - please bring your own beach towel. Everything to enjoy a comfortable cruise with also very good food - breakfast and one lunch or dinner on board!

Kaptain Kosmas Sailboat

Syrolana

SYROLANA is a wooden GULET suitable for group or families up to 16 passengers. She has 2 heavy duty 325HP turbo engines and around 200 square meters sails. There is a tender with outboard engine, 2 VHF, 2 GPS, one radar and the electronic standard equipment. There is always 220AC for charge any telephone or other items like camera or MP3 player. Of course there is an electric fridge, 3000 liters water tanks, hot water and all the equipment expected in such yacht like air conditioning in all the cabins. There is a paddle on board, snorkeling equipment, some fishing lines, and possibility to connect your MP3 player on the yacht stereo. There is WiFi 3G on-board, free for email use (not to download movies ;-). The bar is open for basic beverages (refreshment or beers) and you can also bring and drink your bottles without extra charge. There is a large sunbathing area with sun beds... Everything to enjoy a comfortable cruise with also very good food - breakfast and lunch or dinner on board!

Syrolana Yacht rental

The Skippers

Captain Alex
Captain Alex: The founder of the company and the skipper of the Kapetan Kosmas

Captain Themis
Captain Themis: Son of Captain Alex and skipper of the 88 feet Syrolana

Captain Manolis
Captain Manolis: 'The Cretan' is the skipper of the Anatolie

Our Prices for 2019

For the One Week Cruises
From 1100 Euro per person for the week in a double cabin in low season May or October to 2250 per person in VIP double cabin in very high season.
 We can give you the details when you Contact us for more info.

Prices if you want to charter the entire boat

Sailboat Charter Prices

Customer Comments

Sailboat meal

"Best way to sail Greek Islands!-with Kapetan Kosmas. Best crew-Captain Alex and Varvara. We are sailors and spoiled. We had all our expectations fulfilled and more.Gourme food, drinks. bouzuki musicians on board- especial opening season invite- lucky us! Already looking forward to be on more trips with them." AB 2018

"With Kaptan Kosmas we have experienced a dream trip. The boat is beautiful, the cabins very clean and comfortable. The stops are well-thought and the activities are very pleasant. The Captain and his crew are very experienced and on the lookout for our smallest needs. I keep the best for the end, the food on board is absolutely succulent, fresh and diversified, better than at the restaurant. I recommend this journey without any restriction, only happiness in pure state! I'll be back with joy every year." ML 2018

"A cruise like we dreamed of on the syrolana: A Well-designed itinerary allows you to alternate typical villages and wild landscapes. The good rhythm of the cruise allows you to enjoy swimming in coves and visits of Greek ports. Captain Themis is always good advice, nikos plunges to moor the anchor while Stella prepares us delicious Greek specialities. A very friendly crew and always to the little care! The day begins with a varied breakfast at the stern. After a moment of navigation, little trip on earth closes to discover the port villages and their culinary traditions. Finally, after digestion on board and a little swim, the day ends with an aperitif reported by the sound of the bell of thémis! A Ouzo that smells good the holidays ;) Thank you to thémis, nikos and Stella for this unforgettable cruise: a discovery of the ionian islands combining authenticity and comfort. A 10/10 punctuated by a total eclipse of the moon last night!" JD Oct 2018

"Thank you for this dream week aboard the kapetan kosmas! It was a week out of time, punctuated by heavenly landscapes, the gastronomic meals cooked every day by Barbara and all in fantastic company both of the other passengers and the crew and captain Alexandre MATSAKIS. Everything was absolutely perfect!" MG 2018

"When we booked our trip on the maiden voyage of the 88 foot Kapetan Cosmos with Alex, we had no idea how completely beautiful, restful, adventurous, culinary, colorful, breezy, friendly and perfect a vacation could be. We could not have anticipated the satisfying breakfasts and gourmet lunches on-board every day courtesy of the Captain's wife Varvara... From pastries, to fish, to shrimp, to vegetable canapés, local specialties and produce, fabulous coffee and all the ouzo, beer and wine we could drink. Every intimate cove and beach beckoned us into the crystal waters of the Aegean, as clear as the sky. The waterscapes of islands floating by, winds carrying us along, estuaries lining the rocky shores, spires of rocks and ruins were hypnotizing. In the evenings the quaint towns on each island offered intimate seaside restaurants and shops, cobblestone streets filled with local crafts, cats and kids. There are three beautiful sail boats in The Kapetan's fleet. We met them in two ports, each one as well run and graceful as the next. AND our VIP cabin! The hand made teak cabinets, queen bed and more storage than we could use was our favorite hotel room ever. I had a dressing table and lounge to myself. My husband had enough cabinets to store his photo equipment. The last night topped it off with music from locals and dancing on deck. We will never forget our new friends. One Greek, four French, one Ukrainian, one Latvian and three Americans on deck for the most amazing week of our lives. Thank you Alex!!!" PB 2018

"In July, we experienced for the 6th time the pleasure of navigating around the Greek islands with Captain Alexandre and his crew. This time we cruised in the Sporades on board the Irina. Excellent atmosphere, humour, lots of laugh, excellent food cooked by Varinka, time to explore the lovely the islands, these were all the ingredients which made this cruise an unforgettable experience. Thanks to Alexandre, Varinka and Costia who looked after us so well. As a matter of fact, we plan our 7th cruise next year." NR 2017

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