We were absolutely thrilled with our experience on Ace of Diamonds with Skipper Theodore and Hostess Stefania! The beauty of the Cyclades, fabulous food, and perfect weather in September, had us all swooning.

Theodore knew so many special coves for swimming and beautiful beaches, and took us to the perfect combination of islands we asked for and new places we would never have known to request. He’s clearly an expert sailor, and we felt reassured knowing he brought so much experience to the task. He’s an artist with the boat and snuck us into many a tight Marina for the perfect spot at every island.

Stefania cooked some of the best food we’ve had in our lives—every morning and lunch, she magically produced super local ingredients and whipped up these amazing authentic Greek meals from scratch—from the most sublime yogurt and honey and fresh fruit, to the best lamb and greek salad and treats I’ve ever tasted.

Together, Theodore and Stefanie made us feel so welcome and at home on the boat, and delivered amazing recommendations for dinner restaurants, going out dancing, and the best coffee spot everywhere we went. They were also a blast to hang out with and got along with all 10 of our friends—funny and always willing to share a great story, but also super thoughtful about giving us our space and privacy whenever we needed it. Truly could not have asked for two better guides to the amazing Cyclades.

Shout out to Eugene and the ground support crew at Yacht Sailing who were so lovely to work with as we planned the trip beforehand—super professional, responsive and informative!

Can’t wait to plan our next trip, we’re hooked!

I have wanted to take a trip like this for over a decade and at the end of August a group of friends and I chartered the “Ace of Diamonds” for a week. The experience was absolutely incredible. Everyone with Yacht Sailing Greece was professional and attentive from the beginning. I loved how up front they were with all costs and expectations. We originally reserved a smaller boat but were asked if we wanted to upgrade a few days before because the bigger boat was available, all at no added cost! Theo, our skipper, and Stephanie, our hostess, made sure we had a wonderful time. They were present and attentive but were never intrusive on our group times. Stephanie was a fantastic cook and some of our meals on the boat were better than ones in restaurants. There was a perfect mix of time spent in bays, just basking in the serene and perfectly clear water, and time spent in port. We loved every second of the trip and were not ready for it to end. I cannot recommend this company highly enough and would do this trip a thousand times over if my real life allowed. Trip of a lifetime!

Words do not suffice in fully describing our magical week sailing the Cyclades on the Ace of Diamonds starting with the incredible customer service when we were researching and booking, through planning, boarding and debarking - Eugene, Alex, Maria and Ioanna are incredible. Every single aspect exceeded our expectations - from the crew to the accommodations to the beauty of the islands. Our skipper Cpt Theodor created an immediate sense of confidence and professionalism and throughout the week he generously shared his immense knowledge of, and contagious passion for sailing (even with our relentlessly annoying questions!). And Stephania, our wonderful charming hostess made every meal a delightful tasting of Greek cuisine (as well as accommodating our request for higher waves and bluer water!). The catamaran was very spacious and comfortable for the 8 of us with many sun and shade lounging options, and each bay and port brought opportunities for exploring, dining, swimming and adventuring. A trip of a lifetime which we will never forget. S&K, R&J, D&D, J&J

We had the most amazing time sailing with Theodore and Stephania! Our extended family of 10 adults sailed for a week on the Ace of Diamonds to Kea, Syros, Kythnos, Hydra and Poros.

Theo is hands down the best skipper my family has ever had. We have done several sailing trips around the world and this was by far the best crew and experience we have ever had. Theo loves to sail and his mastery of the craft was thrilling to watch every day! Theo, has wonderful knowledge of the Greek Islands and guided us to less traveled destinations where we felt like the only Americans. He set up amazing dinners in each port stop and we always felt safe and cared for on the boat. I’m so glad we visited Syros and Kythnos especially.

Stephania prepared some of the best meals we’ve had in Greece and the local restaurants had some big time competition with her delicious lunches on the boat! She’s also a ray of sunshine and has such an easy and happy personality. Her infections smile and Theo’s dry humor are a great combination. You can tell they genuinely love their jobs and are good friends too.

If you are considering sailing in Greece look no further. Book with Yacht Sailing and request to sail on the Ace of Diamonds with Theodore and Stephania. It will be the adventure of a lifetime for you and your family!

Yacht sailing is a really fun way to spend time with family and close friends. Since you will be on a boat together for 7 days, you need to choose who is invited wisely. We enjoyed our time on the Ace of Diamonds and Captain Theodore was great. We felt safe, even sailing at 50 knots on one of the crossings, which was quite an adventure. The rest of the trip was relaxing. Lots of good food, swimming and just enjoying the scenery. We decided against a hostess since it would be one more person on the boat. Captain Theodore was more than ideal, he was there when we needed him but gave us plenty of space and privacy. We would do another trip with this company in the future.

This is a trip of a lifetime! It's luxury and adventure all wrapped up in one gorgeous bow! We rented the Ace of Diamonds and it was so clean and well-appointed. Captian Theodore and Nina took amazing care of us (7 people ranging from 9-75!!) . Trust Theodore to take you where he thinks you should go - we just went with the flow and were surprised and thrilled by each destination! We had some long sailing days but worth it for the islands we visited were spectacular. We are pescatarians and Nina accommodated our diet and made some delicious meals...SO MUCH FOOD!!! Take the recommendations they give you for restaurants and activities...we are very much a plan-your-own-adventure family so letting someone else take the lead was hard at first but we soon got used to it. My mom had a COVID scare on the boat so it got a little stressful the last day but Nina and Theodore were kind and professional through all the family drama! I highly recommend Yacht Sailing Greece, the Ace Of Diamonds, Theodore, and Nina!!!

Theodore, our captain, and Stephania, our cook, on The Ace of Diamonds were both outstanding! Beautiful boat, great food. Theodore pointed us in the right direction always, arranged very good guides on our archeological adventures, and was a superb sailor….and a good guy. Stephania did a superb job feeding us with lots of fresh, yummy food., snd winning personality.
The boat was spacious, clean, well designed, and very comfortable for our group of three couples.
Arranging the week was easy and seamless with Eugenes help in the office too. An altogether wonderful trip.

We are a family of 4 from New York who have taken many chartered sailing trips so our perspective is from experience. Since our initial call with Eugene, we felt comfortable with his professionalism and knowledge. The preparations were thorough, even in areas of Covid travel preparation, transportation, restaurants, and accommodations in Athens before our trip began. The boat, Ace of Diamonds, was very comfortable, clean, and had everything we needed (including a great sound system for our music, strong AC, toiletries, etc). It was specially outfitted with extra comfortable lounging areas all over the boat.

What made the vacation especially wonderful were Captain Theodore and our hostess, Evie. Theo is an incredibly qualified captain but also was always ready to give a history lesson or sailing lesson when we wanted it. His itinerary suggestions and restaurant choices were perfect - he knew the coolest and tastiest places to go! Always ready to switch up a plan if the winds changed or there was a more beautiful spot to swim. He was as serious about his responsibilities as he was ready to have fun.

Evie is a master of Greek cuisine - always ready to feed us a delicious traditional Greek meal with a huge smile on her face. Her strapatsada for breakfast and her moussaka for lunch were AMAZING (along with everything else) and she surprised us with a dessert each night when we came back aboard after dinner. We loved being welcomed by her warm smile every morning with our coffee & tea prepared as we each liked it. We would bring Evie home with us if we could!
They were both super fun and a pleasure to be with (and also gave us plenty of family time).

Of all our sailing trips, YachtSailing was the most professional company to deal with, and Theodore & Evie were the best Captain/Hostess crew!

This was the trip of a lifetime. We chartered a beautiful 52 foot catamaran (Ace of Diamonds) for one week with a captain and hostess.

I’m a US citizen and I’ve never visited Greece. I was a little apprehensive about sending a large deposit to a business in a foreign country. Turns out I made the correct choice. Yachtsailing.gr is an outstanding organization. Their staff communicated very well with us (in English). The paperwork and emails were very clear about overall costs for the trip. No hidden fees. They delivered everything they promised and I couldn’t be more pleased with our captain and hostess. Their website provides a lot of information for clients and they were very prompt in answering our additional questions.

If you are considering a charter of the size, I strongly recommend that you spend the extra money for the captain and hostess. It will pay for itself many times over. Not only did they manage all the boat/meal needs, but they provided lots of information about the islands we were visiting. Our captain knows all the hidden anchorages and we saw parts of Greece that others would certainly have missed. Our captain was also amazingly adept at finding port tie ups in the evening. Our hostess Anna provided us with an outstanding array of Greek meals per our request. I couldn’t be more pleased.

The Covid rules mandated that we have Covid tests prior to returning to the US. The staff at yachtsailing.gr made sure that Covid testers were present for us upon our return to Athens at the end of the charter. Everything ran on time and it was all very smooth.

Yachtsailing.gr is it top-notch organization. Thank you Eugene, Joanna, Theodore and Anna!