This was a trip of a lifetime! Our captain was Theodore and I can’t say enough about his knowledge, professionalism and care of our party of 8. The catamaran exceeded my expectations and I really enjoyed the various areas to relax and enjoy the trip. But I truly think it is the captain that can make or break a trip. We were sailing in May so weather is variable. He consulted with us about our “must sees” and made great suggestions to maximize our time through the Cyclades. I ended up enjoying the smaller islands and his knowledge of the people, restaurants and history was second to none. We swam, paddle-boarded, explored historical sites and enjoyed great food. My grandson had his birthday at home and when we called him he even found music for us to sing to him. I felt like he did a great job on the islands exposing us to food we hadn’t tried and making great suggestions. The yacht sailing trip on the Ace of Diamonds and with our captain is a memory all of us will cherish. Thanks again for making our trip so special.

My first trip to Greece was incredible and I’m so glad my friends and I chose The Ace of Diamonds. Our crew Theo and Stefanía were amazing. They made us feel right at home with and created a trip that was perfect based on what we wanted to do. We were able to see so many different places and always felt safe and taken cared of. I would have liked to
Stay another week if time allowed. ⭐️⭐️⭐️⭐️⭐️

Just got off Ace of Diamonds with Theo (captain) and Stefania (hostess) who were an amazing duo to lead our trip. Theo's knowledge of the Cyclades and command of the catamaran were a huge asset. Stefania was a great cook, had local treats on board daily, and made restaurant recos and reservations whenever we asked. And, both of them were so pleasant to be around which is important on a weeklong trip in close quarters.

Working with Yacht Sailing (Eugene) prior to the trip was easy and the entire operation at the marina was impressive. I highly recommend using Yacht Sailing for a trip through the islands of Greece.

This vacation was one of my favorites! I had no idea what to expect but I was amazed every day! The catamaran was wonderful, and it was luxurious in every way. There were so many places beyond the en suite cabins to hang out and enjoy each day and night. Every single person we met at this company, from the owner to Theodore, our phenomenal captain, was so gracious and helpful. It was clear they wanted us to have the best experience possible and would literally do anything in their power to make our lives easier and/or better! Theodore listened to what we wanted to see and experience, and then went out of his way to provide that and more! He heard that we wanted some archaeological experiences so he helped us hike up to the temple of Poseidon. At a different port, Theodore arranged to rent a car and he drove us 30 minutes outside of Nafplio to an archaeological site with a prearranged guide to lead us on a personal tour!! Combined with his amazing chef skills we were simply so lucky to have him as the captain of not just the yacht, but also our vacation!!

Due to a last minute change of holiday plans, we only booked this trip at the end of June. The week with Theodore and Stefanie surpassed all of our expectations. It was simply fab.
It’s a very quick and straightforward transfer from Athens airport. Theodore the captain expertly planned our route with an eye on the winds for the week, to ensure we had good sailing but to lovely port towns and beaches. A warning! Theodore is not a good predictor of the time it will take to get to each place! Apparently he is called Three Hour Theo, but it never takes three hours. No matter. It was fun.
Stefanie cooks great food, especially her yummy Souvlaki. We were well fed and couldn’t have asked for more from our lovely hostess. For a family holiday, we thought they were both great! Even though they introduced us to some strange Greek rules for Uno. What a surprise, unfortunately Theodore won that round (I won the first two, just saying). The only downside to our wonderful week, was the theft of some Haribo, Not pointing any fingers (Theo) but it was almost a firing offence according to the kids and some sea sickness that was dealt with swiftly and sympathetically. Stefanie was amazing with recommending ice cream spots and restaurant recommendations. The islands we visited were spectacular and we saw two turtles and a pod of dolphins and thousands of tropical fish. Our family of four (two girls aged 11 and 10) absolutely loved it. We have no hesitation in recommending this trip, this company, Ace of Diamonds (our boat) and most especially our Captain Theodore and hostess Stefanie. You won’t regret booking this trip. We will be back

We were 2 couples with Great Expectations coming into this trip and they were completely exceeded. I'm sure every experience with this company is amazing but I cannot imagine this trip with our Skipper Theodore and host Stefania, aptly dubbed "Stefania The Great." Theodore's proficiency managing the sailing duties, logistics, recommendations and planning were incredible. Transports and reservations were arranged in such an efficient manor that we were able to completely maximize our experience. Stefania's cooking and exceedingly affable nature were so appreciated. The two of them are innately designed for their positions. As an inquisitive person by nature Theo took the time to explain so many details in regards to the logistics of how he operates the boat. The water toys were amazing, the views phenomenal and the banter and camaraderie were unsurpassed. The knowledge of the local culture, economy, history and cuisine were far above and beyond what we could have imagined. My wife and I are leaving this trip with two new friends and adding a beautiful chapter to our book of life experiences. We would highly recommend this trip and I can assure you Theo and Stefania would be aptly adept at accommodating any family, couples or singles looking for a once in a lifetime Mediterranean sailing experience. We are leaving with minds filled with knowledge, hearts filled with gratitude and a few extra deserved pounds compliments of the culinary experience. Yamas!

We had such a wonderful time and experience on our boat "The Ace of Diamonds". Theadore our captain was the epitome of the very best guide, information provider, language interpreter,historical knowledge and over all knowledge of everything sailing. We would recommend him to anyone wanting to sail in Greece. Our group is going to plan another trip to a different area with captain Theodore as we found him to be so fun to be with and share our evening dinners with.
Maria and Eugene also were very accommodating in planning everything prior to boarding to disembarking and arranging all transportation needs.
Cheers from all of us to you captain Theodore, our experience would not have been so wonderful without you!

What an incredible week! Our boat- Ace of Diamonds, was so fun. They only say I would travel through Greece. Our captain, Theo, was so knowable, amazing planner, and made the trip very special. Our hostess, Stefani, planned the best meals and was super detailed in making our week on the boat very special.

What to say about the week we spent with YachtSailing? AMAZING ALL AROUND. We were four couples from the US sailing on the Ace of Diamonds. Our skipper, Theodore, could not have been more expert in his sailing skills, more attentive to the safety and comfort of all on the catamaran, and was an overall delight to interact with. We discussed which islands we would like to visit and he made it happen. Our hostess, Stephania, was top-notch in cooking traditional Greek dishes for us to enjoy and made sure we had everything we wanted, picking up various treats in the evening for us at many of the islands. The entire team of YachtSailing works like a fine-tuned machine, starting with the initial inquiries one year prior to the trip and ending with disembarkation after a fabulous week of sailing. Every day of the sailing trip was an adventure, including the coves we stopped in for lunch and water sports, to the islands we docked at for the evenings. A highlight was the private tour Theodore set up for us on Delos. Also, just the simple joy of sailing with full sails up catching the wind while enjoying drinks with our friends on the sun-drenched bow is a memory none of us will ever forget. It was clear that the goal of everyone in the YachtSailing organization was to make this a joyous, carefree experience and they exceeded expectations on every level. I run out of superlatives to use when describing this magnificent experience! BRAVO YachtSailing!!

We just had the trip of a lifetime with Theodore and Stephanie on the Ace of Diamonds (June 3-9th). The Greek Islands on their own are exceptional, but what really put this trip over the top were our Skipper, Theo and our host, Stephanie (affectionally referred to for the rest trip as "Stephanie the Great." These two went so far above and beyond to make sure we had an enjoyable trip. Together they provided a very friendly, welcoming, relaxing and inclusive environment. Theo is so good at navigating the winds through the cyclades that he made every port entry look easy. His meticulous attention to detail was very apparent and had our entire crew sailing with ease. Stephanie was our host and to say she is an excellent cook would be an understatement. You will not find a better restaurant on the islands than what Stephanie will freshly prepare for you each day. You can genuinely tell Stephanie loves to provide the guests with great tasting dishes that are unique to the greek experience and most likely not something you have had back in your native country. I really hope our paths cross again!!! These are just two great people providing a once in a lifetime experience. Thank you both!

ACE OF DIAMONDS was exactly that! Had the best trip and most magical week. That was thanks to Theo and Stef who were the very best and took care of us so well! Theo was an amazing captain who navigated seas and all so well and Stef was the best cook and kept all perfectly together! I can’t thank them enough for the great experience and highly recommend them! Can’t wait for the next trip!!

Brilliant week on the Ace of Diamonds. Our captain and crew Theodor and Steph were fantastic hosts
Swimming, relaxing and great food.

Just finished an amazing 7 day trip on the Ace of Diamonds with the incredible duo of Theodore and Stefanie! Theodore is an incredible skipper and navigated expertly through windy conditions and calm seas. We all felt safe and secure with Theodore at the helm. Stefanie is charismatic, fun, attentive, and a fantastic cook. She worked with the many food allergies and preferences seamlessly. I can’t say enough about what an amazing trip this was. The entire group (4 couples) loved the experience. For us - it was the best trip ever. Out only regret is that we didn’t do two weeks instead of one. Next time!

We recently sailed with Theo and Stephanie on the ACE of Diamonds to the Cyclades islands for a week with a group of friends for my 40th birthday.
It was our first time having any sort of sailing experience like this so we weren't too sure what to expect. I must say it was an awesome experience and if we were to do it again we would definitely want to do it with Theo and Stephanie at Yacht Sailing. Theo, as the captain, made some excellent decisions along the way which I am confident kept us safe and gave us the best possible experience with the weather and sailing conditions in mind. He knew we had to get out to the further islands to avoid the serious impending rain event which kept a lot of people in the closer islands boat bound in rain for days.
Instead we had no rain, idealic swim spots and great island experiences. The trade-off is that we did have some quite rough seas as we copped the prevailing northerly wind which is more common in July and August, so some of our team experienced sea sickness, but I'll take that as a bonding experience!
The boat was excellent. We had 7 in our group plus Theo and Stephanie. There are so many places to hang out or sunbake that it was perfect for a group our size or even slighter bigger. Washing machines, aircon, full size fridges, coffee facilities, hair dryer, were all a bonus. One of the big surprises was Stephanie's cooking. She did an excellent job planning, preparing and cleaning up after all of the meals. The quality of her meals was better than most restaurants! We can't believe at one stage we were considering being on a smaller boat and not having a host. The amount of time required to plan, shop, prepare, clean-up, and negotiate on tasks related to meals would have seriously detracted from our experience with a group this size. So if you're questioning whether to get a host, definitely do!
Tips: 1. I would recommend to have some cash on you for the islands for taxis and for mooring fees (there are ATM's on the islands), 2. bring your own amenities onto the boat - soap, shampoo etc as they're not provided, 3. When planning for provisions, remember Stephanie can always go and get more - we underestimated the water requirements but overestimated the alcohol requirements.
All in all it was a wonderful experience! I wish we were still there cruising around all the islands and I hope that we get to do it again one day :)

The boat was great and the crew were fantastic! Theodorus and Stefania were very tuned in to what our group wanted to do and took us to just the right places. They helped us make fond memories that will last a lifetime👍👍

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!

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!

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.

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!!!

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.

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!

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

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!

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!