Turn your sailing fantasy into reality. Let us help you create your ultimate Island Vacation Experience.
Imagine... lounging on the deck of 'your' yacht as you sail past picturesque mountains and rocky cliffs. Enjoy the panoramic view of scenic valleys and sandy beaches as you listen to the thunderous sound of waves crashing on the distant shore. If you prefer, take a turn at the helm, trim the sails, and feel the power of wind and water touch your soul. Later visit a local taverna, order the fresh fish and then we will introduce you to the fisherman who caught it! With Custom Sailing we offer you a true local experience, come sail with friends.
Now in our 11th year, we are Custom Sailing Worldwide, Inc. and we provide customized 'Tailor Made' sailing vacations in New England, the Caribbean, and the Greek Islands. We specialize in the smaller less touristy islands, with us you will see the 'real' Greece! We offer you the best of safety, quality, and comfort. Our Captains are U.S. Coast Guard licensed, and offer more than 20 years experience in the Greek Islands, the Caribbean, and New England.
Join us on our well equipped 50 foot Bavaria Sail boat for the vacation of a lifetime. If you are looking for something larger (up to 300' or smaller) we can help you with that as well.
We have added some trips to Caribbean, please see the website for details!
Remember, there are no limitations with Custom Sailing!! Find out why our guests come back again and again to sail with us!
Keywords: Sailing Yacht, Greece Islands, Adventure, Water sports,
Captain Valerie Weingrad welcomes you aboard for your Custom Sailing holiday. Offering “Tailor made” sailing vacations in New England, the Caribbean and the Greek Islands. Holding a USCG 100T Master Merchant Marine Officers License and current STCW for operation in international waters Valerie is also an ASA certified sailing instructor. Born into a boating family, she has been on the water, in one form or another, her entire life. Her experience includes extensive sailing in the Greek Islands and treks along the entire eastern seaboard, from the last lighthouse in Newport to the tip of Florida's keys. She also brings more than 14 years of experience sailing throughout all of the Caribbean, including the British Virgin Islands, the Grenadine Chain, Trinidad, and Tobago. Between her chef wizardry, her boundless enthusiasm, her far-ranging knowledge, her love of sailing and her distinguished professionalism, you are guaranteed of having fun on Valerie's watch. Her skill and passion for sailing is contagious and will undoubtedly leave you with remarkable memories.
Greece is my second home. The sea, sun and the people are absolutely amazing. It is my privilege to be able to share this place and experience with my guests.
With Custom Sailing you will experience the Greek Islands with friends. In our 13th year we know many taverna owners, shop owners, fisherman, farmers etc who are happy to welcome us to their island. This makes your vacation special!
We are a family of 4, went when our kids were 12 or 13. We have done a fair amount of traveling with them, and this was easily the best experience we have had, we all loved it, which is unusual, as we don't always enjoy the same things... We felt very safe and comfortable with Valerie, always, and she had maria papagiorgio with her as an assistant and cook , the food was spectacular. I still try to replicate some of her recipes. They were both fun, easy to talk to and be with, laid back and flexible. Valerie is an expert captain, well known and connected to others sailing in the area who welcome her at every
Port. Being on a boat was an amazing way to see Greece, never having to pack and unpack and deal with transportation from place to place. I can still Remember the joy and excitement of waking up, going up on deck into the wind and sun and being en route to a new location....
I can't recommend this highly enough, go. Don't miss it. . I can't imagine you and your kids won't love it, and Remember it forever. We still talk about it, Greece is amazing and going with Valerie is the best way I can imagine doing it.
We are back in Boston, having had a wonderful and memorable vacation in Greece. We had a terrific time. Apo and Maria took great care of us and Apo’s skill as a captain was evident on more than one occasion.
Thank you for an experience that we will treasure forever.
After reading the reviews for sailing in the Greek Islands with Captain Valerie and First Mate Maria, I was so excited to spend the week with them. Unfortunately, due to circumstances beyond Valerie’s control, she was not able to join us. I was disappointed to hear that we wouldn’t be sailing with Valerie. However, in the expert hands of Captain Apo and First Mate Maria, I can’t imagine having had a better time! (I’m sure we would have had an amazing time with Valerie, too, and hopefully someday, we will have an opportunity to do so.)
We are a family of 5, including our 3 young adult “kids”. Our trip to Greece was a graduation celebration trip for them (1 from college and 2 from high school), and the sailing portion was such a nice relaxing way to spend a week. The kids love to sleep in and read, and the few hours per day of sailing provided opportunities for them to do so. Maria and Apo skillfully figured out the best islands to visit (after inquiring about what we enjoy doing), when to eat and sail, and that guidance and flexibility was really appreciated. And, we were always to hit the ground running and explore the next island!
We started and ended our island hopping of the Cyclades in Athens and visited the islands of Kythnos, Syros, Paros, Serifos and Kea. We were struck by how unique each of the islands is. It would have been nice to start in Athens and end on an island, and Valerie tried her best to arrange this for us. But, to do so required having the party immediately after ours want to do the reverse trip, and that didn’t work. As it turned out, ending in Athens made for a more relaxing end to the trip, so it worked out well after all. But it’s worth considering if you’re booking a trip.
The boat, Maya, is wonderful! As others have said, for cramped quarters (it’s a sailboat!), you can really spread out. The food (breakfasts and lunches) was wonderful! Maria did most of the cooking, but Apo made breakfast once and lunch twice as well. Everything was prepared with great care.
For me, traveling is as much about the personal connections as it is about the destinations. Spending the week with Apo and Maria was an absolute joy. It felt like we were traveling with friends (who just happened to be great sailors and chefs!). This was the experience of a lifetime. If you can swing it, do it!
Sailed aboard Capella in 2011 and 2012 in the BVI. Capt Val is welcoming and friendly upon arrival. With Capt Val you've got choices of itinerary (within reason and weather), relax, man a winch, raise a sail, hook a ball, steer a course on a 50' footer, whatever YOU enjoy.
My wife and I sailed the Greek Islands with Capt Val and First Mate Maria in 2011 aboard Maya (49' Bavaria). This was "the" vacation trip"! The Greek islands are fantastic. The people are very friendly and inviting. Doesn't matter if you eat on board or ashore, the food is great. One little tip......stay OUT when Maria is cooking, no helping allowed!! Great way to learn a lot about Greek history and culture without any of the crowds or pressure.
My wife and I sailed (bare boated) before (British Virgin Islands, Gulf Islands in Canada etc). We took our family and spent a great week with Valerie and Maria bumping around Greek Islands. What a great experience! Valerie is a fantastic skipper, and one can see it in the way the Greek skippers treat her - with respect and warm friendship. Greek men are generally not much for women showing them how it's done, but Valerie has earned their upmost respect by her skill. She is easy going and looks after the "crew" along with Maria...who is warm, funny and caring. Our kids loved our stops in quiet bays with deep, warm, green-blue water. We were all looking forward evenings, where we explored and ate another great meal...If one is looking for a relaxing vacation in a beautiful place, without the crowds, traffic, crowded pool..this is it! Our only regret was...that we did not book 2 weeks (or more). We will definitely go back to sailing, and definitely with Valerie.
We sailed with Captain Valerie and hostess Maria August 2011. We had the time of our lives! A truly wonderful experience recommended for all. We felt right at home aboard Maya and I am still trying to replicate Maria's tasty recipes! We thoroughly enjoyed ourselves everywhere we went and cannot stop talking about our trip. Hoping to sail again soon with these girls!!!!
We've traveled a lot - we've even been to Greece before - but this was the first time we've sailed in Greece, and I would never want to see it another way after this trip. We invited our adult children on this trip. It turned out to be the most amazing family experience. Lots of time together, but also lots of time in ports, where we could go off in separate directions to explore. It's even amazing how many different nooks there are on a 50-foot sloop for curling up alone with a book. Val was terrific - I had asked not to have the chef so that we could take more people (expecting to do any breakfasts or lunches myself - dinners are in port). Val even took that over, making Greek salads I'll never forget and bringing back delicacies from the local markets. The schedule was ours to make - if we wanted to stay longer on an island, that was fine with Val. But the boat - aaaahhhh. I have never slept so well as I did on that sloop. And there's something about BEING right there - having coffee in the early morning mist on deck in Hydra while the villagers are beginning to bring their donkeys to town and the fishing boats are starting to head out for the day. Coming back to the boat after dinner at a taverna with the moon shining over the harbor and the water gently slapping against the side of the boat. It's a whole experience, not just an accommodation. (Thanks, Val - I would sail with you again anytime, anywhere!!)