Sailing Jollies 

Confidence and experience building in an environment of safety and enjoyment

Joining a Jolly 

Joining a Jolly is easy - just make telephone contact with Rich for a friendly, informal chat with no obligation or pushy sales..  It takes a certain kind of positive, group-minded person to fit on trips like these, so I generally ask for the phone call and a few exchanges by email, WhatsApp / Facebook before you can book to come along.   This ensures that everyone can feel confident that their ship-mates will be like-minded people with a fantastic attitude to making the most of the experience.  

For example, all will take a turn in helping with provisioning, checking the boat, taking out the rubbish, filling the water tanks - and if you wish, you may be as involved as you want in the planning and execution of day to day sailing passages.  "Every man for himself" simply doesn't work on a sailing trip so we want to be sure everyone understands that these are not catered or hosted holidays, but a trip where everyone mucks in for the benefit of all.

Email [email protected] or WhatsApp +447899964267 to arrange your introductory phone call.

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 OK, we've spoken and it all sounds great - what happens next?  How do I book my boat, cabin or berth?

  • Once we're all happy that the trip is right for you and you for it, you pay a 50% deposit which also serves as your Sailing Jollies membership fee, allowing you to join our shared charters (non refundable, though in certain circumstances beyond your control it will be possible to transfer to a future trip), then the balance is due 2 calendar months before the date of your trip.  There are terms to adhere to, and a joining form to complete, then you are all set and your place will be confirmed.  You must also provide evidence of your outbound flight and travel insurance policy, and be willing to partake in Email/Facebook/WhatsApp groups and discussions to introduce yourself, meet your shipmates and ensure you have all the information you need.
  • Regular communication in the build-up to the trip is important, so that everyone can get to know one another and break the ice before we all meet up for the Jolly itself.  We encourage all guests on the multi-yacht trips to be willing to swap yachts for at least one day sail during the trip, which benefits you insofar as you get to sail with another Skipper, but also benefits those new Day Skippers if your experience can help them along the way.
  • Email : [email protected] : Telephone (UK) +447899964267 (WhatsApp is best.)


Our April and October one ways often take in the stunning Corinth Canal, but we also go the 'long way round'..

Testimonials, click for more... 

  "Hey, thanks again for letting me join your trip for the last two weeks. I had an insanely good time sailing with you and felt so safe with the boat in your extremely capable hands. You have a natural talent on the water, and it was fun to watch you work and teach others. I was amazed at how well you dealt with the myriad demands put on you by organizing and managing a trip of such scope, safely moving six boats and about 30 people over such distances while simultaneously managing differences in personalities and expectations, handling conflicts in a professional manner, and creating an environment that encouraged teamwork and socialization. Well done, Rich. I hope we get to sail again together someday!" - CM, Texas, USA  [*** Joining again October 2017 for 2 weeks ***]

"Dear Richard, In the Name of Team 17, we would like again to thank you so much for your patience, kindness, your sailing instructions , safety spirit, and the really good atmosphere that you promote on board during our all sailing week.
As our skipper, your contribution to this week made this holiday something unforgettable. Your future customers will be very lucky ! Personally, I hope I will have again the chance "to share " a beer with you
Cheers man "

Biby ( Amicale du 17 ) (Group of 17 swiss guys, Croatia 2015) 

"Bad situations happen more often because of an accumulation of events that build, and I think that six strangers of initially uncertain experience, three of whom got sick, in an unfamiliar and uncomfortable boat in a force 7 in the channel at night, with foresails that had to be changed on the foredeck and a main that had to be reefed at the mast, plus electronics that turned out to be iffy/ not fully understood had the potential to be unsafe.

As skipper, you were responsible, and you made some judgement calls that I fully support. Indeed, your attitude pulled the crew together and I had total confidence in your competence the whole trip. I appreciated the way that you took account of everyone's needs and opinions and the time that you devoted to skill building. That is what I wanted.

I would be delighted to sail with you again" - MF, milebuilder 2015 

"I had to write this, as i had the best Sailing holiday with Richard and my friends I have ever had ; I got on the boat feeling low as I had a really tough time at home before I left. But hours into the trip I felt better , and as time continued I felt truly happy. Maybe it was the warm Grecian sun, maybe the turquoise sea sparkling. It may have been the quaint Greek architecture in the ports. Everything was special. I felt very safe and in good hands. I know that I speak on behalf of everyone on the boat. A normal holiday now would be out of the question. So back next year for another adventure. Thank-you Richard." - LH, September 2015, Corfu

"Was a great week with loads of time for focused practicing and learning (as well as time for winding down in the evenings with a few drinks and local food :)).

Arrived with a long list of objectives and before the end of the week we had covered almost everything plus a lot more which was added as we went! Feel a lot more confident now about skippering with family and friends. First class instruction from Richard delivered calmly and patiently as always. Thanks again." - Chris B, one-to-one short handed training week, Nov 2014 - Chris has since gone on to charter a bareboat in Croatia for himself, friends and family and has recognised that the training given in that one to one week really enabled him to do that with confidence.

 "The yachts are squeaky clean and in mint condition; like brand new. Clearly maintenance is very high and service excellence exceeded our expectations. We would definitely do the trip again, maybe several times if possible. We learned so much from all the crew and skippers, more than we ever dreamed we could. Thanks again Richard and all the team that make this possible, not forgetting Fanis and Christos of Omega sail." NP&SP, Namibia/S Africa

"We had a really good group of us, there was a great sense of humour around the boat and we all learned some sailing skills along the way" - Alex W, London 

" I was able to see how much Rich involved the others. He was an excellent skipper, giving clear instructions, and at all times (especially during those choppy and rather scary waves) made me, and everyone else, feel safe."   -  Nicola B, London 

"Richard's manner of skippering was first class.  When the serious business needed to be done; it was made clear and precise, and when the business had been done, that was the time to have a bit of fun, and hey, we did! "  -  Matt U, Essex - 


Travel Insurance is a must - I recommend TopSail - click to apply for your policy online. 

2018 events