Sailing Jollies 

Confidence and experience building in an environment of safety and enjoyment


The famous "Sailing Jolly"  ..since 2010

Do you feel you want to improve and develop your skills, build your experience and gain the confidence to be a first time or more refined Skipper, a more competent, more useful, supportive crew, or maybe make that step towards feeling able to charter or buy a boat yourself?

With a beautiful blend of charter holiday with informal, light training and support, the Jolly is the absolutely perfect development opportunity, at every level from complete novice to professional master and instructor.  There truly is something for everyone, for every stage, for every interest, for every taste.   You take exactly what YOU want from your time with us on the water.

A Jolly features elements of a sailing course, a flotilla, a mile-builder, a delivery and a charter holiday, without being any one of those on its own.  Jollies offer a balance of relaxation, enjoyment and learning along the way, are very personalised to you and your wishes, a bespoke service deliberately geared up to getting to know you as an individual and helping you at every stage of your development as you progress on your own sailing journey.  


With an impressive, but perhaps not surprising, 60-75% returning guests every trip, possibly the highest anywhere in the industry, you can be confident that your precious time will be well spent, sailing with enthusiastic, like minded, positive skippers and crews, all keen to help one another to succeed, whatever your particular goal might be. 

All potential new guests are telephone vetted to ensure we have no square pegs in round holes and that everyone should be a great fit for this kind of sailing experience.  Rich has vast experience at matching the right people to the right kind of trip and would prefer you didn't join over coming on one that isn't right for you, wouldn't be enjoyable and might even put you off.  It is often said that Rich knows people better than they know themselves in terms of what they need next, and will always encourage people to wait until they are ready to move to the next level. 

Generally, enthusiastic sailors, keen to learn, usually looking to take their experience and skills to the next level.  Easy going people who enjoy a good time, usually mid 20's to mid 60's bracket whose main focus is on the planning and sailing but who enjoy a few beers at the end of the day.  I'm very happy to take beginners on many routes, but most of clients tend to have some sailing experience - time on family or friends' yachts, or certificates like the RYA Competent Crew, Day Skipper, even Coastal Skipper and Yachtmaster Offshore.


Most are looking for practice and reinforcement, to gain the confidence to charter or purchase their first yacht, or to gain qualifying passages or time as Skipper, towards their next qualification.  Everyone is introduced to one another via Facebook and/or WhatsApp groups beforehand and we work everything out between us, such as the cabin allocations, dietary preferences and what people want out of the week.  All are invited to help to plan the route and the stops they might like to make along the way, based on the conditions of course. 

On a Jolly you will get a full taste of chartering a yacht and all that it involves, from check in, inventory and provisioning, passage planning & route strategy, through to the final handover and sense of achievement from being part of a successful crew.  You will get sea miles, night hours, a 60 mile / overnight passage if feasible, man overboard exercises, advice on sail trimming, helming, berthing, reverse anchoring, departing from a quay, engine maintenance and help with pretty much anything else where we can. 
You may wish to spend some time in the role of 'Skipper', for anything from a simple task to an entire passage.  However it's equally possible to come and relax and not be overly involved - it is entirely up to you.  If you are working towards RYA Coastal Skipper or Yachtmaster Offshore, we will try to accommodate your needs in terms of qualifying passages and time 'skippering'. Everyone can pitch in and play an important part in every aspect of the voyage. 


The Skipper is ultimately in charge, but is happy to sit back and let individuals or groups plan and tackle sections of the trip, only stepping in if there's something awry.   You're never put under pressure to do something, unless you say you want to be pushed - just let your Skipper know.  How do I join?

Professional Skippers & Event Organisers : I offer you the opportunity to charter a yacht alongside mine, on an existing Jolly event and bring your own guests.   I do not 'employ' you, but you can take the yacht and bring your own people.


Qualified (eg RYA Day / Coastal / Yachtmaster Offshore) and experienced Skippers - Are you looking to charter for first time, or want to Skipper but don't have crew?  Once you have completed at least one week on Rich's boat or with another established Skipper, and proven yourself, you may ask to Skipper a Jolly boat on our event.  Bring your family and friends, knowing that at least one other lead or supporting yacht with a known, established, or Professional Yachtmaster Offshore or Coastal Skipper is on hand throughout the trip.  Guidance will be given on destinations, weather, anchorages and harbours. 

Alternatively I can help you fill your yacht with experienced Sailing Jollies guests, who will be happy to for a charter party, to help and support you without being intrusive, allowing you to run the show and be skipper in a friendly atmosphere.

How are the weather conditions generally?


The more adventurous and challenging Jollies are run in the early and late season,  when the conditions can get tough, with fairly rough seas and strong-ish winds, so it pays to be sure of your sea legs taking sensible precautions to avoid sea sickness and bringing a positive sense of being up for longer passages.   We discuss the weather and routing together and info such as the graphic above is shared in the group Whatsapp chat, before and often during the longer passages.

We won't ever recklessly set out in fierce conditions but sometimes being on a deadline means we may make passages that fair weather day sailors would prefer to avoid!  Life jackets and harnesses are provided, but you will need your own wet weather gear.  Since 2015 we have taken ten days to two weeks for our early and late season regattas between Athens and Kefalonia, with a week between Kefalonia and Corfu, taking the time pressure off and giving more time for berthing practice, for example.
I believe that in the world of sailing, we never stop learning, and the day you think you know it all is the day you should pack it in.   Whether it's a new trick from another sailor, or a better way to teach or demonstrate something, there's always something somebody else can bring to the table.  

There's usually more than one way to do something effectively, so two different methods may work equally well, without one being necessarily better than the other.

Some skippers like and dislike certain practices, so as a crew member you should take note, ask before doing something and adapt your knowledge to fit with the yacht and skipper for each particular trip, in order to stay in their good books!

Strong testimonials and a high percentage of repeat bookings speak volumes about the popularity of Sailing Jollies and I believe I am the only one going to such lengths to create a trip that is so personally tailored to whatever each individual guest wants to get from it.  You will be sure to meet like minded, enthusiastic, genuine, fun people, generally all of who are up for learning and developing their sailing skills and experience as much as possible, and no doubt finish the week with a sense of achievement, great memories and having made new friends for life.



 "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." - Courtney M, USA


"We had the pleasure of joining one of Rich's jollies, Athens to Corfu one April, and sailing with Rich through thick and thin. I can honestly say that for the less experienced skipper, this is an excellent way of gaining experience and miles - not as a tightly controlled "flotilla", but as a loose collection of yachts sailing together in company. Rich is sensitive to the needs and concerns of all - skippers and crew alike - and goes out of his way to ensure that everything is as it should be. He really keeps on top of the organisational side of things, is familiar with many sites and has a great network, which enables more experienced skippers who may be new to an area to have a good and relaxing time of it as well. Joining one of Rich's Jollies can also provide the benefit of boat-swapping for crew and, of course, the opportunity for greater social outings and dinners ashore for those so inclined. Or, for an occasional quiet night away from the crowd, such side soirees are accommodated as well. Highly recommended." - David V, pro YM Skipper


 "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


"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, 2 yachts, Croatia)


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 to France


"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, Greece - 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 - 


In2wind Sailing Ltd


[email protected]
+447899964267
Marina Bay & Ocean Village Marinas, Gibraltar