Sailing Jollies Milebuilders, Holidays & Training

complete sailing experiences

Improve your skills, make new friends, build your crewing or skippering experience and gain the confidence to charter yourself - perfect for developing sailors from complete novice to professional YachtMaster.  Jollies bridge the gaps between RYA Courses, Mile-Builders, Flotillas and Charters and provide a balance of relaxation and learning along the way.   An average of 50-75% returning guests every trip - surely the highest in the business - means an opportunity to sail regularly with the nicest bunch of people you could wish for.. our growing Sailing Jollies family.

 "Combining elements of courses, charter holidays, training, flotillas, deliveries & mile-builders"

With the concept of the 'Jolly', I have created an all-round sailing experience, something I felt was missing from the market and which bridges the gap between a course and a holiday.  Jollies are fun and hands on, aimed predominantly at those wishing to develop & improve their sailing, practice their skills and gain in confidence in those weaker areas.  In a relaxed, but at times challenging atmosphere of enjoyment, learning and group camaraderie, you may be as involved as you wish, and get what you want or need, without the constraints of a course syllabus.  See the testimonials for an impression of the success of this concept, which receives many compliments and is bringing clients back time and time again.  

Next Jollies with availability are from March 3rd to April 28th, then May 5-June 9th in Greece, June 23-30 in Scotland, all of July and August in Holland, then October 6 to November 10 back in Greece.

Our usual April one way Athens to Corfu is now three weeks from 7th-28th April, and our special Cyclades 'Meltemi chasing' trip runs out of Syros from 26th May to 9th June.  Trips sell out 6-12 months ahead, so book early.


This new route from Skiathos to Athens was a huge success!  We will bring all 5 boats up from Athens to Skiathos from 5-12 May 2018, with an option to extend by a further week 12-19 May.

Sailing Jollies Facebook Page is the best way to be informed of the latest events and stay in touch with all of our other regular guests.  WhatsApp Rich on +44 7899964267 to arrange a chat.


Sailing Jollies signature events every spring and autumn, moving entire fleets!

Our 9 yacht events take place for 2 weeks (3 weeks spring 2018 due to demand) every April and October, in the springtime up from Athens to Corfu, in the autumn the opposite direction.  We have individual berths, cabins, and whole bareboats, all at very reasonable prices and our yachts are all in excellent condition.  (In October we must bear in mind they have been used all season, but generally they are still in great shape - in any case, things going wrong are great learning opportunities, better to happen while in a big group with professional skippers, instructors, engineers and mechanics who know how to fix things.)

*** NEW FOR 2017-2018 *** Sailing Jollies has created a new relationship with a company to move their fleet of FIVE yachts from Athens to Skiathos in the Sporades, going up in May and returning early October.  Our inaugural trip, with 3 of the 5 this time, took place from 7-14 October, see above.

Facebook group for the April and October one ways

For example, a 2014/15 model 33' yacht is just 900 euros, our 2016 model Sun Odyssey 38' (3 cabin) are just 1100 euros for 7 days (plus end cleaning 100 euros per yacht).  As you work your way up the Jollies' ladder you may ask to charter our 43', 46' or flagship 51', with your own group or eventually with our Jollies clients.  It's quite an accolade to be entrusted with my biggest yacht and my paying guests, and we have several of our 'home grown' skippers now achieving this.

Our celebrated 'anchor star' with all 9 boats anchored, reversed up, sterns tied together in one big, self supporting circle that provides a handy swimming area - a special thing to be part of! 

 From an October Jolly : "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

 *** Ask about our winter sailing options in the Canary Islands, Malta, Gibraltar and the Caribbean ***

Sailing Jollies has consistently received positive feedback for the original and unique concept, turning the delivery needs of charter companies into a wonderful one way holidays that combine a lot of fun with a great deal of learning and confidence building, often with multiple boats travelling together.

Our now famous 'anchor star' 9 yacht formation, that once made the Greek National News!  

 "We had the pleasure of joining one of Rich's jollies, Athens to Corfu, April 2015, 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  

Sailing Jollies going forward :
Rich is now taking bookings for March, April, May and June 2018 and is usually able to cater for individual requests, even creating a Jolly based around the wishes of one or two individuals, just to set the ball rolling.. so if you want to sail but have other dates or venues in mind, don't be shy, let's see what we can build for you.
 Genuinely my own picture, from British Virgin Islands Jolly, February 2017 

Pro Skippers : I offer you the opportunity to charter a yacht alongside mine, on an existing Jolly event and bring your own guests as well as taking on Sailing Jollies clients.   I do not 'employ' you, you can take the yacht at a discounted price, as the company recognises we are helping them by moving the boat, then sell places to guests by berth or cabin.  You make your own profit this way, and of course you earn most if you bring all your own guests.  Clients of mine that you take are subject to a 100 euro commission per guest.

Newly Qualified Day / Coastal / Yachtmaster Skippers

Looking to charter for first time, or want to Skipper but don't have crew?  Sailing Jollies give you the perfect opportunity to bring your family and friends sailing, knowing that a lead yacht with professional Yachtmaster/RYA Instructor skipper is on hand throughout the trip.  Furthermore, alternatively I can help you crew your yacht with experienced Sailing Jollies guests, who will be happy to help and support you without being intrusive, allowing you to run the show and be skipper in a friendly atmosphere without losing face.  Far better this way than to mess up with family, partner, or friends, and have them never come again (let's be blunt, but it's true!)

 Contact Rich for a no-obligation, informal chat about any upcoming sailing trip.  Best way is to WhatsApp +44 7899964267 or add me on Facebook and use Messenger.
 Who goes on a Jolly?

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 happy to take beginners, but most of my clients tend to have some sailing experience - time on family or friends' yachts, or certificates like Competent Crew, Day or Coastal Skipper.

 Most are looking for practice and reinforcement, to gain the confidence to charter their first yacht, or get qualifying passages towards their next qualification.  Everyone is introduced to one another via email and our Facebook 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.  

How do I book?  WhatsApp Rich on +447899964267 or email

Ready for your next RYA Sailing Course?  Ask Rich about doing yours in Scotland, the Solent, Gibraltar, Canary Islands or Greece with Sailing Jollies partner sailing schools. 


How will a Jolly benefit me?

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?


 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 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 and must be worn when asked to do so.  From April 2015 we have decided always to take TWO weeks for our early and late season regattas, taking the time pressure off.

The Sailing Jollies Ethos 

I believe that in the world of sailing, one never stops 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 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 every individual wants to get from it.   You will be sure to meet like minded,genuine, fun people, generally all of whom 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.

 How do I book?

email: or best WhatsApp +44 7899964267

@sailingjollies #sailingjollies 

I look forward to hearing from you!

Sailing Jollies can help with:  Skippered Charter Holidays - One Ways - Round Trips - Deliveries - Assisted Passages - Training - RYA Courses - Competent Crew - Day Skipper - Coastal Skipper - Yachtmaster - Mile Builders - Confidence Boosters - Experience Builders - 60 Mile Passages - Time as Skipper - Night Hours - One to One - Small Group - Private Work - Bareboat Charters - Training

Like Sailing Jollies on Facebook - the easy way to keep in touch.

Sailing Jollies | Promote your Page too

Testimonials and Feedback

  "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, 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 -