Sailing Jollies 

Confidence and experience building in an environment of safety and enjoyment

Mile Builders 

Many people talk about 'getting their miles' as if it's the most important thing in their sailing development.   

Yes, you need them, but if you get 3,000+ miles on a transatlantic crossing where it was all on one tack, no berthing the yacht and nothing to do but read books for 3 weeks, can you call that quality experience?  If you join a pro delivery, the skipper may well not be helpful, you may only motor and you may not be allowed to touch much on the yacht.. same goes for 'freebies' - quid pro quo trips where you help (make tea for) a yacht owner or keep him company but otherwise don't learn a lot, and almost certainly won't be allowed to berth it.  

Mile building with training, skills & drills, berthing, sail trimming, night hours, watches, time as skipper built in - who else gives you that? 

Our main events are the 9 yacht one way from Athens to Corfu every April and the newly established 5 yachts from Athens to Skiathos each May, both fleets returning in October to Athens for winter.

At Sailing Jollies, we say 'Make sure you get decent quality, worthwhile miles and don't just sit there doing not a lot.'   You really should aim to sail on as many different boats, with as many different skippers, in as many different places as possible.  Take on board the good habits and avoid the worst practices of the people you meet and sail with along the way and you won't go far wrong.  Lastly, do not rush to get your next qualification - it's easy to spot somebody who hasn't really had much actual skippering experience - build it up over time and become really confident before moving to the next stage. Why get out of your depth and make the whole thing stressful?  By the time you take your YM exam, it really should just be like taking the examiner out for a nice day's sail.. that's how he wants it to feel, after all - he'll be thinking 'would I let this guy take my family out?'  

 Tanking along in a great breeze on a Bavaria 51 Cruiser, 2011

You get what you pay for... 

There are plenty of opportunities out there to sail for free through crew matching sites, but here are a couple of scenarios to be mindful of before asking yourself if it's a good idea to go with what you don't know..

1. The private owner needing crew, where often 'the wife' is either not interested, or left long ago.  Usually the owner offers free or 'contribution only' sailing in exchange for crewing help or company.  All very well for some miles, but ask : Is the boat properly maintained?  Engine, sails, rigging, safety gear?   Is the owner/skipper interested in helping you develop?  Do you know his experience and qualifications are genuine?  Will he teach you anything?  It can be all about the owner's wishes and you may have no say in where you go, what you do and you may not get to do or touch very much on board, as owners can be very protective of their 'baby'.  Ask for references about the yacht and owner, from people who've sailed with him before - don't be shy to clear up the above points, if they're reluctant to give the info, that is a negative sign.  Whether people would sail with someone again is probably the universal indicator of a good skipper, so do ask if you can speak to previous crew.

2. The professional delivery, where a delivery company or owner pays a professional skipper to take a yacht from A to B.  The delivery company and/or skipper then aims to fill the yacht with enough (unpaid) crew or passengers to get the job done.   Great for miles, sure, but what is in it for you?  Time is money, the skipper is on a deadline, so it often won't be about you getting anything very much out of it, other than doing as you're told.  Delivery skippers can sometimes be uninterested in helping you (from genuine first hand experiences I've heard) and often the yacht has to be effectively 'sterilised' i.e. upholstery covered with bin liners, taped up, you must bring your own sleeping bag, cutlery and crockery.. where's the fun in that?   Plus you sure don't get to see any of the lovely spots along the way, or relax in the sun with a glass of wine or a beer.

Halcyon yachts is a Sailing Jollies recommended partner for Milebuilding on deliveries, where crew are given as many opportunities to participate as possible.


So why do a 'Jolly' instead of a 'freebie'?  

All sailing is valuable experience and the above may be fine too - but our Jollies are deliberately set up for developing sailors at all levels who want more out of a trip than simply the miles.  I take only the positivebest aspects from the different types of sailing (racing, holidays, courses, deliveries and mile-builders) without the down sides, creating a genuinely enjoyable, challenging yet relaxing, educational sailing experience that will leave you wanting nothing more from a week or two on the water each year.   Many of my guests sign up for the next Jolly before we even know where and when it's going to be, and trips are now filling up and selling out 6-12 months in advance.  April 2018 has sold 25 out of 27 boat weeks (9 yachts x 3 weeks) so grab the last places before they fill completely!

Whatsapp Rich on +447899964267 or email [email protected] to book. 

You will actually get to see and experience many of the places you're sailing between, enjoy the atmosphere, take a drink or two, learn, practise and involve yourself in whatever you want or need along the way.. could it be any better?  From around £365 per person, I believe these are the best value trips out there - I can keep it this affordable because I own no boats myself, I only use quality, nearly new charter yachts, often that need to be moved from A to B by the company, therefore we get a discounted rate for doing them a favour.  I therefore have no outgoings, no boat mortgages or loans, no expensive premises, no maintenance, almost zero paid advertising and no year-round berthing costs to pay.. which I am happy to pass on to clients, in very much a 'win, win' situation for all.


"The trip with Sailing Jollies under skipper Richard was only one week, but what I came away with was immense and I have to say also turned out to be one of the most enjoyable holidays I have ever had." - Matt U, Essex 


Why do you do so many one way trips?

I just love to set off knowing that we're on a real, one way mission, that proper planning needs to take place and that we're not just popping out for a day sail in familiar waters.  I also do round trips as relaxed holidays with some training, but the real 'Jolly' for me is a one way mission to get the yacht(s) safely from A to B.  Night sailing, watch systems and 60+ mile passages all play a part in making these trips extra special for skippers and guests alike.

In the early and late season, April, May and October, charter yachts generally need to be moved to and from their seasonal bases.  Rather than the charter company using their own people to do it over a couple of days at their own expense in fuel and manpower, I offer to do it for them and make a 1-3 week long charter trip out of it - the Jolly.  This is great for adventurous sailors looking to build miles, practise drills and learn and revise any aspect of sailing they wish along the way.  I usually try to build in at least one 60 mile / night passage and allow people to skipper sections of the trip to suit their requirements, wherever possible.

Recommended Mile Builders - ask for more information

There are a few trusted Companies and Skippers that Sailing Jollies is happy to endorse and recommend for your mile building adventures - I will never put you on a yacht with someone I don't know or isn't at least very highly recommended by someone I know personally.  My name and reputation are very important to me and I only deal with companies and private individuals of high standing in the sailing community.  Anything you see advertised on this website comes with my full endorsement, unless it states otherwise, in which case you should do your own checks and vetting.  Even if you're due to sail with someone else, I am happy to have a chat with you about what you should check out, if you wish - happy, safe trips are the ethos of the Jolly and always will be.





2018 events