How do I learn to sail…

and where is the best place to do it?

Like so many great questions, the answer is not very straight forward.

The first thing I like to establish, is what the final goal might be.  This typically ranges from, I want to give it a try and learn a new skill to a vision of someone like Dame Ellen who was driven to reach the top of her sport.  here are some lighted tips on learning to sail in the sun:


Work out your budget

Tip One: Come Sailing for as long as you can.

I never had someone for 2 weeks and saw them walk away from sailing saying they wouldn’t go again.

The next question is the tricky one of budget.  The early days of sailing are the most influential and most likely to decide whether you take it up in one way or another. Sailing for a weekend and experiencing bad conditions, is probably the worst of all worlds.  I find over a week, conditions almost always even out, and a first couple of days feeling queasy are quickly forgotten.  If you step off having only experienced that, it may well stay with you.


Stunning Caribbean Beach Scene

Stay in Sailing Heaven for as long as you can afford.

Tip Two:  Sail in the nicest possible place you can afford first time out.

Budget will also drive where you can sail.  If your budget can stretch – it has to be the Carribean and the British Virgin Islands.  This magical archipelago of islands are a sailors dream.  Metronomic Trade winds (less around 6 weeks when tropical storms can come through) and stunning channel that is really well protected from the Atlantic to the East.  The distances are just right to get that perfect balance of holiday and adventure.  The Med and the Baltic are all lovely and you are likely to get a mix bag of conditions.  Greece, Turkey, Italy and Croatia all are wonderful places to learn.


Learning to Sail in the Carribean

Learning to Sail in the Caribbean

Tip Three:  Keep the intensity of your learning to something that matches you final aims.

Next is a formal course, or a Instructional Skipper.  Formal courses are exactly that and if you’re driven to get up the ladder of your chosen system, then go for it!  But if you are looking to learn and don’t like the idea of being held to a syllabus first time out, I never met a skipper yet who wasn’t delighted to pass on his knowledge to willing students.  SailChecker have may bespoke options here with captains qualified to teach sailing and cook!  This way would be more relaxed enabling you to dip in and out as the mood takes you.

Learning to sail in the Caribbean – What does it cost?

Formal Course.  In the Caribbean or the Mediterranean would cost you between $800/ €580 and $1,400 / €945 depending on exact location, boat and deal.  Your flights would be on top.

A less formal Instructional Skipper could start from as little as $600 / €434 if there were 6 to 8 of you, to $2,000+ / €1,500+ for something more luxurious.  Some companies will group people together for this.

So you’re interested? 12 – 19th November – Why wait? have cojoled and persuaded it’s partners to put together a simply unbeatable deal.  We think we have done it, we are offering 7 nights on a luxury 42′ Performance Catamaran in the Caribbean including an Instructional Skipper.

This trip retails normally for $1,995.

What’s included?

Accommodation, Instruction, Breakfast, Lunch, Soft Drinks, Evening Cocktail.

What’s not included?

Flights, Evening & Lunch meals taken ashore, Alcoholic Drinks aboard. Diving, Dinghy Sailing.

Special Offer

For the first 4 to buy this trip will get it for just $649 then remainder will get it for half price.  With very limited availability, we suggest you book very soon.  To help you make up your mind, we allow guests to reserve a place for 3 days without any obligation to buy.

2 places sold – 25/10/13

No obligation reservation






To reserve, just simply click to send us a no obligation email.  Tell us a little about what you want from this amazing trip.

Author: Chris Lait.



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