Sailing holidays

√ Watch/Do-Play √ Culture √ People √ Climate


sailing holidays

For anyone interested in exploring new places on the waves, either alone, in small parties or in the company of a larger group, a sailing holiday can be a very inspiring experience.   And it is not necessarily essential that you have great experience or boating expertise in order to enjoy such a holiday.   Sailing holidays are said to be one of the world’s fastest growing leisure experiences, so you will be in a growing community of enthusiasts if you choose to take such a vacation.


There are possibilities to take a sailing holiday in several parts of the world, from as close to home as the south coast of England, UK, to as far afield as North America and Spain.   The Greek Islands are considered by many to be a popular choice and offer a range of sights, weather conditions, saiiling holiday types and itineraries.


Sailing holidays such as “flotilla holidays” have evolved over the years as the classic way for windsurfers, dinghy sailors and motor boater’s to make the step into sailing.   There is no complicated navigation and most yachts are set up to be easy to handle.   The sails have been cut so that the boat cannot be easily over pressed, and all of the newer yachts feature roller furled sails which can be operated without leaving the cockpit area.   Even the smallest yachts have substantial engines, which are there to get you around when the wind conditions are unhelpful. The engines also keep your beers cool in the fridge!

Newcomers are often surprised at the ease with which they handle their new-found hobby.

Another pleasant aspect to flotilla sailing is the kindred spirits you will meet on the other yachts. Flotilla sailing holidays generally have enthused more people about sailing as a leisure activity in the last twenty years than conventional teaching has in the last hundred years.

The kindly sailing conditions around the Greek islands, together with the security of a gregarious lead crew mean that newcomers will usually find learning a pleasure.


For example, if you are thinking of visiting the Greek Islands, more experienced flotilla sailors enjoy the slightly windier conditions offered at the very beginning and the very end of the summer! You will normally enjoy settled summer sailing conditions from mid-May to mid-October.   There are other sailing holiday opportunities to be found in places like Florida, USA, where you may wish to avoid the windy hurricane season conditions, and you can also consider places like Spain in the Mediterranean, especially from June to September.


Flotilla holidays are normally accompanied by crews who will brief you in plain English and be available to you throughout your holiday. Practical people pick it up very quickly and often go on to do formal sailing qualifications on their return.   But keep in mind that you will be spending quite a bit of time on the waves, where the weather can quickly turn from sunny and hot to wet, windy and cold.   So you will be well advised to ensure you pack a good range of clothes for all conditions, as well as any essentials such as food and drink, plus sun screen.


The environment of the Greek Islands in particular is one of the safest in the world. There are no tides and no significant swell.


You should budget at least £750 for a one week flotilla sailing holiday to the Greek Islands outside the school holidays.   This may not includes return flights or all your meals, so ensure you budget extra for these.


Sailing holidays are enjoyed by a wide variety of people, including movie star Ewan McGregor and Royal, Zara Phillips.

Link to Other Things To Know (Passports, Visas, Health, Security)

You are unlikely to need more than the usual valid passport and visa for a holiday in Europe or North America, though you might need additional sailing qualifications and paper work if you are planning a more adventurous trip.   You can find out exactly what you need by contacting a specialist sailing holiday operator before booking the trip. We suggest you carefully check any prevailing security information in advance of travel, as sailing holidays may venture into territories less safe than that associated with the UK, and can often travel to remote places.

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