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Child learing about sailing

Dee Caffari’s Guide To Choosing Your Perfect Sailing Holiday

Record-breaking yachtswoman and Sunsail ambassador Dee Caffari writes on how to decide which of our sailing holiday options are the right fit for you and your crew.

Booking your annual holiday is always an inspiring time. If it’s your first time opting for a sailing holiday, it can also understandably be a little daunting. You’ve already done the legwork of saving for a memorable excursion. Now, you want to be sure that you and your accompanying crew get the most out of your leisure time together on the water.

As someone who truly relishes every possible outing for nautical escape, I hope this guide helps you feel better-informed when selecting the right holiday for you and your friends and family from the wealth of sailing holiday options.

Know your group

To start, it is a great idea to identify what sailing experience you and your companions (“your crew”) have. In your group, you may have a combination of experience ranging from complete novice to expert sailor. It is a good idea to settle for the type of sailing holiday that will ensure everyone has an enjoyable time.

Fun on flotilla

Families, beginners and people who want a more sociable holiday should consider the option of a flotilla holiday. This type of charter holiday takes form as a group of yachts sailing in company, escorted by a host skipper on a lead yacht. This option provides you with nearly all the advantages of independent yacht chartering but has the added support of a flotilla crew who helps you make the most of your sailing holiday.

Sunsail catamarans front view

Take the helm

For the more experienced and adventurous holiday-makers, there is the freedom-focused bareboat charter option. This style of holiday lets you charter a fully equipped yacht without a professional skipper and crew. You and your group can sail away to explore your chosen destination at a pace to suit.

Familiy enjoying their sailing adventure

The perfect skipper

Interested in something between the two options above? A skippered holiday could be a perfect choice. Experience the same sense of freedom of bareboat sailing with the comfort and reassurance of an experienced skipper at the helm. These types of charters are ideal for the inexperienced or for beginners looking to improve their sailing skills.

A holiday for one or two

If you are a solo holiday-maker or sociable couple and would like to sail with like-minded people, take a look at new Sail By The Cabin holidays. This type of charter gently eases you into the world of sailing holidays and allows you to enjoy the exciting experience without the monetary burden of booking a whole yacht to yourself.

One hull or two

The next decision lies with which vessel suits your on-the-water style. If you’re seeking a more dynamic sailing experience on a classic, performance-driven sailboat, a monohull is a perfect yacht for you. On the other hand, a catamaran fits the bill when holidaying with larger groups and offers a spacious living environment onboard. Helpful tip: catamarans can also travel through waters of any depth.

On board a Sunsail sailboat

The world is your oyster

To determine which destination is best for your group’s sailing holiday, know that some areas of the globe are far more challenging to navigate than others. Whilst I myself have made quite a habit of sailing across the Mediterranean, I wouldn’t recommend it if you are looking for rest and recuperation!

Think about what you want from your trip: Leisurely cruising around idyllic islands? Short hops between destinations? Are you seeking challenge and adventure? Whether you want to undertake a long or short-haul flight to get there will also influence the available options.

Catamaran sailing towards St. Lucia

Destinations to suit your needs

Destinations are graded by levels so that you can make an informed choice about the sailing holiday style that you want. Most destinations provide a choice between a leisurely itinerary or a more challenging course, so consider whether you are after wind strength with fast sailing or sunshine with gentle breeze.

If you are a novice or want to hone your sailing skills, discover which destinations offer the choice to tack on a sailing course or hands-on lessons. You can come away from your trip with a RYA qualification! Consider Sunsail’s largest sailing school, located in the naval heartland of Port Solent, which offers a range of RYA courses to suit any sailor’s or holidaymaker’s experience level.

Explore more ashore

Outside of the epic sailing that you’ll encounter on charter, what else are you wanting from your island-hopping itinerary? A great number of sailing destinations will provide you with a bit of everything in terms of culture and recreation, however, some regions and countries are undeniably better known for certain activities or interests. The Caribbean loves a celebration and well-earned drinks, while Greece favours rich history, culture, and savouring artfully prepared meze platters. For food and wine lovers, Italy beckons, and for idyllic or romantic bays and anchorages, Seychelles hits the spot. Some destinations are ideal if you want to try your hand at more watersporting diversions such as paddle boarding, windsurfing or deep-sea diving and Thailand is home to some of the best dive spots in the world!

Get inspired and get afloat

After all this decision making, you will without a doubt need a holiday! Once booking is complete, start the celebration countdown to your Sunsail holiday. No matter which dreamy waters you find yourself conquering, get ready to see the world, differently, and enjoy your holiday among invigorating winds and endless waves.

Author Name: 

Dee Caffari



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