How to pick the right sailing holiday for you


Sailing holidays can be confusing, and it pays to ask yourself a series of questions before you book, to help narrow your focus to the right package. We caught up with the experts at Sunsail who give us the lowdown on everything you need to know to embark on a sailing adventure.

What type of sailor are you?

First of all, ask yourself where you and your crew fit on the spectrum of sailing experience, from novice to old hand.

Your Experience:

  • Inexperienced/ complete beginner
  • Competent crew
  • Experienced sailor without qualifications
  • RYA Day Skipper looking for experience
  • Expert sailor (ICC/Day Skipper or above and 400+ miles)

Your group:

  • The family sailors
  • The group
  • The couple

This can help you decide on the type of holiday you choose, from flotillas (ideal for families, inexperienced crew or those looking for a sociable sailing holiday) to bareboat (the purist�s option, better suited to more experienced crews).

It can also inform your choice of sailing area, as some places are easier to sail in than others. At Sunsail we grade our sailing areas into levels 1, 2, and 3. More on that below.

Where should I go?

No idea where to go? Ask yourself a few key questions:

What do you want from the sailing part of the holiday:

  • Laid-back easy cruising with short, island hops?
  • Lessons and courses?
  • A mixture of longer and shorter passages?
  • Or more of a challenge, with tricky navigation or stronger breeze?

At Sunsail we grade our destinations by levels, ranging from easy cruising to more challenging conditions. These levels act as a guide to our sailing areas, encompassing tides, wind, weather conditions and navigational challenges that you may encounter.

Level 1


  • Five days or 100 miles as skipper on an equivalent size yacht
  • International Certificate of Competence (ICC). ICC or RYA Day Skipper is compulsory for Croatia,�and Greece.


�Sailing conditions

  • Wind: 5-20 knots
  • Navigation: line-of-sight sailing. Basic knowledge of charts and ability to plot your position required.
  • Moorings: predominantly stern-to mooring in the Mediterranean and buoys in the Caribbean.

Level 2


  • 10 days or 200 miles as skipper on an equivalent size yacht
  • RYA Day Skipper
  • ICC or Day Skipper is compulsory for Croatia, Greece, Italy, and�Spain.


�Sailing conditions:

  • Wind: 10-20 knots
  • Navigation: you�ll need to understand tidal flow and navigate in open water.
  • Moorings: predominantly anchoring. Protected anchorages, Mediterranean-style anchoring and/or marina slips.

Level 3


  • 20 days or 400 miles as skipper on an equivalent size yacht
  • RYA Day Skipper with experience to a higher level
  • RYA Coastal Skipper
  • ICC with experience to a higher level
  • Temporary certificate�of competence is compulsory in Belize



  • Wind: 10-25 knots
  • Navigation: you�ll need to understand large tidal variations, cope with strong currents and make a passage plan.
  • Moorings: predominantly anchoring, some more exposed anchorages with poor anchor holding ground.

But just as important as the sailing is what takes place after a day on the water. So the next question is: What do you want from the shore-side part?

  • Culture and history? Greece
  • Food and wine? Italy
  • A party atmosphere? The Caribbean
  • Quiet bays and anchorages? The Seychelles
  • Bustling towns and harbours? Marina Agana
  • A mixture of the above? Lefkas

Which is the right yacht for me?

Now you know which part of the world you want to sail in, you need decide which yacht to choose.

Monohull - When most people talk about a sailing a yacht, they have the traditional monohull in mind. The classic yacht, they are designed to slice through the water, offering thrilling sailing, but less space than a catamaran. Monohulls have keels that sit much deeper in the water, and so they have to be acutely aware of water depths. These yachts are best for couples, small groups, flotillas and people after a more dynamic sailing experience.

Catamaran - Spread across two hulls, catamarans offer much larger and more spacious living environment, and sit higher on the water, meaning they can explore much shallower areas. They may surrender some upwind performance to the monohulls, but they are a go-anywhere exploring yacht, perfect for large groups.

Types of sailing holiday

Bareboat charter - A bareboat charter puts you in control, as you literally charter the bare boat, without a skipper or crew. Perfect for experienced sailors looking to take the helm and discover true freedom at sea, independently sailing your own yacht. Jump on board our first-class fleet in 25 superb destinations. You will require a qualification and/or certain level of sailing experience to bareboat charter a yacht.

Flotilla holidays - Sail in the company of other yachts, guided by an expert Sunsail lead crew, who will organise your itinerary. Join a Flotilla in the Caribbean or Mediterranean. You will require some experience to join a flotilla without a skipper.

Skippered holidays - Experience sailing in the expert hands of a Sunsail Skipper. Skippered charters are available at every Sunsail base, and are ideal for the inexperienced. These are great for beginners or those looking to improve under the skipper�s watchful eye.

Sailing schools - New to sailing? Start your sailing journey or take your next step with Sunsail and earn an RYA qualification. We have sailing schools in Portsmouth, Lefkas, Marina Agana, and the Whitsundays.

What more do you need?

Now you know pretty much everything you need to begin planning your charter. So what are you waiting for?

To find out more about Sunsail holidays visit

Member Reward Partners offer all RYA members up to 15% off Sunsail bareboat yacht charter or flotilla holidays. Find out more here.