Easy sailing

Sailing holidays

Chilled-out sailing

Sometimes you just want to recline on deck without a care in the world. With simple line-of-sight navigation, short island hops and ample moorings, our easy sailing destinations offer a completely stress-free experience.

Improve your sailing skills and boost your confidence in the calm, warm waters of the Ionian, where navigation is a breeze, as you sail from island to island. Take a break and sail a spacious Sunsail 444 catamaran in the sheltered, blissed-out Bahamas. Choose from a range of charter options for as laid-back or hands-on a holiday as you want. Relax on deck on a skippered charter holiday, or sail with friends on a flotilla at one of our easy sailing destinations.

Our easy sailing destinations are listed as Sunsail Level 1 and Level 1-2 sailing areas. If you have no sailing experience and want to discover the joy of a sailing holiday without having to book the whole yacht for yourself, you can sail by the cabin and meet like-minded holiday makers on a skippered flotilla 

Our easy sailing destinations

Ithaca, Greece

Lefkas Sailing Holidays

  • Easy, rewarding sailing
  • Sail the famous Heptanese Islands
  • Enjoy fantastic watersports
Flotillas Experience level 1-2 Sailing school
Explore Lefkas Sailing Holidays
Hvar Town, Hvar Island

Marina Agana, Croatia

  • Easy line-of-sight sailing
  • Short island hops and longer trips
  • Explore quiet islands and national parks
  • Discover Croatia's rich and two-millennia old history
Flotillas Experience level 1 Sailing school
Explore Marina Agana, Croatia

British Virgin Islands

  • Visit a real-life Treasure Island
  • Steady trade winds, calm currents
  • World-famous yachting destinations
Flotillas Experience level 1
Explore British Virgin Islands

Hire a skipper

A skippered sailing holiday is the ideal way to experience coastal and island sailing in safety, without stepping outside your comfort zone. Hire an expert skipper and benefit from unique local knowledge and recommendations you won’t find anywhere else. Improve your sailing skills and learn as much or as little as you like from a fully qualified skipper available for your whole holiday or for just a day or two, allowing you to be as hands-on or as laid-back as you like.

Book a flotilla holiday

Our flotilla holidays are the most sociable way of experiencing island and coastal sailing. Join with a group of sailors eager to explore an exciting new destination with the help of an expert lead crew. Follow the lead boat on your own, hire an experienced skipper for a couple of days or let your skipper take the reins for the duration of your holiday—the choice is entirely yours. This stress-free approach to sailing holidays allows you to spend as much or as little time with your new flotilla friends as you like, leaving you free to enjoy your holiday your way.