Easy 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 vacation as you want. Choose from a range of charter options for as laid-back or hands-on a vacation as you want. Relax on deck on a skippered charter vacation, 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. 

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 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 vacation 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.