Sailing holidays options

Sail the world with us

Clear waters, warm winds and the thrill of adventure at sea. Whether you’re a newbie looking to find your sea legs, or an old hand who already knows the ropes, we offer sailing holidays for sailors of all ability and experience levels. Go your own way and relish ultimate freedom on a bareboat charter. Or blend superb sailing with lively socials and the support of a lead crew on a Sunsail flotilla. Looking to take things easy? Add a professional skipper and let them tackle the hard work as you enjoy the cobalt seas and chase endless horizons.

Creating the world’s finest charters doesn’t happen overnight. It comes from years of experience. Years spent listening to and acting on what sailors want from a yachting holiday. And we keep refining Sunsail Holidays to make them even better. That way they don’t just live up to your expectations, but go beyond your wildest dreams.

Our sailing holidays span 25 worldwide destinations, from the magical Mediterranean to the colourful Caribbean and even more remote and exotic destinations. We'll take you to the world's best cruising grounds. All you have to do is choose which option suits you best, and prepare to set sail.

We've even grouped our destinations by experience level, so you can find the right sailing ground for your skills, qualifications and desires.

Find out more about our sailing experience levels.

Get inspired for your holiday destination

Feel the romance of a sailing trip for two; indulge in a sailing holiday that shines with some of Europe’s most delicious food; or dive in to a fun-filled family break. We’ll take you wherever you want to go. Wake up to a new view every morning in the Mediterranean, discover pure relaxation in the Caribbean or explore the world’s most remote shores. Get inspired, get afloat and see the world, differently.

Destinations to suit your holiday plans

Find your perfect destination

  • Fantastic local food and wine
  • Island hopping and blue water sailing
  • Ionian, Dalmatian and Amalfi Coasts
Flotillas Experience level 1-3 ICC RYA Sailing school
Explore The Mediterranean
  • Sparking turquoise blue waters
  • Wealth of colonial history & picturesque ports
  • More than 5,000 islands to explore
Flotillas Experience level 1-3 Sailing school
Explore The Caribbean
  • Remote, unspoilt and largely unexplored
  • Stronger winds ideal for experienced sailors
  • Excellent diving, snorkelling and sport fishing
Experience level 3 ICC RYA
Explore Indian Ocean
South Pacific
  • Incredible marine wildlife
  • Exhilarating blue water sailing
  • Intrepid remote island exploration
Experience level 1-2 Sailing school
Explore South Pacific
Southeast Asia- Thailand
  • Sport fishing and excellent diving
  • Year-round sailing, line-of-sight navigation
  • Tropical beaches and dramatic landscapes
Experience level 2 Sailing school
Explore Southeast Asia
Portsmouth, England
  • A rich naval history
  • The famous Cowes Week regatta
  • Strong winds and excellent sailing conditions
Flotillas Experience level 3 Sailing school
Explore The UK