Experienced sailors

Advanced destinations

for experienced sailors

Test your mettle in challenging waters

A taste for adventure, a need to explore. If easy coastal cruising leaves you wanting more, our holidays for experienced sailors offer a greater challenge for intrepid thrillseekers. Stronger winds, changeable weather, broad tidal ranges and exhilarating blue water passages mean these destinations reward the bold and experienced.

Discover the majestic wildlife and immense landscapes of Canada’s Salish Sea, explore the scattered islands of the Seychelles or catch a meltemi wind from Athens through the Cyclades. Our world-class fleet boasts a range of catamarans and monohulls in lengths up to 57 feet, while our charter options let you build your perfect bespoke sailing holiday in some of the world’s premier cruising grounds. 

Our more challenging sailing destinations are Sunsail Level 2-3 and Level 3 sailing areas.

Sailing destinations for experienced sailors

St. Martin sailing holidays

  • Blue water and coastal sailing
  • World-class diving and snorkelling
  • Glamorous resorts and laid-back beaches
Experience level 2-3
Explore St. Martin sailing holidays

Mahé, Seychelles

  • Remote, largely unexplored islands
  • Stable, stronger winds ideal for experienced sailors
  • Good diving, snorkelling and sport fishing
Experience level 3
Explore Mahé, Seychelles

Athens, Greece

  • Ancient relics and ruins
  • Exciting blue water sailing
  • Catch the famous Meltemi wind
Experience level 2-3 ICC
Explore Athens, Greece

Arrange a bareboat charter holiday

Charter a yacht in any of our global destinations and set sail on your own. Venture off the tourist trail in search of scarcely explored islands, virgin coral reefs and playful winds. On a bareboat charter, you have ultimate freedom; you can sail to your own schedule and at your own pace, stopping where and when the mood takes you or pressing on in search of adventure.

Charter a skippered yacht

Skippered holidays are a great way to discover experiences you’d never find on your own. Hire our expert skippers for a day or two and benefit from their local knowledge and unique recommendations, or book a skipper for your entire holiday and just kick back and relax. On a skippered charter, you can take the helm whenever you like or lounge on deck and let your skipper guide you through the highlights of your favourite destination. It’s the most laid-back, flexible way to enjoy a sailing getaway.

Choose Sunsail

Stunning Sailing Destinations 
Flotilla routes
Types of yachts
44 yrs
Creating holidays
4 hr
Service commitment
Consumer protection