Sailing holidays

Sail the world with us

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 everyone. Get the ultimate in freedom and flexibility on a bareboat charter holiday or enjoy social sailing at its best on a flotilla. Or really make the most of your time on the water and add a professional skipper to your private yacht charter or flotilla getaway.

Our sailing holidays take you to the world's best cruising grounds on a private yacht. All you have to do is choose what sailing holiday suits you best.

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

Find out more about our sailing experience levels.

Get inspired for your holiday destination

Whether you’re looking for a romantic trip for two, a sailing holiday tasting some of Europe’s most delicious food or a fun-filled family break over the school holidays, 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. We’ll inspire you to take that trip you’ve been dreaming of.

Destinations to suit your holiday plans

Find your perfect destination

The Mediterranean

  • Fantastic local food and wine
  • Island hopping and blue water sailing
  • Turquoise, Dalmatian and Amalfi Coasts
Flotillas Experience level 1-3 ICC RYA Sailing School
Explore The Mediterranean

The Caribbean

  • Explore over 5,000 tropical islands
  • Line-of-sight and blue water sailing
  • Laid-back island culture and excellent diving
Flotillas Experience level 1-3 Sailing School
Explore The Caribbean

Indian Ocean

  • Remote, unspoilt and largely unexplored
  • Strong winds ideal for experienced sailors
  • Excellent diving, snorkelling and sport fishing
Experience level 3
Explore Indian Ocean
North America

North America

  • Majestic wildlife
  • Challenging coastal sailing
  • Among the world's best cruising grounds
Experience level 3 ICC RYA
Explore North America
South Pacific

South Pacific

  • Incredible marine wildlife
  • Exhilarating blue water sailing
  • Intrepid remote island exploration
Experience level 1-2 ICC RYA Sailing School
Explore South Pacific
Southeast Asia- Thailand

Southeast Asia

  • 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

The UK

  • A rich naval history
  • The famous Cowes Week regatta
  • Strong winds and excellent sailing conditions
Experience level 3 Sailing School
Explore The UK
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Choose Sunsail

Destinations worldwide
Flotilla routes
Types of yachts
40 yrs
Creating holidays
4 hr
Service guarantee
ABTA – The Travel Association
Consumer protection