The Mediterranean

Sailing holidays

Sailing experience level
Day Skipper

Culture, cuisine and gentle cruising

Great food, great wine, a warm and pleasant climate and a relaxed pace of life - that’s what the Mediterranean means to millions of annual visitors. Sailing the Mediterranean offers clear blue waters ideal for swimming and snorkelling, calm conditions and occasional mistral winds that up the ante for those in search of exhilaration, speed and spray.

Discover stunning scenery, ancient history and incredible wildlife as you island-hop through Greece's Ionian Sea, or weave through more than 1,000 sparsely populated islands along Croatia’s Dalmatian Coast. Indulge in the famous cuisine of Italy’s glamorous western shores, and take a trip to the famous Amalfi Coast and Costa Smeralda. Few regions on Earth offer the cultural and geographical variety of the Mediterranean.

From the katabatic meltemi winds of the Aegean to the vibrant and diverse Balearics, Mediterranean sailing has something to surprise and delight sailors of all ages. Whether sailing bareboat, with a skipper or as part of a flotilla, you’re bound to encounter new experiences at every turn. 

Destinations in the Mediterranean

Hvar, Croatia


  • Fine climate and easy sailing
  • Ancient history and rich, varied culture
  • Line-of-sight navigation and island hops
Flotillas Experience level 1-2 ICC RYA Sailing school
Explore Croatia


  • Island hopping and challenging sailing
  • Heptanese, Saronic and Cycladic Islands
  • Incredible ancient ruins and historical sites
Flotillas Experience level 1-3 ICC RYA Sailing school
Explore Greece
Procida, Italy


  • Glamorous towns and quiet villages
  • Unbeatable history, food and culture
  • Line-of-sight cruising and challenging conditions
Flotillas Experience level 2 ICC RYA
Explore Italy


  • Strong winds and open water sailing
  • Excellent nightlife and chilled-out beaches
  • Fantastic diving and snorkelling in underwater meadows
Flotillas Experience level 3 ICC RYA
Explore Spain

Our charter types

Charter your own private yacht and sail the many charming destinations of the Mediterranean, either independently or with the help of an expert skipper. Pick a flotilla holiday and enjoy a more social experience, sailing independently by day and meeting up with your flotilla companions in the evening to enjoy the fantastic restaurants, bars and activities the Mediterranean offers in abundance.

Bareboat charter holidays

Choose a Mediterranean bareboat charter holiday for the most liberating way to sail the diverse countries of the Mediterranean Sea. Take your time and sail at your own pace or squeeze in as much as possible as you island-hop your way along the coast. The choice is yours on a bareboat sailing holiday.

Flotilla sailing holidays

The most social way to sail, a Mediterranean flotilla sailing holiday gives you the chance to enjoy independent island, coastal and blue water sailing by day and group social activities by night. Sail with your family, with friends or on your own, taking in some of the best-loved spots in the Mediterranean along the way.

Skippered charter holidays

Take to the seas in the company of an expert skipper on a skippered charter holiday. Your skipper will be on hand with unmissable tips and recommendations when you need them and discrete enough to give you your own space when you don’t. Hire a skipper for just a day or for your whole holiday, be as hands-on as you like or sit back and let your skipper handle the tough stuff. On a skippered charter holiday it’s entirely up to you.

Choose Sunsail

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