Cultural sailing holidays


Sailing holidays

Noble coastal cities and island empires

Follow in the wake of ancient Greek and Roman mariners on a sailing holiday to the cultural hotspots of Europe. A cultural sailing holiday lets you step back in time and immerse yourself in the heritage of your sailing destination.

Explore the ancient citadels and spectacular Renaissance palaces of the medieval walled city of Dubrovnik, discover Lycian tombs, ruins and historic sites along Turkey’s Turquoise Coast or see an intoxicating fusion of Roman, Greek, Arab and Norman civilisations in Palermo. With so many cultural heritage sites to choose from and destinations to visit, your perfect cultural sailing holiday is right at your fingertips. Set sail on your own on a bareboat charter holiday or enjoy the sights with others in a flotilla.

Our culture-rich sailing destinations

10% off
bareboat and flotilla in 2017

Dubrovnik, Croatia

  • Gentle winds and occasional Mistrals
  • Rich history and spectacular scenery
  • Line-of-sight navigation and island hops
Flotillas Experience level 2 ICC RYA
Explore Dubrovnik, Croatia
10% off
bareboat and flotilla in 2017
Hvar Town, Hvar Island

Marina Agana, Croatia

  • Easy line-of-sight sailing
  • Short island hops and longer trips
  • Explore quiet islands and national parks
Flotillas Experience level 1-2 ICC RYA Sailing school
Explore Marina Agana, Croatia

Fethiye, Turkey

  • Calm conditions and consistent winds
  • Explore the renowned Turquoise Coast
  • Dive, snorkel and kayak the Aegean Sea
Experience level 1-2 ICC RYA
Explore Fethiye, Turkey

Sardinia, Italy

  • Excellent food and wine
  • Glamorous resorts and quiet anchorages
  • Dynamic sailing off famous Costa Smerelda
Experience level 2 ICC RYA
Explore Sardinia, Italy
Palermo, Italy

Palermo, Italy

  • Sicilian food and culture
  • Ideal for experienced sailors
  • Coastal cruising and open water sailing
Experience level 2 ICC RYA
Explore Palermo, Italy

Bareboat charter holidays

Immerse yourself in local traditions, enjoy unique cuisine and explore cultural heritage sites on a bareboat charter holiday. Chartering a yacht in one of our European destinations introduces you to the history of this great region. Go where you want and stay as long as you like—a bareboat charter puts you in control of your schedule.

Skippered sailing holidays

Your skippered sailing holiday lets you sit back and enjoy the culture of Europe with an experienced guide. Our expert skippers have unique local knowledge and recommendations to ensure your sailing holiday is one you won’t soon forget.

Flotilla sailing holidays

If you want to enjoy the social side of sailing along with the culture and sights along the way, opt for a flotilla holiday. You’ll appreciate line-of-sight sailing by day, seeking out medieval walled towns and ancient tombs interspersed along Croatian and Italian islands. By night dine on traditional food and wine in local restaurants with your new friends.

Choose Sunsail

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