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. For more insider knowledge read our Guide for sailing the Mediterranean.

From the ancient ruins and whitewashed walls 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, or by the cabin, 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 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
Explore Italy

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.

Sail By The Cabin

Take advantage of three exclusive dates this summer and book by the cabin on either a Sunsail 53 monohull or a Sunsail 454 catamaran. Your expert skipper will handle the sailing, so you can book a cabin to yourself or with a friend, kick back and enjoy one of three fantastic Mediterranean sailing areas. You and your companions will experience all the fun of a flotilla holiday and make new friendships as you get to know the region’s spectacular coastline with a group of fellow explorers.


We created our Early Boarding* service so you can squeeze every last drop of sunshine out of your Mediterranean sailing vacation. Standard boarding time for all Mediterranean bases is 6 p.m., but you can request a 3 p.m. boarding time for an extra charge. Call your Sunsail Vacation Planning Specialist to request early boarding.

*Early boarding is a pre-paid extra. Subject to availability on request.