Top Sailing Routes For Expert Sailors

Sailing holidays Croatia yacht

Are you an expert sailor looking for the real yachting experience?

Do you search the seas for the ultimate sailing routes when sailing in the Mediterranean?

Well, guess what…

We’ve put together a list of the best expert yacht routes:

Surrounded by the varied coasts of Asia, Africa and Europe, the Mediterranean is a sailing heaven for guests of all different levels of experience. However, for the expert sailor, the waters of the Mediterranean provide a playground of challenges, discovery and breathtaking views.

Unpredictable wind patterns rule the Mediterranean Sea. Many are so prominent they even have names: the ‘Bora’ in Croatia, the ‘Meltemi’ in Greece and Turkey, and the ‘Mistral’ in southern France are just a few of these challenging and powerful wind patterns. In addition to this, sailors in the Mediterranean also have to compete with a harsh, rocky coastline, narrow harbour and marina entrances, and long stretches of open water between ports.

But we know, just as well as you, that facing the challenges of difficult sailing conditions is when the real fun starts.

So check out our list of the top sailing routes for pro sailors, and book your boat now!

The Cyclades

Sailing the Cyclades Islands, Greece

Sailing the Cyclades Islands provides guests with picturesque views of traditionally Greek white-washed houses and sun-drenched hillsides. However, don’t be fooled by this seemingly peaceful archipelago. The Cyclades are situated southeast of Athens and east of Poros, and so are not protected by the mainland.

Here, you should plan a route with beam wind to be prepared for the strong summer north wind, the ‘Meltemi’. The ‘Meltemi’ is extremely unpredictable, and so can create some challenging sailing conditions with winds up to a Force 7 or more.

Although the Cyclades are most popular for the famous islands of Santorini and Mykonos, sailing here – especially during summer – is not recommended for beginner sailors (you can always sail with a skipper, though!). But for those who can take the heat, a sailing route from Athens to Kea, Syros, Mykonos, Paros, Serifos, Cape Sunion and back to Athens is one of the most popular sailing routes in the Greek Islands.

The Dodecanese

Sailing the Dodecanese Islands Greece

The Dodecanese are made up of of 12 gorgeous islands – the most popular islands to sail from are Rhodes and Kos – and this beautiful cluster is the most eastern archipelago in Greece.

Similar to the Cyclades, the Dodecanese lie in the path of the ‘Meltemi’ winds that blow forcefully from the northwest. The ‘Meltemi’ wind patterns are particularly strong off Kos, Patmos, Kalymnos, and the open stretch of sea between Karpathos and Astypalea, so during the summer months it is best to sail in a southerly direction.

If you’re an experienced sailor looking for some exciting sailing conditions, the Dodecanese are the islands for you. We suggest starting your trip in Rhodes and cruising over to Symi, Nissiros, Kos, Tilos, Chalki and heading back to Rhodes.

The Balearic Islands

sailing holidays Croatia yacht

The Balearic Islands lie off the eastern coast of Spain in the western Mediterranean Sea. The three largest islands – Ibiza, Mallorca and Menorca – are some of the most popular holiday destinations in Spain, and play home to millions of travellers each summer.

Sailing season here is year-round, but the marinas and anchorages become overcrowded from June to August. It’s common for patches of unexpected weather to visit, namely the ‘Tramontana’ and ‘Mistral’ winds from the northeast. The island of Menorca usually gets hit the hardest with the northerly swell and powerful winds from the open sea to the north.

A popular sailing route for expert sailors starts in Palma and continues around Ibiza (of course, making a day trip to beautiful Formentera on the way), sailing up to Mahon and Ciudadella on Menorca, and then back down the other side of Mallorca to return to Palma.

The Kornati Islands

Sailing holidays in Zadar, Croatia with Zizoo

Bare, rugged and scattered along the Dalmatian Coast, the Kornati provide an exciting and challenging sailing ground. With hundreds of islands and islets to explore, sailing the Kornati is an interesting and busy sailing route.

The most present winds are the ‘Jugo’ and the ‘Mistral’, but the ‘Bora’ winds bring more powerful wind during the off-season period and sometimes even thunderstorms during July and August.  Care should also be taken when navigating the islands, as underwater rock formations and unexpected rock beds can arise when sailing from island to island.

Dugi Otok, Mali Losinj, Pag and Vir are some of the most popular Kornati islands to sail around, but in amongst these lie hundreds of others. Charter a yacht from Split is generally the best base to explore the Kornati.

The Tuscan Islands

Sailing holidays in the Tuscan Islands, Spain with Zizoo

Tuscany’s archipelago of seven picturesque islands provides gorgeous beaches, a characteristic coastline and an exciting sailing ground for all visitors.

The summer months enjoy moderate to strong northwesterly winds and, while they rarely reach gale force, unpredictable wind patterns are still frequent. Unexpected thunderstorms are known to break out during the summer months, and a rocky coastline covers hidden underwater rock formations that sailors should be aware of.

Some of the most popular routes for sailing the Tuscan Islands begin in Elba and continue on to islands such as Giglio, Giannutri and Capraia.

The Canary Islands

Sailing holidays Canary Islands Zizoo

The beautiful Canary Islands sit just off the west coast of Africa and, while they do provide year round sunshine and perfect temperatures, the sailing conditions can be quite challenging.

The prevailing wind is northeasterly year-round, but the strongest winds are in July and August. Sailors may also experience a funnelling effect produced by the locality of the islands, where wind speed is increased by up to 15 knots in certain areas. The Canary Islands also often experience a high swell due to the thousands of kilometres of open sea.

A popular route for sailing in the Canary Islands starts in Lanzarote, cruising around Gran Canaria and charter a yacht in Tenerife and then back to Lanzarote.


Sailing holidays in Sardinia with Zizoo

Sardinia is the second largest island in the Mediterranean and has a coastline of almost 2000 km made up of small islands, sandy beaches and rocky, unpredictable shores. Portisco is one of the major marinas for visiting sailors, and Caprera, La Maddalena and Cala Santa Maria are also popular spots. Sardinia offers plenty of beautiful beaches to explore.

Sardinia experiences the ‘Mistral’ from the west, the hot ‘Scirocco’ from the southeast and the ‘Ponente’ wind patterns that create challenging sailing conditions. The funnel effect that occurs in the strait of Bonifacio increases wind speed and power, so these types of conditions are best suited to sailors with a bit of experience.

Most popular routes for a sailing holiday in Sardinia begin in Portisco on the Costa Smerelda, then cruising on to Cannigione, Palau, Santa Maria, Bonifacio, Porto Pollo and returning to Portisco.


If you’re keen to visit a sailing hotspot full of medieval old towns, a breathtaking backdrop of mountains, and have plentiful French food at hand, then the island of Corsica is the spot for you. Start off at Macinaggio Bay, a port town where you can pick up some last-minute things and ask all your geographical questions. Then, sail off to Saint-Florent, where you can indulge your historical side by touristing around the sights. Then, get ready to sail to the Girolata, where mysterious coves and grottoes provide an exciting change of scenery. If Corsica’s varied landscape is something you’re here to explore, then this is a good anchorage where you can get a taste of it. Sail to Propriano for some rest among some of the most beautiful beaches around. By the end of this trip, you’ll land square at the other end of the island, from which you can actually hop over to Sardinia. 

expert sailor routes by boat

From Split to Dubrovnik

Everyone knows that Croatia is a sailor’s paradise. From renowned and carefully preserved historical sites, to sparkling waves that seem to welcome all visitors, the coastline of Croatia was truly built for sea lovers. We recommend an itinerary that starts off at Split, where you can visit a venetian palace that’s now a UNESCO site. Then, head off to the Blue Grotto, where a glowingly blue and cold enclave of water and stone awaits adventurers. When you’re done, you can head over to Hvar, where  you can visit the Spanjola fortress and stretch your legs. If you have time, you can hop over to other stops on the way, like Korcula and Mlijet. If not, get ready for a longer trek to Dubrovnik, where you can dock your boat and nourish your bodies with fresh Mediterranean food. 

sailing routes yacht charter

Of course, many of these destinations and routes are suitable for beginner sailors with just a small adjustment to the itinerary, but all of these routes can still be enjoyed by adding an experienced skipper to your booking. Adding a skipper to your trip allows you to kick back, relax and feel the cool breeze as you cruise along under a gorgeous orange sunset.

So, what are you waiting for?

Summer is almost here and the sea awaits, so discover your options and book now!

Thanks to Andrea and James Whitesmith for the awesome images from Flickr. All were under creative commons at the time of use.