Top Sailing Routes For Expert Sailors around the Mediterranean Sea

Need a holiday? Get a free and personalised offer from us!

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

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

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 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:

  • the ‘Bora’ in Croatia
  • the ‘Meltemi’ in Greece and Turkey
  • the ‘Mistral’ in southern France

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

The Cyclades are situated southeast of Athens and east of Poros, and so are not protected by the mainland.

Sailing the Cyclades Islands:

  • Highlights: picturesque views of traditionally Greek white-washed houses and sun-drenched hillsides
  • Sailing conditions: 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.
  • Famous Islands: Santorini and Mykonos
  • Recommendation: sailing in the Cyclades is not recommended for beginner sailors (you can always sail with a skipper)
  • Sailing route ides: Athens – Kea – Syros – Mykonos – Paros – Serifos – Cape Sunion – back to Athens

Read the Guest Post about sailing in the Greek Islands.

The Dodecanese

Sailing the Dodecanese Islands Greece
  • Highlights: 12 gorgeous islands
  • Popular islands: Rhodes and Kos – and this beautiful cluster is the most eastern archipelago in Greece
  • Sailing conditions: 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.
  • Recommendation: 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.
  • Sailing route: Rhodes – Symi – Nissiros – Kos – Tilos – Chalki – back to Rhodes

Charter a yacht in Kos ›

Charter a yacht in Rhodes ›

The Balearic Islands

sailing holidays mallorca spain

The Balearic Islands lie off the eastern coast of Spain in the western Mediterranean Sea.

  • Popular islands: Ibiza, Mallorca and Menorca
  • Sailing season: year-round, but the marinas and anchorages become overcrowded from June to August
  • Sailing conditions: 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.
  • Sailing route: Palma – Ibiza – day trip in Formentera – Mahon – Ciudadella on Menorca – back to Palma

Charter a yacht in Palma ›

Charter a yacht in Ibiza ›

The Kornati Islands

split sailing holiday

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:

  • Sailing conditions: 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.
  • Popular islands: Dugi Otok, Mali Losinj, Pag and Vir

Charter a yacht from Split ›

The Tuscan Islands

Kids on the deck of a boat

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

  • Sailing conditions: 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.
  • Sailing route: Elba – Giglio – Giannutri – Capraia

Charter a yacht from Elba ›

The Canary Islands

cave lanzarote boat holidays

The beautiful Canary Islands sit just off the west coast of Africa.

  • Sailing conditions: provide year round sunshine and perfect temperatures, but 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.
  • Sailing route: Lanzarote – Gran Canaria – Tenerife – Lanzarote

Rent a boat in the Canary Islands ›

Rent a boat in Gran Canaria ›

Charter a yacht in Tenerife ›

Rent a boat in Lanzarote ›


sardinia sailing

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.

  • Main Marinas: Portisco is one of the major marinas for visiting sailors, and Caprera, La Maddalena, and Cala Santa Maria are also popular spots.
  • Beaches in Sardinia: Spiaggia la Celvia, Pevero, Spaggia del Principe, La Maddalena. Check out all the most beautiful beaches in Sardinia.
  • Sailing conditions: There is the ‘Mistral’ wind 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.
  • Sailing route: Portisco – Cannigione – Palau – Santa Maria – Bonifacio – Porto Pollo – Portisco.

Rent a boat in Sardinia ›


  • Highlights: sailing hotspot full of medieval old towns, a breathtaking backdrop of mountains, and amazing French food
  • Sailing route: Macinaggio Bay – Saint-Florent (indulge your historical side by touristing around the sights) – Girolata (mysterious coves and grottoes provide an exciting change of scenery) – Propriano (rest among some of the most beautiful beaches around) – Sardinia

Rent a boat in Corsica ›

sailing in corsica

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.

  • Sailing route: Split (visit a venetian palace that’s now a UNESCO site) – Blue Grotto (a glowingly blue and cold enclave of water and stone awaits adventurers) – Hvar (visit the Spanjola fortress and stretch your legs) – Korcula – Mlijet – Dubrovnik, where you can dock your boat and nourish your bodies with fresh Mediterranean food. 

Charter a sailboat in Split ›

Charter a yacht in Dubrovnik ›

sailing around dubrovnik

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!