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Sailing trip Italy - Sailing with skipper

Experience your dream vacation while sailing in Italy! From the emerald green Costa Smeralda in Sardinia to the cultural diversity of Sicily and the glamorous Amalfi Coast - first-class sailing areas for your sailing vacation in Italy are waiting for you. Sail Italy with an experienced skipper and enjoy la Dolce Vita on the water.

April - October

Olbia / Portisco and Naples / Salerno

4.9/5 Stars

Why a sailing vacation in Italy?

Drei weiße Katamarane ankern in türkisblauen Gewässern bei Sardinien – segeltörn sardinien mit sailwithus

Dreamlike coasts

Sailing Italy means experiencing the Costa Smeralda: emerald green water, white sandy beaches and sophisticated harbors - the perfect backdrop for your sailing trip in Italy.

Culinary delights

Culinary delights

Sailing tour Italy with pleasure: fresh fish, homemade pasta and first-class wines in authentic harbor restaurants - La Dolce Vita when sailing with Italy.

Culture & History

Culture & History

Sailing vacation Italy with culture: From Roman ruins to medieval coastal towns - history and modernity merge when sailing Italy with a skipper.

Our Italy sailing routes

Choose from our most popular sailing areas for your sailing trip in Italy. Each route offers unique highlights and unforgettable experiences.

Drei weiße Katamarane ankern in türkisblauen Gewässern bei Sardinien – segeltörn sardinien mit sailwithus
⭐ Bestseller

Route Sardinia & Corsica

Two dream destinations in one trip! You sail through the La Maddalena archipelago between Sardinia and Corsica with turquoise waters, picturesque coastal towns and Italian-French flair.

Route-Highlights

La Maddalena - Emerald green bays
Bonifacio - Corsican fortress town
Santa Teresa - wild landscape
Lavezzi Islands - fascinating bays
Costa Smeralda - sophisticated harbor towns
Segelcharakter
Diversity: Two countries in one sailing area
Island hopping in the archipelago
Active sailing and relaxing in bays
Pleasant winds with jet effect
Route Amalfi Coast
✨ Glamor

Route Amalfi Coast

Glamor & dolce vita on the Gulf of Naples! Discover the blue grotto of Capri, the thermal springs of Ischia and the path of the gods. Jet-set feeling meets Italian lifestyle.

Route-Highlights

Capri - Blue Grotto & Faraglioni
Positano - picturesque fishing village
Ischia - Thermal springs
Typical trattoria - culinary delight
Sorrento - black cliffs
Segelcharakter
Spectacular cliffs - picturesque places
Light winds and thermal winds
Short distances
Sightseeing from the water - anchoring at buoys
Route Elba & Archipelago
🏝️ Island hopping

Route Elba & Archipelago

The magic of the Mediterranean off Tuscany! Sailing around Elba, Pianosa and Capraia. Turquoise-blue bays, historic Portoferraio and crystal-clear water await you.

Route-Highlights

Portoferraio - Napoleon's exile
Pianosa - Untouched paradise
Capraia - volcanic landscape hike
Palmaiola - lighthouse & bays
Snorkeling - Crystal clear water
Segelcharakter
Varied coastline
Many anchor bays & good marinas
Moderate winds with good sailing wind in the afternoon
Short distances & protected territory

Sailing trip Italy - diverse sailing areas for every taste

From exclusive Sardinia with its turquoise bays to the spectacular Amalfi Coast with its dramatic rocky backdrops - each region has its own character and charm.

Sardinia - The jewel of the Mediterranean

The Costa Smeralda in Sardinia is Italy's premium sailing area. Emerald green water, white sandy beaches and sophisticated harbors such as Porto Cervo make this region a dream destination for sailors. The La Maddalena archipelago offers Caribbean flair with crystal-clear water and secluded bays. The sailing conditions are ideal – moderate winds, short distances and sheltered anchor bays. The Sardinian cuisine with fresh fish, pecorino cheese and Cannonau wine rounds off the experience. From May to October, the conditions are perfect for your sailing trip in Italy.

Elba - Pearl of the Tuscan Archipelago

A sailing vacation around Elba combines the natural beauty of Tuscany with the unique charm of the Mediterranean. The area is characterized by varied waters and moderate winds in summer, making it ideal for relaxed cruises. From the historic capital of Portoferraio with its impressive fortresses to the wild volcanic island of Capraia, the route offers fascinating opportunities. Fantastic bays such as Fetovaia or the Caribbean-like waters off the island of Pianosa invite you to take a long swim. In the evening, you can enjoy the Italian "dolce vita" with local specialties and Tuscan wine in charming harbour towns such as Porto Azzurro. Whether hiking to old watchtowers or relaxing on deck, this variety makes Elba a fantastic destination for an unforgettable sailing trip.

Amalfi Coast - UNESCO World Heritage Site on the water

The Amalfi Coast is one of the most spectacular stretches of coastline in the world. Steep cliffs, pastel-colored houses and luxurious marinas characterize the picture. Positano, Amalfi and Ravello are postcard motifs that are best experienced from the water. The island of Capri with its famous Blue Grotto is a must-see. The sailing conditions are relaxed – sheltered waters, light winds and short distances make the region ideal for families and beginners. The Gulf of Naples also offers cultural highlights such as Pompeii and Herculaneum, which can be visited on shore excursions.

Ready for your Italian adventure?

With our experienced skippers, you can put your skills to the test on an exciting tour through a mostly calm sea area. Start your dream vacation today!