Discover the best sailing holidays in Italy. Explore Tuscany, Sardinia, Sicily, Capri, Ischia, Procida & Aeolian Islands with insider tips from experience.
There is nothing quite like discovering Italy from the water. Having sailed extensively along its coastlines and between its islands, I can say that Italy offers some of the most rewarding sailing holidays in the world. From the rugged shores of Tuscany to the crystal-clear waters of Sardinia, every journey brings new landscapes, cuisines, and unforgettable experiences.
The joy of sailing in Italy lies not just in the scenery, but also in the culture waiting at each port. Small fishing villages, bustling piazzas, and island traditions give every stop a unique personality. Whether you’re chartering a yacht for a week or setting off on a longer voyage, there are countless routes to explore.
The Tuscan Archipelago is a perfect starting point for a sailing holiday. Elba, with its historic harbors and Napoleon connections, offers sheltered bays and sandy beaches. Nearby Giglio and Capraia provide a quieter charm, perfect for those who prefer authentic island life over crowds.
From Tuscany, it’s easy to continue south, stopping at Porto Ercole or sailing towards the Pontine Islands for more secluded adventures.
Ponza is a favorite among Italian sailors, with its pastel-colored houses and dramatic cliffs. It has a lively nightlife and excellent seafood, yet remains relaxed compared to Capri. Ischia is known for its thermal spas and volcanic landscapes, while nearby Procida offers a slower rhythm, perfect for an afternoon anchored in a quiet cove.
These islands combine natural beauty with vibrant culture, making them ideal for sailors who love exploring ashore as much as time on deck.
Capri is iconic, and arriving by yacht makes the experience even more special. Sail around the famous Faraglioni rock formations and anchor in Marina Piccola for breathtaking views. Although it can be crowded in peak season, Capri remains a must-visit stop for its sheer beauty and sense of timeless elegance.
An evening stroll in the Piazzetta, after arriving by tender, captures the essence of Capri’s charm.
Sailing around the Aeolian Islands is an adventure into volcanic landscapes. Stromboli’s glowing crater is an unforgettable sight from the sea, while Lipari offers lively harbors and Aeolian cuisine. Salina, with its vineyards and slower pace, is perfect for relaxation.
From here, Sicily beckons with its dramatic coastline, ancient ruins, and culinary treasures. Taormina and Syracuse are spectacular ports of call for sailors seeking culture and history alongside stunning waters.
Sardinia is a sailor’s paradise. The Costa Smeralda dazzles with turquoise seas, hidden bays, and world-class marinas. Maddalena Archipelago, a UNESCO-protected area, is breathtaking, with wild granite islands and pristine anchorages.
Sardinia’s west coast offers a wilder, less touristy side with long stretches of untouched beaches, while the south provides a gateway to the open Mediterranean routes.
Italy’s sailing season runs from May to October, with July and August being the busiest months. For calmer seas and fewer crowds, consider May–June or September–October. Whether you charter a skippered yacht or sail independently, plan routes with flexibility—Italy is best enjoyed when you allow time for unexpected discoveries.
Each voyage brings a mix of adventure, relaxation, and culture. For me, sailing in Italy has always been about balance: time on the water, time on the shore, and the joy of blending both seamlessly. Once you’ve experienced it, you’ll understand why Italy remains one of the world’s greatest sailing destinations.
