The best places to visit on a sailing holiday to Italy

Imagine going on a sailing holiday where you can have every one of the most important ‘must haves’ ticked off. Sun, sea, history, culture, art, architecture, wonderful cuisine and excellent sailing conditions. It’s not possible, we hear you cry…but it is! On a yacht charter in Italy.

This fascinating Mediterranean gem is quite literally like a world in one country and the diversity found between one end and the other is quite something. To the north, visitors can enjoy the romantic landscapes of Venice, sitting on the coast of the Adriatic Sea. Further south, sunseekers can choose between the azure waters of the Ionian and Tyrrhenian Seas and islands such as Sicily and Sardinia. No two sailing grounds are the same in Italy, and coupled with the vast amount of things to see and do, the country makes for one of the very best, most varied sailing destinations in the world.

With so many places to visit and different sailing conditions on offer, we have pulled together our top places to sail in Italy, to help you plan the perfect Italian yacht charter holiday.

Venice

Sail through the intricate waterways that weave through the romantic city of Venice and enjoy the calm waters of the Adriatic Sea on a sailing holiday to one of the world’s most romantic locations.

Wander around the world famous Piazza San Marco, surrounded by magnificent buildings of Renaissance architecture and enjoy traditional Venetian food at one of the many cafes that line the Square. Visit the city of Torcello where you can see the magnificent sight that is the Cathedral of Santa Maria Assunta, an ornately decorated piece of architecture that was one of the greatest buildings erected in the area during the Byzantine era.

Even though you’ll have your very own yacht to enjoy your sailing adventure in Italy, we recommend swapping your sea vessel for the evening and embarking on a gondola ride where you can sit back and relax as you take in the sights along the Grand Canal and sail under the oldest of cities four bridges, Rialto Bridge.

There are 417 bridges in Venice – 72 of which are private!

Tuscany

When thinking of Tuscany, many automatically picture beautiful sweeping landscapes filled with vineyards and al fresco dining, but the Tuscan riviera has so much more to offer, especially for sailors. There are a multitude of easily accessible mooring locations dotted along the coast, stretching from the north of the region, right down to the more southerly Tuscan ports of Punta Ala and Piombino.

From the northern port of Viareggio, sail south and moor at the Marina de Pisa, where a short journey inland will reward you with stunning views of the famous leaning tower. The port of Castiglioncello in the Livorno province is the perfect gateway to sail to the island of Corsica, an island of outstanding natural beauty where the port of Bastia offers visitors excellent cruising, magical Renaissance architecture and delicious cuisine.

To the south, sail from the marina in Piombino, where you can visit the The Archaeological Park of Baratti and Populonia home to some of the most significant archaeological sites in Italy and an ideal base to explore the island of Elba. From Punta Ala, visit the beautiful beaches of Cala Martina and enjoy a scenic walk up to Castello di Punta Ala.

Loveable Disney character, Pinocchio was the brainchild of Italian writer Carlo Collodi, who was born in Florence in 1826.

Naples

Explore the spectacular ancient Roman ruins of Pompeii, the stylish island resort of Capri and the fashionable city of Sorrento on a bareboat yacht charter from Naples where traditional Italian charm meets chic and stylish culture.

Popular with celebrities and a regular haunt for honeymooners, Sorrento faces the Bay of Naples and offers visitors spectacular views out to sea from the hillside. Enjoy lunch at one of the many cafes that line the Piazza Tasso, and wander through the labyrinthine lanes that lead to 14th Century ecclesiastical buildings and lavishly decorated museums.

Visit the ancient city of Pompeii, where the once thriving Roman city was buried beneath gallons of lava and ash following a catastrophic eruption from Mount Vesuvius which devastated the area. See fully preserved people, homes and belongings of those who suffered during the event and marvel at the undeniable power of Mother Nature.

For an adventure you’ll never forget, sail south to the island of Capri and enjoy a days watersports and cliff diving by the Blue Grotto, where the cobalt coloured seas are as inviting as the people. Venture up Monte Solaro for spectacular views out over the Tyrhrennian Sea, before sampling some of the locally produced limoncello and eating traditional Capri such as ravioli Capresi.

Naples was home to the world’s first pizzeria, Antica Pizzeria Port’Alba, which opened its doors in 1830.

Elba

Often referred to as the most beautiful of the Tuscan islands, Elba is one of the most wonderful places for sailing in Italy, full of quiet anchorages dotted around the rugged coastline with pristine waters that make for the most amazing swimming and snorkelling adventures.  

On the northern coast, visit the Arcipelago Toscano National Park with its dramatic scenery and beautiful walks and the Beach of Samson, a tropical looking beach with gorgeous sand and turquoise waters. To the east, step back in time at the Parco Minerario, an old mining park dedicated to the preservation of the area’s history.

To the south, we highly recommend spending a day in the tranquil setting of Costa dei Gabbiani, the ‘Gulf of seagulls’, a quiet, serene stretch of beach which weaves through multiple coves and is surrounding by magnificent cliffs.

French emperor, Napoleon, was banished to the island of Elba in 1814.

Sardina

The second largest of the Italian islands, Sardinia is rich in history and with over 2,000km of coastline and exhilarating strong summer winds is home to some of the Mediterranean’s most exceptional sailing.

Enjoy the mistral winds of the Costa Smeralda where you can watch fellow sailors taking part in one of the area’s famed regattas. Sunbath on the Grande Pevero beach, lined with powdery sand and see a huge variety of sea life including dolphins when you snorkel and dive in the clear sea. For art lovers, take a hike inland and visit the Stella Maris Church where you can see paintings by El Greco.

Take in breathtaking views of the Straits of Bonfico from the island of La Maddelena and sail further east around the island where you’ll find a number of quiet anchorages, perfect for a day or peace and tranquility. Sardinia is famous for its mouthwatering cuisine, so make sure that you use your time sailing in Sardinia to try as much local food as possible, including freshly caught octopus and squid. Our favourite is seafood fregola with locally grown saffron – delicious.

Sardinia is the only region in Italy not to have a motorway.

Sicily

The largest island in the Mediterranean, Sicily is rich in history and intrigue and home to some of Europe’s most lavish architectural masterpieces, from Byzantine churches to Greek temples. From the northern coast, sail the Aeolian Islands from Palermo or Capo d’Orlando in Messina.

Located in the Tyrrhenian Sea, the islands offer sailors a multitude of deep water anchorages and long passages, ideal for those who are experienced in sailing and looking for an adventurous charter. Instagrammers will fall in love with the picturesque scenery in Salina and a visit to the largest of the islands, Lipari, is a must for history fans, with its ancient acropolis and stone fortress.

Sail to the east coast of Sicily towards Taormina, located between Messina and Catania, and see magnificent Mount Etna before heading ashore to visit the Teatro Antico di Taormina with its breathtaking views.

Sail around the west coast from Palermo and head for Marsala, home to ancient ruins and fortified Marsala wine and visit the Baglio Anselmi Archaeological Museum, where you can see an ancient shipwreck from the Punic War before enjoying some truly spectacular Sicilian cuisine in one of the Island’s many restaurants.

The term, ‘stuck between a rock and a hard place’ originates from the legend of Scylla and Charybdis, sea monsters who guard either side of the messina strait between Sicily and Calabria.

If you want to know more about sailing in Italy, speak to one of our experts who will be happy to share their knowledge with you. Use our price comparison tool to search for charters by date or destination, request a quote or contact our team on 877-292-0737.