Why you should book a holiday with Sailsquare?
The leading sailing holiday marketplace
25,000+ happy travellers, and 10,000+ holidays in 110 destinations worldwide.
Get onboard solo, with your family, or your friends
Reserve a single spot, a cabin, or a whole boat just for you and your friends or family.
Discover who’s already onboard
Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.
Sailing holidays that suit all budgets
Rumour has it that sailing holidays are only for the rich or well-connected. With Sailsquare, that's no longer true. Come and discover a world you never thought was accessible!
Reviews - Sailing holidays in Italy with a local skipper6925 reviews
Would you like some support using the platform? We've (almost) always got the answers!
Can't find the perfect holiday for you?
Use our free holiday concierge tool - and let us find your dream sailing experience for you!Let's find it together!
8 reasons to choose Italy for your next sailing holidays:
- Italy is not only famous for its good food, but beautiful beaches, and rich history. The perfect destination for all those who want to mix a sailing holiday, with a cultural exploration.
- Get lost in the streets of Bonifacio while sailing in Sardinia and enjoy the breathtaking beauty of the Costa Esmeralda.
- With a sailing weekend in Tuscany try the local specialties, from Brunello di Montalcino to Lardo di Colonnata.
- How about an aperitif at sunset off the Ligurian coast? Then set sail towards the wild Sardinia and enjoy a delicious Sardinian Porceddu.
- Sail from Balestrata to Favignana and discover the Sicilian coast with its crystal clear waters - not forgetting to enjoy a good cannolo.
- Experience the unique experience of sailing in Campania. Sail from Naples to Ischia with Vesuvius in sight.
- 7,458 kilometres of coastline, 800 islands and the best food in the world make Italy a true sailing paradise.
- Moor on the coasts of La Maddalena, dive in the crystal clear waters and explore Garibaldi's homeland on the island of Caprera.
The best places & specific destinations to visit during your sailing holidays in Italy:
Italy is the perfect destination for a sailing holiday, with thousands of kilometres of coastline and hundreds of islands, many of which can only be reached by sea, it is a playground for sailors. Sailors in Italy have the fortune of 14 wonderful coastal regions to discover: from the colourful villages of Liguria and Tuscany to Sardinia, Il Giglio, the Pontine Islands, Campania, Sicily and beautiful Salento, Tremiti Islands, the Conero Coast, Venice, and much more. In addition to maritime landscapes, culture also changes every few kilometres - where each region has its own traditions and this is reflected in the cuisine. Enjoy unique and always different dishes after sailing and drink to an unforgettable sailing day.
Italy not only has (arguably) the best food in the world, with a fantastically charming coastline, but also the largest cultural heritage in the world with over 3,400 museums, around 2,100 archaeological treasures, numerous national parks, and 43 UNESCO sites. Your sailing holiday in Italy will be breathtaking not only at sea, but also on land. Find your dream adventure from thousands of sailing opportunities, in every region of the country, with something for each type of budget . From a two-week sailing holiday in Sicily to a sailing weekend in Tuscany, Italy offers a huge variety of sailing experiences.
Sailing along the coast of Sicily and the neighbouring islands of Balestrate, Favignana, Taormina and the Egadi Islands are just some of the destinations to discover in Sicily. It is important not to forget the Sicilian cuisine, including Arancini and Cannoli, which you can enjoy alongside the island’s crystal clear waters.
Discover the land of the Porceddu and the typical masks of the Mamoiada Carnival on a sailing holiday in Sardinia. However, it is not only an area steeped in tradition and culinary richness, The Costa Smeralda, Capo Coda Cavallo, the Rai-coast, and the Paradiso-coast are breathtaking sailing areas, which are among the most beautiful in the world.
Crystal clear waters, just a stone's throw from the Apulian coasts. The most famous island of San Nicola, which resembles an open-air museum is surrounded by coastal beauty - making it an ideal location for snorkelling.
The islands of Elba and Giglio are the most popular areas in Tuscany. They are ideal for those who want to spend a few days on a sailing boat. And, with a bit of luck you might come across some of the dolphins that are native to the area.
The Pontine Islands are a group of 6 beautiful islands, Ponza, Palmarola, Zannone, Gavi, Ventotene, and Santo Stefano. Each of them home to their unique charm, and well worth exploring for yourself.
The Aeolian Islands are among the most unique volcanic islands in the world - from Stromboli, where you can admire the lava flow to the sea, to the island of Vulcano, with only 300 inhabitants. You can also explore the other pretty Aeolians, Lipari, Salina, Filicudi, Alicudi and Panarea.
Tips to help you to better plan for your next sailing holidays in Italy:
All you need to know about your next cruise in Italy aboard a sailboat.
The best time for a sailing holiday in Italy
In Italy you can sail from May to September. The mild climate offers temperatures ideal for this type of holiday - ranging from 20 to 35 degrees, with August being the peak season. You might want to consider avoiding peak season if possible, and choose perhaps June or July instead for your sailing holiday. In these months it is warm, but the sailing areas and cities are much less crowded. You can also save money outside the high season. However, if you still travel in August, sailing in Italy offers the ability to find more secluded bays and coves, tucked away from the “beaten track”, where you can fully embrace the country’s natural beauty.
Sailing holidays in Italy as a family
A holiday in Italy on a sailboat can be suitable for everyone, with its unspoilt nature and crystal clear waters, it is suitable for everyone who longs for the sea and complete relaxation. Sailing in Italy is also ideal for families. In addition, a sailing holiday in Italy is also ideal for couples who want to take a unique break together in romantic locations such as the Aeolian Islands or the Sorrento Peninsula. For the curious culinaries sailing in Italy also has a lot to offer, discover different places where you can try different unique local dishes.
Transport options to and from your holiday
Italy has airports in every major city - Milan, Rome, Bologna, Ancona, Catania, Turin, etc, that are served by budget airlines. However, if you decide to go sailing in August, prices can rise considerably. Alternatively, thanks to the well-developed rail network, you can easily travel by train if you book it at least a few weeks in advance. Ferries also connect the main islands such as Sardinia and Sicily with the rest of Italy. Your skipper will advise you on the best way to reach the port of departure.
How much do sailing holidays in Italy cost?
Prices vary according to destination and duration. You can plan for around €100 per day with an aperitif at sunset. From €300 per person you are looking to sail for a long weekend. If you are looking for a longer experience, for example, you can book 6 nights on the island of Tavolara and the archipelago of La Maddalena for around €600. In short, there is the perfect sailing trip in Italy, with budget friendly options.
Sailing holidays in Italy - why you should travel with a local skipper
If you want to fully enjoy your sailing holiday in Italy in the best conditions, we recommend that you go choose a trip with a local skipper. Travelling with a skipper who has insider knowledge on the area, allows travellers to fully immerse in the pleasure and relaxation of the holiday. Where individuals on the trip wish to learn or practice their sailing skills, skippers will be there to integrate travellers into the responsibilities onboard.
The best sailing holiday itineraries for your next adventure in Italy with a skipper:
- Tuscany: for this route we recommend 7 days, so that you can discover the Tuscan archipelago in a relaxed way. From Punta Alata we go to explore the island of Capraia. After you will spend a few days on the beaches of Portoferraio and can visit the island of Giglio. You will complete your sailing trip in Tuscany on the lesser known island of Giannutri.
- Aeolian Islands: discover the Aeolian Islands between Panarea and Stromboli over a long weekend. Once you have arrived in Stromboli, you will have the opportunity to take a guided excursion to the top of the volcano and end the day in a very good restaurant overlooking the spitting volcano. The next day you sail on to Panarea, past Sciara del Fuoco. Finally you can relax in Panarea or take a trip to the prehistoric village with its breathtaking views.
- North Sardinia: sail for a week in the north of Sardinia and be enchanted by the one of the most beautiful coasts of Italy. Swim in the crystal clear waters and lose yourself in the historical and fascinating places of the island. Sailing highlights in Sardinia include the Maddalena Archipelago, Lavezzi, the Costa Smeralda and Tavolara - some of the most beautiful and famous beaches of the country.
- Pontine Islands: a mixture of relaxation and fun. In the afternoon you can leave for Palmarola, where you will spend the night at anchor. You start the next day by jumping into the refreshing water off the island of Ponza. In the evening you go ashore to celebrate. On Sunday morning you set sail back to Palmarola before returning to Nettuno harbour in the evening.
- Egadi Islands: from the port of Palermo you can explore all three magnificent Egadi islands in one weekend. You'll anchor in the most beautiful bays of the archipelago and explore the charming fishermen's fringes of the islands. In the evening you enjoy a drink ashore and discover the local specialities of the region. In Favignana you toast your sailing day with a glass of wine accompanied by Tonnara, produce of Levanzo. Afterwards you can enjoy an excellent Granita in a bar in the harbour with a breathtaking view, and try a toast at the Scaletta Bar in Marettimo together with the local fishermen.
- Sicily: every itinerary in Sicily is exciting - this suggestion: Start from Catania and sail towards Acitrezza to spend the night on board and admire the magnificent panorama of the full moon rising in the background of Faraglionis. This will be accompanied by a generous aperitif with typical local food and drink rounded off with the famous Sicilian wines. And hey, why not swim at night in the crystal clear waters of the Cyclops Coast?