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Yacht sailing holidays & skippered tours in Italy

Yacht sailing holidays & skippered tours in Italy

Discover the beauty of Italy and treat yourself to a sailing holiday of relaxation, fun, and unique landscapes. Sail around the beautiful islands of Sicily and Sardinia, discover the Lipari, Pontine and Aegadian Islands by boat or anchor in the romantic bays of Tuscany or Cinque Terres.

  • Sailing Holidays
  • Italy

FLEXIBLE CANCELLATION.

Stress-free booking: you can cancel up to 24 hours before departure!

  • 43 reviews
    4 discounted
    spots

    AperiVela: sailing + all-inclusive aperitif

    from 25 May - One day
    Lazio Italy
    Join in on this experience!
    75 59€ Per person
  • 11 reviews
    almost
    confirmed

    Longing for the sun !!!!!!

    from 25 May - One day
    Lake Garda Italy
    Join in on this experience!
    100€ Per person
  • 25 reviews

    Whale watching cruise with WWF researcher - Ischia and Procida

    from 26 May - 3 nights
    Gulf of Naples Italy
    1 person interested
    in this holiday
    429€ Per person
  • 31 reviews
    confirmed

    Leave with us: 2 boats to discover the splendid Capraia

    from 26 May - 3 nights
    Tuscany Italy
    5 people
    are onboard
    265€ Per person
  • 19 reviews
    confirmed

    Portovenere and the Gulf of Poets - Hostess on board!

    from 26 May - 3 nights
    Liguria Italy
    7 people interested
    in this holiday
    376€ Per person
  • 11 reviews
    almost
    confirmed

    Longing for the sun !!!!!!

    from 26 May - One day
    Lake Garda Italy
    Join in on this experience!
    100€ Per person
  • 41 reviews
    confirmed

    Isola di Capraia .. "I'll walk around you until you return" :-)

    from 26 May - 3 nights
    Tuscany Italy
    5 people
    are onboard
    318€ Per person
  • Holiday between culture, sport and food and wine between Cinque Terre and Lunigiana

    from 27 May - 6 nights
    Liguria Italy
    Join in on this experience!
    859€ Per person
  • 6 discounted
    spots

    Weekend for sea lovers: relaxation aboard an ancient 17m sailing ship

    from 27 May - 2 nights
    Pontine Islands Italy
    Join in on this experience!
    400 389€ Per person
  • 4 reviews

    The most beautiful period Ponza and palmarola

    from 27 May - 2 nights
    Pontine Islands Italy
    Join in on this experience!
    361€ Per person
  • 7 reviews

    Fantastic Gargano and wild Tremiti

    from 27 May - 5 nights
    Tremiti Islands Italy
    1 person
    is on board
    368€ Per person
  • 13 reviews
    almost
    confirmed
    whole boat only

    EARLY BOOKING - Weekend in Ogliastra, the heart of the most beautiful Sardinia - ALL INCLUSIVE!

    from 27 May - 2 nights
    Southern Sardinia Italy
    Reserve this boat!
    (5 spots available)
    403€ Per person
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Reviews - Yacht sailing holidays & skippered tours in Italy

8256 reviews
20 / 10
Samantha B.

Samantha B.

review about May weekend on the island of Elba .... sailing, nature and characteristic villages May 2022

10 / 10
Magical experience Thank you then Skipper Marco who immediately put us at ease. A beautiful group for a truly dream weekend! Super recommended!
Fabio  A.

Fabio A.

review about Sailing in company between Elba, Giglio and Giannutri August 2021

10 / 10
Thanks to Daniele I lived, together with my wife, not only one of the most beautiful holidays of our life but he managed to let us enter in a way known really by few (the sea), thanks skipper it was all fantastic
Spartaco M.

Spartaco M.

review about CrazySail Skipper Academy Lite: Punta Ala - April 30th April 2022

10 / 10
Great Inti! The most ''ganzo'' skipper (tuscan like me) I have met so far. Really engaging and dynamic person from a human point of view, but technical at the same time in pointing out some dangerous situations to the skipper or helmsman on duty, always with a smile or a joke that does not hurt. I hope to have the opportunity to sail with you again Good wind and see you soon
Francesco Maria V.

Francesco Maria V.

review about CrazySail Skipper Academy Lite: Lake Garda - April 9th April 2022

10 / 10
Matteo was the skipper of a day on Lake Garda, a precise and helpful attentive person, with the joke ready even in more complicated situations. I recommend it for your raids at sea!
Giuseppe B.

Giuseppe B.

review about The Gargano and the Tremiti April 2022

10 / 10
Thank you guys for welcoming us in your boat with all its comforts and the precautions reserved for us you have made us this Easter special. Everything was perfect... The ability of andrea and his partner to sail even with sea always formed in maximum tranquility and carefree the enchanted places visited at the tremiti the walks in the villages evenings and dinners on the boat spent in joy with the fantastic companions ... leave an indelible memory and new true friendships Thank you for the wonderful holiday I highly recommend to try all these beautiful emotions
Arturo M.

Arturo M.

review about Tartare, prawns and bubbles in Santa Margherita Ligure - all inclusive! March 2022

10 / 10
What can I say, beautiful We is beautiful company. Giorgio, in addition to being a very good skipper, is a fan of good food and bubbles. We drank and ate very well, really!! The boat is brand new and very comfortable. I recommend this experience to everyone!!
LAURA M.

LAURA M.

review about Sailing & Trekking to the Aeolian Islands March 2022

10 / 10
Season still cold but when you need a holiday you go ... The weather was not on our side but the attentive and professional reliable crew made these cold days of March a beautiful experience. Mario precise and available to our many requests. The boat is spacious, well equipped and well maintained in its interior.... with the new sails it will be super!
Carla L.

Carla L.

review about BARCOLANA 53 ° - The biggest regatta in the world! October 2021

10 / 10
Joy and extreme competence here is the atmosphere that you breathe on the boat with Martin. An unforgettable experience
Marialuisa S.

Marialuisa S.

review about Sailing in the Maddalena archipelago and southern Corsica on a brand new Lagoon46 August 2021

10 / 10
What a fantastic experience! Gianni is a very experienced skipper and a wonderful guy, He made us feel at home on Marelia and took us to some of the most beautiful bays in Sardinia and Corsica, we swam, dived, waterskied, cooked, drank and laughed together. Marelia is an amazing catamaran, spacious, brand new and with all the comforts including air con and sound system. I can’t wait to sail again with Gianni and the #Lagoon’sLovers ?? #bagnetto #birretta ———— Che esperienza fantastica! Gianni è uno skipper molto esperto e un ragazzo meraviglioso ?? ci ha portato in alcuni dei posti più belli della Sardegna e della Corsica, abbiamo nuotato, fatto immersioni e sci d’acqua, abbiamo cucinato, bevuto e riso insieme. Marelia è un catamarano bellissimo, spazioso, nuovo e dotato di tutti i comfort, aria condizionata e sound system inclusi! Non vediamo l’ora di poter veleggiare di nuovo con Gianni e i #LagoonLovers ?? #bagnetto #birretta Mari & Carlo
Sara G.

Sara G.

review about Week between the island of Elba and Capraia - Relax, sun and good wine September 2021

10 / 10
Unforgettable holiday! Luca dedicated himself completely to us putting us at ease. Super helpful, prudent, kind, polite, proactive. He cradled us for 7 days on the coast of the Island of Elba without missing anything!!! Wonderful sunrises and sunsets, hidden coves where we could only get there by swimming. Endless aperitifs with background music. In short... Fun!! Luca introduced us to the island in a different way and pampered us as best we could wish for!!! THANK YOU!!!
Lucia B.

Lucia B.

review about Sailing, Diving, Snorkeling, Trekking, Abbufate almost never rests September 2021

10 / 10
Beautiful experience! Despite having left alone, I found a captain who welcomed me with great warmth and was able to amalgamate all the crew members. Spotless boat, great food, incredible landscapes, breathtaking sea, combined with the long sailing experience of the skipper, the love for the sea and for their land, made the week unforgettable. I will not easily forget the melody of the waves and the themed music selection ???? ???? I will be back with my friends and with a tiny backpack ???? Thanks Dario ????
Rafael G.

Rafael G.

review about Sardinia, from Barcelona: high altitude crossing and well-deserved relaxation September 2021

10 / 10
Alfons and Gonzalo on the boat and Inma on land form a great and compact team, the trip has been an experience, the crossing from Bcn to Alguero is a mini challenge for those who are thinking about being on the high seas without having to cross the Atlantic.... ;) Sardinia keeps multiple secrets, the visits we did very well but the island gives of itself to return again Thanks for the expedition
Valentina C.

Valentina C.

review about Aeolian Islands in Catamaran: lots of relaxation, good food and adventures September 2021

10 / 10
More than a holiday it was a journey within a journey! Contact with the sea is assured and not at the expense of comfort. To be redone!
Stefania A.

Stefania A.

review about Cruise Tremiti Islands / Vieste / Rodi Garganico, departure from Termoli September 2021

10 / 10
Perfect holiday! Marco good skipper and exquisite person. Very well maintained boat and, more unique than rare, everything you touch on board, WORKS! The itinerary between Tremiti and Gargano is also well chosen. Thank you
Maddalena G.

Maddalena G.

review about Sailing lessons on a cruise in the Flegrean islands August 2021

10 / 10
The holiday I was looking for! Beyond the tour that we managed to do, touching Ischia, Procida and Amalfi (which is worth visiting) what I have left most is the passion and the will of Eugenio to appreciate life on the boat for what it is ... team spirit, organization, collaboration. he is really very prepared, precise, patient and available to make you participate in the navigation. I was so comfortable on the boat and with the rest of the crew, that I didn't even feel the need to get off to visit when we were stopped in port. It was an experience that opened me up to a world I didn't know. it has enriched me so much on a human level. Eugenio and Anna (his partner) were two excellent travel companions.
Laura B.

Laura B.

review about Weekend to discover the western Riviera - Sailing between nature and fun August 2021

10 / 10
Beautiful weekend! Perfect tour from every point of view: Marco and Cristina are very professional and pleasant and have put everyone at ease, providing all participants with many notions on sailing techniques. Boat kept in excellent condition, clean and comfortable. The good weather and great company were the icing on the cake to make this holiday a real escape of reality!.
Elena G.

Elena G.

review about Exclusive cruise between Capraia, Elba Island and Corsica! August 2021

10 / 10
Beautiful holiday. The boat is really spacious, elegant, sporty. Simón is very attentive, kind and helpful, and we went sailing whenever the weather allowed. We had fun and relaxed. In short, we recommend everyone a week on Sean with Simón! Elena and Fabio
Massimiliano T.

Massimiliano T.

review about A week to discover the Tuscan islands August 2021

10 / 10
I spent this holiday among the Tuscan islands and in the wonderful blue waters of the Island of Elba. With a fantastic crew and a wonderful skipper giving me and the whole crew the memory of a week at sea that will remain indelible in our hearts. Thank you so much Ilario I think it is for me and on behalf of all Thank you Until next time Good wind
Monica B.

Monica B.

review about Have fun and relax while discovering Elba and Capraia islands August 2021

10 / 10
An unforgettable week: our first sailing experience was exciting thanks to the competence, availability and passion of the skippers. Excellent accommodation on the boat that was comfortable and always clean.
Laura A.

Laura A.

review about Around Ventotene Ponza and Palmarola departing from Torre Annunziata August 2021

8 / 10
In addition to being a good professional, Paolo is a beautiful person, able to entertain you and make you smile with his stories. He made us live an experience that we will not forget!
MARIANGELA I.

MARIANGELA I.

review about Northern Sardinia and Southern Corsica on an exceptional 47-foot sailboat for 4 privileged people August 2021

10 / 10
Our holiday of almost 2 weeks between South Corsica and North-East of Sardinia was wonderful! Everything could not be better, enchanting places visited, protected bays, every day awakenings in enchanted places and sunsets over shimmering seas, despite it being August. The Soledonna boat is really special with every possible sail imaginable, you will sail even with a thread of wind, a boat not for charter but for racing, with the most comforts to be able to make an extraordinarily comfortable holiday. The last but not the least Antoine and Fides special people, who made us feel at home from the first day, immediately tried to understand our needs and did everything to make us ferns! And they succeeded"! Leaving Soledonna and Antoine and Fides was hard, but we will meet again! I recommend everyone to travel with them, you really feel privileged! Good wind! Seas
Isabel M.

Isabel M.

review about Exciting tour of the Aeolian Islands led by captain Elvira, in love with the sea August 2021

10 / 10
Nicola is a professional and a successful business man. We delayed our flight and found the solution so that no one would be harmed. Raffaelle his assistant was always looking out for us.
Francesco S.

Francesco S.

review about Five days between Trieste and Istria! August 2021

10 / 10
Alberto is an experienced skipper, a mountain guide and a lover of the sea and nature with a great desire to share curiosities and the basics of sailing. With him we felt safe and involved in the travel choices (we had booked the entire boat) having had to undergo a one-day stop due to the strong bora that died on Trieste. To complete the crew we were lucky enough to have Federica who supported Alberto in the management of the boat, the galley and really pampered us throughout the holiday. Rely on her and you will not regret it. Finally the boat was absolutely up to our expectations, with comfortable indoor and outdoor spaces for 6/8 people and everything you need to enjoy a nice holiday. In short, it was our first time on the boat for several days and removed that minimum of spirit of adaptation that is required, the holiday was the right compromise between relaxation and adventure. SUPER!
Gabi C.

Gabi C.

review about Gulf of Trieste August 2021

10 / 10
Congratulations to the skipper Mauro very attentive to everything. Sunsets aperitifs and dives that say a holiday overlooking the sea, top super recommended!
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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 holidays in Sicily

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.

Sailing holidays in Sardinia

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.

Sailing holidays in the Tremiti Islands

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.

Sailing holidays in Tuscany

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.

Sailing holidays in the Pontine Islands

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.

Sailing holidays in the Aeolian Islands

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?

Italy: the most beautiful places to sail

  • Aeolian Islands (469)
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  • Northern Sardinia (398)
  • Pontine Islands (287)
  • Aegadian islands (197)
  • Liguria (112)
  • Gulf of Naples (106)
  • Southern Sardinia (83)
  • Lake Garda (72)
  • Amalfi Coast (44)

Italy: next departures

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Italy: best travel ideas

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Top Destinations

  • Italy
  • Greece
  • Tuscany
  • Aeolian Islands
  • Northern Sardinia
  • Pontine Islands
  • Ionian Islands
  • Aegadian islands
  • France
  • Croatia
  • Cyclades
  • Spain
  • Liguria
  • The Balearic Islands
  • Gulf of Naples
  • Southern Sardinia
  • Split Archipelago
  • Dodecanese
  • French Riviera and Porquerolles
  • Saronic Islands and Athens area
  • Amalfi Coast
  • Corsica
  • Caribbean
  • Canary Islands
  • Grenadines & Martinique
  • Brittany and Normandy
  • Sicily
  • Venice and the Gulf of Trieste
  • Guadeloupe
  • The Maldives

Top Travel Ideas

  • Adventure
  • Catamaran
  • Courses & regatta
  • Day trips
  • Flotilla
  • Gulet and sailing ship
  • Monohull
  • Offshore
  • Sport & wellness
  • Whole boat with skipper
  • All inclusive
  • Crewed
  • WWF Sailing Cruises
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