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Sailing holidays in Italy with a local skipper

Sailing holidays in Italy with a local skipper

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

COVID‑19

Book without stress paying a small deposit, cancellation is free!.

  • 3 reviews
    4 discounted
    spots

    BARCOLANA 53 ° - The biggest regatta in the world!

    from 9 October - 3 nights
    Venice and the Gulf of Trieste Italy
    Join in on this experience!
    608 555€ Per person
  • confirmed

    DOLOMITI SHORT BREAK - 4 days of skiing, 2 ski passes included!

    from 4 March - 3 nights
    Dolomites Italy
    Join in on this experience!
    359€ Per person
  • confirmed

    Weekend in Matera with horseback riding

    from 5 March - 2 nights
    Basilicata Italy
    Join in on this experience!
    169€ Per person
  • confirmed

    White Experience Bormio - Weekend of skiing and relaxation (1 skipass included)!

    from 5 March - 2 nights
    Alps and Prealps Italy
    Join in on this experience!
    199€ Per person
  • 7 reviews

    Weekend between the Pontine islands, having fun between Ponza and Palmarola

    from 5 March - 2 nights
    Pontine Islands Italy
    Join in on this experience!
    273€ Per person
  • 3 reviews

    Spring in Venice on a sailing boat!

    from 5 March - 2 nights
    Venice and the Gulf of Trieste Italy
    Join in on this experience!
    210€ Per person
  • 6 reviews
    2 discounted
    spots

    Sailing in winter - Offshore sailing

    from 5 March - 2 nights
    Tuscany Italy
    4 people interested
    in this holiday
    191 170€ Per person
  • 2 reviews
    3 discounted
    spots

    Gulf of tigullio, between sailing culture and fun.

    from 5 March - 2 nights
    Tuscany Italy
    Join in on this experience!
    314 293€ Per person
  • 35 reviews

    If you are passionate about sailing this is the we for you

    from 5 March - 2 nights
    Tuscany Italy
    Join in on this experience!
    158€ Per person
  • 41 reviews

    NAVIGATION COURSE with FIV instructor

    from 5 March - 2 nights
    Lazio Italy
    Join in on this experience!
    210€ Per person
  • 10 reviews
    3 discounted
    spots

    Sailing weekend in Ponza - Convenient boarding in Ostia

    from 5 March - 2 nights
    Pontine Islands Italy
    Join in on this experience!
    209 198€ Per person
  • Weekend sailing between Ponza and Palmarola

    from 5 March - 2 nights
    Pontine Islands Italy
    1 person interested
    in this holiday
    284€ Per person
  • 1
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Reviews - Sailing holidays in Italy with a local skipper

6787 reviews
20 / 10
Francesco M.

Francesco M.

review about Boat week on Elba. Covid19 proof safe holiday August 2020

10 / 10
Massimo è uno Skipper di grande esperienza, gentile e disponibile. Ci ha fatto passare veramente un'ottima vacanza!
Claudio V.

Claudio V.

review about Offshorse Salining course towards Elba Island or Capraia December 2020

10 / 10
molto bene tutto
Carlotta C.

Carlotta C.

review about Give yourself an experience aboard a "comfortable" sailboat in the Aeolian Islands October 2020

8 / 10
Roberto è stato uno skipper molto simpatico e di compagnia, la pulizia sulla barca era impeccabile. Barca comodissima per 4 persone più skipper, credo che in 6 ci si sarebbe stati un po’ sui piedi. Mi sarebbe piaciuto se si fosse andati un po’ più a vela che a motore, ma forse le condizioni non erano le più ottimali. Inoltre sarebbe carino fornire più informazioni turistiche (idee per escursioni, suggerimenti per ristoranti, calette da visitare, tour a cui ci si può unire ecc) ma anche in questo caso capisco che probabilmente in bassa stagione ed in pieno COVID l’offerta in generale fosse ridotta. In ogni caso consiglio questo genere di vacanza anche a persone che non siano mai state in barca, a noi è piaciuta molto!
Edoardo C.

Edoardo C.

review about A weekend for those who love the sea on a sailing boat at the Barcolana, the most famous regatta in the world October 2020

10 / 10
Una bella esperienza. Barca in ottime condizioni: bella, comoda e veloce! A bordo ci siamo subito amalgamati con spirito di collaborazione e voglia di divertirsi. Quindi siamo stati molto bene sia a terra che veleggiando. Angelo è Comandante di grande esperienza al timone e guida nel far conoscere i luoghi in cui si naviga. Grazie.
Salvatore B.

Salvatore B.

review about Experience the Egadi Islands, an archipelago of beauties. September 2020

10 / 10
AMAZING! Thanks to Giuseppe and his outstanding service and fantastic catamaran, we had a fantastic time. Very knowledgeable, he was able to listen and adapt to our needs to make sure we could relax, see incredible places and get the best out of an unforgettable week. We got spoiled with a perfect catamaran, delicious tuna (Giuseppe is a great cook too!), a tour of Marettimo, Levanzo, Favignana but also San Vito lo Capo (one of the best beaches in the whole Italy). I can't thank enough Giuseppe for all his efforts and attention to every single details. We cannot wait to book another week with him!
Giovanna F.

Giovanna F.

review about Aeolian Islands in Gulet September 2020

8 / 10
Viaggio bello e interessante . Caicco condotto con maestria seguendo secondo il meteo le migliori possibilità di navigazione. Personale valido e estremamente disponibile.
Costanza N.

Costanza N.

review about September on Elba! September 2020

10 / 10
Luca è uno skipper super! Disponibile, attento, sa gestire bene il gruppo e ci ha regalato un fine settimana meraviglioso! Sicuramente tornerò a bordo.
Renato M.

Renato M.

review about Weekend in Ponza and Palmarola, 2 nights. Half board included September 2020

10 / 10
Ringrazio Nicola e Carlo per la splendida vacanza sulla splendida goletta. Navigazione gradevole puntuale. Gli spazi sono ampi, prendisole per tutti e le cabine comodissime. Nicola è comandante attento e premuroso ma anche un ottimo chef... che dire dei paccheri... buonissimi!!!! Sicuramente torneremo a bordo ma nel frattempo consiglio a tutti una crociera con loro. Buon vento Renato
Angela P.

Angela P.

review about Gulf of tigullio, between sailing culture and fun. September 2020

10 / 10
Prima volta in barca a vela per me e la mia famiglia, barca molto bella e comoda. Alberto ci ha fatto sentire a casa nostra e ci ha fatto scoprire posti bellissimi. Esperienza da ripetere!!!
Ignazio D.

Ignazio D.

review about Relax and navigation from the Egadi islands to Palermo September 2020

10 / 10
ottimo Skipper, ottima vacanza.
Patrizia R.

Patrizia R.

review about Relaxing weekend at the Pontine Islands September 2020

10 / 10
Dario è una persona simpatica e molto alla mano e disponibile mi ha fatto molto piacere di conoscerla!
Laura A.

Laura A.

review about Week in the Pontine and Ischia islands August 2020

10 / 10
Bellissima esperienza, posti incantevoli e skipper più che professionale malgrado la giovane età! Federico si è dimostrato esperto e competente in ogni situazione! Da ripetere
Lucia D.

Lucia D.

review about Wandering around Salento August 2020

10 / 10
E' stata un'esperienza rigenerante. Mario è uno skipper attento e scrupoloso a cui affidarsi con serenità. Gentile e sempre pronto a spiegare rotte e manovre senza stancarsi mai, comunicando con apertura e disponibilità le scelte di volta in volta a seconda del vento, venendo incontro generosamente alle diverse esigenze dei membri dell'equipaggio. Simpatica e piacevole la sua compagnia. Salento meraviglioso. Da ripetere volentieri in altri mari! Grazie!
Silvia G.

Silvia G.

review about get on board to experience the magic of the Aeolian islands together August 2020

8 / 10
Giovanni è uno skipper super paziente e con una barca di sole donne ce n'è voluta molta! è una persona di cuore e molto simpatica. In navigazione è molto bella la flottiglia a cui si è legati, che allarga la rete delle amicizie e delle attività da condividere. Eolie top!
MASSIMILIANO M.

MASSIMILIANO M.

review about Between mines and tuna traps, between culture, food and the beauties of the Iglesiente August 2020

10 / 10
È stata una vacanza fantastica, conoscere e visitare nuovi posti tramite barca a vela è stata un'esperienza unica e molto positiva. Luigi mette a proprio agio gli ospiti, anche chi, come me è la prima volta che ha messo piede su una barca, facendomi scoprire la magia della navigazione. Questo skipper è molto competente, sia riguardo la navigazione sia la conoscenza dei posti. E cosa che non guasta è un ottimo cuoco. Sicuramente ritornerò a navigare.
Marzia C.

Marzia C.

review about A week in the Tuscan islands (Elba, Giglio, Giannutri) August 2020

10 / 10
Bellissima esperienza settimana di mare, sole, vento e buona compagnia
Francesco M.

Francesco M.

review about Pontine Islands in 20 meters catamaran with private bathroom August 2020

10 / 10
Uno Skipper preparato, professionale capace di gestire qualsiasi situazione. Enrico é grande anche nel fare festa ed accontentare l'equipaggio per qualsiasi esigenza. Ci sono stati dei problemi nella gestione della vacanza non da imputare allo Skipper, ma agli armatori. Per Enrico chapeaux!!!
Francesca D.

Francesca D.

review about Pure holiday and fun in the North of Sardinia - La Maddalena, Costa Smeralda August 2020

10 / 10
Esperienza Fantastica! Organizzazione perfetta, ambiente accogliente e disponibilità elevata. Umberto è una persona molto disponibile che a fine vacanza lascia su terra ferma con nozioni di base della barca a vela e un accrescimento generale e personale. Consiglio vivamente e spassionatamente.
Rita M.

Rita M.

review about Sailboat cruise respecting the sea and nature August 2020

10 / 10
Antonio un perfetto capitano con cui abbiamo passato una splendida settimana navigando tra le isole dell arcipelago toscano e sempre pronto a soddisfare ogni nostra esigenza!!!
Elena L.

Elena L.

review about Discovering the Egadi: wind and relaxation in a dream sea August 2020

10 / 10
Nicola è competente, preciso, premuroso e disponibile. Amante del mare e dei suoi silenzi, della barca a vela e del suo lento, morbido andare. È stato collaborativo, ma mai invadente, autorevole ma paziente con i nostri errori da prima volta in barca a vela. È un maestro nell'insegnare l'amore ed il rispetto per il mare!
Claudia L.

Claudia L.

review about Sailing between Capraia and northern Corsica August 2020

10 / 10
Josuah è stato un fantastico compagno di viaggio oltre che il nostro skipper. Simpatico e alla mano, sempre disponibile ad ogni nostra richiesta. Insieme alla sua compagna si sono presi cura di noi e che dire della meravigliosa piadina di Monica? Strepitosa!!!!! Grazie mille ragazzi per questa settimana in mezzo al mare fra Capraia e Corsica! Alla prossima!!!
Emanuele P.

Emanuele P.

review about August in the Aegadian Islands August 2020

10 / 10
Abbiamo trascorso una settimana fantastica in compagnia di uno skipper ed una ciurma eccezionale! Nicolò non solo è stato un abile velista e una guida formidabile grazie alla sua conoscenza della Sicilia , ma anche un divertentissimo compagno di viaggio che ci ha regalato un'esperienza a 360° oltre a essere un ottimo cuoco :-) Siamo già pronti a prenotare la prossima vacanza con lui e farci di nuovo un sacco di risate!
Sonia M.

Sonia M.

review about Sardinia Wind Flotilla - North Sardinia for Sailing, Sun and Fun August 2020

10 / 10
ciao, normalmente non lascio mai le recensioni ma ora lo faccio perché Luca lo merita per davvero. il nostro skipper è stato a dir poco eccezionale. non è la prima volta che faccio charter e, posso serenamente evidenziare come sia il migliore che io abbia mai incontrato. professionale, preparato, gentile, disponibile, sempre sorridente, con un carattere dolce ma fermo. tornerò senz'altro se ci sarà Luca!
Margherita P.

Margherita P.

review about Sailing week with hostess on board. Flexible dates and itinerary. Relax, sea, adventure. August 2020

10 / 10
Voto 10: il meglio che potessimo sperare! Grande professionalità di Enrico e Daniela che sono due grandi conoscitori del mare, lo si percepisce subito e ci si sente a proprio agio fin dall’inizio. Ospitalità: cordiali e piacevoli rendono la vacanza rilassante e allo stesso tempo divertente. Cucina: Daniela cucina molto bene riuscendo sempre a soddisfare le esigenze di tutti. Itinerario: flessibile anche qui a seconda delle esigenze. Le spiagge più belle e il mare blu sono assicurati ! Consigliamo al 100%, anche a chi, come eravamo noi, é alla prima esperienza in barca a vela!
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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 (349)
  • Tuscany (285)
  • Northern Sardinia (190)
  • Liguria (140)
  • Aegadian islands (134)
  • Pontine Islands (130)
  • Gulf of Naples (53)
  • Southern Sardinia (40)
  • Sicily (28)
  • Puglia (18)

Italy: next departures

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Italy: best travel ideas

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Top Destinations

  • Italy
  • Greece
  • Aeolian Islands
  • Tuscany
  • Northern Sardinia
  • France
  • Ionian Islands
  • Liguria
  • Aegadian islands
  • Pontine Islands
  • Cyclades
  • Caribbean
  • Saronic Islands and Athens area
  • Spain
  • The Balearic Islands
  • French Riviera and Porquerolles
  • Corsica
  • Croatia
  • Brittany and Normandy
  • Gulf of Naples
  • Split Archipelago
  • Guadeloupe
  • Grenadines & Martinique
  • Dodecanese
  • Sicily
  • Amalfi Coast
  • Kornati Islands
  • BVI - British Virgin Islands
  • Bahamas
  • Seychelles

Top Travel Ideas

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  • Catamaran
  • Courses & regatta
  • Day trips
  • Flotilla
  • Gulet
  • Monohull
  • Offshore
  • Sport & wellness
  • Whole boat with skipper
  • All inclusive
  • Premium
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