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Sailboat holidays & skippered tours

The thrill of sailing, the chance to discover places only accessible by sea and to meet new friends are what make a sailing holiday magical. Treat yourself to a week or weekend where you can wake up in the roadstead and have breakfast with the sea around you.

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5.0

Super!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

4 departures available

June - September

Starting from

€800

€720

Per person

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4.6

Between the Pontine Islands and the Phlegrean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

5 departures available

July - September

Starting from

€759

€683

Per person

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4.9

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

12 departures available

June - October

Starting from

€550

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

5 departures available

June - September

Starting from

€793

€714

Per person

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5.0

Super!

Aeolian Islands - A week on a sailing boat with skipper and assistant

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

June - September

Starting from

€935

€748

Per person

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4.7

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

Italy: Northern Sardinia

6 days - 7 nights

13 departures available

June - September

Starting from

€650

Per person

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4.8

Super!

Flottiglia Sun & Fun Marmaglia - Età 25-40 anni

Croatia: Kornati Islands

7 days - 7 nights

2 departures available

August

€1,100

€950

Per person

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5.0

Super!

Blu Pontino - Evasione infrasettimanale

Italy: Pontine Islands

4 days - 3 nights

2 departures available

August - October

Starting from

€180

Per person

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4.8

Super!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

11 departures available

June - September

Starting from

€650

Per person

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4.9

Super!

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

11 departures available

August - October

Starting from

€220

€187

Per person

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5.0

Super!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

12 departures available

June - October

Starting from

€550

Per person

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4.8

Super!

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

€1,190

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

The world's largest marketplace for sailing holidays

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

Get onboard solo, with your family or your friends

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

Find out before you book who's waiting for you on board

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Sailboat holidays & skippered tours

15952 reviews

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Life-changing experiences: Four days in the Pontine Islands

06/13/2025

Cristiano P.

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Italy

Fantastico. Esperienza meravigliosa. Divertente, bella, ho solo aggettivi positivi
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Weekend at the Pontine a stone's throw from Rome

06/12/2025

armando a.

-

Switzerland

È stata una bellissima esperienza con Antonio! Posti fantastici! Sarebbe stato ancora più bello navigare solo con le vele ma purtroppo le condizioni meteo e dell' equipaggio non lo permettevano. Da rifare sicuramente ;)
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Weekend at the Pontine a stone's throw from Rome

06/12/2025

Daniela B.

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Italy

Una barca d’epoca curata e amata, uno skipper di esperienza con competenze e grandi doti da intrattenitore (anche ottimo cuoco), un equipaggio piacevole e rispettoso e isole che ti rubano il cuore. Questo in sintesi il nostro we con Antonio e la sua barca, ma non possiamo ridurre a poche righe il nostro weekend. Antonio è un vero “lupo di mare” e grazie alle sue competenze ci ha raccontato storie di mare, di uomini, di isole, di uccelli migratori, di palme e di antichi romani. Le sue capacità come restauratore di barche d’epoca si apprezzano vivendo sulla sua barca che mantiene immutato il fascino di un tempo. Abbiamo visitato calette e grotte accompagnate dallo skipper che con il tender ci ha portato dove la comoda barca da 15m non poteva arrivare, dormito in rada e veleggiato quando il tempo lo consentiva. Un’esperienza da ripetere che ci ha rapito il cuore.
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

06/11/2025

Gemma M.

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Italy

Un soggiorno meraviglioso reso speciale da Andrea e Marta, due persone splendide che ci hanno fatti sentire subito a casa. La barca è bellissima, curata e in perfette condizioni. Andrea, skipper esperto e sempre disponibile, ci ha accompagnati con il gommone alla scoperta dei luoghi più belli e nascosti, lasciandoci sempre liberi di scegliere il ritmo della giornata. Marta, cuoca eccezionale, ha preparato piatti deliziosi e ha mantenuto la barca sempre pulita e in ordine con una discrezione e una dedizione davvero ammirabili. La compagnia di Matthias, cane dolce e affettuoso, è stata un piacevole valore aggiunto. Un’esperienza davvero unica.

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