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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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4.6

Enjoy: in the blue of the Aeolian Islands

Italy: Aeolian Islands

6 days - 6 nights

18 departures available

May - September

Starting from

€600

€540

Per person

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4.4

The unspoiled paradise of the BVI

Caribbean: BVI - British Virgin Islands

10 days - 10 nights

One departure available

March

€1,350

€1,147

Per person

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4.9

Relaxing weekend in the Aeolian Islands: Lipari, Vulcano and Salina

Italy: Aeolian Islands

3 days - 2 nights

One departure available

October

€320

Per person

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4.2

Sailing holiday on the Côte d'Azur: experience the charm of the French Riviera

France: French Riviera and Porquerolles

6 days - 7 nights

13 departures available

June - September

Starting from

€730

€657

Per person

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4.8

Thailand: a dream to discover sailing with a hostess

Thailand: Phuket, Krabi and Phi Phi Islands

7 days - 7 nights

4 departures available

January - December

€1,050

Per person

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4.8

New Year's Eve wandering among the islands of Thailand with hostesses

Thailand: Phuket, Krabi and Phi Phi Islands

11 days - 11 nights

One departure available

December - January

€1,646

Per person

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5.0

Split archipelago, Hvar islands, Brac - with Hostess and full board

Croatia: Split Archipelago

7 days - 7 nights

20 departures available

June - October

Starting from

€1,100

Per person

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4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

21 departures available

May - October

Starting from

€590

Per person

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New

Cruise between the Maddalena archipelago and South Corsica

Italy: Northern Sardinia

7 days - 7 nights

One departure available

October

€585

Per person

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5.0

Raja Ampat: New Year's Eve in the last paradise

Indian Ocean: Indonesia

12 days - 12 nights

One departure available

December - January

€2,070

Per person

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4.5

Ibiza & Formentera: an exclusive journey between sky and sea

Spain: The Balearic Islands

6 days - 6 nights

11 departures available

June - September

Starting from

€736

Per person

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4.6

Experience the sea, feel the wind

Italy: Aegadian islands

6 days - 7 nights

3 departures available

July

Starting from

€790

€711

Per person

Why book a holiday with Sailsquare?

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

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

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

19278 reviews

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IBIZA and FORMENTERA - ALL INCLUSIVE with skipper and skipper

10/17/2026

Elena V.

We really needed this holiday! Filippo is a wonderful host: attentive skipper (also ready to involve those who show interest in sailing), excellent cook, great entertainer and even singer. The weather was not the best, which changed the itinerary and it was a great shame, but it is the risk of every holiday, even more so in those by boat. The latter is equipped with interesting "pluses" (BBQ, fishing rods, SUP). It is comfortable, but it is "lived" practically all year round as it is basically Filippo's home and this means that it is not a 5-star hotel on the water where everything is impeccable. A thread of sporting spirit and sharing is needed, as clearly written in the announcement. Finally, I cannot fail to mention Nao, a wonderful sailing companion always ready to be cuddled and try to save you when you go down into the water. And if I loved it because I don't have any particular liking for dogs, you can trust it. Ps: you will go home with a couple of extra kilos on you, but it's worth it

Learn to sail in Liguria: First level sailing course

10/17/2026

Nicole C.

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IT

Unforgettable experience on the legendary [hidden]. Even before getting on board, Orazio, with great professionalism, deepened the previous experiences of his crew with whom he shared choices and organization. Once on board, we were greeted by wonderful people and we were amazed by the beauty of the boat, perfectly tidy, clean and welcoming. It is said that when you are at sea all your thoughts remain on land and so it was, between many laughs and exquisite company, we also learned new notions of sailing and life at sea in general. Super recommended experience. Nicole and Matteo from Aosta.
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Sailing paradise in Greece on a big 50 ft boat: the best local experience

10/16/2026

Francesca D.

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CH

Aga and Jerry are excellent hosts and sailors. Aga goes above and beyond to make guests feel welcome, organising restaurant bookings, taxi boats, recommendations and gorgeous breakfasts. Jerry is an experienced sailor, always calm, with plenty of stories to share, and happy to offer hands-on sailing opportunities to those interested. The boat is comfortable, clean and well maintained. Unfortunately, I cannot give the highest rating due to the high overall cost, lack of transparency around the common fund and poor communication. Having experienced similar holidays, we found the price significantly higher than comparable offers. It was also the first time we encountered a flat per-person common fund with no breakdown of actual expenses. Given the additional €250 per person (including children), totalling €1,750, I would have appreciated a summary of costs, particularly as this covered bed linen, four nights in harbour, breakfasts and lunches, as well as a few restaurant dinners joined by Aga or Jerry. Finally, just days before departure, we were informed of an alleged bedbug outbreak in Athens, which we could not verify through any online sources. This meant sealing all our belongings before boarding, adding considerable packing time and taking up valuable luggage space. Had we been informed earlier, I might have chosen a different holiday.

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

10/15/2026

Lara R.

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CH

We had a wonderful time and the crew took good care of everything we could have wished for. Thank you very much for the great experience!

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