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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

New

Stintino, Asinara and South Corsica

Italy: Northern Sardinia

7 days - 7 nights

One departure available

September

€620

€590

Per person

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4.2

Discover the South of Sardinia by sailing, white beaches and tradition

Italy: Southern Sardinia

6 days - 7 nights

2 departures available

August

Starting from

€896

€806

Per person

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Odysseus trip to Zakynthos - Kefalonia-Ithaka

Greece: Ionian Islands

7 days - 7 nights

One departure available

October

€890

Per person

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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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5.0

New

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

One departure available

October - November

€250

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

2 departures 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

2 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

Why book a holiday with Sailsquare?

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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

19275 reviews

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!

A taste of the magnificent Island of Elba

10/14/2026

Annachiara P.

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IT

It was a beautiful weekend!! Alberto is an experienced and prepared skipper who is totally dedicated to what he is passionate about. We really appreciated his willingness to meet us and, compatibly with weather conditions and times, to adapt the weekend to our needs: although we were licensed, we needed to regain confidence with going to sea (sailing!), without giving up relaxation. Alberto was a great teacher and we learned so much! He took us to beautiful places and we really enjoyed our time together (and the classical guitar under the stars added that extra touch :D). A special thanks to Claudia for her company and for the super aperitifs she prepared for us! The boat is beautiful, maintained with great care, order and cleanliness. They were two wonderful days. Thank you very much Alberto and Claudia!! We hope to repeat it soon!
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The Saronic Islands sailing, skippered and on-board kitchen

10/14/2026

Kaija H.

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FI

Annalisa and Emanuel hosted a very nice and safe sailing trip in their boat involving everyone. Despite the changed route plans due to bad weather the previous week, they were able to replan us a nice trip in the Cyclades Islands. We visited beautiful natural bays, enjoyed sailing, swimming, snorkling, sun bathing, fishing, ancient historical places and delicious fresh home-cooked food. Annalisa and Emanuel are the best and most patient hosts I have ever had!
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Sailing and Trekking in the Aeolian Islands

10/14/2026

Massimo G.

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IT

A week in full relaxation in the Aeolian Islands.Mario is a professional and helpful skipper with his customers, putting them immediately at ease, For your holiday in this archipelago I highly recommend to contact him .... MARIO

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