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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!

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

Greece: Ionian Islands

7 days - 7 nights

19 departures available

April - October

Starting from

€460

Per person

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5.0

Super!

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

17 departures available

May - October

Starting from

€689

Per person

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4.6

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

Italy: Northern Sardinia

6 days - 7 nights

16 departures available

May - October

Starting from

€650

€585

Per person

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4.9

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

27 departures available

April - November

Starting from

€650

€618

Per person

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4.8

Super!

Lefkas, Kefalonia & Ithaca: 7 days of relaxation and fantastic bays

Greece: Ionian Islands

7 days - 7 nights

9 departures available

May - July

Starting from

€650

€585

Per person

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4.8

Super!

Ios, Sikinos, Folegandros and Anafi: the fantastic Cyclades of the South

Greece: Cyclades

7 days - 7 nights

2 departures available

August

€990

Per person

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4.8

Super!

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

12 departures available

May - September

Starting from

€1,300

€1,170

Per person

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5.0

Super!

The Sporades Islands: A Hidden Paradise of Greece

Greece: Sporades

7 days - 7 nights

5 departures available

July - September

Starting from

€650

Per person

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4.8

Super!

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

20 departures available

May - October

Starting from

€590

Per person

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4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

22 departures available

May - November

Starting from

€600

€540

Per person

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4.8

Super!

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

21 departures available

May - October

Starting from

€640

€576

Per person

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4.6

Weekend "nel Blu dipinto di Blu" - Ponza & Palmarola

Italy: Pontine Islands

3 days - 2 nights

7 departures available

May - June

Starting from

€230

€207

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

17626 reviews

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Easter on the Island of Elba

04/9/2026

Miriam C.

-

Italy

Very pleasant sailing experience. The boat was in good condition. Everything went according to expectations and the navigation was safe and relaxing. The only negative note concerns the owner, Enrico. During communications he was often grumpy, with a rather rigid attitude and not inclined to confrontation. This made the interaction less pleasant, especially at times when more availability and friendliness would have been useful. Overall, I recommend the experience for the quality of the boat and the service at sea, but I suggest the owner to improve the approach with customers to make everything really impeccable.
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Easter in Capraia and Corsica

04/9/2026

Monica L.

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Italy

Weekend absolutely up to expectations. Marco is a trained skipper, with great experience, very helpful, kind and caring towards his crew. His boat is hospitable and excellently cared for by him. All positive!!
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Easter: Whale Watching Expedition in Pelagos Sanctuary with WWF Guide

04/8/2026

Agnese F.

-

Italy

Unique experience, with excellent chances of whale sighting. In 3 days we made 3 close sightings of dolphins and bottlenose dolphins
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Easter in Capraia and Corsica

04/8/2026

Giovanni G.

-

Italy

Unique and beautiful experience, from start to finish. Starting with the skipper: exceptional, inclusive and very experienced of the sea and the places visited, always constructive and aimed at making us live a positive experience; the places visited were beautiful, with exceptional views, small villages in the middle of nature, with trekking, walks and stops for local shopping; The company of the whole crew (and friendly boats) was fun and collaborative, aimed at creating an enjoyable group experience; The perfect boat, equipped with every comfort, including USB recharges for almost every bed just to give an example. An experience certainly to be repeated and that I recommend

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