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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

26 departures available

March - October

Starting from

€460

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

28 departures available

April - November

Starting from

€650

€618

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

18 departures available

May - October

Starting from

€689

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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5.0

Super!

The Sporades Islands: A Hidden Paradise of Greece

Greece: Sporades

7 days - 7 nights

8 departures available

July - September

Starting from

€650

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

17 departures available

May - October

Starting from

€650

€585

Per person

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5.0

Super!

In the heart of the Cyclades, from Milos to Athens (Lavrio)

Greece: Cyclades

5 days - 6 nights

One departure available

June

€580

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

14 departures available

May - September

Starting from

€1,200

€1,080

Per person

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4.8

Super!

From Milos to Athens: the fantastic Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€750

Per person

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4.8

Super!

Paros Serifos Kytnos the fantastic Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

August

€950

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

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

17617 reviews

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Four days in the paradise of the San Blas Islands - All inclusive

02/26/2026

Gianluca A.

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United States

Luigina and Alessandro made us feel at home since the very first moment. They cooked incredible meals, were always attentive to our needs, and we truly enjoyed spending time with them. It was probably one of our best family sailing adventures. On top of that they made us discover the San Blas islands: crystal clear water, white sand beaches, snorkeling, paddle boarding and of course sailing between the islands. So much to do and a joy doing it with them especially thanks to their deep knowledge of the are. Definitely highly recommended!!
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Thailand: a dream to discover while sailing

02/2/2026

Giovanna C.

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France

Giovanni and Raffaela are two skippers with their hearts in their hands. In addition to being excellent sailors, they are extremely hospitable people, helpful and attentive to every need of guests. professionalism in managing all aspects of navigation, always calmly and safely, and care for the well-being of everyone on board. It was our first trip to Thailand - short but we will be back An experience that we absolutely recommend! Joan and Mary
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Cape Horn and Patagonia Glaciers Expedition 15 days/14 nights

01/31/2026

Francesco C.

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Italy

A dream that has become reality! Passing Cape Horn under sail cannot be described. The expedition both from a sailing and naturalistic point of view was fantastic. Laurent is a very good skipper from all points of view, the emotions in crossing certain landscapes are incredible. The on-board company is just as pleasant. However, the difference is made by Laurent: prepared, reliable, calm, helpful and much more. An experience that I recommend to all sailors! Thank you Laurent !!
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Midweek special on the island of Elba, 2 nights

01/24/2026

Sara M.

-

Italy

I left with my brother: there were 7 of us, plus Marco. It was our first boat experience and we couldn't ask for anything better! Marco was extremely kind, helpful and attentive to every detail. The combination of the boat excursion and the trekking on the island was simply fantastic, everything impeccably organized. In addition, there was also the opportunity to enjoy free time in total relaxation. I absolutely recommend this experience with Marco!

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