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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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4.8

Super!

Midweek weekend in Elba: sea, scents, colors

Italy: Tuscany

2 days - 2 nights

2 departures available

September

€200

Per person

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4.8

Super!

Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

Italy: Tuscany

6 days - 6 nights

3 departures available

August - September

Starting from

€980

Per person

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4.8

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

3 departures available

September - October

Starting from

€600

€540

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

4 departures available

August - September

Starting from

€730

€657

Per person

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5.0

Super!

Ibiza & Formentera: one week with cook on board

Spain: The Balearic Islands

6 days - 6 nights

One departure available

September

€750

€713

Per person

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5.0

Super!

Long weekend on a sailing boat Cous Cous Festival in San Vito Lo Capo

Italy: Sicily

4 days - 3 nights

2 departures available

September

€345

Per person

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5.0

Super!

Saronic Gulf Cruise: Aegina, Poros, Hydra, Athens Surroundings

Greece: Saronic Islands and Athens area

6 days - 6 nights

One departure available

September

€650

Per person

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4.6

The Island of Elba, to make you live a special experience!

Italy: Tuscany

6 days - 5 nights

One departure available

August

€700

Per person

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5.0

Super!

A sailing story between Favignana, Levanzo and Marettimo

Italy: Aegadian islands

7 days - 7 nights

3 departures available

August - September

Starting from

€620

Per person

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5.0

Super!

Corsica as you've never seen it before!

France: Corsica

7 days - 7 nights

One departure available

August

€1,050

Per person

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4.9

Super!

Sailing course in the Cyclades

Greece: Cyclades

7 days - 7 nights

2 departures available

October

Starting from

€950

Per person

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4.7

Kornati: the pearl of Croatia

Croatia: Kornati Islands

6 days - 7 nights

One departure available

August

€800

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

18478 reviews

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A week sailing in the most beautiful places in the world

08/13/2026

Elena T.

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IT

Piero and Giusy are the best that a sailing experience can offer. Excellent sailors, they give the opportunity to try and apply themselves in maneuvers if you wish. Excellent guides and connoisseurs of the area, it is easy to get lost talking about anything with them. Finally, Giusy's ability in the kitchen and in the management of the kitchen / galley is something that borders on perfection. You can't ask for anything better. Priceless availability, patience and kindness!! ❤️❤️❤️
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Sailing cruise in the Greek islands - The Saronic Islands

08/13/2026

Bruno P.

Not even closer to the good experience we had last year.

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

08/13/2026

Florian H.

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DE

The Tour was great - we had a marvelous time with our family (including two 14-year-old boys) and the other guests. Skipper Tom and our host Aga are very kind and professional. We enjoyed the cuisine and the tour plan including a trip to Hydra. Tom was one of the best skippers I have been with, combining an eye for safety with calm and decisive seamanship. Aga made everything else possible be it recommending places and restaurants but also considering allergies and other specifics. The sea and the landscape are fantastic. Big thanks to the entire team!

Long weekend among the queens of the archipelago - Elba and Capraia

08/13/2026

Gabriele B.

-

IT

Nice experience, Edoardo kind and helpful, to be done again.

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