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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

Tuscany and Corsica: sailing sun adventure good food energy and well-being

Italy: Tuscany

3 days - 3 nights

4 departures available

August - September

Starting from

€350

Per person

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4.7

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

11 departures available

August - November

Starting from

€700

€665

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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4.8

Super!

Five days barefoot between Tuscany and Corsica

Italy: Tuscany

5 days - 4 nights

4 departures available

August - September

Starting from

€490

Per person

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4.8

Super!

Weekend on Elba, sea, colors and scents.

Italy: Tuscany

2 days - 2 nights

One departure available

September

€200

Per person

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4.8

Super!

Summer is made for the Aeolian Islands! Weekly cruise

Italy: Aeolian Islands

6 days - 7 nights

One departure available

August - September

€750

Per person

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4.9

Sailing in the magical Sardinia of the South

Italy: Southern Sardinia

6 days - 7 nights

5 departures available

August - September

Starting from

€790

Per person

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4.2

New

Dreamy Saronics: turquoise waters and relaxation just a stone's throw from Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

3 departures available

September - October

Starting from

€990

€842

Per person

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5.0

Super!

Saronic Islands and surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

September

€620

Per person

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4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

August

€1,075

€690

Per person

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5.0

Super!

From Skiathos to Athens

Greece: Sporades

7 days - 7 nights

One departure available

September

€620

Per person

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5.0

Super!

Lose yourself in the magic of the Southern Ionian Islands

Greece: Ionian Islands

7 days - 6 nights

One departure available

August

€1,100

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

18486 reviews

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Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

08/15/2026

Michele A.

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NL

With Luca and Tommy fantastic holiday guaranteed!
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Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/15/2026

Vittorio C.

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IT

Saving Marco and Filippo, good skippers and nice guys, bad organization, and I would avoid going into details because there were many ambiguous things, as shared among the 80 participants. I do not recommend

Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/15/2026

Gianluca I.

-

IT

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

08/14/2026

Gian Luca P.

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IT

Week under the sign of the sun together with a dynamic and efficient group, authoritative skipper, of extreme experience and awareness in sailing safely. Sometimes not very malleable in the decisions, and in comparison with the crew, but a good dose of empathy, persuasion, on the part of all, every goal, desire, need was achieved, thus crowning a wonderful week of magnificent places and healthy fun. Recommended. Gian Luca .

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