573

experiences

573

experiences

4.7

From Rhodes to Lycia, a gem of the Turkish coast

Duration:

6 days - 7 nights

Turkey:

Turkey

Marinella

€648

€720

Per person

5.0

Aeolian Islands: between sea and authentic flavours

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

123 travellers

Starting from

€585

€650

Per person

5.0

Super!

Weekend between the Gargano and the Tremiti

Duration:

2 days - 2 nights

Italy:

Tremiti Islands

Give this experience a try!

€284

€315

Per person

5.0

Super!

Sailing cruise on the French Riviera between the Lerins Islands

Duration:

6 days - 7 nights

France:

French Riviera and Porquerolles

19 travellers

Starting from

€810

€900

Per person

5.0

Relaxing holiday on the Côte d'Azur

Duration:

7 days - 6 nights

France:

French Riviera and Porquerolles

Give this experience a try!

Starting from

€531

€590

Per person

5.0

Sailing for a weekend at Elba Island - Spring/Summer

Duration:

3 days - 2 nights

Italy:

Tuscany

6 travellers

€261

€290

Per person

5.0

Super!

On board with the chef at the Egadi Islands

Duration:

7 days - 7 nights

Italy:

Aegadian islands

96 travellers

Starting from

€675

€750

Per person

5.0

Sailing WellEssere in Ionian Greece

Duration:

7 days - 7 nights

Greece:

Ionian Islands

7 travellers

Starting from

€1,215

€1,350

Per person

5.0

Magical weekend in Palmarola and Ponza

Duration:

3 days - 2 nights

Italy:

Pontine Islands

39 travellers

Starting from

€288

€320

Per person

5.0

Andalucía and Gibraltar

Duration:

6 days - 6 nights

Spain:

Andalusia

8 travellers

Starting from

€765

€850

Per person

4.7

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

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

91 travellers

Starting from

€585

€650

Per person

4.7

From Fethiye, on the spectacular Turkish coast, to Rhodes, Greece

Duration:

6 days - 7 nights

Turkey:

Turkey

3 travellers

€621

€690

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.

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Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

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On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Sailboat holidays & skippered tours

15837 reviews

Sailing cruise in the Greek islands - The Saronic Islands

05/12/2025

Monika L.

Germany

Skipper Bertrand machte einen super Job! Wir sind unerfahrene Segler und fühlten uns absolut sicher und sehr gut aufgehoben. Auf die mehrtägige Flaute (und seine sehr unterschiedlichen Gäste an Bord) hat Bertrand total flexibel und entspannt reagiert. Mach bitte weiter so! Auch die Orga mit sailsquare war perfekt- wir sind glücklich und sehr zufrieden von Bord gegangen und empfehlen Euch gern weiter!

Weekend in Capraia, the island with timeless sunsets

05/12/2025

Stefano F.

Italy

Marco è un vero appassionato di barche e, per questo, ti fa assaporare ogni momento che si trascorre a bordo

Stuffed anchovies: magical weekend from Genoa

05/12/2025

Maurizio S.

4 stelle perché c’è sempre la possibilità di migliorare, Bella esperienza che va senz’altro rifatta in luoghi diversi.

Weekend sailing course from Bandol

05/12/2025

Arthur N.

France

Nous avons passé un séjour formidable ! Notre skipper Nicolas a été à l'écoute de nos attentes, il a su adapter l'itinéraire en fonction de nos envies et nous a énormément appris sur le fonctionnement du voilier. Bienveillant, pédagogue, drôle... nous repartirons avec lui les yeux fermés !

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