573

experiences

573

experiences

Sailing the Small Cyclades

Duration:

7 days - 7 nights

Greece:

Cyclades

2 travellers

€788

€876

Per person

4.9

From the Pontine to the Egadi Islands - Adventure, Navigation, and Relaxation - One Way

Duration:

6 days - 6 nights

Italy:

Aegadian islands

2 travellers

€531

€590

Per person

Summer 2025 - Catamaran week in the Pontine Islands

Duration:

7 days - 7 nights

Italy:

Pontine Islands

14 travellers

Starting from

€1,080

€1,200

Per person

4.7

1st One-Way Special - Between the island of Elba, Corsica and Sardinia

Duration:

6 days - 6 nights

Italy:

Northern Sardinia

Give this experience a try!

€774

€860

Per person

5.0

Weekend in Ogliastra, super Sardinia with skipper and hostess

Duration:

3 days - 2 nights

Italy:

Southern Sardinia

12 travellers

€612

€680

Per person

4.7

From Fethiye to Antalya: the beautiful Turquoise Coast

Duration:

6 days - 7 nights

Turkey:

Turkey

3 travellers

€648

€720

Per person

4.9

Super!

Midweek on Elba, from Monday to Thursday

Duration:

3 days - 3 nights

Italy:

Tuscany

23 travellers

Starting from

€356

€395

Per person

4.3

Sardinia by sailing: from Asinara to La Maddalena and Strait of Bonifacio

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

Give this experience a try!

€720

€800

Per person

4.3

Sailing in the natural parks of Sardinia, from La Maddalena to Asinara

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

2 travellers

€810

€900

Per person

4.3

Sailing holiday on the Côte d'Azur: discover the charm of the French Riviera

Duration:

7 days - 7 nights

France:

French Riviera and Porquerolles

48 travellers

Starting from

€585

€650

Per person

5.0

Talamone and Giglio Sailing Weekend with Geniale Vento, Mare, Libertà

Duration:

3 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€405

€450

Per person

5.0

Super!

Ibiza & Formentera All inclusive week with Cook

Duration:

6 days - 6 nights

Spain:

The Balearic Islands

96 travellers

Starting from

€711

€790

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.

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.

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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

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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