573

experiences

573

experiences

4.8

Vacanza a piedi nudi: Weekend tra Elba e Capraia su barca 15m

Duration:

2 days - 2 nights

Italy:

Tuscany

37 travellers

Starting from

€225

€250

Per person

4.7

The beautiful Tuchese Coast between Antalya and Fetihie

Duration:

6 days - 7 nights

Turkey:

Turkey

3 travellers

€648

€720

Per person

Sailing Cruise - The Odyssey - Egadi Islands - Sicily

Duration:

6 days - 6 nights

Italy:

Aegadian islands

Give this experience a try!

€855

€950

Per person

4.9

Super!

Sunny weekend on Elba from Friday to Sunday

Duration:

3 days - 2 nights

Italy:

Tuscany

32 travellers

Starting from

€275

€305

Per person

4.9

Super!

Sailing week in the Tuscan Archipelago

Duration:

7 days - 6 nights

Italy:

Tuscany

9 travellers

Starting from

€630

€700

Per person

4.5

Short sailing cruise in the Gulf of Naples

Duration:

3 days - 3 nights

Italy:

Naples & Amalfi Coast

8 travellers

€315

€350

Per person

5.0

Super!

Week in Corsica with wellness programme

Duration:

6 days - 7 nights

France:

Corsica

10 travellers

Starting from

€898

€998

Per person

5.0

Magical week in the Pontine Islands (and Phlegraeans)

Duration:

7 days - 7 nights

Italy:

Pontine Islands

Give this experience a try!

€864

€960

Per person

4.3

From Alghero to Carloforte and Teulada discover the west coast of Sardinia

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

Give this experience a try!

€810

€900

Per person

4.9

Super!

A week in the Aeolian Islands - 6 islands in seven days

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

37 travellers

Starting from

€477

€530

Per person

4.5

Between the Pontine Islands and the Phlegrean Islands by Sailing Boat

Duration:

7 days - 7 nights

Italy:

Pontine Islands

88 travellers

Starting from

€647

€719

Per person

5.0

Super!

Weekend Elba o Capraia

Duration:

2 days - 2 nights

Italy:

Tuscany

34 travellers

Starting from

€264

€293

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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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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