572

experiences

572

experiences

5.0

Super!

Secret Aegean with skipper and kitchen on board from Kalymnos to Samos

Duration:

7 days - 6 nights

Greece:

Dodecanese

3 travellers

€560

€800

Per person

5.0

Super!

Secret Aegean with skipper and kitchen on board from Samos to Mykonos

Duration:

7 days - 6 nights

Greece:

Sporades

3 travellers

Starting from

€665

€950

Per person

Sailing and Hiking in the Cyclades

Duration:

7 days - 7 nights

Greece:

Cyclades

Give this experience a try!

Starting from

€798

€997

Per person

Sailing & Diving in the Small Cyclades

Duration:

7 days - 7 nights

Greece:

Cyclades

10 travellers

Starting from

€816

€1,020

Per person

4.7

Ibiza All Inclusive on an 18m ketch with skipper and skipper

Duration:

6 days - 7 nights

Spain:

The Balearic Islands

41 travellers

Starting from

€960

€1,200

Per person

5.0

Super!

Secret Aegean with skipper and kitchen on board from Kos to Rhodes

Duration:

7 days - 6 nights

Greece:

Dodecanese

13 travellers

Starting from

€840

€1,050

Per person

5.0

Oslofjord - East Coast Norway - Round trip

Duration:

6 days - 5 nights

North Sea:

Norway

Give this experience a try!

€480

€600

Per person

5.0

Oslofjord - West Coast of Sweeden - Round trip

Duration:

6 days - 5 nights

North Sea:

Norway

Give this experience a try!

€480

€600

Per person

5.0

Super!

Secret Aegean with skipper and kitchen on board from Santorini to Kos

Duration:

7 days - 6 nights

Greece:

Cyclades

8 travellers

€840

€1,050

Per person

4.8

Super!

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

64 travellers

€990

€1,190

Per person

5.0

Super!

Unspoilt Balearic Islands for max 4 guests: north Mallorca and south Menorca

Duration:

6 days - 6 nights

Spain:

The Balearic Islands

12 travellers

Starting from

€765

€900

Per person

4.8

Come and discover the Saronic Islands from Poros

Duration:

6 days - 6 nights

Greece:

Saronic Islands and Athens area

14 travellers

Starting from

€497

€585

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.

Find out before you book who's waiting for you on board

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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

15836 reviews

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 !

Sailing course on the Côte d'Azur aboard a 15-metre sailboat

05/9/2025

Caroline T.

France

Un super stage !!! Cyril est très pédagogue et sait s'adapter à ses moussaillons. Il fait partager son experience et donne des conseils pertinents. Quel plaisir d'entendre ses anecdotes ! Côté bateau rien à redire c'est parfait : spacieux, bien pensé, un vrai bateau à vivre. Merci encore

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