573

experiences

573

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.

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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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