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Sailboat holidays & skippered tours

The thrill of sailing, the chance to discover places only accessible by sea and to meet new friends are what make a sailing holiday magical. Treat yourself to a week or weekend where you can wake up in the roadstead and have breakfast with the sea around you.

572

experiences

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5.0

Super!

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

Duration:

7 days - 6 nights

Greece:

Dodecanese

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3 travellers

€560

€800

Per person

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5.0

Super!

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

Duration:

7 days - 6 nights

Greece:

Sporades

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3 travellers

Starting from

€665

€950

Per person

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Sailing and Hiking in the Cyclades

Duration:

7 days - 7 nights

Greece:

Cyclades

Give this experience a try!

Starting from

€798

€997

Per person

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Sailing & Diving in the Small Cyclades

Duration:

7 days - 7 nights

Greece:

Cyclades

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10 travellers

Starting from

€816

€1,020

Per person

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4.7

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

Duration:

6 days - 7 nights

Spain:

The Balearic Islands

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41 travellers

Starting from

€960

€1,200

Per person

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5.0

Super!

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

Duration:

7 days - 6 nights

Greece:

Dodecanese

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13 travellers

Starting from

€840

€1,050

Per person

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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

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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

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5.0

Super!

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

Duration:

7 days - 6 nights

Greece:

Cyclades

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8 travellers

€840

€1,050

Per person

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4.8

Super!

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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64 travellers

€990

€1,190

Per person

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5.0

Super!

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

Duration:

6 days - 6 nights

Spain:

The Balearic Islands

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12 travellers

Starting from

€765

€900

Per person

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4.8

Come and discover the Saronic Islands from Poros

Duration:

6 days - 6 nights

Greece:

Saronic Islands and Athens area

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14 travellers

Starting from

€497

€585

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

The world's largest marketplace for sailing holidays

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

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

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

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

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

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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
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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.
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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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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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