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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.

569

experiences

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From Paros to Milos, the hidden gems of Cyclades

Duration:

5 days - 5 nights

Greece:

Cyclades

Give this experience a try!

Starting from

€765

€900

Per person

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4.5

June 2 long weekend between Ischia, Procida and Ventotene from Naples

Duration:

4 days - 3 nights

Italy:

Pontine Islands

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Gennaro

€357

€420

Per person

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4.8

Super!

Lampedusa, Lampione e Linosa fra colori magici

Duration:

7 days - 7 nights

Italy:

Pantelleria and Lampedusa

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34 travellers

€595

€700

Per person

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4.7

Two boats walking on the island of Elba: the magic of the roadstead!

Duration:

6 days - 5 nights

Italy:

Tuscany

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2 travellers

Starting from

€638

€750

Per person

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4.6

Cruise to the Maddalena Archipelago and South Corsica

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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30 travellers

Starting from

€667

€785

Per person

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5.0

Poetic Gulf of Poets

Duration:

3 days - 2 nights

Italy:

Liguria

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13 travellers

Starting from

€170

€200

Per person

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Two boats walking on the island of Elba: the magic of the roadstead!

Duration:

6 days - 5 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€850

€1,000

Per person

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Paros-Naxos and Small Cyclades

Duration:

5 days - 5 nights

Greece:

Cyclades

Give this experience a try!

Starting from

€765

€900

Per person

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4.8

Super!

Flottiglia Sun & Fun Marmaglia - Età 25-40 anni

Duration:

7 days - 7 nights

Croatia:

Kornati Islands

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28 travellers

€950

€1,100

Per person

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4.9

Super!

Fast sailing holiday in the Cyclades with gourmet cuisine on board

Duration:

6 days - 7 nights

Greece:

Cyclades

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4 travellers

€780

€890

Per person

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4.9

Super!

Long weekend on Elba: 4 days of sun and sailing

Duration:

3 days - 3 nights

Italy:

Tuscany

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18 travellers

Starting from

€342

€380

Per person

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4.3

Sailing holiday in the archipelago of La Maddalena and Costa Smeralda

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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4 travellers

Starting from

€720

€800

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

15833 reviews

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

05/9/2025

Caroline T.

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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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1 May long weekend sailing with RICCARDO PROFESSIONAL SKIPPER COOK

05/8/2025

Maria Pia D.

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Italy

TOP
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

05/7/2025

Janette G.

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Australia

After sailing in the teeth of the Meltemi in the eastern Aegean 2 years ago Chris and I were happy to accept an invitation from friends to sail with Sail square in the gentle waters of the southern Corfu strait. Our hopes for a relaxing week on the water were fulfilled, largely due to the sailing skill and the care of Alessandro and his crew. We and our friends were comfortably accommodated in 2 cabins, each with a bathroom. All was clean and well-maintained. Our hostess, Marta, provided delicious Greek breakfasts and lunches. While sailing in the beautiful waters between Corfu, Paxos and Antipaxos, there were many opportunities for swimming at lovely beaches and walking in the islands. Alessandro and his crew, including the ship’s dogs, were exceptionally good hosts and we recommend this experience unreservedly. Lucy and Chris Costas May 2025
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A long weekend of sea and freedom from Argentario to Elba

05/7/2025

RAFFAELE L.

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Italy

Per il ponte del 1 maggio 2025 siamo stati a bordo di OTHELLO per una minicrociera di 4 giorni. La barca è molto bella, elegante ma estremamente funzionale e curata, comoda e con molte dotazioni. I bagni riservati nelle singole cabine sono stati per noi un dettaglio importante, come gli ampi spazi anche all’interno. L’atmosfera da subito è stata accogliente e simpatica grazie ad Enrico che si è dimostrato per tutta la vacanza uno skipper straordinario sia per le sue doti tecniche che come persona. Tonia, la compagna di Enrico, ha completato la splendida atmosfera respirata sulla barca con la sua simpatia, empatia e accoglienza. Il gruppo quindi si è amalgamato in modo molto speciale. Un meteo favorevole ci ha permesso di svolgere il programma previsto: Argentario, isola del Giglio ed Isola D’Elba. Enrico, con la sua esperienza ha organizzato le tratte in modo sicuro, considerando venti e correnti. E’ stato molto bravo a coinvolgerci in tutte le fasi della navigazione, a secondo dei livelli di conoscenza e di interesse individuali. Mia moglie ed io consigliamo vivamente un’esperienza con Enrico e Tonia, che con tutti i loro racconti ci hanno lasciato una grande voglia di tornare su OTHELLO e di visitare tanti altri luoghi.

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