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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.

562

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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39 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

15832 reviews

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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.

-

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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Weekend in Capraia, the island with timeless sunsets

05/7/2025

Leonardo R.

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Italy

Marco è un grande appassionato di vela ed un professionista del settore della nautica. Lo capisci subito perché ti coinvolge nel suo mondo sin dal primo minuto e condivide con gli ospiti le sue esperienze e le attività di bordo, sempre e solo in piena sicurezza. Sono stati due giorni divertenti; lo consiglio a chi ha voglia anche di imparare e di rilassarsi allo stesso tempo!

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