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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.

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5.0

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

28 departures available

March - October

Starting from

€460

Per person

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5.0

Super!

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

18 departures available

May - October

Starting from

€689

Per person

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4.8

Super!

Come and discover Guadeloupe and its archipelago: a paradise on the water

Caribbean: Guadeloupe

7 days - 7 nights

2 departures available

January - March

€850

Per person

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4.9

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

33 departures available

March - November

Starting from

€650

€618

Per person

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4.9

Super!

Rhodes Kalymnos South Dodecanese on magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

2 departures available

July - August

Starting from

€1,000

Per person - min 2 pax

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4.9

Super!

From Kalymnos to Samos Dodecanese North on a magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

One departure available

August

€1,200

Per person - min 2 pax

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4.8

Super!

From Ios to Milos, the best of the Central Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€750

€675

Per person

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4.8

Super!

Come and discover Guadeloupe and its archipelago: a paradise on the water

Caribbean: Guadeloupe

6 days - 6 nights

2 departures available

February - March

€730

Per person

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4.8

Super!

Ios, Sikinos, Folegandros and Anafi: the fantastic Cyclades of the South

Greece: Cyclades

7 days - 7 nights

2 departures available

August

€990

€891

Per person

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4.8

Super!

Lefkas, Kefalonia & Ithaca: 7 days of relaxation and fantastic bays

Greece: Ionian Islands

7 days - 7 nights

10 departures available

May - July

Starting from

€650

€585

Per person

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4.8

Super!

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

22 departures available

May - October

Starting from

€1,100

€990

Per person

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4.8

Super!

The Small Cyclades and spectacular Santorini

Greece: Cyclades

7 days - 7 nights

2 departures available

August - September

Starting from

€940

€846

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

17620 reviews

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Thailand and the Andaman Sea

01/9/2026

Paola V.

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Italy

Gianluca is an amazing skipper. He knows the places he takes you to very well and is attentive to the needs of guests. Sailing with him is safe and pleasant. The boat is beautiful and always clean. Wonderful holiday that I will take in my heart Highly recommended
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New Year's Eve in Thailand: 10 days of magic in the Andaman Sea

01/7/2026

angelo r.

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Italy

They promised me a boat not crowded with random people, they promised me a competent skipper or at least conscious and prepared in knowing how to lead an entire crew. They promised me incredible roadsteads and dream beaches. They promised me that we would almost never go ashore and that we would wash little. In one way or another I still managed to wash myself: for the rest they were right. Left with strangers, returned with friends. Not recommended for lovers of trashy tracks, group dances, annoying drunks and Sunday skippers: because Sunday is the only day you will have to let the skipper take a nap. I would leave tomorrow.
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New Year's Eve on the French Riviera between relaxation Provençal scents and sailing

01/6/2026

Fabrizio D.

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Italy

The French Riviera in winter is an experience to try if we then add a very prepared skipper and crew of beautiful people I could not wish for more, and then the weather gave us a big hand
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Come and discover Guadeloupe and its archipelago: a paradise on the water

12/24/2025

Manfred B.

-

Austria

It was a great week with Sabine and Patrick! They are very flexible and strive to accommodate every request! Every day a new adventure! Sailing, shore excursions, snorkeling......, - there is something for everyone

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