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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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4.8

Super!

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

Caribbean: Guadeloupe

7 days - 7 nights

9 departures available

January - December

€850

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

4 departures available

February - December

€730

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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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

2 departures available

October

€337

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

10 departures available

July - October

Starting from

€1,100

€1,045

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

26 departures available

March - September

Starting from

€650

€618

Per person

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4.9

Super!

Cyclades and Microcyclades with a magnificent 15-meter boat

Greece: Cyclades

7 days - 7 nights

3 departures available

May - June

Starting from

€750

Per person

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4.8

Super!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

14 departures available

June - September

Starting from

€625

Per person

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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

33 departures available

March - November

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

One departure available

October - November

€583

Per person

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4.8

Super!

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

Caribbean: Guadeloupe

5 days - 5 nights

One departure available

December

€650

Per person

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4.8

Super!

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

24 departures available

May - October

Starting from

€600

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

17597 reviews

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

10/19/2025

Catherine S.

My first sailing experience was simply extraordinary! ⛵️ Unforgettable moments spent at sea, surrounded by incredible people. Anna Lisa and Emmanuel were amazing hosts! Thank you to everyone for your good humor, your kindness and this unique adventure. Can't wait to do it again! 🌊✨
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Secret Aegean with skipper and kitchen on board - Rhodes to Kos

10/19/2025

Olivier P.

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France

Some sailings leave a softer trace than that of the boat's wake. The sailing week was perfect: beautiful sailing, delicious food and a friendly atmosphere. Thank you to them for this wonderful interlude — I will leave without hesitation!
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

10/19/2025

Jean-Loup N.

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Switzerland

Hello! We had a wonderful time with Andrea and Marta around the islands of Corfu, Paxos, and Antipaxos, discovering their hidden gems. The boat was spotless and spacious (we were five on board); everything was perfectly taken care of, and all I had to do was relax on the deck. As is often the case in the Mediterranean, sailing conditions aren’t always ideal, and our skipper preferred using the motor rather than the sails — which made the trip smooth and relaxing as we cruised from one beautiful anchorage to another. A special note for fans of the Netflix series Maestro in Blue: you might even come across the filming set — or the director and crew — during your cruise! Thank you again, Andrea and Marta! Cheers!
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Unspoilt Balearic Islands for max 4 guests: north Mallorca and south Menorca

10/18/2025

John D.

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Switzerland

Great skipper with excellent knowledge of the different harbours and coves in Mallorca and Menorca.. Enrico is very flexible and can adjust to changing weather.. Many thanks to our skipper and fantastic cook for making this voyage safe, smooth, and and simply unforgetable!

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