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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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4.7

Experience the Befana as you have never seen it before... by boat!

Italy: Tuscany

4 days - 4 nights

One departure available

January

€270

Per person

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5.0

It's time for sun and sea!

Italy: Liguria

2 days - 1 night

10 departures available

April - June

Starting from

€300

Per person

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4.4

New Year's Eve on the French Riviera between relaxation Provençal scents and sailing

France: French Riviera and Porquerolles

6 days - 5 nights

One departure available

December - January

€690

€621

Per person

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New Year's Eve in Thailand: 10 days of magic in the Andaman Sea

Thailand: Phuket, Krabi and Phi Phi Islands

10 days - 10 nights

One departure available

December - January

€2,150

€1,500

Per person

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5.0

Tuscany and Liguria, we sail between the Apuan Alps and the Gulf of Poets

Italy: Liguria

2 days - 2 nights

2 departures available

May

€200

Per person

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4.9

Sailing course in the Cyclades

Greece: Cyclades

7 days - 7 nights

8 departures available

May - October

€990

Per person

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5.0

Wellness Adventure Retreat

Caribbean: San Blas Islands - Panama

10 days - 10 nights

6 departures available

February - June

Starting from

€3,000

€2,100

Per person

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4.9

Day at the Gulf of Tigullio on a Sailing Boat - All inclusive!

Italy: Liguria

1 day - 0 nights

9 departures available

June - August

€155

Per person

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4.9

10 EPIC DAYS: From the Dodecanese to Milos with Hostess on board

Greece: Cyclades

8 days - 9 nights

One departure available

August

€1,430

Per person

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4.9

Aeolian Islands under the Stars: 5 Nights of Volcanoes, Sea and Magic

Italy: Aeolian Islands

5 days - 5 nights

15 departures available

May - August

Starting from

€590

Per person

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4.9

100% female sailing cruises

Greece: Cyclades

7 days - 7 nights

2 departures available

May - October

€990

Per person

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5.0

North-Eastern Sardinia: a paradise of nature and emotions

Italy: Northern Sardinia

6 days - 6 nights

One departure available

July

€1,450

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

17617 reviews

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

12/24/2025

Manfred B.

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

12/16/2025

Johannes T.

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Germany

That was a great, wonderful week. Many thanks to Sabine and Patrick! Best wishes Carola and Johannes
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Weekend on Elba "Only for four" for maximum comfort

11/25/2025

D. D.

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Italy

Great weekend! Impeccable welcome on Friday evening, really much appreciated. Very professional and prepared skipper (also the other crew members) - experienced hands-on in the challenging (but fun) crossing. I learned a lot (main objective - achieved). I hope to have the chance of another experience together soon.
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A day sailing in the fantastic Gulf of Trieste

11/11/2025

Armin F.

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Italy

Everything worked out great, Paolo was super helpful!!!! Advice 100%

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