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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!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

6 departures available

June - September

Starting from

€800

€720

Per person

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5.0

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Sailing, swimming and aperitif at sunset ... What else?

Italy: Lake Garda

1 day - 0 nights

52 departures available

April - August

Starting from

€59

Per person

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4.8

Super!

7 days between Capri, Amalfi and Sorrento: dream sailing cruise

Italy: Naples & Amalfi Coast

7 days - 7 nights

5 departures available

July - August

Starting from

€900

Per person

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A weekend of sailing in Capraia

Italy: Tuscany

2 days - 2 nights

6 departures available

February - April

€220

Per person

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5.0

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Sporades Experience: Freedom, Turquoise Sea and Greek Magic

Greece: Sporades

6 days - 7 nights

17 departures available

May - September

Starting from

€650

Per person

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4.9

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Sailing in the Cyclades

Greece: Cyclades

7 days - 7 nights

14 departures available

April - October

Starting from

€1,080

Per person

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Spring on Lake Garda

Italy: Lake Garda

1 day - 0 nights

One departure available

May

€99

Per person

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5.0

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Weekend in the Tuscan Archipelago with PROFESSIONAL COOK SKIPPER

Italy: Tuscany

2 days - 2 nights

4 departures available

May - June

Starting from

€250

€238

Per person

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4.8

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Capri LightBlue and Positano BluSKy

Italy: Naples & Amalfi Coast

3 days - 2 nights

4 departures available

April - July

Starting from

€275

Per person

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A wonderful day.... sul Garda - ALL INCLUSIVE

Italy: Lake Garda

1 day - 0 nights

45 departures available

April - August

Starting from

€99

Per person

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Island of Capraia sailing and wild nature

Italy: Tuscany

4 days - 4 nights

One departure available

May - June

€500

€450

Per person

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Isola del Giglio - Festa dell'Uva e delle Cantine aperte

Italy: Tuscany

3 days - 3 nights

One departure available

September

€280

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

17619 reviews

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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.

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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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