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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!

Weekend on Elba, sea, colors and scents.

Italy: Tuscany

2 days - 2 nights

One departure available

September

€200

Per person

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4.7

Lampedusa, Linosa and Lampione, islands on the high seas

Italy: Pantelleria and Lampedusa

6 days - 7 nights

2 departures available

September - October

Starting from

€860

Per person

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4.8

Super!

Vacation between Tuscany and Corsica on a magnificent 17m boat

Italy: Tuscany

6 days - 7 nights

One departure available

August - September

€900

€820

Per person

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4.8

Super!

Summer is made for the Aeolian Islands! Weekly cruise

Italy: Aeolian Islands

6 days - 7 nights

One departure available

August - September

€750

Per person

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5.0

Super!

Corsica as you've never seen it before!

France: Corsica

7 days - 7 nights

One departure available

August

€1,050

Per person

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4.9

Sailing in the magical Sardinia of the South

Italy: Southern Sardinia

6 days - 7 nights

4 departures available

August - September

Starting from

€790

Per person

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4.2

New

Dreamy Saronics: turquoise waters and relaxation just a stone's throw from Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

3 departures available

September - October

Starting from

€990

€842

Per person

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5.0

Super!

Saronic Islands and surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

September

€620

Per person

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4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

August

€1,075

€690

Per person

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4.9

Super!

Holidays on the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€716

Per person

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4.7

Week between the Tuscan Islands and Northern Corsica

Italy: Tuscany

7 days - 6 nights

3 departures available

September

€700

Per person

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4.9

Super!

Giglio Island - Festival of Grapes and Open Cellars

Italy: Tuscany

3 days - 3 nights

One departure available

September

€280

Per person

Why book a holiday with Sailsquare?

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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

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 more about the skipper and travellers who have already booked the holiday, to find out more about the

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

18646 reviews

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Istria and Kornati Islands

08/20/2026

STEFANO A.

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IT

Excellent compromise between the pleasure of a holiday in enchanting places and the learning of the basic rudiments. A special appreciation to Lara and Gianluca for their passion and patience in teaching.
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Island of Elba and South Corsica fantastic week

08/20/2026

Mirko G.

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IT

All great!!
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Learn to sail in a week in the Tuscan Archipelago

08/20/2026

cathy n.

-

FR

First experience for us on a sailboat. We will keep wonderful memories of it. It was an incredible adventure! Thank you sincerely Marco for everything, we enjoyed it immensely.

Weekend Elba or Capraia

08/20/2026

Riccardo I.

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IT

A nice alternative weekend, especially for mid-August, with people we didn't know but we immediately got on well. Special mention for the skipper Sebastiano who in addition to sympathy also taught us something in terms of sailing. The only thing that my friends and I recommend to review to improve, is the departure time, since in the end we left on Saturday morning and we found it a bit useless to sleep the first night docked at the port.

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