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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!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

5 departures available

July - October

Starting from

€600

€540

Per person

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5.0

Super!

Ibiza & Formentera: one week with cook on board

Spain: The Balearic Islands

6 days - 6 nights

One departure available

September

€750

€675

Per person

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4.8

Super!

A week of sea, volcanoes and fun in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

6 departures available

July - September

Starting from

€690

€621

Per person

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4.8

Super!

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

5 departures available

August - October

€650

Per person

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4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

2 departures available

September

€441

Per person

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4.8

Super!

From the Pontine to the Aeolian Islands - Adventure, Navigation, and Relaxation - One Way

Italy: Aeolian Islands

5 days - 6 nights

One departure available

July

€590

Per person

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4.8

Super!

Let's sail together in Southern Sardinia

Italy: Southern Sardinia

6 days - 7 nights

8 departures available

July - September

Starting from

€900

€855

Per person

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5.0

Come and discover the Egadi Islands! Nature, relaxation and crystal clear waters

Italy: Aegadian islands

7 days - 7 nights

8 departures available

July - September

Starting from

€700

Per person

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5.0

Holiday in the Aeolian Islands: comfort, adventure and music! - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

One departure available

August

€1,050

Per person

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4.8

Super!

Let's enjoy the wonders of the Tyrrhenian Sea - Elba, Capraia and Corsica

Italy: Tuscany

7 days - 6 nights

One departure available

August

€801

€761

Per person

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5.0

Super!

ONE WAY Marina River - Porto Vecchio

France: Corsica

3 days - 3 nights

One departure available

August

€290

Per person

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4.4

Magnificent weekend of approach to sailing on the island of Elba

Italy: Tuscany

2 days - 2 nights

2 departures available

July

€250

Per person

Why book a holiday with Sailsquare?

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

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

17931 reviews

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Four days in the Pontine Islands, just a stone's throw from Rome

07/1/2026

Stefano A.

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IT

We had a great time, we were lucky enough to have good weather (a bit warm), a group to have fun with and a skipper who, in addition to being a nice storyteller, solves one of the main critical issues: he cooks! A great

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

07/1/2026

Rory D.

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IE

Francesco was incredibly nice, welcoming and good fun to be around. He was very accommodating, thoughtful and was always looking for a way to make our trip more enjoyable. He also sought to align the route with our preferences. The boat was very clean, well equipped and the beds were much larger than they appear in the photos! As a skipper, he was very organised and experienced. He was always tracking the weather and considered our safety a priority. On top of that, he knew the islands, bays, harbours and routes inside out!

Long live Elba and Capraia

07/1/2026

Marina M.

Beautiful experience. Filippo is a professional and experienced skipper. We sailed both under sail and by motor in complete safety, the skipper was available to explain the maneuvers, involving the crew members who wanted to do it in the management of the boat. Clean, comfortable, efficient, well-equipped boat. Very beautiful island of Capraia perfect for a three-day weekend.
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Four days in the Pontine Islands, just a stone's throw from Rome

07/1/2026

Gea O.

-

IT

The experience with Antonio was beautiful. he took us to discover the Pontine Islands, between stories and making us explore the caves with the tenderino. In addition.... He is an excellent cook!! I hope to get back on his boat soon. Thank you Antonio!

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