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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!

Aeolian Islands in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

3 days - 2 nights

10 departures available

June - August

Starting from

€390

€351

Per person

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4.9

Super!

Life Changing Experiences - Arcipelago La Maddalena

Italy: Northern Sardinia

6 days - 6 nights

3 departures available

August

€1,100

Per person

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5.0

Super!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

3 departures available

August

Starting from

€1,100

€990

Per person

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5.0

Super!

Zakynthos and the Strofades Islands: a unique route in Ionian Greece

Greece: Ionian Islands

6 days - 6 nights

4 departures available

June - July

Starting from

€850

Per person

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4.9

Super!

Weekend at the Pontine. Travel with photographer-Life changing experiences

Italy: Pontine Islands

3 days - 2 nights

10 departures available

June - September

Starting from

€370

€352

Per person

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4.8

An unforgettable week between Capri, Positano, Amalfi, Ischia, Procida...

Italy: Naples & Amalfi Coast

7 days - 7 nights

2 departures available

August

Starting from

€977

€879

Per person

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5.0

Super!

From Piraeus to Mykonos: the Aegean by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

June

€1,000

Per person

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4.9

Super!

A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

Italy: Tuscany

2 days - 2 nights

5 departures available

May - September

Starting from

€220

Per person

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4.9

Super!

Weekend in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

3 departures available

July

Starting from

€390

Per person

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5.0

Super!

Tuscan Archipelago: night and day sailing

Italy: Tuscany

4 days - 3 nights

One departure available

August

€320

€272

Per person

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4.9

Super!

Three days of adventure in the Aeolian Islands

Italy: Aeolian Islands

3 days - 3 nights

3 departures available

June - September

Starting from

€400

Per person

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4.9

Super!

Wind, sea and freedom: a week between Corsica and the Tuscan archipelago

Italy: Tuscany

7 days - 6 nights

8 departures available

August - September

Starting from

€650

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

17657 reviews

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Weekend in the Pontine Islands

05/6/2026

Emanuele A.

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Italy

Memorable experience. Fabio is an exceptional person... nice, easy-going, and expert in navigation and all the gems of the Pontine Islands. The crew, whom I did not know, was a great discovery, and a rare harmony was immediately created, thanks to the love for the sea that naturally united everyone. Definitely to be redone! Thank you Fabio, thank you sea!
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Weekend in the Pontine Islands

05/6/2026

Antonio A.

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Italy

EXCELLENT SKYPPER WITH GREAT EXPERIENCE OF THE PONTINE. BOAT VERY WELL MAINTAINED AND COMFORTABLE. RECOMMENDED

May 1st long weekend between Elba and Capraia - 2 boats in company

05/6/2026

Massimo A.

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Italy

Matteo is the most knowledgeable person on sailing I have ever met, and his boat has a comfort far superior to normal charters, having 18 meters in length. Perfect organization and reliability. The tour of Elba is easy but wonderful

May Day between Elba and Capraia

05/6/2026

Silvia V.

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Italy

Very competent skipper, with a choice of stages always careful and well thought out to avoid possible inconveniences and please everyone. Thanks to the good weather and the favorable wind, it was the perfect combination of sailing and moments of relaxation and conviviality."

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