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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

In the blue of Capri and the infinity of the Amalfi Coast

Italy: Naples & Amalfi Coast

2 days - 2 nights

7 departures available

May - October

Starting from

€320

€272

Per person

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4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

5 departures available

June - September

Starting from

€999

€949

Per person

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4.8

Super!

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

Greece: Ionian Islands

7 days - 7 nights

9 departures available

June - September

Starting from

€600

€540

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

14 departures available

May - October

Starting from

€230

Per person

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4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

3 departures available

July - September

Starting from

€390

Per person

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4.9

Super!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

8 departures available

June - October

Starting from

€650

Per person

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4.8

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

21 departures available

May - November

Starting from

€650

€618

Per person

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4.9

Super!

Trip with photographer to the Pontine - Life changing experiences

Italy: Pontine Islands

4 days - 3 nights

8 departures available

June - October

Starting from

€420

€399

Per person

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5.0

Super!

Sailing in the magical Sardinia of the South

Italy: Southern Sardinia

6 days - 7 nights

14 departures available

June - September

Starting from

€790

Per person

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4.8

Super!

A week in the Aeolian Islands - 6 islands in seven days

Italy: Aeolian Islands

6 days - 7 nights

7 departures available

June - September

Starting from

€583

€525

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

12 departures available

May - September

Starting from

€400

€380

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

12 departures available

May - October

Starting from

€230

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

17658 reviews

1st May: Whale watching expedition with WWF guide on an 18-meter schooner

05/6/2026

rosanna b.

-

Italy

I am satisfied with the knowledge that Laura has transmitted to us about cetaceans, dolphins etc. the knowledge on where and how they live on what they feed and what we humans could do if we were human, to help them live better, the explanations were very simple but effective and clear Laura is very competent in the subject. Pleasant destinations for the search for cetaceans, hearing their chatter through the headphones was very pleasant. The crew helpful, the boat a little too spartan. overall it was a good experience.
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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.

-

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.

-

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

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