638

experiences

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

4.7

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

Italy: Naples & Amalfi Coast

2 days - 2 nights

8 departures available

May - October

Starting from

€320

€272

Per person

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

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

11 departures available

June - September

Starting from

€600

€540

Per person

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

4.9

Super!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

7 departures available

June - October

Starting from

€700

Per person

4.8

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

22 departures available

May - November

Starting from

€650

€618

Per person

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

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

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

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

5.0

Super!

The Sporades Islands: A Hidden Paradise of Greece

Greece: Sporades

7 days - 7 nights

6 departures available

July - September

Starting from

€650

Per person

Why book a holiday with Sailsquare?

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Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

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On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Sailboat holidays & skippered tours

17651 reviews

Weekend "nel Blu dipinto di Blu" - Ponza & Palmarola

05/5/2026

Jacopo G.

Italy

Three fantastic days in the Pontine Islands together with an excellent company that was able to bond right away. Matteo is an experienced and very capable skipper who never gives up on his knowledge and is also very nice and very skilled in the kitchen! The boat is gorgeous!! Large, spacious and equipped with every possible service. Definitely highly recommended!!

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

05/5/2026

Diego M.

Italy

A beautiful experience, I would do it again 1000 times. Starting from the beauty of the boat, to hospitality and the possibility of being able to actively collaborate in daily activities. The presence of hydrophones on board is very interesting. Awesome people and great experience!

May Day between Elba and Capraia

05/5/2026

Eugenia C.

Italy

We had a good time, company as unlikely as it is fun. Fantastic weather, beautiful sea

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

05/4/2026

simone m.

Italy

Matteo is super fantastic, professional to the max with a pinch of irony that puts all his guests at ease!!

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