629

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

4.8

Super!

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

Italy: Tuscany

2 days - 2 nights

12 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

8 departures available

June - September

Starting from

€650

€585

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

€650

Per person

5.0

Super!

Sailing in the magical Sardinia of the South

Italy: Southern Sardinia

6 days - 7 nights

13 departures available

June - September

Starting from

€790

Per person

5.0

Super!

Weekend at the Pontine Islands between Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

4 departures available

June - July

Starting from

€285

Per person

4.6

Different flotilla in Ionian Greece: nature, new friends and fun

Greece: Ionian Islands

7 days - 7 nights

2 departures available

August

Starting from

€874

€699

Per person

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

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

4.7

Weekend of sea and colors between Ischia, Procida and Vivara

Italy: Naples & Amalfi Coast

2 days - 2 nights

7 departures available

May - October

Starting from

€275

€234

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!

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

Italy: Tuscany

2 days - 2 nights

11 departures available

June - October

Starting from

€230

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

17667 reviews

Weekend among the most beautiful coves of Elba

05/18/2026

Stefania V.

Italy

Marco and Carmen wonderful people. As if we had known each other forever. There was harmony and understanding on everything. We will definitely repeat!

Sailing weekend to the Columbretes Islands

05/18/2026

Elodie P.

France

We have spent an incredible weekend. The boat is very stylish, well made and comfortable. Alex is an amazing person, very interesting, pedagogue and always ready to share moments! It has adapted to everything we wanted to do and has allowed us to do a route on earth, bathe, etc This trip would stay in our memory!!

Weekend among the most beautiful coves of Elba

05/17/2026

Giulia L.

Italy

New experience for me and my partner, excellent company, beautiful places, well organized trip, Carmen and Marco nice and easy-going, they were able to put us all at ease, we will remain a beautiful memory!

Let's discover the Aeolian Islands together by sailing

05/17/2026

Tim D.

Germany

Mario is an excellent skipper. Through him we were able to see the most beautiful corners of the Aeolian Islands. His local knowledge and contacts on all the islands gave us an unforgettable trip. We were also lucky enough to have his incredibly lovely wife on board. Even though communication was not easy (we didn't speak Italian and she didn't speak English), she made the trip even more beautiful. We thank them very much for this wonderful sailing holiday.

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