635

experiences

5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

3 departures available

May - July

Starting from

€350

Per person

New

Egadi mon amour: seven days to fall in love, be amazed and relax.

Italy: Aegadian islands

7 days - 7 nights

12 departures available

May - September

Starting from

€600

€540

Per person

4.9

An Aeolian adventure: sailing, nature and relaxation in the Aeolian Islands

Italy: Aeolian Islands

6 days - 7 nights

6 departures available

June - September

Starting from

€750

Per person

4.9

Super!

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

Italy: Tuscany

2 days - 2 nights

4 departures available

June - September

€280

Per person

4.9

Super!

Weekend in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

2 departures available

July

Starting from

€390

Per person

4.9

Super!

Long weekend among the queens of the archipelago - Elba and Capraia

Italy: Tuscany

4 days - 3 nights

4 departures available

July - August

Starting from

€480

€432

Per person

5.0

Super!

Weekend in the Pontine Islands between Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

3 departures available

June - July

Starting from

€285

Per person

4.9

Super!

Cruise-Coastal Navigation Course Porquerolles-Calanque Cassis

France: French Riviera and Porquerolles

6 days - 7 nights

4 departures available

July - August

€800

Per person

4.4

Sailing holiday on the Côte d'Azur: experience the charm of the French Riviera

France: French Riviera and Porquerolles

6 days - 7 nights

13 departures available

June - September

Starting from

€730

€657

Per person

5.0

Super!

Sailing cruise between the Maddalena archipelago and Corsica

Italy: Northern Sardinia

7 days - 7 nights

7 departures available

June - August

Starting from

€850

Per person

4.7

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

40 departures available

January - December

Starting from

€300

€270

Per person

5.0

Super!

A sailing holiday: discovering the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

One departure available

August

€650

Per person

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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

17668 reviews

2-day course in the Pertuis Charentais

05/21/2026

Geoffroy P.

France

An excellent sailing weekend with Fabienne as skipper. Professional, an excellent sailor and a great teacher, she knows how to transmit with calm and precision while putting everyone at ease on board. I particularly appreciated his ability to give his place to everyone according to his level, allowing both beginners and more experienced to fully enjoy the navigation and progress. A very nice human and maritime experience that I recommend without hesitation.

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!

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