635

experiences

5.0

Super!

Sailing, swimming and aperitif at sunset ... What else?

Italy: Lake Garda

1 day - 0 nights

25 departures available

June - August

Starting from

€79

Per person

4.8

Super!

A sailing trip through history and food and wine to the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

5 departures available

July - August

Starting from

€900

Per person

4.8

Super!

Athens to Paros: the best of the Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

August - September

€950

Per person

5.0

Super!

Corfù Paxos Antipaxos

Greece: Ionian Islands

6 days - 6 nights

2 departures available

September

€900

Per person

5.0

Super!

Learn to sail in a week in the Tuscan Archipelago

Italy: Tuscany

6 days - 6 nights

4 departures available

August

Starting from

€849

Per person

5.0

Super!

Ibiza & Formentera: one week with cook on board

Spain: The Balearic Islands

6 days - 6 nights

2 departures available

September

€750

€675

Per person

5.0

Super!

Long weekend in Sardinia

Italy: Northern Sardinia

4 days - 3 nights

One departure available

June

€450

Per person

5.0

Super!

A sailing holiday: discovering the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

3 departures available

August

€650

Per person

4.6

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

€1,260

€1,134

Per person

4.8

All Inclusive: Procida, Capri, Positano, Amalfi, Cetara, Sorrento

Italy: Naples & Amalfi Coast

6 days - 6 nights

3 departures available

June - August

Starting from

€1,150

Per person

5.0

Super!

Week in Ponza Palmarola and Ventotene COMODI – Max 4 people

Italy: Pontine Islands

6 days - 6 nights

One departure available

July - August

€1,150

€978

Per person

4.7

Whale watching cruise with WWF guide in the Corfu archipelago

Greece: Ionian Islands

6 days - 7 nights

2 departures available

July - August

Starting from

€1,052

€999

Per person

Why book a holiday with Sailsquare?

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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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