325

experiences

4.7

Flotilla Marmaglia Sun & Fun - Croatia - WOMEN SEATS ONLY - BUS INCLUDED!

Croatia: Kornati Islands

7 days - 7 nights

One departure available

August

€1,180

€800

Per person

4.8

Super!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August

€920

Per person

4.7

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

One departure available

August - September

€795

Per person

4.8

Super!

Sailing and Freediving in the sea of Sardinia and Corsica

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August

€870

Per person

4.8

Super!

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

9 departures available

August - October

Starting from

€1,300

€1,040

Per person

4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

4 departures available

August - October

Starting from

€700

Per person

4.7

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

Italy: Naples & Amalfi Coast

2 days - 2 nights

4 departures available

October

Starting from

€275

Per person

4.8

Super!

Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

Italy: Tuscany

6 days - 7 nights

One departure available

August

€1,100

Per person

5.0

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

6 departures available

September - October

Starting from

€570

Per person

5.0

Super!

Learn to sail in Liguria: First level sailing course

Italy: Liguria

2 days - 1 night

One departure available

October

€220

Per person

5.0

Super!

Sailing week North Sardinia and South Corsica

Italy: Northern Sardinia

6 days - 6 nights

One departure available

August - September

€950

Per person

5.0

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

August - October

€690

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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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

18389 reviews

A week of sea, volcanoes and fun in the Aeolian Islands

08/9/2026

Marigra L.

SKIPPER not at all attentive to everyone's needs!! Interested only in a woman of his CLOSE acquaintance, it seemed like his vacation! Everything revolved around his personal interest! All this led to complaints from all the people who were on board so much so that one of us HAD to take him back to remind him to take the reins of the situation and be attentive to the needs of the group. I would absolutely never take a holiday with him again! The boat was clean and well maintained with plenty of room for improvement! The amazing places, the islands experienced from the sea are a marvel.

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

08/9/2026

Gloria G.

As a first sailing experience, everything was perfect exceeding expectations. Frank was an excellent skipper, he welcomed us on his boat with extreme professionalism and sympathy, he knew how to listen to our needs and made us discover wonderful places. We highly recommend this experience. fair winds!

Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/9/2026

Gizi L.

First time on a sailing boat and I must say that with such a staff it was difficult for it to go wrong. Prepared, always super helpful and friendly. They never let us miss anything. Great girls! Beautiful experience

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

08/9/2026

Juliana S.

Fantastic experience, our skipper Luca exceptional!

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