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Sailboat holidays & skippered tours

The thrill of sailing, the chance to discover places only accessible by sea and to meet new friends are what make a sailing holiday magical. Treat yourself to a week or weekend where you can wake up in the roadstead and have breakfast with the sea around you.

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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

7 departures available

August - October

Starting from

€1,300

€910

Per person

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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

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4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

September - October

Starting from

€700

Per person

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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

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4.7

Feast of Santa Candida in Ventotene

Italy: Pontine Islands

3 days - 3 nights

One departure available

September

€420

€378

Per person

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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

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5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

5 departures available

September - October

Starting from

€570

Per person

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4.8

Super!

Week end in Costa Azzurra

Italy: Liguria

2 days - 2 nights

2 departures available

August - September

Starting from

€360

€300

Per person

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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

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5.0

Super!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

6 departures available

September - October

Starting from

€570

Per person

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4.8

Super!

Cast off for a week at sea, a thousand ways to experience it!

Greece: Saronic Islands and Athens area

7 days - 7 nights

5 departures available

September - November

Starting from

€585

€527

Per person

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4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

September - October

Starting from

€750

€675

Per person

Why book a holiday with Sailsquare?

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80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

Get onboard solo, with your family or your friends

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

Find out before you book who's waiting for you on board

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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

18700 reviews

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The Wild Flotilla: dive into the wilderness of Tuscany & Corsica

08/23/2026

Claryssa S.

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IT

Unfortunately, the experience of the flotilla holiday was far below expectations, especially with regard to the organization, which I consider the main and most serious flaw. The first problem was precisely the organization of the group: the boat group was formed only a week before departure, leaving very little time to get to know each other, coordinate and above all adequately organize the galley. For a holiday of this type, where a good part of the experience depends on the collaboration between the participants, I think it is definitely not enough time. The weather was certainly a factor independent of the organization, but precisely in adverse weather conditions one would expect greater management capacity and above all an alternative plan. The itinerary initially planned included Elba, Capraia and Corsica, with return to the port of Scarlino scheduled for Friday evening. The return was instead brought forward to Thursday after lunch, without any real alternatives being proposed to save at least part of the holiday. The only proposal was a day at the spa, a solution that I personally consider inconsistent with a sailing holiday and, above all, not very suitable as an alternative in August. Even in terms of sociality and flotilla life, the organization was practically non-existent. No evenings or dinners have been organized all together and, in fact, each boat has always organized itself. This is particularly disappointing considering that the very concept of flotilla should promote knowledge between people and the sharing of common moments. Even the catamaran, which should represent the landmark and the centerpiece of the flotilla, was used only once for an aperitif. Also on that occasion there was even a lack of a cable for music, so the aperitif took place without music and without a real organization of the event. On the last evening, however, an evening on the catamaran was organized, but in the rain, when the holiday was practically over. I also found the involvement of the skippers in the creation of the group very lacking. In a flotilla, the skipper should not limit himself to the technical management of the boat, but should also contribute to promoting socialization and integration among the participants. In this sense, involvement has been practically non-existent. The only aspect that I would like to evaluate positively is precisely the composition of the boat groups: I must admit that the boats were well formed and the people got along well with each other. I would almost say "thank goodness", because it was the group of the single boat that saved most of the experience. In conclusion, the problem was not the weather, which obviously cannot be controlled, but the management of what happened because of the weather. A holiday can be affected by bad weather, but a good organization should be able to propose alternatives, keep the spirit of the flotilla alive and create opportunities for aggregation. The way it was managed, I had the feeling of a holiday in which each boat was left to organize itself, completely losing the added value that should distinguish a flotilla from a simple boat holiday with friends. I expected much more in terms of organization, management of unforeseen events and above all the ability to create a real group. The potential was there, but it was very little exploited.

Sailing to discover the Tuscan Archipelago and Corsica

08/23/2026

Elisa O.

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IT

A beautiful week of dives, chats, aperitifs and songs. Enrico is a very prepared skipper and always made us feel at ease. His boat is very nice and cozy. The crossing between Corsica and Elba was exciting. Highly recommended!

Whale watching cruise with WWF guide between Northern Corsica and the Tuscan Archipelago

08/23/2026

Fabrizio r.

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IT

Positive experience for the nice group of people and for the atmosphere created on board. With reference to the scientific and cetacean observation part, due to the adverse weather the original program has been modified and in the routes we have made the sightings have been practically zero unfortunately
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Sailing holiday on the Côte d'Azur: experience the charm of the French Riviera

08/23/2026

Sara S.

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IT

Beautiful experience! The skipper Enrico helpful, kind and always ready to share his great knowledge. We visited beautiful places and swam in crystal clear waters. Super recommended! Thank you Enri <3

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