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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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5.0

Super!

Long Weekend Santa Candida - Ventotene

Italy: Pontine Islands

5 days - 4 nights

One departure available

September

€550

Per person

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4.8

Super!

Week end in Costa Azzurra

Italy: Liguria

2 days - 2 nights

One departure available

August - September

€360

€324

Per person

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4.8

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

2 departures available

September - October

€600

€540

Per person

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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

One departure available

September

€650

Per person

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5.0

Super!

Weekend of the Pontine Islands to discover Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

2 departures available

September

€490

€441

Per person

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4.8

Super!

Five days barefoot between Tuscany and Corsica

Italy: Tuscany

5 days - 4 nights

4 departures available

August - September

Starting from

€490

Per person

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5.0

Tuscany and Corsica: sailing sun adventure good food energy and well-being

Italy: Tuscany

3 days - 3 nights

2 departures available

September

€350

Per person

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5.0

Super!

Barcolana 58: a day at the most famous regatta in the world

Italy: Venice and the Gulf of Trieste

1 day - 1 night

One departure available

October

€280

Per person

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5.0

Super!

Come and discover the Egadi Islands! Nature, relaxation and crystal clear waters

Italy: Aegadian islands

7 days - 7 nights

4 departures available

August - September

Starting from

€700

Per person

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4.9

Super!

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

Italy: Tuscany

2 days - 2 nights

One departure available

September

€280

Per person

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4.8

Super!

Midweek weekend in Elba: sea, scents, colors

Italy: Tuscany

2 days - 2 nights

2 departures available

September

€200

Per person

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4.8

Super!

All-Inclusive Sailing: Capri, Positano, Amalfi

Italy: Naples & Amalfi Coast

3 days - 2 nights

One departure available

September

€790

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

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

18879 reviews

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Unforgettable adventure in the Aeolian Islands

08/27/2026

Daniele R.

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IT

An unfortunately very negative experience caused by a truly endless series of problems with the boat, such as: - boat refrigerator not working and replaced with one of the dimensions absolutely not suitable to accommodate 7 people, - faulty alternator that did not allow the battery to be recharged during motor navigation with substantial problems for all the electrical instrumentation on board -Gas cylinder finished after 2 days of navigation severely limiting us in the preparation of meals, which following recharging had already proved to be partially discharged and therefore not refilled from the last charter -Too superficial cleaning of the boat since the last charter Added to this is the lack of prior communication of the skipper change, with a person who did not speak Italian and which made general communication difficult while sailing with us, the skippers of the other boats and the port insiders, this lack of prior communication is really incomprehensible, was there a fear that people would cancel the experience? We got to get to most of the islands, but we didn't get to visit them as it should have been, because most of the time we spent in the ports fixing boat problems or waiting for technicians to do it. I think it would have been right for Gaetano to recognize and take responsibility for these inconveniences by reimbursing us at least part of the fee paid for this (non) holiday, instead he has always minimized every issue by demonstrating little intellectual honesty and little care of his customers. Unfortunately, a mention must also be made of Sailsquare, which, aware of the situation we were facing, left us at the mercy of the problems without offering us concrete and valid support. I leave only 3 stars to the destination because in fact we saw and enjoyed it very little, 1 star with our eyes closed for the skipper and the boat. Too bad.
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

08/27/2026

Sandra M.

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IT

The holiday with Andrea was perfect! Andrea is a very good skipper, who makes guests feel at ease with simplicity, always kind and helpful, generous in making the most beautiful bays and beaches known by tender, where we have experienced unforgettable baths and moments. Very clean boat thanks to Carol, the hostess, who in addition to taking care of the spaces, prepares really good breakfasts and lunches, with the added value of having tasted typical Greek dishes. The travel program was nice, I enjoyed dining on land and visiting the delightful villages along the itinerary, it made the holiday even more varied and complete. After many years of sailing holiday, this experience has stood out for its organization, care and quality of service. Thanks to Andrea, Mattias (the loving poodle who conquers everyone) and Carol for the beautiful week. Super-recommended!

Amazing Pontine Islands on a sailing boat

08/27/2026

Rita G.

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IT

We spent 3 wonderful and unforgettable days. Carlo is a very good skipper with a great deal of experience and a lot of passion for sailing.
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Magical Pontine: full sail to discover the archipelago

08/27/2026

Enrico V.

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IT

I would say that the experience did not go badly but my expectations were a little higher. The crew was excellent company and a nice group was created that was able to manage all the various difficult situations in the best possible way.

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