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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

8 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

4 departures available

August - 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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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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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

8 departures available

August - 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

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

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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?

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

18592 reviews

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Unforgettable adventure in the Aeolian Islands

08/17/2026

Nicole K.

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IT

A nightmare week. The experience is called "unforgettable adventure in the Aeolian Islands" and unfortunately I will never forget it. It is not my first experience on a sailing boat and I know perfectly well that during a week of navigation unforeseen events and breakdowns can occur. A troubled battery, an electrical glitch or a technical problem can happen – it's part of life at sea. But when incidents follow one after the other, involve essential aspects of security and are inadequately managed, it becomes difficult to simply speak of "bad luck". 1% bad luck, 99% organizational and managerial inability. Then there is an aspect that I find particularly serious right from the beginning of the experience: we had booked the charter with Gaetano [hidden], but at the time of departure Gaetano did not show up and we found ourselves on board with another skipper, without having been informed in advance of the change. It was therefore not the person with whom we had chosen and booked the experience. And, as we were later told by Sailsquare when we contacted them during the week, they did not appear to have been informed of the change of skipper either. During the week we had repeated problems with the batteries, refrigerator and on-board instrumentation not working, problems with the electrical panel, strong smell of burning and abnormal voltage, as well as several situations during navigation and maneuvers that made us feel concretely in danger. The most serious moment was in Lipari, when a line ended up in the propeller, causing the engine to shut down and leaving the boat adrift a few meters from the gas station, other boats and rocks. In that situation it was me, my boyfriend and I who had to intervene materially to try to secure the boat and limit the damage. Added to this is what happened during a disturbance on Stromboli, when we found ourselves having to independently manage the return on board in sea conditions that we considered unsafe, without receiving adequate assistance or communication from the skipper or Gaetano. I won't go into all the individual circumstances here, but it really was a nightmare week. What I can say is that we never really felt calm or adequately protected during this experience. At a certain point, our only concern was to be able to get off the boat and go back to land. The behavior of the organization also contributed heavily to our negative experience. Sailsquare's assistance was, from our point of view, totally absent when we needed it most. In a situation of this type we would have expected a concrete intervention, a control and above all someone who would take responsibility for assisting us and verifying the conditions in which we were sailing. I therefore do not dispute the fact that a boat can have a breakdown. I dispute the way a number of issues were handled and, above all, the fact that the safety of the guests seemed to take a back seat. As far as I'm concerned, this was not a simple "unlucky" holiday: it was a nightmare week, during which we were afraid for our safety several times. It is an experience that, in light of what happened, I absolutely do not feel like recommending.

A sailing holiday: discovering the Pontine Islands

08/17/2026

Monica F.

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IT

Beautiful places, lovely sea. A special thanks to Luca, our super captain, who with his experience and generosity made our holiday special. The only negative note: the boat for 6 people was a bit small; A bit tiring to organize the space in the fridge and galley.
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Sea, scents and colors on Elba

08/17/2026

Alberto B.

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IT

A beautiful experience, to be repeated. Thanks to Ivo, a very experienced skipper, available to teach those who want to learn the basics of sailing! Elba Island perfect for sailing, with its beautiful bays, plus Ivo adapted the route according to our preferences. Too bad for periods with little wind, but it is not to be taken into account.
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Gulf of Poets

08/17/2026

VALENTINA R.

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IT

An experience above my expectations. They were three days of lightness, laughter, sea and beautiful people, the kind that arrive perhaps just when you need it most and fill your heart. Giovanni was a wonderful skipper: professional, attentive, helpful and able to create a serene and familiar atmosphere right from the start. He was able to make us experience the boat naturally, letting us enjoy every moment and making the experience even more special. I left with expectations and I come back with much more: beautiful memories, lots of laughter and a much fuller heart. Thank you Giovanni, and thank you to all the crew for these three days that I will take with me. I really hope that this is just the first of many other times at sea. ⛵️❤️

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