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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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4.9

Super!

Three days of adventure in the Aeolian Islands

Italy: Aeolian Islands

3 days - 3 nights

One departure available

September

€400

Per person

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4.9

Super!

Cyclades from Milos to Milos

Greece: Cyclades

7 days - 7 nights

One departure available

September

€800

Per person - min 2 pax

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5.0

Super!

From Mykonos to Athens by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

September - October

€950

€760

Per person

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4.8

Super!

All Inclusive Tour: Capri, Amalfi, Cetara, e Sorrento

Italy: Naples & Amalfi Coast

5 days - 5 nights

One departure available

September

€1,150

Per person

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5.0

Super!

From Milos to Mykonos by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

September

€1,000

€750

Per person

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5.0

Super!

Croisière de rêve sous voiles dans les îles de la société 14 Jours

Pacific Ocean: French Polynesia

13 days - 13 nights

One departure available

October - November

€2,090

Per person

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4.8

Super!

A taste of the magnificent Island of Elba

Italy: Tuscany

2 days - 2 nights

3 departures available

September

€300

Per person

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4.8

Super!

Come and discover the Saronic Islands from Poros

Greece: Saronic Islands and Athens area

6 days - 6 nights

One departure available

September

€600

Per person

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4.9

Super!

Four days in the Aeolian Islands from Capo D'Orlando

Italy: Aeolian Islands

4 days - 4 nights

One departure available

September

€400

Per person

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5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

5 departures available

September - October

Starting from

€370

Per person

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4.7

Voices of the Pelagos: artistic-scientific whale watching expedition with WWF guide

Italy: Tuscany

4 days - 4 nights

One departure available

October

€453

€430

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

3 departures available

September

Starting from

€490

€466

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

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

19016 reviews

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The Island of Elba, to make you live a special experience!

09/4/2026

Gianluca D.

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IT

Very positive experience in a week in which the weather, due to the temperatures, did not help us much. Livio was always a center of gravity to which everyone on board referred, An extremely pleasant person and an excellent captain. Precise, prudent, fussy, aggregating and companion when it was time to relax. In addition to Livio, the real luck was to meet extremely pleasant and intelligent people who, despite not having a long experience of life on board like me, were able to live the holiday with the spirit necessary in this particular context. All this made the objective discomforts a minor thing and ignited my emotions making me live a week in which I never for once thought of anything other than what I was experiencing, for me it is a rare commodity ... The boat is to all intents and purposes Livio's second home so you have to tune in with this spirit and adapt to some lack of comfort compared to other more modern boats. Nothing that cannot be overcome with the right spirit... even the alcoholic one of the goliardic evenings that I will not forget ...

Unforgettable adventure in the Aeolian Islands

09/4/2026

Andrea E.

Extremely negative experience – technical problems, maintenance and management absolutely to be reviewed.

Discovering the Aeolian Islands Between Nature, Relaxation and Fun

09/4/2026

Alberto B.

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IT

The holiday was better than I expected. Giovanni was an excellent captain, an excellent cook, an extra friend! I would go back a hundred more times !
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Sailing week in the Tuscan Archipelago

09/4/2026

Beatrice M.

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CH

How many laughs, when well-being! We spent a week sailing around Elba in the company of Paolo. The boat is a gem and Paolo is an experienced skipper; He took care of everything leaving us the freedom to enjoy the experience. In addition to his professional skill he is also an interesting and nice person. We left in 4, and on the boat we met a third couple with whom we immediately integrated. And with 7 total people on the boat we found our harmony without ever feeling cramped. There are very precise rules that must be followed, ask Paolo as soon as you embark and if you follow them everything will be fine haha We spent a very special week made up of many baths in a beautiful sea, many peaceful roadsteads, many chats, lots of laughter and a record amount of beers! If you want to live a real experience and not just a holiday, it is the right boat for you :) p.s Paolo we will see you again soon!

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