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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!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

5 departures available

July - August

Starting from

€850

€765

Per person

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5.0

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

Greece: Ionian Islands

7 days - 7 nights

17 departures available

June - October

Starting from

€570

Per person

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4.9

Super!

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

4 departures available

July - August

Starting from

€410

€369

Per person

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New

Egadi mon amour: seven days to fall in love, be amazed and relax.

Italy: Aegadian islands

7 days - 7 nights

12 departures available

May - September

Starting from

€600

€540

Per person

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4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

17 departures available

June - November

Starting from

€600

€540

Per person

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4.9

Super!

Cruise-Coastal Navigation Course Porquerolles-Calanque Cassis

France: French Riviera and Porquerolles

6 days - 7 nights

3 departures available

July - August

€800

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

6 departures available

July - September

Starting from

€900

Per person

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5.0

Super!

Split archipelago, Hvar islands, Brac - with Hostess and full board

Croatia: Split Archipelago

7 days - 7 nights

10 departures available

July - October

€1,250

Per person

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5.0

Super!

Sailing cruise between the Maddalena archipelago and Corsica

Italy: Northern Sardinia

7 days - 7 nights

7 departures available

June - August

Starting from

€850

Per person

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5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

2 departures available

June - July

Starting from

€350

Per person

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4.9

An Aeolian adventure: sailing, nature and relaxation in the Aeolian Islands

Italy: Aeolian Islands

6 days - 7 nights

6 departures available

June - September

Starting from

€750

Per person

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4.7

Youth cruise (18-23 years): whale watching with WWF between the Tuscan Archipelago and Northern Corsica

Italy: Tuscany

6 days - 7 nights

2 departures available

July - August

Starting from

€999

€949

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

17686 reviews

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

05/30/2026

Alessandra C.

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IT

Beautiful experience, very pleasant crew. Gennaro really made a difference both for his experience but also for his kindness! Highly recommended!!

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

05/30/2026

Vincenzo D.

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IT

For us it was the first experience on a sailing boat and it couldn't have gone better. In our opinion, behind the experience, there are the people: Gennaro, the skipper, was the real wild card as well as the glue of this magnificent weekend. An exquisite person. We couldn't have wished for anything better. A guy (I hope he won't be offended) with whom every chat was constructive and full of ideas. Furthermore, to end on a high note, a further point of awareness that I took home is that thanks to him and this adventure I decided to want to obtain my boat license soon. We highly recommend this lifetime experience!
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Sailing weekend in Istria

05/30/2026

Vittoria B.

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IT

Wonderful experience! Mirco is a reliable skipper, very attentive to all aspects of safety and excellent company. The boat is spacious and is kept in perfect condition. I had never sailed in this area and it was a pleasant surprise, perfect itinerary for a weekend, we will definitely be back!

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

05/26/2026

Roberto L.

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IT

A great weekend! Beautiful places visited, particular attention was paid to organizing the tour in maximum safety in navigation and in maximum comfort. The skipper Gennaro is very prepared, a well-equipped boat, very comfortable and externally clean. Highly recommended

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