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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!

Weekend between Ponza and Palmarola Comfortable - max 4 people

Italy: Pontine Islands

3 days - 2 nights

2 departures available

June - July

Starting from

€440

Per person

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5.0

Super!

Aeolian Islands in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

3 days - 2 nights

10 departures available

June - August

Starting from

€390

€351

Per person

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4.8

Super!

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

10 departures available

June - October

Starting from

€500

Per person

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4.9

Super!

Sailing weekend in Istria

Croatia: Istrian peninsula

3 days - 2 nights

7 departures available

June - October

€260

Per person

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5.0

Super!

Weekend of emotions in Ponza and Palmarola!

Italy: Pontine Islands

3 days - 2 nights

One departure available

June

€300

Per person

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4.8

Super!

A sailing trip through history and food and wine to the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

5 departures available

July - August

Starting from

€900

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

4 departures available

June - September

€280

Per person

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4.8

Super!

Athens to Paros: the best of the Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

August - September

€950

Per person

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5.0

Super!

Sail in Menorca with a cook on board!

Spain: The Balearic Islands

5 days - 5 nights

3 departures available

June - August

Starting from

€950

€808

Per person

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5.0

Super!

Corfù Paxos Antipaxos

Greece: Ionian Islands

6 days - 6 nights

2 departures available

September

€900

Per person

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5.0

Super!

Learn to sail in a week in the Tuscan Archipelago

Italy: Tuscany

6 days - 6 nights

4 departures available

August

Starting from

€849

Per person

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5.0

Super!

Ibiza & Formentera: one week with cook on board

Spain: The Balearic Islands

6 days - 6 nights

2 departures available

September

€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

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.

-

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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