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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!

Gulf of Poets

Italy: Liguria

3 days - 2 nights

5 departures available

August - September

Starting from

€280

Per person

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4.9

Super!

Weekend in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

3 departures available

July

Starting from

€390

Per person

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4.9

Super!

Long weekend among the queens of the archipelago - Elba and Capraia

Italy: Tuscany

4 days - 3 nights

2 departures available

August

€510

€459

Per person

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5.0

Super!

Weekend in the Pontine Islands between Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

3 departures available

June - July

Starting from

€285

Per person

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5.0

Super!

A sailing holiday: discovering the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

One departure available

August

€650

Per person

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4.6

Island of Elba and South Corsica fantastic week

Italy: Tuscany

7 days - 6 nights

4 departures available

June - August

Starting from

€700

Per person

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5.0

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August - September

€1,020

Per person

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4.9

Super!

Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

Italy: Tuscany

6 days - 6 nights

11 departures available

June - September

Starting from

€980

Per person

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5.0

Super!

Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

Italy: Aeolian Islands

6 days - 7 nights

11 departures available

May - October

Starting from

€800

€720

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

July - September

Starting from

€350

Per person

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4.7

Whale watching cruise with WWF guide in the Corfu archipelago

Greece: Ionian Islands

6 days - 7 nights

One departure available

July - August

€1,052

€999

Per person

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5.0

Super!

Four days in Ponza and Palmarola

Italy: Pontine Islands

4 days - 3 nights

2 departures available

June - July

Starting from

€420

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

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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