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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

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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4.9

Super!

Adventure weekend in the Egadi Islands

Italy: Aegadian islands

3 days - 2 nights

One departure available

May

€350

Per person

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4.6

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

€1,260

€1,134

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!

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

11 departures available

May - October

Starting from

€500

Per person

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4.9

Super!

Sailing weekend in Istria

Croatia: Istrian peninsula

3 days - 2 nights

8 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

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

17683 reviews

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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Weekend Elba o Capraia

05/26/2026

Sabrina S.

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IT

Fantastic holiday with the guidance of Francesco who involved us a lot in managing the destination and the boat, taught us how the sea can create bonds.
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Weekend among the most beautiful coves of Elba

05/26/2026

Samantha G.

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IT

We were literally welcomed by Marco and Carmen, it seemed to have known them for a lifetime. Evidently they attract beautiful people because the rest of the crew was also wonderful. Beautiful sailings (you can move as little as possible), but managed in full comfort. Finally, an excellent knowledge of the places that does not hurt and makes you enjoy unforgettable coves
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Tuscan archipelago between nature and relaxation

05/26/2026

Francesco D.

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IT

Riccardo is a true professional, a reliable person and also an excellent travel companion. He was able to perfectly interpret our requests with availability and empathy, becoming in a few minutes a friend, an accomplice in adventures, a trusted person, as if we had always known each other ... Not just a skipper! Thanks to Riccardo and "[hidden]" for this wonderful experience!

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