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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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4.9

Super!

Weekend in the Gulf of Alassio and Gallinara Island

Italy: Liguria

2 days - 2 nights

9 departures available

June - August

Starting from

€250

Per person

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4.5

Unforgettable adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

19 departures available

June - November

Starting from

€420

€399

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

An unforgettable week between Capri, Positano, Amalfi, Ischia, Procida...

Italy: Naples & Amalfi Coast

7 days - 7 nights

2 departures available

August

Starting from

€977

€879

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

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

3 departures available

August - September

Starting from

€1,020

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

17693 reviews

Weekend among the most beautiful coves of Elba

06/1/2026

Francesca C.

-

IT

I had never had a multi-day experience on a boat, let alone on a sailboat, but I couldn't imagine a better experience than the one Marco and Carmen offered me. The [hidden] is comfortable and equipped and Marco and Carmen make it a home for the time of the experience, managing to create cohesion and participation in the group. On the [hidden] you are a crew, you learn, you collaborate and you get to know each other. The itinerary is beautiful, with crystal clear water and incredible views. I saw dolphins for the first time up close, very close. I saw fish and birds whose names I knew and for the first time I slept lulled by the waves. I really spent three beautiful days, with a nice crew that immediately, thanks above all to the energy transmitted by Carmen and Marco, cohesive and collaborated for the success of the trip. So what can I say, fair winds! I really think I will make it again and I will certainly recommend it to everyone!
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Traveling and Dreaming in the Gulf of Poets - All inclusive

06/1/2026

Maria Giovanna D.

-

IT

We spent a weekend on a sailing boat with the skipper Giorgio and Francesca, two really wonderful, welcoming and professional people. Unfortunately, our holiday was abruptly interrupted by a domestic emergency that forced us to return early. In a moment of great stress for us, the skipper and his wife showed a rare empathy and flexibility: they immediately took action to reorganize and concentrate the itinerary, allowing us to still enjoy a taste of the holiday before the forced return. In addition to the beauty of the sea, we will take with us the memory of their great kindness and humanity. Highly recommended, we hope to be back soon to finish the trip!
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Adventure weekend in the Egadi Islands

06/1/2026

Marta D.

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IT

Beautiful experience! Vittorio always very helpful, he took us to beautiful and uncrowded coves! Highly recommended!

Weekend of approach to sailing in the setting of the Gulf of Poets

06/1/2026

Tommaso d.

-

IT

Fantastic weekend with the charm of sailing at least for a while.together with a competent and nice skipper hidden behind the bark of the sea dog. Great company.

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