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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!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

One departure available

July

€410

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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4.4

Sailing holiday on the Côte d'Azur: experience the charm of the French Riviera

France: French Riviera and Porquerolles

6 days - 7 nights

13 departures available

June - September

Starting from

€730

€657

Per person

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5.0

Super!

The Sporades Islands: A Hidden Paradise of Greece

Greece: Sporades

7 days - 7 nights

3 departures available

July - September

Starting from

€750

Per person

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5.0

Super!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

3 departures available

July - August

Starting from

€850

€765

Per person

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4.8

Super!

Lefkas, Kefalonia & Ithaca: 7 days of relaxation and fantastic bays

Greece: Ionian Islands

7 days - 7 nights

One departure available

June

€750

€675

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

11 departures available

June - October

Starting from

€1,200

Per person

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5.0

New

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

Italy: Aegadian islands

7 days - 7 nights

7 departures available

June - September

Starting from

€650

€585

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

Per person

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4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

2 departures available

July - September

€400

Per person

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4.5

Unforgettable adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

17 departures available

July - November

Starting from

€540

€513

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

16 departures available

June - October

Starting from

€570

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

17773 reviews

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Afternoon, aperitif and sunset on Verbano - Lake Maggiore

06/14/2026

Enrico C.

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IT

We had a wonderful day on board Stefano's sailboat, a very kind and helpful person. We visited the three major islands and even managed to swim. Finally, we had a pleasant aperitif at sunset in front of the Hermitage of Santa Caterina. It was a wonderful experience, which I recommend to anyone who wants to spend a relaxing day.
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A sensory sailing journey between volcanoes and a marine paradise

06/14/2026

Diana B.

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IT

The experience spent on board was really positive. Mario was always very attentive and helpful. Every day spent on board was marked by big smiles, organization and relaxation. His boat is a SHOWSTOPPER, beautiful, comfortable and impeccably maintained. Special mention to the meals prepared on board that made the cruise look like an event organized by Slow food! Mario, with the precious help of Gaia, made a week of vacation special. Thank you
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North Sardinia and Corsica: blue seen from a sailboat

06/14/2026

Matteo B.

The most beautiful sailing holiday ever had! Absolutely recommended 🙌
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Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

06/14/2026

Maddalena G.

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ES

We spent 6 days on a boat in the Aeolian Islands and it was a truly memorable experience. The itinerary allowed us to discover wonderful islands, spectacular bays and unforgettable sunsets. Life on board was pleasant and relaxing, and discovered fantastic places to take a dip. Bledar proved to be professional, helpful and attentive to safety, as well as knowing the area very well and being able to recommend the most beautiful places to visit. The boat was comfortable and well organized for a multi-day vacation. An experience that I recommend to those who want to experience the sea from a different perspective, and discover the Aeolian Islands in the most authentic way possible. Definitely a holiday that I will carry with me in my memories.

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