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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!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

7 departures available

June - October

Starting from

€650

Per person

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4.9

Super!

Trip with photographer to the Pontine - Life changing experiences

Italy: Pontine Islands

4 days - 3 nights

7 departures available

June - October

Starting from

€420

€399

Per person

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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

3 departures available

June - July

€410

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

10 departures available

July - October

Starting from

€230

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

17 departures available

June - October

Starting from

€570

Per person

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4.7

Weekend of sea and colors between Ischia, Procida and Vivara

Italy: Naples & Amalfi Coast

2 days - 2 nights

6 departures available

June - October

Starting from

€275

€234

Per person

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4.8

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

19 departures available

June - November

Starting from

€700

€665

Per person

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4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

16 departures available

June - November

Starting from

€600

€540

Per person

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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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4.8

Super!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

10 departures available

June - October

Starting from

€230

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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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

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

17697 reviews

Cast off for a week at sea, a thousand ways to experience it!

06/2/2026

Fabienne H.

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BE

An unforgettable week on a sailboat! It was my very first sailing experience and I couldn't have asked for anything better. From the beginning, Alex, our skipper, has listened to our desires, expectations and needs, while adapting to our pace. Her enthusiasm, sense of adventure and good humour made this week particularly enjoyable. He knows how to share his passion with simplicity: we even had the opportunity to learn some navigation techniques and participate in the maneuvers, which made the experience even more fun. Sailing with the wind provides an incredible feeling of freedom, far from everyday life. Between the beautiful landscapes, the moments of relaxation and the small adventures at sea, each day was unique. I leave with a head full of memories and the desire to do it again. I recommend this experience 100% to anyone who dreams of discovering sailing, whether for the first time or for sailing enthusiasts. Roxane

Weekend among the most beautiful coves of Elba

06/2/2026

Annalisa D.

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IT

It was a beautiful experience. Marco and Carmen guided us and accompanied us on a wonderful journey. The luck of meeting a group of beautiful people made everything much easier and even the small difficulties were overcome with ease. This time I think I can really say...... FAIR WINDS TO ALL!!!!
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Gulf of Poets

06/2/2026

Flavia B.

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IT

Giovanni is the most beautiful discovery of this trip. After so many bad experiences, finally a person attentive to the needs of the crew, reserved but at the same time open and welcoming. Thanks to him we discovered magnificent coves, stories and magical places. We will definitely be back!
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Weekend among the most beautiful coves of Elba

06/2/2026

Gianmario B.

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IT

We spent the weekend with two professional, attentive and caring people towards guests. Carmen and Marco are people who enter into symbiosis right away, giving full availability to make you feel at ease and as if you have always known them. Boat in excellent condition, nothing is missing, you obviously need a spirit of adaptation not being in your bathroom at home. The relationship that is created during the experience with all the guests is also beautiful, in this experience we met wonderful people. We recommend everyone and Fair Winds

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