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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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4.7

Feast of Santa Candida in Ventotene

Italy: Pontine Islands

3 days - 3 nights

One departure available

September

€420

Per person

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4.8

Super!

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

4 departures available

September - October

€1,300

Per person

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4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

2 departures available

September - October

Starting from

€700

Per person

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4.8

Super!

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

Greece: Saronic Islands and Athens area

7 days - 7 nights

4 departures available

September - November

Starting from

€585

€527

Per person

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5.0

Super!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

4 departures available

October

€570

Per person

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5.0

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

4 departures available

September - October

Starting from

€570

Per person

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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

4 departures available

September - October

€370

Per person

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5.0

Super!

Saronic Islands and surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

September

€620

Per person

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4.8

Super!

COUS COUS FEST: Un Week End di Mare, Vela, Cous Cous e Musica!

Italy: Sicily

4 days - 3 nights

2 departures available

September

€345

Per person

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4.9

Super!

The fantastic Saronic Islands and the surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

2 departures available

October

€750

Per person

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5.0

New

Learn to sail in Liguria: First level sailing course

Italy: Liguria

2 days - 1 night

One departure available

October

€220

Per person

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4.8

Super!

Five days barefoot between Tuscany and Corsica

Italy: Tuscany

5 days - 4 nights

One departure available

September

€490

€440

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

19150 reviews

Wellness, sun, sea and adventure: a weekend full of sailing!

09/15/2026

rosanna n.

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IT

We had a beautiful we on a sailing boat. Daniele and Maria Pia are wonderful in putting everyone at ease. Excellent company, the itinerary and the food prepared by Pia who is a wonderful cook, able to find any variation she is asked for. Daniele gladly lent himself to a change of cove for an unforgettable swim, due to the headwind compared to the established itinerary. Everything perfect.
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Sailing weekend in Istria

09/15/2026

Simona G.

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IT

Mirco top as captain 😊 you will only find out why by sailing with him 😝 boat in perfect conditions, cozy and equipped with all comforts. I will definitely be back at sea with Mirco. Thank you for everything !!

Week end in Costa Azzurra

09/15/2026

Massimiliano M.

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CH

Really beautiful experience! Alessandro was an extremely professional, competent and attentive commander, but above all kind and helpful. We were with three children under 4 years old, including a 10-month-old girl, and she was able to meet our needs with great patience and naturalness, making us experience and appreciate the boat (first time)! She took care of every organizational / logistical aspect to perfection, but her way of relating to the children was really an added value, fundamental to make the weekend serene and pleasant for everyone. An exquisite person and a captain of great professionalism. An experience that made us want to do it again soon! Thank you very much. Stefania + Massimiliano + Lori
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Week between the Tuscan Islands and Northern Corsica

09/15/2026

Silvia M.

-

IT

Beautiful experience, beautiful places, close-knit group and Francesco.. a real sea dog!

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