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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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4.8

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

8 departures available

August - October

Starting from

€1,300

€910

Per person

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4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

September - October

Starting from

€700

Per person

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4.7

In the blue of Capri and the infinity of the Amalfi Coast

Italy: Naples & Amalfi Coast

2 days - 2 nights

4 departures available

October

Starting from

€275

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

One departure available

August

€1,100

Per person

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5.0

Super!

Educational cruise in the Tuscan archipelago and Cetacean sanctuary

Italy: Tuscany

7 days - 7 nights

One departure available

August

€865

Per person

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5.0

Super!

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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5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

5 departures available

September - October

Starting from

€570

Per person

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4.7

Feast of Santa Candida in Ventotene

Italy: Pontine Islands

3 days - 3 nights

One departure available

September

€420

€378

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

7 departures available

August - October

Starting from

€570

Per person

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5.0

Super!

Sailing week North Sardinia and South Corsica

Italy: Northern Sardinia

6 days - 6 nights

One departure available

August - September

€950

Per person

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4.8

Super!

Week end in Costa Azzurra

Italy: Liguria

2 days - 2 nights

2 departures available

August - September

Starting from

€360

€300

Per person

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5.0

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

August - October

€690

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

18652 reviews

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Pula and the enchanting Kvarner islands: special price private cruise

08/20/2026

Alessio L.

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IT

A beautiful week in the full spirit of the sailing holiday, you sleep in the roadstead and sail as soon as the wind allows it, minimizing motor navigation. Ilaria and Maurizio, both sailing instructors, are very good at creating aggregation and putting all participants at ease both by supporting (as far as possible) the needs of life on board, and by extinguishing notions of sailing in order to make, based on interest and previous knowledge, the whole crew participate in the maneuvers and management of the boat while sailing The boat is very comfortable and cozy and impeccably maintained In addition to the bays, fun and sailing, the sailing holiday is beautiful if it is in contact with the sea, with nature and respect for its rhythms, Ilaria and Maurizio best interpret this spirit
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Aeolian Islands in the name of sailing, fishing and relaxation

08/20/2026

Eleonora M.

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IT

Antonio is a skipper and a very prepared and helpful person, he handled every situation with promptness and control making us feel safe and comfortable. The boat and organization were comfortable. The itinerary, although short, offers several possibilities for all tastes and splendid landscapes. Recommended experience
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Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

08/20/2026

Valentina S.

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IT

Lovely trip, very nice boat and beautiful places. Very knowledgeable skipper
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Cruise course in Sardinia

08/20/2026

Marta G.

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IT

Very nice experience. In addition to seeing wonderful places we had a great time. Throughout the week we found the ideal weather windy but not too much and allowed us to go sailing every day. The boats are not very big, we were 5 students plus the skipper for each boat (two boats in all) but in this way we could spend more time maneuvering and learn everyone. It is a basic course suitable even for those who have never been on a boat, but also very fun for those like me who had already been there. The holiday, and also the boats, are very rustic, we stayed every night sleeping in the bay at anchor, except one evening when we went to port in Bonifacio. The spaces are tight so you have to have a lot of spirit of adaptation but this also makes the holiday magical. For those who have never been on a boat I can say that it is like a camper on water. I recommend bringing a small rechargeable fan with USB (but that can go without power!), sometimes the evenings are a bit hot and not always so much air passes through the hatches. Although it was a course, the atmosphere was still relaxed, the skippers were very knowledgeable and we had a great time. Absolutely recommend.

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