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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

6 departures available

September - October

Starting from

€1,300

€1,040

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

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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5.0

Super!

Long Weekend Santa Candida - Ventotene

Italy: Pontine Islands

5 days - 4 nights

One departure available

September

€550

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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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

5 departures available

September - November

Starting from

€585

€527

Per person

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4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

2 departures available

September

Starting from

€441

€419

Per person

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4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

September - October

Starting from

€750

€675

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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5.0

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

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - October

€690

Per person

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5.0

Super!

Weekend of the Pontine Islands to discover Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

One departure available

September

€490

€441

Per person

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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

6 departures available

September - October

Starting from

€370

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

19020 reviews

Maddalena Archipelago, southern Corsica: wonderful Sardinia

09/5/2026

Alessandro C.

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IT

With Massimo skipper and collaborator Valentina it was a really positive experience, with a very close-knit group; we visited beautiful bays both in the archipelago of La Maddalena and in the south of Corsica. The sail to Bonifacio with the overnight stay in the port is very beautiful. A special applause for the lunches and dinners on the boat truly worthy of the best restaurants, Thank you for the beautiful week spent at sea. Alexander

A week in the Aeolian Islands - 6 islands in seven days

09/5/2026

Antonella B.

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GB

The skipper was the only negative part of the experience. Rude, directive, judgmental and controlling. Would lose temper over small things without actually teaching anything. Arrogant and entitled. Do not recommend him. He also took advantage of the trip to bring his fiance and son onboard for a total of 4 nights over the 6 we had paid for making the space more crowded than it should have been. “Please” “thank you” are not part of his vocabulary. Felt a bit on a disciplinary experience at time. Boat not spacious enough for 9 people (including the two extra guests we were informed of only after departure - no permission asked, just communicated) Beautiful destination, I truly love Eolian islands. And my friend are the best company, always!
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Discovering the Aeolian Islands Between Nature, Relaxation and Fun

09/5/2026

Helena A.

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IT

An amazing week in the Aeolian Islands: incredible sea, islands that never disappoint and that beauty that gets under your skin. Too bad only for the little wind and the very heat, but they did not take anything away from the experience. I have never been bored: gossip, controversy, quarrels, laughter... A perfect mix that made this holiday unforgettable. I met wonderful people, each with their own story, their own character, their own light. And then there is Giovanni, our skipper: professional, patient, attentive. An excellent cook and a person who first studies, observes, understands... And only then does it open up, showing its truest side, the dedicated one, that of the smiles that come when it decides you can see them. Thank you from the Mad Mermaid 🚨🤣, who has lived it all this week, up to the last wave.
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Lampedusa, Linosa and Lampione, islands on the high seas

09/5/2026

Jacopo V.

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IT

Beautiful experience, super experienced skipper! The islands of Lampedusa and Linosa are enchanting and the skipper Lorenzo is 10 out of 10: he has a great deal of experience and knows the place perfectly. It made us experience a beautiful and different holiday than usual, despite the weather was not totally on our side (very hot week and incessant sirocco). The only constructive criticism goes to the [hidden] boat: it is rather dated and the spaces on board are a bit tight. There were 9 of us in total (7 guests + skipper and assistant skipper), perhaps a little too high for the type of boat. Reducing the number of participants would greatly improve comfort. Apart from that, the holiday remains absolutely recommended and promoted with flying colors for the itinerary and management!

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