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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

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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4.7

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!

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!

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

3 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

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

19012 reviews

Pontine and Flegree on a comfortable 15 meters: an adventure in the Mediterranean

09/3/2026

Martina P.

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IT

A truly unforgettable experience! Not only for the location. The skipper was just amazing: always attentive and helpful with all of us. Thanks to his great expertise, he was able to manage wind and sea perfectly, giving us breathtaking stops and coves in total safety and relaxation.
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Egadi Sail & Relax: the archipelago to experience

09/3/2026

Leandro D.

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IT

A truly unforgettable sailing holiday! A beautiful experience, made even more special by Paolo's professionalism and sympathy. A prepared, competent person who is always attentive to everyone's needs, capable of transmitting confidence and at the same time creating a relaxed and pleasant atmosphere. A special mention also to his qualities as a cook, he prepared typical dishes of Sicilian cuisine in a truly impeccable way. Between sea, sunsets, good food and lots of tranquility, it was a holiday that I would absolutely do again. Highly recommended for those who want to experience the sea in an authentic way, with a skipper who really makes the difference.

7 days of sailing between beautiful Croatian islands and crystal clear waters

09/3/2026

Domenico F.

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IT

A very special holiday! Emilio is a skipper with a great deal of experience, but above all a calm, patient person with a huge passion for sailing. It was nice to see him involved in trying to make us experience the sea to the fullest. He gave me valuable advice to steer the boat leaving me the helm to practice and he was very happy to let me do it, correcting me and patiently explaining everything he could help me improve. Something that I really appreciated. In addition, Emilio is an open, nice and helpful person. During the holiday he was much more than a skipper: it was like having another friend on board with whom to share days, laughter, swimming and beautiful bays of Croatia. He faced every situation with tranquility, always finding the right solution and trying to satisfy us in our requests, especially when we wanted to discover new bays or simply stop for a swim. It is rare to find a skipper who can convey so much experience and passion without ever making it a burden on the crew. A great experience, which I would definitely do again. Emilio super recommended! ⛵️
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Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

09/3/2026

Walter G.

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IT

7 dream days with the skipper Luke, always vigilant, attentive, prepared and available to the various proposals of the crew, among the most beautiful waters of the central Tyrrhenian Sea, the Phlegraean and Pontine islands. Ventotene is a piece of the heart now, Palmarola where the boats fly Procida a living postcard, Ponza is unique The Gem is a comfortable, reliable, safe, fun and equipped boat, The only small observation just to look for a flaw? refrigerators could yield a little more, but with careful management of the galley you still do not run any risk. I confirm right now my next participation in this experience which has been part of my blood count since 2025. Happy birthday guys, we would certainly have to hear from each other again, a big hug to his nephew LUKE, you are really a very good boy🫂to hear us again YOUNG MAN in the ass of the whale,,,,,that I don't know anyway!!!! 🤣🤣🤣🤣🤣

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