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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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5.0

Super!

Cruise for Singles from Sanremo to Saint-Tropez

France: French Riviera and Porquerolles

8 days - 7 nights

One departure available

August

€650

Per person

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4.8

Super!

7 days between Capri, Amalfi and Sorrento: dream sailing cruise

Italy: Naples & Amalfi Coast

7 days - 7 nights

4 departures available

August

€990

Per person

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4.8

An unforgettable week between Capri, Positano, Amalfi, Ischia, Procida...

Italy: Naples & Amalfi Coast

7 days - 7 nights

One departure available

August

€977

€879

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

5 departures available

September - October

Starting from

€275

Per person

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4.6

Week between the Tuscan Islands and Northern Corsica

Italy: Tuscany

7 days - 6 nights

7 departures available

July - September

Starting from

€700

Per person

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5.0

Aeolian Islands in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

3 days - 2 nights

5 departures available

July - August

Starting from

€425

€383

Per person

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4.8

Super!

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

5 departures available

August - October

€650

Per person

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5.0

Super!

EXPERIENCE THE MAGIC! Sailing and relaxing in a maritime wonderland!

Croatia: Istrian peninsula

7 days - 7 nights

4 departures available

August - September

€649

Per person

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4.9

Super!

Weekend in the Gulf of Alassio and Gallinara Island

Italy: Liguria

2 days - 2 nights

5 departures available

July - August

Starting from

€250

Per person

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4.8

Super!

Let's sail together in Southern Sardinia

Italy: Southern Sardinia

6 days - 7 nights

6 departures available

July - September

Starting from

€900

€855

Per person

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5.0

Egadi Sail & Relax: the archipelago to experience

Italy: Aegadian islands

7 days - 7 nights

8 departures available

July - September

Starting from

€550

€495

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

3 departures available

July - October

Starting from

€420

€399

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

18073 reviews

Weekend in the Pontine Islands between Ponza and Palmarola

07/14/2026

Federica M.

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IT

Our skipper of the sailboat [hidden] was very good, young, smart, born on boats, the sea is his dimension, he always took care that the boat was safe and anchored in places where the undertow was not too strong, so as not to make us feel bad. Always kind and smiling, he also organized the Saturday evening on land, booking us an excellent restaurant in Ponza and showing us a nice place to spend the evening. He booked us the taxi boat to go and return from the port. The boat has an elongated awning to offer a greater onbra, and a nice sun mattress under the mainsail. The gas only had a small working flame and it took a while to boil the pasta, but we were on vacation and there was no hurry, I'm sure it will be fixed soon. We had a Sup for swimming and masks for snorkeling. Mattia was always very kind, courteous and helpful, he transmits security and reliability. And it has a great playlist too! We had a really good time. Highly recommended!!
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Mini whale watching cruise with WWF guide between Ponza and Palmarola

07/14/2026

Leonardo C.

It was an experience we will remember for a long time! Special thanks go to skipper Luca and guide Andrea, who made this day truly extraordinary. Andrea is an extremely prepared, competent person capable of transmitting his passion for the sea and marine fauna in an engaging way. You can feel how much he loves his job and how much he cares about sharing his knowledge with those who participate in the excursion. Luca, with great professionalism and availability, has led the boat impeccably, involving and opening the doors to anyone interested in the world of sailing. Together they have done much more than was planned: they have committed themselves far beyond what was required of them, modifying the route when possible, making us discover wonderful places not planned and dedicating time and energy to give us a truly unique experience. We did not feel like simply participants in an excursion, but guests accompanied by two people who put heart, passion and dedication into what they do. It is rare to meet professionals who are so attentive and eager to offer the best. I recommend this experience to anyone who loves the sea and nature: if you are lucky enough to have Luca and Andrea with you, you will experience a day that will go far beyond expectations. Thank you very much!
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Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

07/14/2026

Lidia Giulia D.

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IT

An extremely prudent sailing experience, suitable for those seeking maximum tranquility. I state that I have several sailing holidays behind me, so I know the rhythms on board and the fundamental role of the skipper. Precisely for this reason, I would like to leave a balanced and objective review, which highlights both the positive sides and the aspects that have limited our experience. Starting from the positive notes, the boat itself is very comfortable and spacious, equipped with 4 cabins and 4 bathrooms, which guaranteed excellent livability on board even during an important crossing such as the one to reach Corsica. In addition, the skipper is an elderly and highly experienced person, who puts the safety of the crew and the boat first. He has always made himself available to accompany us ashore with the tender whenever we needed it, guaranteeing us comfortable and safe disembarkations. However, in other respects, the holiday was affected by a management that was perhaps too rigid. The aspects of navigation that most influenced the week were the management of the draft and the very conservative moorings. The boat has a large draft, which undoubtedly requires attention. However, the skipper's caution was in my opinion excessive. We stopped almost exclusively in roadsteads well known to him and very sheltered, often far from the most famous and evocative points, such as Isola Piana, which we were able to see only after much insistence. Coves with shallow waters and turquoise waters were systematically avoided, always keeping a safe distance well above what was necessary. In addition, there were few trips once at the destination. Although they covered an important route arriving in Corsica, once they arrived there, daily travel was reduced to a minimum. It became very difficult and rare to move to change bays or explore the surroundings once the anchor was dropped. During the journeys, navigation took place far offshore. Even during longer transfers, the skipper tended to always sail in very open seas, staying at a great distance from the mainland, which did not allow us to enjoy the coastal views. This also affected the logistics of the bathrooms and activities. Always mooring at a great distance from the shore, it was not possible to enjoy the sea swimming, and in SUP we struggled a lot to cover the distances starting directly from the boat. This has limited a bit the spontaneity and freedom typical of a holiday at sea. Finally, we did little sailing. Despite the days of good wind, navigation took place mainly by motor. In summary, it was a holiday with a very quiet pace and a strongly conservative approach. I think it is ideal for those who are at their first experience and are looking for very calm rhythms and maximum caution; those who already have experience and are looking for the spirit of sailing and active exploration of the coves may find this style a little too limiting.

Gulf of Poets

07/14/2026

Robin H.

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DE

We had an unforgettable sailing trip! It was an incredibly beautiful experience that we would do again at any time. Giovanni was incredibly warm, attentive and made sure we felt comfortable the whole time. Due to his open and friendly manner, we felt at home on the ship from the first moment. The atmosphere on board was relaxed, the landscape fantastic and the entire trip was simply perfectly organized. Thank you very much for this special experience – we can heartily recommend the sailing trip with Giovanni!

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