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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!

Ibiza & Formentera: one week with cook on board

Spain: The Balearic Islands

6 days - 6 nights

One departure available

September

€750

€675

Per person

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4.8

Super!

A week of sea, volcanoes and fun in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

6 departures available

July - September

Starting from

€690

€621

Per person

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5.0

Super!

A sailing holiday: discovering the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

3 departures available

August

€650

Per person

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5.0

Super!

Ogliastra to go crazy, mini-cruise among the wonders of Sardinia

Italy: Southern Sardinia

4 days - 3 nights

2 departures available

July - September

€740

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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4.9

Super!

Sailing weekend in Istria

Croatia: Istrian peninsula

3 days - 2 nights

6 departures available

July - October

€260

Per person

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4.8

Super!

From the Pontine to the Aeolian Islands - Adventure, Navigation, and Relaxation - One Way

Italy: Aeolian Islands

5 days - 6 nights

One departure available

July

€590

Per person

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4.8

Super!

Weekend on Elba, sea, colors and scents.

Italy: Tuscany

2 days - 2 nights

2 departures available

July - September

Starting from

€200

Per person

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4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

14 departures available

July - November

Starting from

€600

€540

Per person

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5.0

Come and discover the Egadi Islands! Nature, relaxation and crystal clear waters

Italy: Aegadian islands

7 days - 7 nights

9 departures available

July - September

Starting from

€700

Per person

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5.0

Egadi Sail & Relax: the archipelago to experience

Italy: Aegadian islands

7 days - 7 nights

10 departures available

July - September

Starting from

€550

€495

Per person

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New

Week end in Costa Azzurra

Italy: Liguria

2 days - 2 nights

4 departures available

June - July

Starting from

€300

€270

Per person

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On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Sailboat holidays & skippered tours

17853 reviews

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Weekend Elba or Capraia

06/23/2026

Andrea B.

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IT

I write this review with regret and with a constructive spirit, because I rarely leave negative judgments. Capraia, the water and the sea were very beautiful; Unfortunately, the overall management of the experience did not reflect the expectations created by the announcement. On the listing page consulted before departure, check-in was at 20:00; We arrived at 19:00. On our arrival we were challenged for a delay by referring to a different time, which we had not clearly received before departure. The ad described night browsing as a possibility, not a guaranteed service. In our experience it was not carried out: we were told that the weather conditions were favorable, but that, given the time that the skipper considered late, he would need to rest. The start therefore took place the following morning, significantly reducing the time actually usable over the weekend. I understand that the itinerary and stops may depend on operational needs, weather and safety. In our case, however, the program was much more limited than we expected and requests to evaluate further stops, sunset or alternatives received little or no follow-up. In addition, some of the equipment indicated in the ad was not available during our experience: the SUP was not on board, the awning was not present and the bow sundeck was not usable during navigation because it was occupied by the tender. For what I paid, I would have waited for clearer communications, equipment consistent with what was indicated in the announcement and a management more attentive to the needs of the group. I hope that these comments can be received constructively and contribute to improving the service.

Weekend at the Pontine Islands between Ponza and Palmarola

06/23/2026

sophia jasmine t.

-

IT

I had never slept on the boat it was a fantastic experience, marco and benedetta were professional and kind. I highly recommend this adventure!
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Weekend Elba or Capraia

06/23/2026

Michela I.

-

IT

The evaluation for me is negative and the reason for some points: from the site it says check-in time at 8 pm at the port we arrived at 7 pm and on arrival the skipper (Nicola's replacement) tells us that we had to be in port at 5 pm. A few days earlier a chat had been made with both skippers in question but neither of the 2 said that the time was different from the one written on the site, so the 9 people participating arrived by 19/20. This led to a change in the departure because the skipper did not really want to consider the option of leaving in the evening to be at his destination already in the morning as written on the website. We left on Saturday morning at 8.15 with the forced choice to go to Capraia because Elba was too far away. Once in Capraia we stayed in only one cove because the skipper did not want to move. Since Capraia is very small you could see at least 2 coves in one day. It was not possible to see the sunset from the boat for the same reason, we had to move. On Sunday, we did the same thing only one cove. We then move on to "what you find on board" written on the site: there was no awning and in order not to die in the sun we created it with some towels, sup was not there, bow sundeck occupied by the tender during navigation because the skipper did not want to put it in the sea. All seasoned with the rudeness with which the answers were given both by the skipper on board and by Nicola in the chat to all the participants who pointed out the problems just described. Island of Capraia very beautiful and crystal clear water, too bad we saw little. Excellent sea conditions practically a board.
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Weekend on the Island of Elba

06/23/2026

Chiara P.

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IT

It wasn't just a weeekend, it was a dream! It was my first experience on a sailing boat with a group of people I didn't know, and everything was perfect, Marco accompanied us in the best way, always in maximum safety, and took us to wonderful places, the starry sky of the first night at anchor I will never forget. His boat is well maintained and tidy, we will certainly schedule other outings with him!

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