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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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4.9

Super!

Trip with photographer to the Pontine - Life changing experiences

Italy: Pontine Islands

4 days - 3 nights

6 departures available

July - October

Starting from

€420

€399

Per person

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5.0

Super!

Tuscany and North Corsica on a sailing boat

Italy: Tuscany

7 days - 7 nights

One departure available

August

€1,060

Per person

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4.8

Capri Light Blue - Two boats in company!

Italy: Naples & Amalfi Coast

3 days - 2 nights

2 departures available

September - October

€242

€218

Per person

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5.0

New

Egadi mon amour: seven days to fall in love, be amazed and relax.

Italy: Aegadian islands

7 days - 7 nights

7 departures available

June - September

Starting from

€600

€540

Per person

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4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

2 departures available

July - September

€400

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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4.8

Super!

A sailing trip through history and food and wine to the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

3 departures available

July - August

Starting from

€900

Per person

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5.0

Super!

Luxury routes among the wonders of Northern Sardinia with hostess

Italy: Northern Sardinia

6 days - 6 nights

8 departures available

July - September

€1,600

Per person

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5.0

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August - September

€1,020

Per person

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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

One departure available

July

€410

Per person

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5.0

Super!

Learn to sail in a week in the Tuscan Archipelago

Italy: Tuscany

6 days - 6 nights

2 departures available

August

Starting from

€849

Per person

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5.0

Super!

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

5 departures available

September - November

€250

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

17855 reviews

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Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

06/23/2026

Kim W.

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CA

An amazing experience, not simply a choice destination (nature, culture, cuisine, weather) but truly memorable from the standpoint of staffing, communication and service. From the moment you book the trip, Bledar is in contact, verifying your needs. I felt 100% certain my celiac daughter would be well-supported on the journey with an unusual sophistication of dietary understanding. Bledar is an excellent chef for celiacs and non-restricted diets alike. In addition to his captain credentials, he is a delight to talk with and the purveyor of fun. His magnetic personality gives him so many connections to the community that you will be guaranteed to enjoy the best nature, eating, shopping spots. Whatever you desire Bledar and his first mate Alesandro will make the memory possible! I would go back and sail with them in a heartbeat.

Amazing Pontine Islands on a sailboat with private bathrooms

06/23/2026

Giulia C.

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IT

Wonderful first sailing experience! Comfortable boat, adequate space. Carlo and Barbara super nice and easy-going. The swim at the Cathedrals is super recommended. Absolutely recommended experience
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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.

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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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