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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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4.6

"Nel Blu dipinto di Blu" - midweek in Ponza, Palmarola and Ventotene

Italy: Pontine Islands

4 days - 3 nights

3 departures available

June

Starting from

€320

€288

Per person

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4.7

Lampedusa, Linosa and Lampione, islands on the high seas

Italy: Pantelleria and Lampedusa

6 days - 7 nights

9 departures available

August - October

Starting from

€860

€774

Per person

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4.8

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

19 departures available

May - October

Starting from

€640

€576

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

10 departures available

June - September

Starting from

€825

€743

Per person

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4.9

Super!

Sailing holiday in the turquoise blue waters of Corsica

Italy: Tuscany

7 days - 7 nights

7 departures available

June - August

Starting from

€680

Per person

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4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

5 departures available

August - September

Starting from

€1,041

€989

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

9 departures available

May - October

Starting from

€320

€272

Per person

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4.9

Super!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

7 departures available

June - October

Starting from

€700

Per person

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4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

3 departures available

July - September

Starting from

€390

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

9 departures available

June - October

Starting from

€420

€399

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

15 departures available

May - October

Starting from

€230

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

13 departures available

May - September

Starting from

€400

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

17632 reviews

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Sailing in the Cyclades

04/22/2026

Miguel M.

-

Spain

Exceptional experience!! Yann is a skipper who knows the navigation area and the most suitable anchorages and ports well. In addition to being an excellent sailor, he is an endearing person who seeks the well-being of his "crew", carrying out activities on land such as hikes or visits to interesting places that give added value. His boat "[hidden]" is a sailboat of the highest level, very comfortable and designed to sail in extreme conditions and therefore absolutely safe. Yann keeps it in pristine condition and is spotlessly clean. In short, it is a highly recommended experience.
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Weekend among the most beautiful coves of Elba

04/21/2026

SARA N.

-

Italy

Unforgettable sailing experience with Marco and Carmen! 🌊⛵ From the first moment we felt welcomed as friends: professional, helpful and always attentive to every detail. The weekend was well organized, with breathtaking views, moments of relaxation, aperitifs and lots of laughter. We sailed to the island of Elba, saw dolphins and caught some excellent fish that we then cooked and ate together. All wonderful! Marco is an experienced skipper who conveys safety and passion for the sea, while Carmen adds a special touch with her kindness, sympathy and care for guests. I recommend this experience to anyone who wants to experience the sea in an authentic and relaxing way. Definitely to be redone, we will see each other 😜 again
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Sailing cruise in the Greek islands - The Saronic Islands

04/15/2026

Goutham B.

-

Germany

I had a wonderful week of sailing with this team. Skipper is super cool and I enjoyed his company a lot. He was happy to customize the sailing plan according to each of our requirements and was friendly to even cook for us a few times (The pasta was delicious). Bertrand even allowed me to stay on the boat for few extra days at Aegina. However, for my bad luck, an unfriendly couple was part of the crew and they were neither willing to pay for the skipper's food, nor willing to cook which was clearly mentioned in the advertisement as the responsibility of the whole crew. Even then the skipper was cool enough to invite us all to dinner in order to build up a family feeling between the crew members. Despite all this effort, It's unfortunate to see them giving a bad review about their sailing experience here. But other than this, personally I enjoyed the whole sailing week with Bertrand and his team. I am looking forward to sail with your team in the future.

Sailing cruise in the Greek islands - The Saronic Islands

04/15/2026

Thomas S.

-

United Kingdom

The captain (Alex) asked us to lie to the police as soon as we got there about being his friends and not chartering this boat. Something about not having a charter lisence, which made us feel very uncomfortable, even though Bertrand now denys it. The toilets stank and the shower was very uncomfortable to use, but I guess thats just how boats are. It leaked when it rained and it is fairly cramped, and we left asking why we paid that price for that boat. We didn't feel like we got value for our money at all and the organiser was very rude to us when we brought up our concerns. At least the islands were nice.

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