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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

Aeolian Islands: wellness, taste, fun with fabulous cook on board

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

July - August

Starting from

€920

€828

Per person - min 2 pax

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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

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

8 departures available

July - September

Starting from

€795

€716

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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4.6

Week between the Tuscan Islands and Northern Corsica

Italy: Tuscany

7 days - 6 nights

10 departures available

June - September

Starting from

€650

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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4.8

Super!

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

Italy: Tuscany

2 days - 2 nights

17 departures available

April - October

Starting from

€230

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

8 departures available

May - October

Starting from

€320

€272

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

12 departures available

May - September

Starting from

€400

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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4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

4 departures available

June - September

Starting from

€360

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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

17630 reviews

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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.
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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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Easter in Capraia and Corsica

04/14/2026

Giunio M.

-

Italy

Wonderful days in the company of quiet people and lovers of the sea and sailing
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Offshore and night navigation course on cabin cruisers

04/13/2026

Marco B.

-

Italy

Sailing course... but also a holiday. Navigation to Giglio and back via Elba with departure at night. Despite the little wind that blew in those days, Paolo was able to convey notions and make the students practice, all with the utmost sympathy ... Be prepared to be made fun of, especially if you're an engineer.

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