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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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4.8

Super!

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

24 departures available

May - October

Starting from

€1,200

€1,080

Per person

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4.8

Super!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

17 departures available

June - October

Starting from

€660

Per person

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4.8

Super!

Cast off for a week at sea, a thousand ways to experience it!

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

October - November

€585

Per person

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5.0

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

34 departures available

March - October

Starting from

€460

Per person

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4.9

Super!

Cruise-Coastal Navigation Course Porquerolles-Calanque Cassis

France: French Riviera and Porquerolles

6 days - 7 nights

8 departures available

July - August

Starting from

€800

Per person

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4.9

Super!

SLOW SAIL - sailing from San Vincenzo to Capraia and Corsica

France: Corsica

7 days - 6 nights

4 departures available

August

Starting from

€750

Per person

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4.8

Super!

Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

Italy: Tuscany

6 days - 6 nights

13 departures available

June - September

Starting from

€990

Per person

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4.9

Super!

Lefkas, Kefalonia & Ithaca: 7 days of relaxation and fantastic bays

Greece: Ionian Islands

7 days - 7 nights

10 departures available

May - July

Starting from

€650

€585

Per person

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5.0

Super!

Daily sailing trips to Ortigia and Plemmirio

Italy: Sicily

1 day - 0 nights

20 departures available

October - November

€150

Per person

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5.0

Super!

Dream Cruise Under Sail in the Society Islands 14 Days

Pacific Ocean: French Polynesia

13 days - 13 nights

One departure available

October - November

€2,090

Per person

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4.8

Super!

A taste of the magnificent Island of Elba

Italy: Tuscany

2 days - 2 nights

5 departures available

October - November

€300

Per person

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4.9

Super!

Sailing adventure in Norway: chasing the Northern Lights - COTTAGE + SAILBOAT

North Sea: Norway

7 days - 7 nights

7 departures available

January - November

Starting from

€1,200

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

19274 reviews

A taste of the magnificent Island of Elba

10/14/2026

Annachiara P.

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IT

It was a beautiful weekend!! Alberto is an experienced and prepared skipper who is totally dedicated to what he is passionate about. We really appreciated his willingness to meet us and, compatibly with weather conditions and times, to adapt the weekend to our needs: although we were licensed, we needed to regain confidence with going to sea (sailing!), without giving up relaxation. Alberto was a great teacher and we learned so much! He took us to beautiful places and we really enjoyed our time together (and the classical guitar under the stars added that extra touch :D). A special thanks to Claudia for her company and for the super aperitifs she prepared for us! The boat is beautiful, maintained with great care, order and cleanliness. They were two wonderful days. Thank you very much Alberto and Claudia!! We hope to repeat it soon!
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The Saronic Islands sailing, skippered and on-board kitchen

10/14/2026

Kaija H.

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FI

Annalisa and Emanuel hosted a very nice and safe sailing trip in their boat involving everyone. Despite the changed route plans due to bad weather the previous week, they were able to replan us a nice trip in the Cyclades Islands. We visited beautiful natural bays, enjoyed sailing, swimming, snorkling, sun bathing, fishing, ancient historical places and delicious fresh home-cooked food. Annalisa and Emanuel are the best and most patient hosts I have ever had!
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Sailing and Trekking in the Aeolian Islands

10/14/2026

Massimo G.

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IT

A week in full relaxation in the Aeolian Islands.Mario is a professional and helpful skipper with his customers, putting them immediately at ease, For your holiday in this archipelago I highly recommend to contact him .... MARIO

Barcolana Weekend: experience the largest regatta in the world

10/13/2026

Francesco S.

-

IT

Ilaria in a nutshell Great skipper Great cook Super nice

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