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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

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

Greece: Saronic Islands and Athens area

6 days - 7 nights

2 departures available

October

€1,300

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

2 departures available

October - November

€585

Per person

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4.9

Super!

The fantastic Saronic Islands and the surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

October

€750

Per person

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4.7

Voices of the Pelagos: artistic-scientific whale watching expedition with WWF guide

Italy: Tuscany

4 days - 4 nights

One departure available

October

Starting from

€453

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

2 departures available

October

€570

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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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

One departure available

October

€370

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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5.0

Super!

Daily sailing trips to Ortigia and Plemmirio

Italy: Sicily

1 day - 0 nights

26 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

€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

19265 reviews

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Sailing in the magical Sardinia of the South

10/8/2026

Sebastiano F.

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IT

I was looking for a super sea to continue improving my sailing knowledge... With the staff of [hidden] I was able to find all this combined with irony and lightness that never hurt! P.S. Extremely recommended for sailing enthusiasts who want to grow Thank you very much to Gianluca, Valeria and Michela!
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From Mykonos to Athens by sail, with skipper and on-board kitchen

10/7/2026

manuela c.

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IT

Annalisa and Emanuel were professional and nice, we unfortunately had the worst week of wind in sailor's memory and we were forced to always stay still without sailing except for 3 hours on the first day so I can't talk about the cruise destinations except for syros that they propose and that, unlike other islands, it is not crowded and therefore maintains something of the Greek spirit with beautiful villages and has beautiful trekking and beaches (the beaches unfortunately due to wind were not frequentable but I saw them in the treks). Beautiful and spotless boat absolutely comfortable. What can I say? Hope to see you again next year! Maybe with better luck for the climate! Thank you

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

10/6/2026

Iris D.

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BE

Such a wonderful experience! As a solo traveller I had a great time during this trip, Aga and Arnon were very welcoming and took good care of us. The places we visited were stunning, the food Aga prepared for us was excellent, and the overall vibes were 10/10.
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Experience the sea in October!

10/6/2026

Luigi V.

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IT

Super experienced and helpful skipper. He helped us learn the basics of sailing and life on a sailing boat. Great chef skills!

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