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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!

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

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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

2 departures available

October

€230

Per person

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4.9

Super!

Adventure weekend in the Egadi Islands

Italy: Aegadian islands

3 days - 2 nights

3 departures available

October - November

€350

Per person

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5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

One departure available

October

€370

Per person

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4.8

Super!

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

Greece: Ionian Islands

7 days - 7 nights

16 departures available

June - September

Starting from

€600

€540

Per person

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4.9

Super!

NEW YEAR's Eve between sea and land in Norway: chasing the Northern Lights - COTTAGE + SAILBOAT

North Sea: Norway

11 days - 11 nights

One departure available

December - January

€1,300

Per person

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4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

One departure available

October

€750

€675

Per person

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5.0

Super!

Relaxing holiday on the Côte d'Azur

France: French Riviera and Porquerolles

7 days - 7 nights

9 departures available

April - August

Starting from

€540

€486

Per person

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5.0

Super!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

36 departures available

March - October

Starting from

€460

Per person

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4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

3 departures available

August

Starting from

€1,040

Per person

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4.8

Super!

Experience the sea in October!

Italy: Tuscany

2 days - 2 nights

3 departures available

October

€200

Per person

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4.9

Super!

Week on the Côte d'Azur between Porquerolles and Calanques

France: French Riviera and Porquerolles

6 days - 7 nights

7 departures available

July - August

Starting from

€800

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.

-

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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