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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

E-bike & Sailing Experience with wine tasting on Elba - 2 boats

Italy: Tuscany

3 days - 2 nights

One departure available

October

€250

€238

Per person

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4.0

European Mile Builder - Leg 2: Gibraltar to Las Palmas

Atlantic islands: Canary Islands

6 days - 6 nights

One departure available

November

€660

Per person

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5.0

2 days sailing between Palermo and Cefalù - All inclusive & flexible dates

Italy: Sicily

2 days - 1 night

3 departures available

October

€215

Per person

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4.4

From Martinique to Guadeloupe riding the trade winds

Caribbean: Guadeloupe

10 days - 10 nights

One departure available

February

€1,250

€1,125

Per person

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5.0

Unspoilt Balearic Islands for max 4 guests: Mallorca and/or Menorca

Spain: The Balearic Islands

6 days - 6 nights

One departure available

October

€950

Per person

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5.0

New

Cruise to the Golden Islands via the capes and bay of St Tropez

France: French Riviera and Porquerolles

5 days - 4 nights

27 departures available

February - October

Starting from

€595

Per person

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4.1

Totano's cup 2027 weekend of sailing and party on the island

Italy: Tuscany

3 days - 2 nights

One departure available

October

€350

Per person

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New

Sailing Week Sardinia and Corsica

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

October

€600

Per person

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4.4

L'Île de Beauté: sailing in Corsica with night return

France: Corsica

6 days - 7 nights

5 departures available

July - August

Starting from

€750

Per person

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4.7

Four days on a sailing boat

Italy: Tuscany

4 days - 4 nights

One departure available

June

€625

Per person

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5.0

New

Stintino, Asinara and South Corsica

Italy: Northern Sardinia

7 days - 7 nights

One departure available

September

€620

€590

Per person

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Odysseus trip to Zakynthos - Kefalonia-Ithaka

Greece: Ionian Islands

7 days - 7 nights

One departure available

October

€890

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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