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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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4.7

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

4 departures available

October - November

€700

€665

Per person

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4.7

Tenerife and La Gomera aboard an 18 m ketch

Atlantic islands: Canary Islands

6 days - 7 nights

10 departures available

January - December

Starting from

€900

Per person

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5.0

New

Basic and advanced sailing courses

Italy: Liguria

2 days - 1 night

3 departures available

October - November

Starting from

€220

€198

Per person

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New

Weekend in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

2 departures available

May

€450

Per person

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4.7

From Funchal to Lanzarote: adventure and unforgettable emotions

Atlantic islands: Canary Islands

6 days - 7 nights

One departure available

December

Starting from

€900

Per person

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4.3

The perfect holiday on Europe's hottest and most glamorous island

Malta: Malta

6 days - 6 nights

One departure available

October

€690

Per person

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4.7

Tuscany and Liguria, we sail between the Apuan Alps and the Gulf of Poets

Italy: Liguria

2 days - 2 nights

2 departures available

April - October

Starting from

€250

Per person

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4.1

Corso di vela RYA Day Skipper Pratical sailing

Italy: Tuscany

4 days - 4 nights

11 departures available

October - December

€1,400

Per person

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5.0

Sailing excursion from Naples to Procida or Sorrento

Italy: Naples & Amalfi Coast

1 day - 0 nights

34 departures available

October - December

€100

Per person

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4.4

The British Virgin Islands, an enchanted paradise

Caribbean: BVI - British Virgin Islands

10 days - 10 nights

One departure available

March

€1,350

€1,147

Per person

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4.1

Capraia & Corsica del Nord — 7 days of sailing in the blue

Italy: Tuscany

7 days - 6 nights

9 departures available

July - September

Starting from

€850

€723

Per person

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5.0

Raja Ampat: beyond the known routes

Indian Ocean: Indonesia

10 days - 10 nights

2 departures available

January - February

€1,570

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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