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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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4.1

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

36 departures available

January - December

Starting from

€275

€248

Per person

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4.1

Corso di vela RYA Day Skipper Pratical sailing

Italy: Tuscany

4 days - 4 nights

9 departures available

October - December

€1,400

Per person

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4.4

Caribbean by boat, the Grenadines and Tobago Cays

Caribbean: Grenadines & Martinique

7 days - 7 nights

3 departures available

January

€950

€855

Per person

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5.0

Weekend in Tuscany between Argentario and Giglio Island

Italy: Tuscany

3 days - 2 nights

3 departures available

October - November

€280

Per person

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5.0

Let's discover Portofino, Santa Margherita and Sestri Levante together

Italy: Liguria

2 days - 2 nights

2 departures available

October - November

Starting from

€430

Per person

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4.5

Wild Corsica: The Magic of a Boat Trip

France: Corsica

7 days - 7 nights

4 departures available

July - August

Starting from

€1,000

Per person

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4.8

Thailand: a dream to discover while sailing

Thailand: Phuket, Krabi and Phi Phi Islands

14 days - 14 nights

One departure available

January

€2,100

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

2 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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4.7

Island of Elba and South Corsica fantastic week

Italy: Tuscany

7 days - 6 nights

11 departures available

June - August

Starting from

€660

Per person

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4.9

Life Changing Experiences - Week in the Pontine Islands with photographer on board

Italy: Pontine Islands

6 days - 6 nights

4 departures available

July - August

Starting from

€1,037

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

19286 reviews

Squid Regatta

10/20/2026

Valentina M.

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IT

Wonderful weekend with participation in the squid regatta that allowed us to appreciate Francesco's skills as a captain. It was fun to get involved in conducting! [hidden] is a gem of a boat: convenient spaces, clean and comfortable.
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The fantastic Saronic Islands and the surroundings of Athens

10/20/2026

manuela c.

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IT

I had a great time on the boat with Ale, a professional, kind, helpful person who tried to please everyone (and it's not easy!) and super nice. I saw very beautiful places despite the islands being quite man-made, took nice baths in magnificent roadsteads and visited beautiful villages with even some trekking. Beautiful, solid and comfortable, the boat, suitable for any navigation, I have always felt safe. Ale also always available to cook for everyone! Experience to be done again next year in other islands. Thank you
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It's time for sun and sea!

10/19/2026

Francesco G.

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IT

A special thanks goes to Carlo, exceptional owner and skipper, super welcoming, prepared and smart. He managed to make us feel immediately at ease by transmitting his passion for the sea and guaranteeing us a stay in total relaxation and safety. Very nice, comfortable and clean boat. Highly recommended experience for anyone who wants to unplug and experience the sea in an authentic way.
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IBIZA and FORMENTERA - ALL INCLUSIVE with skipper and skipper

10/19/2026

Chloe Maira G.

-

IT

fabulous hour spent with Filippo and his beloved dog NOA, professionalism, humor, good food, great sailings all the desirable

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