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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

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

37 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

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Sailing week of yesteryear in the clear waters of Sardinia

Italy: Southern Sardinia

6 days - 6 nights

3 departures available

October

€750

Per person

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5.0

A dream trip for 2 people in the wilderness - All inclusive

Caribbean: San Blas Islands - Panama

6 days - 6 nights

8 departures available

October - December

Starting from

€1,925

€1,733

Per person

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5.0

New

From the Côte d'Azur to Corsica: between wild coves and the open sea

France: Corsica

5 days - 4 nights

3 departures available

April - June

€795

Per person

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4.9

Weekend of relaxation and fun to discover the Island of Elba

Italy: Tuscany

3 days - 2 nights

One departure available

October

€250

Per person

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5.0

New

Corfu: sailing, dream bays and walks in the villages - hostess on board

Greece: Ionian Islands

6 days - 6 nights

3 departures available

October

Starting from

€1,200

€500

Per person

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4.6

School-holiday cruise from Marina di Pisa to Cagliari

Italy: Southern Sardinia

10 days - 10 nights

2 departures available

July

Starting from

€1,350

€1,282

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

Why book a holiday with Sailsquare?

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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

19254 reviews

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Maddalena Archipelago, southern Corsica: wonderful Sardinia

10/5/2026

Michelle B.

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US

Mossimo and Valentina were superb! Incredible sailing, delicious food, taking us to stunning locations it far exceeded my expectations! I highly recommend sailing with them. Cheers! Michelle

Egadi paradise for sailing and snorkeling

10/4/2026

Luzia K.

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DE

Unfortunately, a wonderful week has come to an end. Mario is a great skipper and host. I can't even list all the bays where we swam in the crystal clear water. Gaia took very good care of us. Nice people, sun, absolutely relaxed.

We have known the Aeolian Islands for 20 years, live them with us!

10/4/2026

Livia R.

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IT

Everything perfect.. Very well organized. Very nice and engaging experience.
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Corfu between bays, taverns and myths.

10/4/2026

Clara M.

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ES

A very pleasant and peaceful experience. Despite being the last outing and carrying the exhaustion of the season, they did everything possible to make us comfortable and the alternatives they gave us when there was bad weather were very good ideas. The treatment is very nice, the kitchen too. The beautiful sailboat, very cozy, you feel at home. The only thing is that we thought we were going to make more stops and sailing trips and discover more hidden places and we were left wanting more, but it was mainly because of two days of bad weather. We will repeat the experience for sure

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