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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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4.4

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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4.7

Lampedusa, Linosa and Lampione, islands on the high seas

Italy: Pantelleria and Lampedusa

6 days - 7 nights

One departure available

October

€740

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

4 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

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4.7

Da Lanzarote a Tenerife, avventura ed emozioni indimenticabili

Atlantic islands: Canary Islands

6 days - 7 nights

One departure available

December

Starting from

€900

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

19249 reviews

Sailing, swimming and aperitif at sunset ... What else?

10/3/2026

Victoire D.

-

FR

Perfect afternoon with Emanuele! Wonderful host, generous food and drink and the boat is beautiful and welcoming Many thanks!!
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

10/3/2026

Marina G.

-

IL

Thank you for a lovely holiday! ❤️

Sailing, sun and sea in the Tuscan Archipelago

10/3/2026

Luca P.

-

IT

Overall the experience was positive: it was my first time on a sailing boat and I was left with a great desire to repeat a trip of this type, especially thanks to the good harmony that was created with the group. However, there were some organizational and management aspects that deserve room for improvement: Management and navigation: Claudio is a very nice person, but a more precise planning of the itinerary would have made the difference. By not booking ports in advance, last-minute searches often proved fruitless. In addition, we almost always sailed by motor instead of sailing (used only on two occasions), which is a bit of a shame for a holiday of this type. Movements on land: On the days at anchor near the ports there was little availability in the use of the tender to take us ashore; fortunately we were able to remedy this thanks to the support of a more experienced travel companion. Itinerary: Unfortunately we were unable to reach either Capraia or the Island of Giglio. The adverse weather certainly complicated things, but probably with a different management of the stops at least one of the two stages could have been reached. Boat: The boat itself was beautiful, but in my opinion not suitable for comfortably accommodating 8 people. Also worth mentioning is a small plumbing problem in one of the bathrooms (the backflow of water after draining). Overall an adventure that I would gladly do again, with the hope that these details can be taken as ideas for improvement.

Split archipelago, Hvar islands, Brac - with Hostess and full board

10/3/2026

Jean michel S.

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BE

What a dream week! Cecilia, Tommaso... and their sailboat Cassiopeia are fabulous and passionate hosts! Coves with crystal clear waters, aperitifs and meals with little onions, discoveries of ports and original restaurants, guitar and singing evenings, discussions in the moonlight and always in a good mood. I highly recommend this experience Jean Michel

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