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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

Relaxing weekend in the Aeolian Islands: Lipari, Vulcano and Salina

Italy: Aeolian Islands

3 days - 2 nights

One departure available

October

€320

Per person

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4.2

Sailing holiday on the Côte d'Azur: experience the charm of the French Riviera

France: French Riviera and Porquerolles

6 days - 7 nights

13 departures available

June - September

Starting from

€730

€657

Per person

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4.8

Thailand: a dream to discover sailing with a hostess

Thailand: Phuket, Krabi and Phi Phi Islands

7 days - 7 nights

4 departures available

January - December

€1,050

Per person

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4.8

New Year's Eve wandering among the islands of Thailand with hostesses

Thailand: Phuket, Krabi and Phi Phi Islands

11 days - 11 nights

One departure available

December - January

€1,646

Per person

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5.0

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

Croatia: Split Archipelago

7 days - 7 nights

20 departures available

June - October

Starting from

€1,100

Per person

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4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

21 departures available

May - October

Starting from

€590

Per person

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5.0

Raja Ampat: New Year's Eve in the last paradise

Indian Ocean: Indonesia

12 days - 12 nights

One departure available

December - January

€2,070

Per person

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4.5

Ibiza & Formentera: an exclusive journey between sky and sea

Spain: The Balearic Islands

6 days - 6 nights

11 departures available

June - September

Starting from

€736

Per person

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4.6

Experience the sea, feel the wind

Italy: Aegadian islands

6 days - 7 nights

3 departures available

July

Starting from

€790

€711

Per person

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4.4

Guadalupe to St. Martin via Antigua, Barbuda, St. Barth, and Anguilla

Caribbean: Saint Martin

14 days - 14 nights

One departure available

February

€1,490

€1,341

Per person

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5.0

3 days in the wild Aeolian Islands - All inclusive & flexible dates

Italy: Aeolian Islands

2 days - 2 nights

2 departures available

October - November

€723

Per person

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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

33 departures available

April - November

Starting from

€650

€618

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

19284 reviews

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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.

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IT

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

The fantastic Saronic Islands and the surroundings of Athens

10/19/2026

ASLIHAN A.

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TR

Alessandro was the best captain one could ask for. I had to leave after two nights because of a health emergency back home. He offered me a free sailing trip im April.

Magical Barcolana Weekend: the most famous regatta!

10/19/2026

LUIGI L.

-

IT

Wonderful experience with a wonderful team. Strongly suggested

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