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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

New Year's Eve on the French Riviera between relaxation Provençal scents and sailing

France: French Riviera and Porquerolles

6 days - 5 nights

One departure available

December - January

€690

€621

Per person

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5.0

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

Italy: Liguria

2 days - 2 nights

2 departures available

May

€200

Per person

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5.0

Sailing adventure in Guna Yala (San Blas Islands) - All inclusive

Caribbean: San Blas Islands - Panama

7 days - 7 nights

One departure available

December

€860

Per person

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4.9

Sailing course in the Cyclades

Greece: Cyclades

7 days - 7 nights

9 departures available

May - October

€990

Per person

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5.0

Wellness Adventure Retreat

Caribbean: San Blas Islands - Panama

10 days - 10 nights

6 departures available

February - June

Starting from

€3,000

€2,100

Per person

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4.9

Day at the Gulf of Tigullio on a Sailing Boat - All inclusive!

Italy: Liguria

1 day - 0 nights

9 departures available

June - August

€155

Per person

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4.9

10 EPIC DAYS: From the Dodecanese to Milos with Hostess on board

Greece: Cyclades

8 days - 9 nights

One departure available

August

€1,430

Per person

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4.9

100% female sailing cruises

Greece: Cyclades

7 days - 7 nights

2 departures available

May - October

€990

Per person

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5.0

North-Eastern Sardinia: a paradise of nature and emotions

Italy: Northern Sardinia

6 days - 6 nights

2 departures available

July

€1,450

Per person

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5.0

Scopriamo insieme Portofino, Santa Margherita e Sestri Levante

Italy: Liguria

2 days - 2 nights

4 departures available

April - May

€450

Per person

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4.8

Long weekend on Elba: 4 days of sun and sailing

Italy: Tuscany

3 days - 3 nights

7 departures available

July - September

Starting from

€410

€369

Per person

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4.4

Sailing holiday in the archipelago of La Maddalena and Costa Smeralda

Italy: Northern Sardinia

6 days - 7 nights

One departure available

September

€850

€765

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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

17616 reviews

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Weekend on Elba "Only for four" for maximum comfort

11/25/2025

D. D.

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Italy

Great weekend! Impeccable welcome on Friday evening, really much appreciated. Very professional and prepared skipper (also the other crew members) - experienced hands-on in the challenging (but fun) crossing. I learned a lot (main objective - achieved). I hope to have the chance of another experience together soon.
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A day sailing in the fantastic Gulf of Trieste

11/11/2025

Armin F.

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Italy

Everything worked out great, Paolo was super helpful!!!! Advice 100%
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Squid Festival: let's close the season on a high note! - on board a 17mt boat

11/10/2025

giulia f.

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Italy

I participated in the weekend on a sailing boat organized for the Squid Festival and I couldn't ask for anything better! It was a wonderful experience, between sea, wind and excellent company. The crew was great: nice people and with a great desire to have fun. The skipper is super professional, but also helpful and attentive to let us experience sailing in a relaxed and fun way. I can't wait to get back on board for the next adventure! ⚓️🐙✨ Giulia, Eva and Martina
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Squid Festival: let's close the season on a high note! - on board a 17mt boat

11/5/2025

Marco F.

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Switzerland

Matteo is a professional skipper and above all a pleasant person, who steers the boat and situations with lightness and experience. Luke [hidden] a well-maintained and decidedly comfortable and spacious boat. Nice opportunity and fantastic company / crew, not to be forgotten and to be seen again with pleasure in a next navigation, between sea aperitifs and laughter.

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