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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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5.0

New

Just relaxing while sailing on the Côte d'Azur

France: French Riviera and Porquerolles

2 days - 2 nights

One departure available

September

€450

Per person

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4.9

Sporades Experience: Freedom, Turquoise Sea and Greek Magic

Greece: Sporades

6 days - 7 nights

2 departures available

September

Starting from

€750

Per person

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4.7

Squid Regatta

Italy: Tuscany

2 days - 2 nights

One departure available

October

€180

Per person

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5.0

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

Italy: Liguria

2 days - 2 nights

6 departures available

September - November

Starting from

€380

Per person

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4.8

EGADI AND COUSCOUS FEST of San Vito Lo Capo

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€630

Per person

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4.0

Sailing and Hiking in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€1,290

€1,161

Per person

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5.0

It's time for sun and sea!

Italy: Liguria

2 days - 1 night

One departure available

October

€350

Per person

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4.4

The Canary Islands seen from the boat and beyond

Atlantic islands: Canary Islands

10 days - 10 nights

One departure available

November

€890

Per person

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4.4

Premium

Cruise to discover Corfu and Ionian Greece - Hostess & Half Board

Greece: Ionian Islands

7 days - 7 nights

3 departures available

September - October

Starting from

€845

€676

Per person - min 2 pax

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4.8

Sunny weekend on Elba from Friday to Sunday

Italy: Tuscany

3 days - 2 nights

3 departures available

September - October

€325

€309

Per person

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4.9

Weekend sailing course from Bandol

France: French Riviera and Porquerolles

2 days - 1 night

6 departures available

September - November

€301

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

4 departures available

September - October

Starting from

€1,100

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

19077 reviews

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Sailing weekend with skipper cook

09/8/2026

Flavia G.

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IT

Weekend with perfect conditions to relax! Flavio was discreet but of company and cooks in an excellent way!! The Trieste and Slovenian coasts are beautiful and we found beautiful water!! We also loved the boat!
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Five days at the Pontine from Ostia - Sailing course and more!

09/8/2026

Giuseppe G.

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IT

This experience also included a sailing course. The skipper Enzo is an excellent instructor, competent, patient and always ready to involve the crew in steering the boat. We sailed a lot. The boat is well maintained, comfortable and clean. The dolphins also noticed it and accompanied us both in the navigation to Palmarola and in the one for the return to Ostia. Enzo knows the Pontine very well, we enjoyed the most beautiful coves without haste and always in safety. Also thanks to the favorable weather that gave us a beautiful relaxing but also active holiday for those who wanted to participate in the management of the boat during the numerous sailings.
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Five days at the Pontine from Ostia - Sailing course and more!

09/8/2026

Coretta P.

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IT

Beautiful holiday that I recommend to anyone who wants to experience the sea in the most intense and authentic way, with a discreet spirit of adaptation and a great desire to sail, learn and regenerate. Enzo proved to be a particularly professional, patient and prepared skipper, able to convey his experience by enriching every moment with many ideas and interesting topics. I sincerely thank all the crew for the fun and the many laughs shared!

Gulf of Poets

09/8/2026

Silvia M.

-

IT

Giovanni super skipper, kind, helpful is a super pleasant company! Very nice destination, especially on the first day of sailing. Definitely recommended experience!

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