header cover
logo

Log in

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.

cover image
avatar image

4.9

Super!

Holidays on the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

5 departures available

August - September

Starting from

€716

Per person

cover image
avatar image

New

Corsica Sailing Experience for only 4 people

France: Corsica

7 days - 6 nights

One departure available

August

€900

Per person

cover image
avatar image

5.0

Super!

ONE WAY Marina River - Porto Vecchio

France: Corsica

3 days - 3 nights

One departure available

August

€290

Per person

cover image
avatar image

4.7

Week between the Tuscan Islands and Northern Corsica

Italy: Tuscany

7 days - 6 nights

6 departures available

August - September

Starting from

€700

Per person

cover image
avatar image

4.4

L'Île de Beauté: sailing in Corsica with night return

France: Corsica

6 days - 7 nights

One departure available

August

€749

Per person

cover image
avatar image

5.0

Super!

Sail in Menorca with a cook on board!

Spain: The Balearic Islands

5 days - 5 nights

One departure available

August

€950

€855

Per person

cover image
avatar image

4.8

Super!

All-Inclusive Sailing: Capri, Positano, Amalfi

Italy: Naples & Amalfi Coast

3 days - 2 nights

3 departures available

September

€790

Per person

cover image
avatar image

5.0

Super!

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

3 departures available

October - November

€250

Per person

cover image
avatar image

4.8

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

4 departures available

September - October

Starting from

€600

€540

Per person

cover image
avatar image

4.8

Super!

From Milos to Athens: the fantastic Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€750

Per person

cover image
avatar image

5.0

Wellness, sun, sea and adventure: a weekend full of sailing!

Italy: Tuscany

3 days - 2 nights

One departure available

September

€230

Per person

cover image
avatar image

4.9

Super!

Quattro giorni all'Elba - Hostess a bordo

Italy: Tuscany

4 days - 5 nights

One departure available

August

€800

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

18197 reviews

avatar image

Sailing from Tuscany to South Corsica

07/26/2026

Serena P.

-

IT

Beautiful experience, super comfortable boat, brilliant and knowledgeable skipper took us to beautiful places and sailing with the wind in our sails ,!! To be done again bye Marco
avatar image

Aeolian Islands: sun, sport, music, good food... The rest is magic!

07/26/2026

Benedetto R.

-

IT

Great skipper Captain Dario, professional and precise in the management and management of his [hidden]. It makes you feel immediately at ease in a boat equipped with every comfort. I hope to see you again soon at sea. Fair Winds 🌬️ greetings Benedict
avatar image

Sailing adventure in the sea of Ulysses - Stewardess on board

07/26/2026

Francesco Saverio C.

-

IT

I don't think it could have gone better than this. A mixture of adventure, fun and mystery that I will hardly forget! Probably the best choice at this time of my life! A round of applause to the skipper Leo and the hostess Ilda who were always present in all the needs of the guests on board with a sympathy and empathy that I still feel now! The only unexpected thing was that the fridge broke but we improvised with ice and it went great anyway! All the shades of green and blue that I have seen, the paradisiacal beaches, the lunches and dinners in joy, will haunt me in my dreams ... for a long time!

Aeolian Islands: sun, sport, music, good food... The rest is magic!

07/26/2026

Camilla V.

-

IT

Experience to be redone! A group of nice people and a professional skipper who over time has made himself loved 😂❤️ We recommend everyone a nice week in the Aeolian Islands with the [hidden].

Customer Support

customer support

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964