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

4.7

Kornati: the pearl of Croatia

Croatia: Kornati Islands

6 days - 7 nights

2 departures available

August

Starting from

€800

Per person

cover image
avatar image

4.8

Super!

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

4 departures available

August - October

€650

Per person

cover image
avatar image

4.8

Super!

Midweek weekend in Elba: sea, scents, colors

Italy: Tuscany

2 days - 2 nights

2 departures available

September

€200

Per person

cover image
avatar image

4.7

Week between the Tuscan Islands and Northern Corsica

Italy: Tuscany

7 days - 6 nights

5 departures available

August - September

Starting from

€700

Per person

cover image
avatar image

5.0

Super!

Sailing Holiday with a Hostess Among the Wonders of Northern Sardinia

Italy: Northern Sardinia

6 days - 6 nights

4 departures available

August - September

Starting from

€1,450

Per person

cover image
avatar image

5.0

Super!

Vento di Sicilia: from the Aeolian Islands to Trapani

Italy: Aegadian islands

7 days - 7 nights

One departure available

August

€920

Per person

cover image
avatar image

5.0

Super!

Ibiza & Formentera: one week with cook on board

Spain: The Balearic Islands

6 days - 6 nights

One departure available

September

€750

€675

Per person

cover image
avatar image

4.7

Whale watching mini-cruise in the Pelagos Sanctuary with WWF guide

Italy: Liguria

4 days - 4 nights

One departure available

September

€609

€579

Per person

cover image
avatar image

4.5

Ibiza & Formentera: an exclusive journey between sky and sea

Spain: The Balearic Islands

6 days - 6 nights

2 departures available

August - September

Starting from

€1,010

Per person

cover image
avatar image

5.0

Super!

Long weekend on a sailing boat Cous Cous Festival in San Vito Lo Capo

Italy: Sicily

4 days - 3 nights

2 departures available

September

€345

Per person

cover image
avatar image

4.8

Super!

All Inclusive: Procida, Capri, Positano, Amalfi, Cetara, Sorrento

Italy: Naples & Amalfi Coast

6 days - 6 nights

One departure available

August

€1,290

Per person

cover image
avatar image

5.0

Super!

Saronic Gulf Cruise: Aegina, Poros, Hydra, Athens Surroundings

Greece: Saronic Islands and Athens area

6 days - 6 nights

One departure available

September

€650

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

18257 reviews

avatar image

Sailing cruise to the Pontine: wonders a stone's throw from Rome

07/30/2026

Valeria M.

-

IT

Antonio is a great cook! He cooked great dishes! Very nice! During meals it is nice to listen to his stories. He knows the sea very well, he is attentive and scrupulous. Recommended holiday to experience a week of relaxation in a fabulous sea!

Egadi mon amour: seven days to fall in love, be amazed and relax.

07/30/2026

raffaella s.

-

IT

Giuseppe captain of excellence! He taps his experience and knowledge of the seas he sails, attentive and helpful. He conveys confidence and also a lot of love for his work, his family and for the crew. Listen carefully to all the information and advice he offers you, they are always very useful!! We spent a fantastic week, lulled by crystal clear waters, paradisiacal landscapes and lots of fun. Embark as strangers and disembark as friends!! Don't be surprised if once you get on the ground you are ready to start again: it is the [hidden] effect! Raffaella: if today I dive fearlessly it is thanks to Giuseppe!! Marco: Giuseppe? One of us! Not the Skipper but one of the group Chiara: I brought more seasickness pills than swimsuits, but with Giuseppe at the helm and his tips I didn't use a single one. Great navigation and zero drama! Federico: Giuseppe? A super captain who made me live and appreciate my first boat experience to the fullest. Federica: a huge thank you to Giuseppe for making us live this experience from A to Z... complete with a sailor's shower included in the package. Davide: Giuseppe super Skipper available and always present, he made us spend a wonderful week on a sailing boat. Tiziana: Giuseppe, with his boat [hidden], just like the moon guides you, cradles you, takes you to the stars and the three sister islands

The Island of Elba, to make you live a special experience!

07/30/2026

Giovanna F.

-

IT

Beautiful first experience on a sailing boat, with a skipper attentive to the needs of his guests and scrupulous. Livio, known (for me) as "Lucio", in addition to sailing, with his infinite stories makes you fly to spaces and places of other times ... But be careful not to take away the cookies for breakfast, he could get very angry!! Joke: peaceful and very discreet person. See you soon!
avatar image

Three days wandering among the Ionian islands

07/30/2026

Nicolas G.

-

CH

Wonderful stay aboard Dario and his wife's sailboat! They showed us some great anchorages in the Ionian Islands, as well as some very good authentic Greek restaurants, away from the tourist crowds. Dario and his wife are lovely and really laid back, a real pleasure to sail with. I recommend without hesitation!

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