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

5.0

Egadi Sail & Relax: the archipelago to experience

Italy: Aegadian islands

7 days - 7 nights

8 departures available

July - September

Starting from

€550

€495

Per person

cover image
avatar image

4.8

Super!

A sailing trip through history and food and wine to the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

3 departures available

July - August

Starting from

€900

€720

Per person

cover image
avatar image

4.8

Super!

Midweek weekend in Elba: sea, scents, colors

Italy: Tuscany

2 days - 2 nights

4 departures available

July - September

Starting from

€200

Per person

cover image
avatar image

5.0

Super!

Learn to sail in a week in the Tuscan Archipelago

Italy: Tuscany

6 days - 6 nights

One departure available

August

€949

Per person

cover image
avatar image

5.0

Super!

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

4 departures available

September - November

€250

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

5.0

Super!

Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

Italy: Aeolian Islands

6 days - 7 nights

3 departures available

August - September

Starting from

€950

Per person

cover image
avatar image

4.7

Amazing Pontine Islands in 4 days

Italy: Pontine Islands

4 days - 3 nights

2 departures available

July - August

Starting from

€437

Per person

cover image
avatar image

4.7

Whale watching cruise with WWF guide between Liguria and the French Riviera

Italy: Liguria

6 days - 6 nights

2 departures available

July - August

Starting from

€946

Per person

cover image
avatar image

4.8

New

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

Italy: Aegadian islands

7 days - 7 nights

5 departures available

July - September

Starting from

€600

€540

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

cover image
avatar image

4.8

Super!

All in the family: 5 days between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

4 departures available

July - September

Starting from

€490

€466

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

18084 reviews

Cast off for a week at sea, a thousand ways to experience it!

07/15/2026

Michael J.

-

DE

Our one-week sailing trip through the Saronic Gulf deserved a definitive 5-star rating for its perfect blend of adventure and incredible food. We explored the car-free streets of Hydra and swam in the crystal-clear, secluded bays of Dokos. Captain Alexandre amazed us, especially with a rich, authentic Bolognese that tasted like it simmered for hours. Our stops in Spetses and Poros offered beautiful views, but the true highlight was dining right on deck. Captain Alexandre's perfectly creamy risotto easily rivaled any high-end restaurant we found onshore. Each night ended with stargazing and the gentle rocking of the yacht under the Greek sky. This five-star combination of spectacular island views and gourmet sailing cuisine made for an unforgettable journey.

Corfu between bays, taverns and myths.

07/15/2026

Chrystel O.

-

FR

Wonderful experience ! Nice and friendly people on board. Beautiful landscapes. Would definitely book again with this crew anywhere :)
avatar image

The Sporades Islands: A Hidden Paradise of Greece

07/15/2026

Valerio R.

-

IT

Fantastic experience

Weekend in the Pontine Islands

07/15/2026

Sara F.

-

IT

Dream experience! Thank you Dario, skipper attentive to his guests and their needs, very prepared and a great connoisseur of the Ponza/Palmarola area. I definitely recommend a weekend to enjoy this adventure

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