495

experiences

5.0

Super!

EXPERIENCE THE MAGIC! Sailing and relaxing in a maritime wonderland!

Croatia: Istrian peninsula

7 days - 7 nights

4 departures available

August - September

€649

Per person

4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

2 departures available

September

€441

Per person

4.8

Super!

Let's sail together in Southern Sardinia

Italy: Southern Sardinia

6 days - 7 nights

7 departures available

July - September

Starting from

€900

€855

Per person

5.0

Come and discover the Egadi Islands! Nature, relaxation and crystal clear waters

Italy: Aegadian islands

7 days - 7 nights

8 departures available

July - September

Starting from

€700

Per person

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

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

Per person

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

5.0

Super!

Luxury routes among the wonders of Northern Sardinia with hostess

Italy: Northern Sardinia

6 days - 6 nights

7 departures available

July - September

Starting from

€1,450

Per person

4.9

Super!

Life Changing Experiences - Week in the Pontine Islands with photographer on board

Italy: Pontine Islands

6 days - 6 nights

2 departures available

August - September

€1,100

Per person

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

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

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

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

18018 reviews

Corfu between bays, taverns and myths.

07/11/2026

Stefania A.

Beautiful holiday, definitely to be redone! Very knowledgeable and welcoming crew Great cooks... (which doesn't hurt) All positive

Kornati: the pearl of Croatia

07/11/2026

Silvia M.

Wonderful week with good winds, beautiful coves, the company and guidance of Marco!

Let's discover the Aeolian Islands together by sailing

07/10/2026

Davide R.

Unforgettable holiday! Mario is the skipper everyone wants. He knows Aeolian Islands inside out, and everyone knows him there. Thank you for everything. I hope to see you again soon! :)

Midweek sailing trip in the Gulf of Naples

07/10/2026

Raquel Leonor C.

Best of all, Sandro the Skipper 🇮🇹 Amazing 👌 ⭐️⭐️⭐️⭐️

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!

Call us at

+44 20 3514 4220

Read our

Contact & Support

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!