482

experiences

4.8

Super!

Flottiglia Sun & Fun Marmaglia - Età 25-40 anni

Croatia: Kornati Islands

7 days - 7 nights

2 departures available

August

Starting from

€1,100

€950

Per person

4.8

Super!

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

One departure available

August

€1,190

Per person

5.0

Super!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

August

€900

Per person

4.6

Between the Pontine Islands and the Phlegrean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

4 departures available

July - September

Starting from

€719

Per person

4.8

Super!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

5 departures available

July - September

Starting from

€650

Per person

5.0

Super!

North and south Sardinia of Corsica sailing

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

July - August

Starting from

€900

€810

Per person

4.9

Super!

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

2 departures available

August - October

Starting from

€200

Per person

4.7

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

Italy: Northern Sardinia

6 days - 7 nights

8 departures available

July - September

Starting from

€650

Per person

4.9

Super!

Week of sea, nature and fun in the Egadi Islands!

Italy: Aegadian islands

7 days - 7 nights

5 departures available

August - September

Starting from

€690

€621

Per person

4.8

Super!

Sardinia and Strait of Bonifacio on a 50-foot sailboat

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August

€820

Per person

4.9

Super!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

7 departures available

July - October

Starting from

€751

Per person

4.8

Super!

From the Pontine to the Amalfi Coast by sailboat

Italy: Naples & Amalfi Coast

8 days - 7 nights

2 departures available

July - September

Starting from

€680

€598

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

16187 reviews

Secret Aegean with skipper and kitchen on board from Kos to Rhodes

07/12/2025

Attilio A.

Italy

Excellent welcome, well-designed itinerary, excellent on-board cuisine.

Weekend on Elba Island

07/12/2025

Roberta C.

Antony is a generous and very active person. Capable in managing the boat and a skilled and organized cook. Nice experience.!

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

07/12/2025

IOANNIS P.

Greece

Everything was perfect

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

07/12/2025

Melissa Sara C.

Italy

Abandon yourself to the colors and flavors of the islands, the sea and the wind. The summary of a week perfectly lulled by the waves in which to breathe freedom on a perfectly maintained boat thanks to the attention that Dario the skipper gives to all things. An extremely experienced navigator, he also knows how to involve in on-board operations as well as direct to the focal points of the sea and land islands, trying to answer all my countless curiosities. For those who love sailing, top experience!

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 2035144220

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!