629

experiences

4.8

Super!

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

Italy: Northern Sardinia

6 days - 7 nights

14 departures available

June - September

Starting from

€680

Per person

4.8

Super!

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

21 departures available

May - October

Starting from

€590

Per person

4.8

Super!

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

11 departures available

May - September

Starting from

€1,300

€975

Per person

4.8

Super!

Sardinia and Corsica on a Classic Sailing Ship 4 cabins plus crew

Italy: Northern Sardinia

6 days - 7 nights

12 departures available

June - September

Starting from

€550

€523

Per person

4.7

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

7 departures available

July - September

Starting from

€795

€716

Per person

4.7

Whale watching cruise with WWF guide for children 14-17 on an 18-meter schooner

Italy: Tuscany

6 days - 6 nights

4 departures available

June - August

Starting from

€1,052

€999

Per person

5.0

Super!

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

13 departures available

June - October

Starting from

€689

Per person

5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

7 departures available

June - September

Starting from

€825

€743

Per person

5.0

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

14 departures available

May - October

Starting from

€570

Per person

4.9

Super!

Sailing holiday in the turquoise blue waters of Corsica

Italy: Tuscany

7 days - 7 nights

4 departures available

June - August

Starting from

€680

Per person

4.6

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

Italy: Northern Sardinia

6 days - 7 nights

16 departures available

May - October

Starting from

€650

€585

Per person

4.7

In the blue of Capri and the infinity of the Amalfi Coast

Italy: Naples & Amalfi Coast

2 days - 2 nights

5 departures available

September - October

Starting from

€320

€272

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

17667 reviews

Weekend among the most beautiful coves of Elba

05/18/2026

Stefania V.

Italy

Marco and Carmen wonderful people. As if we had known each other forever. There was harmony and understanding on everything. We will definitely repeat!

Sailing weekend to the Columbretes Islands

05/18/2026

Elodie P.

France

We have spent an incredible weekend. The boat is very stylish, well made and comfortable. Alex is an amazing person, very interesting, pedagogue and always ready to share moments! It has adapted to everything we wanted to do and has allowed us to do a route on earth, bathe, etc This trip would stay in our memory!!

Weekend among the most beautiful coves of Elba

05/17/2026

Giulia L.

Italy

New experience for me and my partner, excellent company, beautiful places, well organized trip, Carmen and Marco nice and easy-going, they were able to put us all at ease, we will remain a beautiful memory!

Let's discover the Aeolian Islands together by sailing

05/17/2026

Tim D.

Germany

Mario is an excellent skipper. Through him we were able to see the most beautiful corners of the Aeolian Islands. His local knowledge and contacts on all the islands gave us an unforgettable trip. We were also lucky enough to have his incredibly lovely wife on board. Even though communication was not easy (we didn't speak Italian and she didn't speak English), she made the trip even more beautiful. We thank them very much for this wonderful sailing holiday.

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!