379

experiences

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!

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!

From Cagliari to Cannigione.. exploring the east coast of Sardinia

Italy: Southern Sardinia

6 days - 7 nights

One departure available

May

€550

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

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

Italy: Tuscany

6 days - 6 nights

5 departures available

June - August

Starting from

€1,052

€999

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

5.0

Super!

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

Italy: Aeolian Islands

7 days - 7 nights

15 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

9 departures available

June - September

Starting from

€825

€743

Per person

4.9

Super!

Sailing holiday in the turquoise blue waters of Corsica

Italy: Tuscany

7 days - 7 nights

4 departures available

July - August

Starting from

€890

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

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

4 departures available

August - September

Starting from

€1,041

€989

Per person

4.7

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

Italy: Naples & Amalfi Coast

2 days - 2 nights

8 departures available

May - 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 yacht sailing holidays & tours in Italy

12680 reviews

1st May: Whale watching expedition with WWF guide on an 18-meter schooner

05/4/2026

Marzia L.

Italy

Unique experience! Laura is a fantastic guide and communicator! We heard the clicks of sperm whales that were probably hunting deep under our boat, crossed paths with a turtle and discovered many secrets about cetaceans. I highly recommend this holiday. The schooner that hosted us is mostly built of wood, so it seems to be on a pirate boat! Particular mention for the two sailors Melissa and Alejandro, two really talented and empathetic guys. Thank you and fair winds!

Long weekend among the wonders of Elba and Capraia

05/4/2026

Emanuela A.

Italy

Company is key... the only flaw. Marco excellent moderator gz see you next time

Weekend "nel Blu dipinto di Blu" - Ponza & Palmarola

05/4/2026

Mara B.

Italy

The weekend with Matteo in Ponza/Palmarola was super pleasant. Matteo is an excellent skipper, the right mix of experience, availability and sympathy. Super recommended!

Relaxing weekend in the Pontine Islands

05/4/2026

Paolo C.

Italy

Beautiful experience thanks to the great skills of Stefano and Adriano: the places they made us discover, the way and the climate on board with the crew made this long weekend in the Pontine Islands unforgettable.

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!