experiences

5.0

Super!

Afternoon sailing and barbecue evening

Italy: Lake Garda

1 day - 0 nights

One departure available

August

€149

Per person

4.9

Super!

Trekking and sailing weekend on the island of Elba

Italy: Tuscany

3 days - 2 nights

One departure available

September

€340

€323

Per person

4.7

Weekend a Capraia, trekking e natura

Italy: Tuscany

3 days - 2 nights

2 departures available

September - October

€200

Per person

5.0

Selvaggio Blu in Sardinia, Sail & Trek with Alpine Guide on board

Italy: Southern Sardinia

5 days - 6 nights

2 departures available

October - November

€1,450

€1,300

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 - Sport & wellness yacht sailing holidays & tours in Italy

730 reviews

Weekend a Capraia, trekking e natura

07/21/2025

Lorena C.

Italy

A 5 star captain who also caught and cooked an unforgettable tuna for me and the crew for my birthday! Thank you for your professionalism and availability. Until next time... fair winds

Sailing and yoga: discovering Elba and the north of Corsica

07/21/2025

Rossella L.

Italy

Filippo is a very prepared and helpful skipper!! He guided us in a punctual and clear way and immediately made us become familiar with the activities of the boat!! A good cook and speaker, he was able to create a good atmosphere on the boat right from the start!! Thank you Filippo until next :):)

Weekend a Capraia, trekking e natura

07/5/2025

Sonia G.

Italy

I had never been on a boat before... it was my first time... you have to say that it was a beautiful experience... An unforgettable weekend.. that I will always carry in my heart.... the skipper Francesco a formidable person.... nice... kind...... available... and above all very good in the kitchen too... surprised us with his really very good first courses... Definitely an experience to be repeated...

Weekend a Capraia, trekking e natura

06/22/2025

Leonardo D.

Italy

Advised!

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!

Italy: the best travel ideas

Sailboat (925)Whole boat with skipper (750)Cooking service onboard (125)All inclusive (100)Catamaran (100)Family sailing cruises (90)Day trips (85)Courses & regatta (60)Sport & wellness (20)WWF Sailing Cruises (15)

Other travel ideas

Sailboat (326)Whole boat with skipper (267)Cooking service onboard (76)All inclusive (56)Catamaran (53)Exotic destinations (38)Courses & regatta (26)Family sailing cruises (24)Day trips (21)Offshore (16)