header cover
sailsquare logo

Sport & wellness yacht sailing holidays & tours in Italy

Discover more than 10 opportunities to get on board a Sport & wellness adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

cover image
avatar image

4.6

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

Italy: Tuscany

3 days - 3 nights

2 departures available

September

Starting from

€420

Per person

cover image
avatar image

4.6

Long weekend of whale watching with a WWF guide between the Amalfi Coast, Ischia and Capri

Italy: Naples & Amalfi Coast

3 days - 3 nights

2 departures available

September

Starting from

€452

€429

Per person

cover image
avatar image

4.9

Super!

Trekking & Sailing Experience-Weekend lungo a Capraia in compagnia

Italy: Tuscany

4 days - 3 nights

One departure available

September

€440

€418

Per person

cover image
avatar image

4.9

Super!

LET'S GO TO TOTANI - Festival in Capria

Italy: Tuscany

3 days - 3 nights

One departure available

October - November

€420

Per person

cover image
avatar image

4.8

Trekking and sailing weekend on the island of Elba

Italy: Tuscany

3 days - 2 nights

One departure available

September

€340

Per person

cover image
avatar image

5.0

Long weekend on a sailing boat Cous Cous Festival in San Vito Lo Capo

Italy: Sicily

4 days - 3 nights

2 departures available

September

€410

Per person

cover image
avatar image

4.7

Weekend a Capraia, trekking e natura

Italy: Tuscany

3 days - 2 nights

4 departures available

September - October

€200

Per person

cover image
avatar image

4.7

COUS COUS FEST: A Weekend of Sea, Sailing, Cous Cous and Music!

Italy: Sicily

4 days - 3 nights

2 departures available

September

Starting from

€390

€351

Per person

cover image
avatar image

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

cover image
avatar image

4.8

Cous cous Festival in San Vito lo Capo and the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€600

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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

737 reviews

avatar image

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
avatar image

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 :):)
avatar placeholder

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...
avatar image

Long weekend of whale watching with a WWF guide between the Amalfi Coast, Ischia and Capri

06/25/2025

NINA B.

-

Italy

Beautiful trip, guided and accompanied with care and wisdom!

Customer Support

nightLifeGeneralInfo

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!

search

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

Other travel ideas

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964