header cover

Offshore yacht sailing holidays & tours in Italy

Discover more than 22 opportunities to get on board a Offshore adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

22

experiences

cover image
avatar image
From Piombino to Sicily - First stop

Duration:

6 days - 6 nights

Italy:

Pontine Islands

Give this experience a try!

€500

Per person

cover image
avatar image

4.8

Week 2 June at the Egadi Islands between Nature, Relaxation & Fun

Duration:

6 days - 7 nights

Italy:

Aegadian islands

avatar placeholder
avatar placeholder
avatar placeholder

+4 travellers

have booked

€595

Per person

cover image
avatar image

4.8

ONE WAY Aeolian Islands by catamaran with hostess - from Palermo to Lipari

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

avatar placeholder
avatar placeholder

+2 travellers

have booked

€1,000

Per person

cover image
avatar image

5.0

Exclusive itinerant route: Catania - Taormina - Tropea - Aeolian Islands

Duration:

8 days - 8 nights

Italy:

Sicily

Give this experience a try!

€799

Per person

cover image
avatar image

5.0

Cruising Alghero to Olbia across the Maddalena and Emerald Coast

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

Give this experience a try!

€650

Per person

cover image
avatar image

4.5

OneWay Tropea/Olbia - Live the experience of offshore sailing

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

Give this experience a try!

€980

Per person

cover image
avatar image

4.2

Itinerant summer in the Tyrrhenian Sea: One way from San Vincenzo to Saint Florent

Duration:

6 days - 7 nights

Italy:

Tuscany

Give this experience a try!

€850

Per person

cover image
avatar image

5.0

Olbia to Ponza crossing and the archipelago

Duration:

7 days - 7 nights

Italy:

Pontine Islands

Give this experience a try!

€600

Per person

cover image
avatar image

4.8

Giglio Archipelago and Pontine Islands - Oneway -

Duration:

6 days - 7 nights

Italy:

Pontine Islands

avatar image
avatar placeholder
avatar placeholder

+6 travellers

have booked

€635

Per person

cover image
avatar image

4.9

Magical Aeolian Islands by catamaran with hostess on board - ONE WAY

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

avatar placeholder
avatar placeholder
avatar placeholder

+3 travellers

have booked

€1,000

Per person

cover image
avatar image

5.0

Pontine Islands off season

Duration:

7 days - 7 nights

Italy:

Pontine Islands

Give this experience a try!

€650

Per person

cover image
avatar image

4.9

Learn to sail with a fantastic holiday in the south of Sardinia

Duration:

6 days - 6 nights

Italy:

Southern Sardinia

avatar placeholder
avatar placeholder
avatar placeholder

+6 travellers

have booked

Starting from

€846

€890

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 - Offshore yacht sailing holidays & tours in Italy

391 reviews

avatar image

Aeolian and Egadi Islands - 2 weeks with embarkation and disembarkation in Naples

10/2/2023

Ida G.

-

Italy

Esperienza semplicemente FANTASTICA. 15 giorni immersi tra mare, vento, natura e tanto divertimento. Emiliano e Gennaro skipper unici, esperti e prudenti. Hanno reso la nostra vacanza a bordo meravigliosa. La loro barca uno spettacolo. Spaziosa, comoda, pulita e ordinata. Notti in rada, navigazione notturna, tantissima vela e tante risate! Grazie ragazzi........ci rivedremo presto!
avatar image

Aeolian and Egadi Islands - 2 weeks with embarkation and disembarkation in Naples

10/1/2023

Stéphanie B.

-

Switzerland

Ce séjour à la voile dans les îles Éoliennes et Égades a été tout simplement extraordinaire ! Les skippers, avec leur professionnalisme, ont su nous guider en toute sécurité à travers les magnifiques eaux de la Méditerranée. Leur expertise en navigation et leur amour pour la mer nous a permis de découvrir le monde de la voile. Le bateau était impeccablement entretenu, offrant tout le confort nécessaire pour profiter pleinement de cette aventure. Nous avons eu la chance de déguster des spécialités locales qui ont ajouté une touche authentique à notre voyage. Les skippers ont été incroyablement attentionnés, veillant à ce que chacun de nous se sente à l'aise. Leur connaissance des îles Éoliennes et Égades nous a permis de découvrir des endroits cachés et des plages isolées que nous n'aurions jamais pu trouver seuls. Ce séjour à la voile a dépassé toutes mes attentes. Je suis reconnaissante envers les skippers pour cette expérience inoubliable. Merci Emiliano et Gennaro!
avatar image

From the AEOLIAN to the PONTINE - Adventure, Navigation and Relaxation - One Way

09/29/2023

Maya P.

-

Italy

Professionalità simpatia serietà ma soprattutto un insegnante fantastico: chiarezza, disponibilità, e conoscenza trasmesse in ogni istante con spontanea semplicità con al primo posto sempre la sicurezza di tutti. Grazie cercavo una vacanza scuola me la immaginavo proprio così. Oggi mi porto a casa molte nozioni interessanti che non vedo l’ora di mettere in pratica di nuovo e approfondire, ma anche tanto relax e un soffio di vento nei capelli ??????????????????????
avatar placeholder

Alghero to the Costa Smeralda

09/26/2023

Bruno T.

-

France

Nous avons passé une très bonne semaine avec Tommaso sur son beau voilier. Le temps n'a pas toujours été idéal pour la navigation, et le programme n'a pas pu être réalisé, mais notre skipper nous a trouvé des visites, des restaurants et des balades sympathiques pour nous consoler. Nous avons découvert la vie à bord et appris la conduite du bateau. Dommage pour la Maddalena, nous n'avons plus qu'à recommencer. Avec Tommaso peut être !

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

MastercardVisaAmerican ExpressApple pay

© 2023 Sailsquare Srl SB • All rights reserved - VAT IT07860990964