218

experiences

218

experiences

5.0

Weekend in Capraia, the island with timeless sunsets

Duration:

2 days - 2 nights

Italy:

Tuscany

+12 travellers

have booked

€275

Per person

4.8

Weekend 2 June in the colours of Elba on board a classic Ketch

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€240

Per person

4.8

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

Duration:

6 days - 7 nights

Italy:

Aegadian islands

+5 travellers

have booked

€595

Per person

4.2

Relaxing weekend between Portovenere and the 5 Terre

Duration:

2 days - 2 nights

Italy:

Liguria

christian v.

has booked

Starting from

€280

Per person

5.0

Weekend getaway in Capraia

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€350

Per person

4.9

A day of sailing in the Gulf of Trieste

Duration:

1 day - 0 nights

Italy:

Venice and the Gulf of Trieste

Give this experience a try!

€99

Per person

Tour in the marine protected area of Tavolara and Cala Moresca

Duration:

1 day - 0 nights

Italy:

Northern Sardinia

Give this experience a try!

€70

Per person

4.8

Weekend cruise from Trieste in Slovenia

Duration:

2 days - 2 nights

Italy:

Venice and the Gulf of Trieste

Give this experience a try!

Starting from

€250

Per person

4.5

An unforgettable week in the Tuscan Archipelago

Duration:

7 days - 7 nights

Italy:

Tuscany

Give this experience a try!

€1,280

Per person

W.E Golfo Dei Poeti-Portovenere-Rosse-Ferale

Duration:

2 days - 2 nights

Italy:

Liguria

+36 travellers

have booked

€210

Per person

4.7

Two hearts and a sailboat: discovering the Phlegrean Islands

Duration:

2 days - 2 nights

Italy:

Gulf of Naples

Give this experience a try!

€250

Per person

5.0

Weekend with wine tasting between Santa Margherita Ligure and Portofino

Duration:

2 days - 2 nights

Italy:

Liguria

+11 travellers

have booked

Starting from

€289

€340

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 - Yacht sailing holidays & skippered tours in Italy

10891 reviews

Luxury sailing in the Gulf of Poets

04/15/2024

Antonio C.

Italy

Giornata splendida, mare e barca perfetti, altissimo valore aggiunto l’equipaggio, simpatico gentile preparato ma soprattutto disponibile, e Costanza ottima cuoca, esperienza fantastica, da ripetere!!

Veleggiata verso il farò di Cecina con Aperitivo a bordo

04/11/2024

maurizio r.

Italy

Grazie per la bella domenica di relax in barca Maurizio e Giuliana

Moorings and manoeuvres course - Night Navigation and Signals - Anchorages

04/10/2024

Stefano P.

Italy

Corso vela, efficace, utilissimo, sintetico essenziale in una parola strepitoso. Skipper istruttore preparato, simpatico ed all'altezza del ruolo.

A weekend of sailing between Capraia and the island of Elba

03/20/2024

davide C.

Italy

Enrico è un comandante che sa mettervi a proprio agio in un equilibrio di libertà e professionalità . Se vi piace oltre al vento il buon cibo siete sulla barca giusta ..

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!