experiences

4.8

Super!

All Inclusive Tour: Capri, Amalfi, Cetara, and Sorrento

Italy: Naples & Amalfi Coast

5 days - 5 nights

2 departures available

June - August

Starting from

€1,115

€1,059

Per person

5.0

Super!

A fantastic day on a boat in the blue sea of Tuscany

Italy: Tuscany

1 day - 0 nights

38 departures available

June - August

Starting from

€125

Per person

5.0

Super!

A day sailing in the fantastic Gulf of Trieste

Italy: Venice and the Gulf of Trieste

1 day - 0 nights

2 departures available

June - July

€99

Per person

5.0

Super!

A wonderful day.... on Lake Garda - ALL INCLUSIVE

Italy: Lake Garda

1 day - 0 nights

31 departures available

June - September

Starting from

€99

Per person

4.8

Super!

All Inclusive: Procida, Capri, Positano, Amalfi, Cetara, Sorrento

Italy: Naples & Amalfi Coast

6 days - 6 nights

3 departures available

July - September

Starting from

€1,385

€1,316

Per person

5.0

Super!

Sailing, swimming and aperitif at sunset ... What else?

Italy: Lake Garda

1 day - 0 nights

26 departures available

June - September

Starting from

€79

Per person

5.0

Super!

Day trip on a sailing boat

Italy: Tuscany

1 day - 0 nights

24 departures available

June - July

Starting from

€150

Per person

4.8

Super!

All-Inclusive Sailing: Capri, Positano, Amalfi and Sorrento Coast

Italy: Naples & Amalfi Coast

3 days - 2 nights

3 departures available

June - July

€865

Per person

5.0

Super!

The awakening of the lake

Italy: Lake Garda

1 day - 0 nights

2 departures available

July

€69

Per person

5.0

Super!

Afternoon sailing and barbecue evening

Italy: Lake Garda

1 day - 0 nights

5 departures available

June - August

Starting from

€129

Per person

4.9

Day at the Gulf of Tigullio on a Sailing Boat - All inclusive!

Italy: Liguria

1 day - 0 nights

15 departures available

June - August

€150

Per person

4.9

Aperitif Trip to the Gulf of Tigullio - All inclusive!

Italy: Liguria

1 day - 0 nights

6 departures available

June - August

€89

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 - All inclusive yacht sailing holidays & tours in Italy

516 reviews

Gulf of Poets and Cinque Terre

06/4/2025

alessia a.

Italy

Sono stata con amiche sulla barca di Giorgio per due giorni, siamo state veramente molto bene. Giorgio è uno skipper attento, e premuroso. Ci ha coccolato preparandoci ottimi pasti! We assolutamente consigliato!

A day on a sailing boat to Gallinara Island or the Dianese Gulf

05/21/2025

Roberta N.

Italy

Bellissima giornata nelle acque liguri, Matteo skipper professionale e simpatico ha insegnato a me ed alla mia amica le basi del veleggiare ottimo l’aperitivo, peccato nn aver visto i delfini sarà x la prossima uscita 😊

A day on a sailing boat to Gallinara Island or the Dianese Gulf

05/20/2025

Sabrina L.

Italy

A day sailing in the fantastic Gulf of Trieste

05/20/2025

dino m.

Italy

Giornata splendida per il tipo di esperienza, per l’ambiente e per la preparazione dello skipper che è stato ottimo anche per tutte le informazioni su quel tratto di costa che ci ha fornito. Molto preparato.. Persona gentile e cordiale, Ci siamo divertiti. Esperienza da ripetere!!

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!