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All inclusive yacht sailing holidays & tours in Italy

Discover more than 36 opportunities to get on board a All inclusive adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

36

experiences

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Intro sail Liguria

Duration:

1 day - 0 nights

Italy:

Liguria

Give this experience a try!

€125

Per person

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4.8

Sorrento Coast, Capri, Positano, Amalfi. Inclusive.

Duration:

3 days - 2 nights

Italy:

Amalfi Coast

Give this experience a try!

Starting from

€550

Per person

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5.0

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

Duration:

1 day - 0 nights

Italy:

Lake Garda

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+4 travellers

have booked

Starting from

€69

Per person

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4.0

All-inclusive Sardinia & Corsica Cruise (per cabin)

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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+106 travellers

have booked

Starting from

€1,445

Per person

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Sailing and Aperitif at Porto Venere - All Inclusive

Duration:

1 day - 0 nights

Italy:

Liguria

Give this experience a try!

Starting from

€90

Per person

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Sardinia and Costa Smeralda in Comfort - with Hostess - All Inclusive

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

Give this experience a try!

Starting from

€1,690

Per person

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Eolie a vela con skipper ed hostess, all inclusive con cucina vegana

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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Pietro

has booked

Starting from

€1,500

Per person

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5.0

All Inclusive Cruise to the Egadi Islands

Duration:

7 days - 6 nights

Italy:

Aegadian islands

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+77 travellers

have booked

Starting from

€1,064

€1,120

Per person

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5.0

Weekend in Ogliastra, breathtaking Sardinia with skipper and hostess

Duration:

2 days - 2 nights

Italy:

Southern Sardinia

Give this experience a try!

€417

Per person

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5.0

Sailing Summer Campus in Sardinia - ONLY FOR BOYS aged 9 to 18

Duration:

6 days - 6 nights

Italy:

Northern Sardinia

Give this experience a try!

Starting from

€790

Per person

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4.9

Gulf of Tigullio on a Sailboat - All inclusive!

Duration:

1 day - 0 nights

Italy:

Liguria

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+152 travellers

have booked

Starting from

€149

Per person

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5.0

The awakening of the lake

Duration:

1 day - 0 nights

Italy:

Lake Garda

Give this experience a try!

Starting from

€59

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 - All inclusive yacht sailing holidays & tours in Italy

428 reviews

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Take part in the 55th Barcolana with everything included

10/11/2023

Peter C.

-

Italy

Fantastica esperienza! Nonostante il vento quasi inesistente Alberto e Federica ci hanno fatto sentire tutta l'energia della Barcolana! Grazie!
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All inclusive weekend in the Gulf of Alassio

10/6/2023

John C.

-

Italy

Sarà stata la sfortuna o l’improvvisazione ma non abbiamo navigato con Daniele e nonostante l’impegno di Carmen il we “non ha girato” (barca bloccata in porto da “problemi burocratici”) Mi spiace ma non riproverò
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Day Trip Sailing around the Golfo Di Paradiso towards Portofino ALL INCLUSIVE - FLEXIBLE DATES

10/5/2023

Pietro R.

-

Italy

Kit e sua moglie Alice sono stati degli ospiti eccezionali. Torneremo presto a trovarli.
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LAST MINUTE! - Lampedusa and Linosa, Islands on the high seas - All Inclusive

10/2/2023

Angela Loredana D.

-

Italy

OLTRE OGNI ASPETTATIVA! La vacanza sul TANIMAR è stata un'esperienza unica. Emanuela e Lorenzo ci hanno coccolato e prestissimo c'è stata grande empatia. Gli skipper hanno accolto la nostra richiesta di rimanere la notte in rada più volte durante la settimana ed hanno preparato ottime pietanze con pesce fresco e prodotti tipici del luogo. Anche l'isola di Linosa e la cena a casa di Margaret sono state esperienze autentiche e belle. Non sono mancate lunghe veleggiate (a vele poco gonfie - ahimè - per carenza di vento) ed emozionanti ed unici tramonti conditi da aperitivi ed ottima musica. Se proponete altre rotte io ci torno volentieri sul TANIMAR. Consigliatissima esperienza!

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