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Private yacht sailing holidays with skipper in Italy

Chartering a sailing boat in Italy will let you discover a new way of travelling new way of travelling in complete freedom. Choose between a catamaran or a sailing boat and embark with an experienced skipper to discover Tuscany, Sicily, Tuscany, Sicily, Sardinia and many other destinations.

145

experiences

145

experiences

4.5

North Sardinia and South Corsica by catamaran with flybridge

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

87 travellers

Starting from

€799

€940

Per person

5.0

Route to the Egadi Islands: Wind, Flavors and Sea

Duration:

7 days - 7 nights

Italy:

Aegadian islands

Give this experience a try!

Starting from

€585

€650

Per person

5.0

Super!

On board with the chef at the Egadi Islands

Duration:

7 days - 7 nights

Italy:

Aegadian islands

56 travellers

Starting from

€675

€750

Per person

4.7

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

67 travellers

Starting from

€495

€550

Per person

5.0

Super!

Easter and Easter Monday with whoever you WANT! to the Pontine Comfortable max 4 pers

Duration:

5 days - 4 nights

Italy:

Pontine Islands

Give this experience a try!

€590

€656

Per person

5.0

Super!

Weekend SS. Peter and Paul at the Pontine

Duration:

3 days - 2 nights

Italy:

Pontine Islands

Give this experience a try!

€441

€490

Per person

5.0

Super!

Famo Ponte on April 25th Palmarola Ponza ! COMODI MAX 4 Pers

Duration:

5 days - 5 nights

Italy:

Pontine Islands

Give this experience a try!

€585

€650

Per person

5.0

Super!

Bridge on May 1, 2025 between Palmarola and Ponza: maximum comfort for 4 people

Duration:

4 days - 4 nights

Italy:

Pontine Islands

Give this experience a try!

€522

€580

Per person

5.0

Aeolian Islands - A week on a sailing boat with skipper and assistant

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

3 travellers

Starting from

€786

€873

Per person

5.0

Island of Capraia sailing and wild nature

Duration:

4 days - 4 nights

Italy:

Tuscany

4 travellers

€405

€450

Per person

5.0

Aeolian Islands: between sea and authentic flavours

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

44 travellers

Starting from

€765

€850

Per person

4.9

Super!

Easter sailing between the islands: Elba and Capraia

Duration:

4 days - 3 nights

Italy:

Tuscany

Give this experience a try!

€356

€395

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 - Private yacht sailing holidays with skipper in Italy

1241 reviews

Weekend of theoretical and practical course

12/8/2024

Fabio M.

Italy

Gianpaolo è un bravissimo skipper, ha saputo coinvolgere tutto l'equipaggio. Utilissimi i suoi consigli

Weekend of theoretical and practical course

11/27/2024

Matteo S.

Italy

Gianpaolo è stato straordinario. Pozzo di conoscenza e di voglia (e pazienza) di condividerla in maniera efficace e pratica. Accogliente sia lui che la barca. Comodo anche arrivare al molo e parcheggiare eventuale mezzo di trasporto. La barca (per quella che è la mia poca esperienza in merito ancora) si è dimostrata molto adeguata alle applicazioni sia teoriche che pratiche e per imparare. Da rifare sicuramente, consiglio decisamente !!!

Capraia and Totani, let's go!

11/10/2024

Pablo C.

Italy

Ci siamo trovati molto bene con Ivo: skipper professionale, cuoco provetto e persona gioviale con tanto da raccontare! La sua barca è in ottime condizioni e ben pulita. Torneremmo volentieri in barca con lui.

Capraia and Totani, let's go!

11/4/2024

MATTEO R.

Italy

Skipper molto esperto, preciso e disponibile. Ottimo cuoco e pescatore!! Molto attento (anche troppo) alla cura della sua barca e alla sicurezza dell’equipaggio. Qualche costo extra (cambusa a forfait e tesseramento asd) da mettere in conto, ma nel complesso, consigliato!!

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