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Whole boat with skipper yacht sailing holidays & tours in Pontine Islands

Discover more than 33 opportunities to get on board a Whole boat with skipper adventure in Pontine Islands. A unique experience with a local skipper, starting at €350 a week.

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4.6

Between the Pontine Islands and the Phlegrean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

5 departures available

July - September

Starting from

€759

€683

Per person

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5.0

Super!

Blu Pontino - Evasione infrasettimanale

Italy: Pontine Islands

4 days - 3 nights

2 departures available

August - October

Starting from

€180

Per person

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4.9

Super!

Life-changing experiences - Escape to the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

9 departures available

June - September

Starting from

€370

€352

Per person

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5.0

Super!

Weekend di emozioni nel Blu Pontino

Italy: Pontine Islands

3 days - 2 nights

One departure available

October - November

€180

Per person

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4.8

Super!

Weekend sailing in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

3 departures available

June - July

Starting from

€330

Per person

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4.9

Super!

Life-changing experiences: Four days in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

7 departures available

June - September

Starting from

€420

€399

Per person

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4.8

4 days in the Pontine Islands (sailing school)

Italy: Pontine Islands

4 days - 3 nights

7 departures available

June - September

Starting from

€220

Per person

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7 days of sea and sailing in the fantastic blue of the Pontine

Italy: Pontine Islands

7 days - 7 nights

3 departures available

July - August

Starting from

€500

Per person

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5.0

Super!

Weekend between Ponza and Palmarola Comfortable - max 4 people

Italy: Pontine Islands

3 days - 2 nights

3 departures available

July - September

Starting from

€475

€428

Per person

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4.9

Super!

Life Changing Experiences - Week in the Pontine Islands

Italy: Pontine Islands

6 days - 6 nights

2 departures available

August

€1,100

Per person

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5.0

Super!

Four days in Ponza e Palmarola

Italy: Pontine Islands

4 days - 3 nights

2 departures available

July

€390

Per person

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4.5

Feast of Santa Candida in Ventotene

Italy: Pontine Islands

3 days - 3 nights

One departure available

September

€395

Per person

Why book a holiday with Sailsquare?

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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 - Whole boat with skipper yacht sailing holidays & tours in Pontine Islands

231 reviews

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Life-changing experiences: Four days in the Pontine Islands

06/13/2025

Cristiano P.

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Italy

Fantastico. Esperienza meravigliosa. Divertente, bella, ho solo aggettivi positivi
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Weekend at the Pontine a stone's throw from Rome

06/12/2025

armando a.

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Switzerland

È stata una bellissima esperienza con Antonio! Posti fantastici! Sarebbe stato ancora più bello navigare solo con le vele ma purtroppo le condizioni meteo e dell' equipaggio non lo permettevano. Da rifare sicuramente ;)
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Weekend at the Pontine a stone's throw from Rome

06/12/2025

Daniela B.

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Italy

Una barca d’epoca curata e amata, uno skipper di esperienza con competenze e grandi doti da intrattenitore (anche ottimo cuoco), un equipaggio piacevole e rispettoso e isole che ti rubano il cuore. Questo in sintesi il nostro we con Antonio e la sua barca, ma non possiamo ridurre a poche righe il nostro weekend. Antonio è un vero “lupo di mare” e grazie alle sue competenze ci ha raccontato storie di mare, di uomini, di isole, di uccelli migratori, di palme e di antichi romani. Le sue capacità come restauratore di barche d’epoca si apprezzano vivendo sulla sua barca che mantiene immutato il fascino di un tempo. Abbiamo visitato calette e grotte accompagnate dallo skipper che con il tender ci ha portato dove la comoda barca da 15m non poteva arrivare, dormito in rada e veleggiato quando il tempo lo consentiva. Un’esperienza da ripetere che ci ha rapito il cuore.
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Magical weekend in Palmarola and Ponza

06/10/2025

Katia C.

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Italy

Piacevolissima vacanza in compagnia di Federico e Costanza. La Compagnia e la barca hanno reso tutto indimenticabile.

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