header cover
sailsquare logo

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

Discover more than 22 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.

cover image
avatar image

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

€719

Per person

cover image
avatar image

4.9

Super!

Life-changing experiences - Escape to the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

7 departures available

July - September

Starting from

€370

€352

Per person

cover image
avatar image

4.8

Super!

ONE WAY From the Phlegraean to the Pontine Islands

Italy: Pontine Islands

8 days - 7 nights

3 departures available

July - September

Starting from

€680

€544

Per person

cover image
avatar image

4.9

Super!

Four days of sea, nature and fun in the Pontine Islands!

Italy: Pontine Islands

4 days - 3 nights

One departure available

July

€420

Per person

cover image
avatar image
7 days of sea and sailing in the fantastic blue of the Pontine

Italy: Pontine Islands

7 days - 7 nights

One departure available

August

€600

Per person

cover image
avatar image

4.8

4 days in the Pontine Islands (sailing school)

Italy: Pontine Islands

4 days - 3 nights

3 departures available

July - September

Starting from

€270

Per person

cover image
avatar image

4.9

Super!

Life-changing experiences: Four days in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

5 departures available

July - September

Starting from

€420

€399

Per person

cover image
avatar image

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

cover image
avatar image

4.8

Super!

A sailing trip through history and food and wine of the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August

€950

Per person

cover image
avatar image

4.5

Feast of Santa Candida in Ventotene

Italy: Pontine Islands

3 days - 3 nights

One departure available

September

€395

Per person

cover image
avatar image

4.9

Cruise to discover the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

One departure available

July

€390

Per person

cover image
avatar image

5.0

Pontine Islands aboard a splendid 16-meter sailboat

Italy: Pontine Islands

4 days - 3 nights

3 departures available

July

Starting from

€440

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

258 reviews

avatar placeholder

Four days in the Pontine archipelago

07/2/2025

Eleonora F.

-

Italy

Abbiamo vissuto un'ottima esperienza! Abbiamo visto posti magnifici con buoni consigli di Antonio e abbiamo anche veleggiato!
avatar image

4 days relaxing in the Pontine Islands

07/2/2025

Simone S.

-

Italy

Tutto top tranne… ahimè… Sailsquare. Bruno è un ottimo skipper, ha grande esperienza e conosce bene le bellissime zone in cui naviga. La sua barca è bella, comoda e ben equipaggiata. Inoltre viverla massimo in 4 persone è un grande vantaggio… Maggiori spazi, maggiore comodità e maggiori comfort. Assolutamente una vacanza in barca TOP!!! Consigliata e da rifare assolutamente!!! Ahimè nella nostra vacanza abbiamo avuto un imprevisto non dipeso da nessuno. Cose che possono semplicemente accadere. Bruno l’ha gestito al meglio, ha cercato individuare la natura del problema, di riparare il danno, di trovare la soluzione migliore per l’equipaggio e per la sicurezza di tutti siamo rientrati con un giorno di anticipo rispetto al programma. Era assolutamente la cosa giusta da fare. Avendo prenotato tramite Sailsquare eravamo tutti convinti di poter contare su loro per compensare il giorno perso ma invece… nulla! Declino totale di ogni forma di assistenza e soluzione al problema. Abbiamo chiamato più volte e in modo educato e garbato ci hanno detto “vedetevela voi”. Grande grande grandissima delusione. Ho prenotato tramite Sailsquare, riconoscendo loro una commissione del 20%, convinto di poter contare sulla loro assistenza e supporto e invece, nel momento del bisogno a commissioni incassate, tanti saluti a voi. Bruno 5 stelle Barca 5 stelle Destinazione 5 stelle Sailsquare zero totale
avatar image

Relaxing weekend in the Pontine Islands

07/1/2025

Fabio D.

-

Italy

Stefano skipper dí grande esperienza e professionalità, insieme a suo figlio Adriano, ci hanno guidato in una fantastica avventura nelle isole pontine
avatar image

Weekend di emozioni nel Blu Pontino

07/1/2025

Marianna M.

-

Italy

Lele è stato molto gentile, preparato e di ottima compagnia... Ha creato una bella atmosfera ! Consigliatissimo!

Customer Support

nightLifeGeneralInfo

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!

search

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!

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964