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Sailboat holidays & skippered tours

The thrill of sailing, the chance to discover places only accessible by sea and to meet new friends are what make a sailing holiday magical. Treat yourself to a week or weekend where you can wake up in the roadstead and have breakfast with the sea around you.

631

experiences

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4.9

Capraia under full sail / trekking on the island

Duration:

3 days - 2 nights

Italy:

Tuscany

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+4 travellers

have booked

Starting from

€240

Per person

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4.9

Between sunsets and aperitifs on a sailing boat

Duration:

7 days - 6 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€400

Per person

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4.9

Weekend at the Pontine Islands: Ponza and Palmarola

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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+3 travellers

have booked

€240

Per person

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4.9

Weekend in the Pontine Islands

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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+15 travellers

have booked

Starting from

€269

Per person

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5.0

Relaxing weekend in the Pontine Islands

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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+33 travellers

have booked

Starting from

€230

Per person

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4.5

Weekend in the Pontine Islands

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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+5 travellers

have booked

Starting from

€269

Per person

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4.8

Weekend between Amalfi, Positano and Capri

Duration:

3 days - 2 nights

Italy:

Amalfi Coast

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+18 travellers

have booked

€450

Per person

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Mini-cruise to the Aeolian Islands

Duration:

3 days - 2 nights

Italy:

Aeolian Islands

Give this experience a try!

Starting from

€219

€230

Per person

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5.0

Weekend in the coves of Ponza and Palmarola

Duration:

2 days - 2 nights

Italy:

Pontine Islands

Give this experience a try!

€275

Per person

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4.6

Educational weekends: manoeuvres and mooring in Tuscany 

Duration:

2 days - 3 nights

Italy:

Tuscany

Give this experience a try!

€200

Per person

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4.9

Sailing weekend in Ponza and Palmarola!

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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+30 travellers

have booked

Starting from

€248

€275

Per person

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5.0

Aperitif on a Sailing Boat and - All inclusive!

Duration:

1 day - 0 nights

Italy:

Liguria

Give this experience a try!

€90

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 - Sailboat holidays & skippered tours

14275 reviews

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25 April - 4 days sailing between La Maddalena and Bonifacio

05/3/2024

Bart S.

-

Spain

Excellent sailing trip in a comfortable boat with a great captain!! Grazie per tutto Leo & Crew!!!
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Sailing, early sun and aperitif at sunset ... What else?

05/3/2024

Cristiana L.

-

Italy

Giornata stupenda! lo skipper Emanuele molto simpatico, alla mano e soprattutto molto preparato e affidabile. Abbiamo veleggiato con un bel vento, io sono interessata alla vela ed Emanuele mi ha spiegato tante cose, fatto fare delle manovre e riposto pazientemente a tutte le mie tante domande. Abbiamo anche fatto un bellissimo aperitivo all'ancora. Non posso che consigliare vivamente questa esperienza!
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May 1st on Elba - Stewardess on board -3 Cab./ 3 Bathrooms

05/2/2024

susanna s.

-

Italy

una splendida vacanza . Fabio e Angela gentilissimi mi hanno offerto ogni confort a bordo e insegnato i primi rudimenti della vela .
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25 April - Whale watching expedition with WWF researcher in Liguria

05/2/2024

Rossella D.

-

Italy

Esperienza complessivamente decisamente positiva, nonostante le importanti difficoltà causate dalle pessime condizioni meteorologiche. L'estrema professionalità dello skipper e delle guide di whale watching, insieme al grande affiatamento e collaborazione che si è creato con tutto l'equipaggio, hanno fatto in modo che l'intera esperienza si vivesse nel migliore dei modi, in totale armonia, portando a casa anche grandi soddisfazioni di avvistamento di delfini, balenottere e tartarughe! Un'esperienza davvero indimenticabile, grazie di cuore!

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