header cover

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.

628

experiences

cover image
avatar image
Intro sail Liguria

Duration:

1 day - 0 nights

Italy:

Liguria

Give this experience a try!

€125

Per person

cover image
avatar image

4.9

The fantastic Saronic Islands and the surroundings of Athens

Duration:

6 days - 7 nights

Greece:

Saronic Islands and Athens area

avatar image
avatar image
avatar placeholder

+7 travellers

have booked

Starting from

€618

€650

Per person

cover image
avatar image

5.0

Sailing Cyclades

Duration:

6 days - 7 nights

Greece:

Cyclades

avatar image
avatar image
avatar image

+91 travellers

have booked

Starting from

€920

Per person

cover image
avatar image

5.0

Ibiza & Formentera All inclusive week with Cook

Duration:

5 days - 6 nights

Spain:

The Balearic Islands

avatar image
avatar image
avatar image

+27 travellers

have booked

Starting from

€570

€600

Per person

cover image
avatar image

4.8

Gone with the Wind, Corfu and the Poseidon Islands

Duration:

6 days - 7 nights

Greece:

Ionian Islands

Give this experience a try!

€570

Per person

cover image
avatar image

4.8

An unforgettable sail to discover the Egadi Islands

Duration:

3 days - 4 nights

Italy:

Aegadian islands

avatar placeholder
avatar placeholder
avatar placeholder

+17 travellers

have booked

€350

Per person

cover image
avatar image

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

cover image
avatar image

4.9

Educational course From Athens to Kos on a comfortable and fast Kufner 54

Duration:

9 days - 10 nights

Greece:

North Egean Islands

avatar placeholder
avatar placeholder
avatar placeholder

+4 travellers

have booked

€890

Per person

cover image
avatar image

4.4

Sailing course on the Côte d'Azur aboard a 15-metre sailboat

Duration:

4 days - 3 nights

France:

French Riviera and Porquerolles

avatar image
avatar placeholder
avatar placeholder

+3 travellers

have booked

€440

Per person

cover image
avatar image

5.0

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

Duration:

1 day - 0 nights

Italy:

Lake Garda

avatar image
avatar placeholder
avatar placeholder

+6 travellers

have booked

Starting from

€69

Per person

cover image
avatar image

4.9

Crossing to the northwest: sailing weekend in Sicily

Duration:

3 days - 2 nights

Italy:

Sicily

avatar placeholder
avatar placeholder
avatar placeholder

+4 travellers

have booked

€300

Per person

cover image
avatar image

5.0

Weekend sailing in the Pontine Islands

Duration:

2 days - 2 nights

Italy:

Pontine Islands

Give this experience a try!

Starting from

€250

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

avatar image

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!!!
avatar image

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!
avatar image

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 .
avatar image

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!

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

MastercardVisaAmerican ExpressApple pay

© 2023 Sailsquare Srl SB • All rights reserved - VAT IT07860990964