577

experiences

577

experiences

Sailing and Hiking in the Cyclades

Duration:

7 days - 7 nights

Greece:

Cyclades

Give this experience a try!

Starting from

€798

€997

Per person

Sailing & Diving in the Small Cyclades

Duration:

7 days - 7 nights

Greece:

Cyclades

8 travellers

Starting from

€736

€920

Per person

4.7

Ibiza All Inclusive on an 18m ketch with skipper and skipper

Duration:

6 days - 7 nights

Spain:

The Balearic Islands

37 travellers

Starting from

€960

€1,200

Per person

5.0

Oslofjord - East Coast Norway - Round trip

Duration:

6 days - 5 nights

North Sea:

Norway

Give this experience a try!

€480

€600

Per person

5.0

Oslofjord - West Coast of Sweeden - Round trip

Duration:

6 days - 5 nights

North Sea:

Norway

Give this experience a try!

€480

€600

Per person

4.8

Super!

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

62 travellers

€990

€1,190

Per person

5.0

Super!

May Day long weekend to discover the islands of Elba and Capraia

Duration:

4 days - 4 nights

Italy:

Tuscany

Give this experience a try!

€380

€460

Per person

5.0

Super!

Settimana in barca a vela tra Toscana e Corsica

Duration:

7 days - 6 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€1,275

€1,500

Per person

5.0

Super!

Unspoilt Balearic Islands for max 4 guests: north Mallorca and south Menorca

Duration:

6 days - 6 nights

Spain:

The Balearic Islands

12 travellers

Starting from

€765

€900

Per person

Escape to the Magical Blue of the Pontine Islands

Duration:

4 days - 3 nights

Italy:

Pontine Islands

Give this experience a try!

€353

€415

Per person

From Paros to Milos, the hidden gems of Cyclades

Duration:

5 days - 5 nights

Greece:

Cyclades

Give this experience a try!

Starting from

€765

€900

Per person

4.8

Super!

Lampedusa, Lampione e Linosa fra colori magici

Duration:

7 days - 7 nights

Italy:

Pantelleria and Lampedusa

34 travellers

€595

€700

Per person

Why book a holiday with Sailsquare?

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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 - Sailboat holidays & skippered tours

15813 reviews

First spring getaways in the company of the sea

04/29/2025

Raffaella Valeria R.

Italy

Esperienza in barca vela TOP!!! Carlo è uno skypper super preparato, professionale, attento ad ogni dettaglio e capace di trasmettere tutta la sua passione e conoscenza del mare e della vela con gentilezza. Partecipare attivamente alle manovre e alle analisi meteo ti fa vivere al 100% l'andare in vela. Grazie Carlo!

From Sanremo sailing holiday to discover the Côte d'Azur

04/29/2025

Alessandra V.

Italy

Esperienza molto positiva. Sono rientrata a casa rigenerata!!!! Accoglienza, organizzazione, sistemazione, competenza , consigli ed insegnamenti durante la navigazione davvero di qualità. Skipper molto preparato anche nel gestire situazioni e persone, sempre disponibile ad insegnarci, a coinvolgerci con fiducia in modo simpatico. e divertente. Meteo buono , giusto vento, e grande fortuna con compagni di viaggio conosciuti sul posto ma che si sono rivelati simpaticissimi e con cui abbiamo condiviso risate sia a bordo che bei momenti a terra. Consigliatissimo tutto. Grazie ragazzi per questa bella mini vacanza.

25 April long weekend between Capraia and Northern Corsica

04/29/2025

VERONICA D.

Italy

Un esperienza meravigliosa. Complimenti al capitano, bravissimo nel creare gruppo e un ottimo amico di bordo. A presto Francesco

Day trip with aperitif at sunset!

04/28/2025

Silvia Maddalena V.

Italy

Bellissima giornata in ottima compagnia!

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