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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.

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5.0

Super!

Mykonos and the Western Cyclades by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

2 departures available

September

Starting from

€1,000

€750

Per person

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4.9

Super!

Sail to the edge of the world among the wonders of the North (cottage + sailboat)

North Sea: Norway

7 days - 7 nights

One departure available

October

€1,200

Per person

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4.9

Super!

Sailing holiday among the wonders of the Cyclades from Athens

Greece: Cyclades

6 days - 7 nights

One departure available

September - October

€835

Per person

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4.9

Super!

Baie and fast sailing from Milos to Paros

Greece: Cyclades

6 days - 7 nights

One departure available

September

€980

Per person

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4.9

Relaxing weekend in the Aeolian Islands: Lipari, Vulcano and Salina

Italy: Aeolian Islands

3 days - 2 nights

7 departures available

September - October

€320

Per person

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5.0

Tuscany and Corsica: sailing sun adventure good food energy and well-being

Italy: Tuscany

3 days - 3 nights

2 departures available

September

€350

Per person

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4.3

New

Dreamy Saronics: turquoise waters and relaxation just a stone's throw from Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

September - October

€890

Per person

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4.1

Conquering the Aeolian Islands - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

2 departures available

September - October

Starting from

€680

Per person

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4.7

Amazing Pontine Islands on a sailboat with private bathrooms

Italy: Pontine Islands

3 days - 2 nights

2 departures available

September

Starting from

€312

Per person

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4.4

Atlantic crossing by sailboat from Tenerife to the Caribbean

Caribbean: Grenadines & Martinique

20 days - 20 nights

One departure available

November - December

€3,900

Per person

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4.8

Egadi paradise for sailing and snorkeling

Italy: Aegadian islands

6 days - 7 nights

One departure available

September - October

€600

Per person

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4.8

Sailing in the magical Sardinia of the South

Italy: Southern Sardinia

6 days - 7 nights

One departure available

September

€790

Per person

Why book a holiday with Sailsquare?

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

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

19039 reviews

Aeolian Islands on a luxury sailing boat

09/6/2026

Palma A.

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IT

We spent a lovely week among magical places in a comfortable boat and above all in the company of an excellent staff ! Super recommended
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Come and discover the Egadi Islands! Nature, relaxation and crystal clear waters

09/6/2026

Orazio F.

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IT

Wonderful holiday among the most beautiful coves of the Egadi Islands. Alessandro is a fantastic skipper, very nice and competent and is able to delight the crew with real chef dishes even in the middle of the sea. Cala Rossa remains in the heart. Highly recommended!"
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The Island of Elba, to make you live a special experience!

09/6/2026

Andrea C.

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IT

Wonderful sailing holiday! Livio is a great skipper, he always made us feel safe, sharing his knowledge and experience and allowing us to understand what was happening to the boat at every moment of navigation. The boat has its respectable age, and if it is probably less comfortable than other more recent models, it has however arrived 7 times in the Caribbean: and what latest model can boast so many Atlantic crossings? Let Livio tell us about them, who also gave us the gift of his jovial company, not to mention his pasta with sauce with olives, capers and chilli, which ignites the conversation as well as the palate! I conclude with a greeting to my travel and goliardy companions, a nice lively and cohesive group, please, see you on the mainland!!
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A week in the Aeolian Islands - 6 islands in seven days

09/6/2026

Giorgia Z.

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IT

Unforgettable experience and wonderful places, definitely worth coming back to. A group that soon found its balance. Extremely competent and passionate skipper who involved the group in decisions, offering valuable advice based on his experience of the sea and the islands. From day one he took care that the group was balanced and that everyone participated in the daily management of the activities, an approach based on respect for the rules and common sense that is fundamental in a sailing holiday. I appreciated honesty, clarity and passion, direct communication and without formalism, which brings out authenticity and maintain a collaborative atmosphere. Qualities that on a boat are worth much more than words of circumstance. See you soon [hidden], see you soon Nik!!

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