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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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4.8

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

4 departures available

September - October

Starting from

€600

€540

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

7 departures available

September - October

Starting from

€230

Per person

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4.8

Super!

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

4 departures available

August - October

€650

Per person

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5.0

Super!

A sailing story between Favignana, Levanzo and Marettimo

Italy: Aegadian islands

7 days - 7 nights

3 departures available

August - September

Starting from

€620

Per person

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4.7

Lampedusa, Linosa and Lampione, islands on the high seas

Italy: Pantelleria and Lampedusa

6 days - 7 nights

4 departures available

August - October

Starting from

€860

Per person

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5.0

Super!

Kefalonia to Corfu

Greece: Ionian Islands

6 days - 6 nights

One departure available

August - September

€900

Per person

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4.4

Unforgettable adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

10 departures available

August - November

Starting from

€540

€513

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!

A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

Italy: Tuscany

2 days - 2 nights

2 departures available

September

€280

Per person

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4.9

Super!

Holidays on the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€716

Per person

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4.9

Super!

Rhodes Kalymnos South Dodecanese on magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

One departure available

August

€1,200

Per person - min 2 pax

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5.0

Super!

Corfù Paxos Antipaxos

Greece: Ionian Islands

6 days - 6 nights

One departure available

September

€900

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

18420 reviews

Let's sail in relaxation on Lake Garda - All Inclusive

08/10/2026

Marcus K.

-

AT

The day with Fabio was perfect, very nice sailing experience, delicious regional food, enough stops for swimming and very good conversations! We highly recommend it.

Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/10/2026

Marco B.

-

IT

Very prepared skippers. Well done
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North Sardinia and Corsica: blue seen from a sailboat

08/10/2026

Ciro C.

-

IT

Some considerations: 1) The reported age of some participants was incorrect, two were 55 and 58 years old instead of 49 and 51 as erroneously reported. 2) There were 5 of us sharing the same bathroom as some participants agreed to use the bathroom exclusively. This did not create problems for me but it is good to point it out 3) There are skippers who tend to group up with the participants and others do not... Leonardo and the lady who helps him tend to see guests predominantly as customers. A certain detachment is perceived. . It is not a criticism, it is an observation. 4) The boat, even if it is about 30 years old, is well maintained. You have to get used to a few steps below deck
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Wind, sea and freedom: a week between Corsica and the Tuscan archipelago

08/10/2026

Carmelo C.

-

IT

Josuah hello made us feel from the first minutes an integral part of the boat, he accompanied us to unique and enchanting places, on board the other fantastic guests, great harmony and understanding. We will bring this positive experience into the future and coves with sunsets and starry nights that I had never encountered. JOSUAH great Captain.

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