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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!

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

Italy: Tuscany

7 days - 7 nights

3 departures available

September - October

€650

Per person

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4.9

Super!

NEW YEAR's Eve between sea and land in Norway: chasing the Northern Lights - COTTAGE + SAILBOAT

North Sea: Norway

11 days - 11 nights

One departure available

December - January

€1,300

Per person

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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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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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4.7

Palma de Mallorca All Inclusive on 18m Ketch

Spain: The Balearic Islands

6 days - 7 nights

One departure available

September

€1,290

Per person

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4.1

Conquering the Aeolian Islands - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

3 departures available

September - October

Starting from

€680

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

A sailing story between Favignana, Levanzo and Marettimo

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€620

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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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

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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

19022 reviews

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

09/5/2026

Valentina R.

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IT

Very nice boat, excellent skipper and owner, delicious food. Costs a little too high given the decidedly downsized changes of course.
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Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

09/5/2026

Daniela B.

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IT

Luca and Tommaso are two mature professionals both from a nautical and hospitality point of view. Luca has a lot of dedication to his boat, which he has renovated inside and out with great care and can count on a good network of other "captains" friends with whom to refine routes and choice of roadsteads. Thomas is an experienced sailor, a thoughtful cook, and a pleasant conversationalist. Thanks to them, my son and I had a very pleasant experience on the boat.

Maddalena Archipelago, southern Corsica: wonderful Sardinia

09/5/2026

Alessandro C.

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IT

With Massimo skipper and collaborator Valentina it was a really positive experience, with a very close-knit group; we visited beautiful bays both in the archipelago of La Maddalena and in the south of Corsica. The sail to Bonifacio with the overnight stay in the port is very beautiful. A special applause for the lunches and dinners on the boat truly worthy of the best restaurants, Thank you for the beautiful week spent at sea. Alexander

A week in the Aeolian Islands - 6 islands in seven days

09/5/2026

Antonella B.

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GB

The skipper was the only negative part of the experience. Rude, directive, judgmental and controlling. Would lose temper over small things without actually teaching anything. Arrogant and entitled. Do not recommend him. He also took advantage of the trip to bring his fiance and son onboard for a total of 4 nights over the 6 we had paid for making the space more crowded than it should have been. “Please” “thank you” are not part of his vocabulary. Felt a bit on a disciplinary experience at time. Boat not spacious enough for 9 people (including the two extra guests we were informed of only after departure - no permission asked, just communicated) Beautiful destination, I truly love Eolian islands. And my friend are the best company, always!

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