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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!

All in the family: 5 days between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

3 departures available

September

€490

€466

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

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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4.8

Super!

From Tavolara to Ogliastra, the great emotions of Eastern Sardinia

Italy: Southern Sardinia

5 days - 4 nights

One departure available

September

€1,200

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

€940

Per person

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5.0

Super!

Weekend in the Tuscan Archipelago with PROFESSIONAL COOK SKIPPER

Italy: Tuscany

2 days - 2 nights

One departure available

September

€250

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

Voices of the Pelagos: artistic-scientific whale watching expedition with WWF guide

Italy: Tuscany

4 days - 4 nights

One departure available

October

€453

€430

Per person

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4.7

Palma de Mallorca All Inclusive on 18m Ketch

Spain: The Balearic Islands

6 days - 7 nights

2 departures available

September

€1,290

Per person

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5.0

Weekend in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

One departure available

September

€295

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

18971 reviews

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A sailing holiday: discovering the Pontine Islands

08/31/2026

Matilde C.

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IT

Fantastic experience! Fabio is a competent and attentive skipper, both to the weather conditions and to the needs of the group. He guided us between Palmarola, Ponza and Ventotene to discover beautiful bays and caves, also involving us in the maneuvers and handling of the boat and making us live the sailing experience to the fullest! The only flaw is the space: the boat is small and has only one bathroom, so in 6 plus the skipper it is a bit cramped.
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Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

08/31/2026

Antonio C.

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IT

To be clear: excellent experience, do it. Pros: - convenient departure, parking in Punta Ala, boarding and disembarking luggage directly in front of the boat; - A great skipper, nice, we sailed whenever we could, that is a lot of hours; - if you are sick of the sea, traveling by sail, only with the sound of the sea and the wind, is an experience; - the roadsteads visited are more than enchanting, so the dozens of baths taken are one better than the other; - the skipper guides the shopping and cooks VERY WELL. Fish couscous, hummus with octopus... So it optimized all the times and at the same time satisfied every palate. In addition, he went out of his way for every need. Cons: - serious voice: you sleep in extremely small spaces, several days it was hot and humid and the ventilation in the stern is entrusted to a small porthole. Fortunately, he has installed a fan in each room, but the noise is remarkable. In short, sleeping is a bit of a problem; - Not very relevant article: there is a lack of communication. Better to clarify, perhaps from Maps, which parking lot can be used. That on Mondays we need a car for shopping, what if we were all on the train? Extremely positive experience, I thank the skipper Riccardo. Don't deny it.
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Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

08/31/2026

Giovanna B.

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IT

Super positive sailing experience! Alberto took us to beautiful places... postcard sea and beaches.... exciting and numerous sails.... fairness and infinite availability in providing us with information and clarifications on the fabulous world of sailing !!! Top cleanliness .... !! Boat very well maintained !! The only flaw...... Time literally flew !!

Wind, sea and freedom: a week between Corsica and the Tuscan archipelago

08/31/2026

Luigi M.

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IT

Magnificent experience, perfect Joshua, beautiful places, wonderful travel companions... And I would definitely do it a thousand times over

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