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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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4.7

Flotilla Marmaglia Sun & Fun - Croatia - WOMEN SEATS ONLY - BUS INCLUDED!

Croatia: Kornati Islands

7 days - 7 nights

One departure available

August

€1,180

€800

Per person

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4.8

Super!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August

€920

Per person

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4.7

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August - September

Starting from

€795

Per person

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4.8

Super!

Sardinia and Corsica on a Classic Sailing Ship 4 cabins plus crew

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August

€850

Per person

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4.8

Super!

Sailing and Freediving in the sea of Sardinia and Corsica

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August

€870

Per person

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4.8

Super!

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

9 departures available

August - October

Starting from

€1,300

€1,040

Per person

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4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

4 departures available

August - October

Starting from

€700

Per person

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4.7

In the blue of Capri and the infinity of the Amalfi Coast

Italy: Naples & Amalfi Coast

2 days - 2 nights

4 departures available

October

Starting from

€275

Per person

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4.8

Super!

Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

Italy: Tuscany

6 days - 7 nights

One departure available

August

€1,100

Per person

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5.0

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

6 departures available

September - October

Starting from

€570

Per person

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5.0

Super!

Learn to sail in Liguria: First level sailing course

Italy: Liguria

2 days - 1 night

One departure available

October

€220

Per person

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5.0

Super!

Sailing week North Sardinia and South Corsica

Italy: Northern Sardinia

6 days - 6 nights

One departure available

August - September

€950

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

18380 reviews

Week end in Costa Azzurra

08/8/2026

Alina S.

-

IT

Beautiful experience! The owner of the boat is generous and nice. I state that it was my first time of such a stay on the boat, so being part was difficult for me at times (sway effect), but despite this Alessandro did not make us weigh this and spoiled us by treating us as real guests of honor. Thank you for your patience and hospitality. I recommend this type of experience to everyone to experience the sea 100%, especially those who are sea addicted like me🩵
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Sailing among the Islands of Ulysses. Stewardess on board

08/8/2026

Francescu G.

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FR

A very pleasant trip. Hansel and Éléonore are adorable, knew how to make us discover magnificent coves, listen to the passengers and take into account everyone's desires. We highly recommend!!
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Aeolian Islands: between sea and authentic flavours

08/8/2026

Irene S.

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IT

Carlo was a fantastic skipper: attentive, professional and passionate. He guided us between the islands with confidence and passion, making us experience for the first time the beautiful feeling of turning off the engine and sailing! Always ready to answer our thousand questions about boating with infinite patience, and then how can we not mention that delicious calamarata, prepared with fish caught right among the boats? One of the best memories of this experience. Life on a boat is all about shared spaces, collaboration and small compromises, but waking up to the sound of the waves and falling asleep under a sky full of stars is worth it all. It is an experience that we recommend to everyone. Unfortunately, due to the weather and strong winds, we were unable to see two of the planned islands. It will definitely be a good excuse to come back!

Discover the beautiful scenery of the Pink Granite Coast

08/8/2026

Benjamin B.

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DE

Our sailing trip led from Trébeurden via Trégastel to the area of Roscoff, where we visited various anchorages and learned a lot of interesting things. Excursions into the interior are also possible on request (also together on request). Overall, Olivier is very much oriented towards the individual wishes of his guests - and of course his decisions are also dependent on the weather. We were on board as a couple with Olivier and always had the impression that we could enjoy our freedom as well as experience a nice sailing adventure together with our skipper. We would recommend Olivier, his boat and the sailing area at any time. Dear Olivier, we were looking for a skipper – and found a friend! All the best to you and your loved ones!

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