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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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4.9

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

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4.7

La Dolce Vita on a sailboat: discovering the Côte d'Azur

France: French Riviera and Porquerolles

7 days - 6 nights

One departure available

August

€649

Per person

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4.9

Super!

Midweek between Elba and Capraia

Italy: Tuscany

4 days - 4 nights

One departure available

September

€400

Per person

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4.8

Super!

The fantastic Saronic Islands and the surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

3 departures available

September - October

Starting from

€750

€713

Per person

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4.9

Super!

Four days in the Aeolian Islands from Capo D'Orlando

Italy: Aeolian Islands

4 days - 4 nights

One departure available

September

€400

Per person

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4.8

Super!

Five days barefoot between Tuscany and Corsica

Italy: Tuscany

5 days - 4 nights

4 departures available

August - September

Starting from

€490

Per person

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4.8

Super!

Weekend on Elba, sea, colors and scents.

Italy: Tuscany

2 days - 2 nights

One departure available

September

€200

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

€1,000

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

18381 reviews

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

08/9/2026

pietro b.

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IT

Luca accompanied us for a fantastic week of sailing, snorkeling and a lot of relaxation, infecting us with his cheerfulness, his knowledge of the history of the island, its geology and marine fauna. The boat is spartan but comfortable, and the kitchen equipped (and excellent if Luca cooks). That's why we highly recommend it! Thanks Luca, see you next time!

Week end in Costa Azzurra

08/8/2026

Alina S.

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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!

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