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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!

Midweek weekend in Elba: sea, scents, colors

Italy: Tuscany

2 days - 2 nights

2 departures available

September

€200

Per person

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5.0

Super!

Sailing Holiday with a Hostess Among the Wonders of Northern Sardinia

Italy: Northern Sardinia

6 days - 6 nights

4 departures available

August - September

Starting from

€1,450

Per person

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4.7

Amazing Pontine Islands on a sailboat with private bathrooms

Italy: Pontine Islands

3 days - 2 nights

4 departures available

August - September

Starting from

€312

Per person

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4.8

The gems of the Amalfi Coast: Capri Light Blue, Positano Blue Sky, Amalfi Dreaming History

Italy: Naples & Amalfi Coast

4 days - 3 nights

One departure available

September

€333

Per person

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5.0

Super!

Ibiza & Formentera: one week with cook on board

Spain: The Balearic Islands

6 days - 6 nights

One departure available

September

€750

€713

Per person

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4.7

Whale watching mini-cruise in the Pelagos Sanctuary with WWF guide

Italy: Liguria

4 days - 4 nights

One departure available

September

€609

€579

Per person

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4.5

Ibiza & Formentera: an exclusive journey between sky and sea

Spain: The Balearic Islands

6 days - 6 nights

2 departures available

August - September

Starting from

€1,010

Per person

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5.0

Super!

Long weekend on a sailing boat Cous Cous Festival in San Vito Lo Capo

Italy: Sicily

4 days - 3 nights

2 departures available

September

€345

Per person

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5.0

Super!

Saronic Gulf Cruise: Aegina, Poros, Hydra, Athens Surroundings

Greece: Saronic Islands and Athens area

6 days - 6 nights

One departure available

September

€650

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!

Corsica as you've never seen it before!

France: Corsica

7 days - 7 nights

One departure available

August

€1,050

Per person

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4.8

Super!

A sailing trip through history and food and wine to the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August

€990

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

18305 reviews

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Five days in Croatia with skipper, instructor and cook

08/3/2026

nicol c.

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IT

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

08/3/2026

maria antonella p.

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IT

It was the perfect holiday, an experience that I highly recommend to anyone who wants to visit enchanting places in total relaxation and live in contact with nature. Andrea, Carol and little Mattias are a very experienced and generous team, always careful to create a welcoming atmosphere that makes the customer feel pampered. Andrea, the skipper, will take you on a tour of unspoilt coves, tell you travel anecdotes and challenge your competitive skills by playing beach volleyball with you. Carol, the hostess on board, will prepare delicious and fresh dishes for you, cheering you with her sweetness and helpfulness and allowing you to spend a holiday in total relaxation and in a very clean and comfortable environment. Finally, what about Mattias the dog?! His love of addiction! Highly recommended experience!!

Midweek getaway between Elba and Capraia

08/2/2026

Barbara B.

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IT

Beautiful experience, perfect skipper, super company, lots of nature, absolutely recommended

Leave everything for the Island of Elba

08/2/2026

Gianmarco N.

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IT

We had a simply unforgettable experience aboard Josuah's boat. Two days that we will carry with us for a long time, between breathtaking landscapes, crystal clear sea and moments of pure relaxation. But what really made this experience special was Josuah's hospitality: an exceptional skipper, always available, attentive and able to make you feel at home from the first moment. His passion for the sea and what he does can be felt in every detail and makes the journey even more authentic. It was not just a boat trip, but an experience full of emotions, sharing and beautiful company. If you're looking for something more than just hiking, this is the way to go. Thank you very much, Josuah. We hope to return to sail with you soon!

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