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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!

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

3 departures available

October

€1,300

Per person

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4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

One departure available

September - October

€700

Per person

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4.8

Super!

Cast off for a week at sea, a thousand ways to experience it!

Greece: Saronic Islands and Athens area

7 days - 7 nights

2 departures available

October - November

Starting from

€585

€527

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

3 departures available

October

€570

Per person

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5.0

Super!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

4 departures available

October

€570

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

3 departures available

October

€230

Per person

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4.9

Super!

The fantastic Saronic Islands and the surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

2 departures available

October

€750

Per person

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5.0

Super!

Barcolana 58: a day at the most famous regatta in the world

Italy: Venice and the Gulf of Trieste

1 day - 1 night

One departure available

October

€280

Per person

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4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - October

Starting from

€750

€675

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

Starting from

€453

Per person

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4.8

Super!

Squid Festival on the Island of Capraia - 2 boats in company (22 seats)!

Italy: Tuscany

3 days - 2 nights

One departure available

October

€280

Per person

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4.8

Super!

All-Inclusive Sailing: Capri, Positano, Amalfi

Italy: Naples & Amalfi Coast

3 days - 2 nights

One departure available

September

€790

Per person

Why book a holiday with Sailsquare?

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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

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

19198 reviews

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Pack your suitcase and we'll take care of the rest!! Stewards on board!

09/23/2026

Pamela T.

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IT

It was my first boating holiday and I couldn't have imagined a better experience. Alessandro and Carlo are prepared, attentive and welcoming. Eros, the third member of the staff, an added value. A perfect triptych as a corollary of a try that speaks for itself. Two smart ideas: - travel in tandem with the boat of Andrea, Alessandro's brother - the beach game in the shoal, certainly the funniest memory as well as an excellent team-building initiative. Saying goodbye to them and putting their shoes back on was very difficult! ;)
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Amazing Pontine Islands on a sailboat with private bathrooms

09/23/2026

Fabrizio T.

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IT

A weekend on a sailing boat in the Pontine Islands with this skipper was a fantastic experience, combining safety, sympathy and excellent company. Skipper Dario faced a storm on Friday night with great professionalism and confidence, proving to be a responsible and active professional. He was always available and prepared at every moment of navigation. Enrica was also on board, a welcoming and kind presence that made the atmosphere even warmer and more familiar. The boat is nice and functional, although a little dated, but equipped with everything you need to experience the sea in comfort and safety. Highly recommended for those who want to experience the authentic sea with a highly reliable crew

North Corsica & Tuscan Archipelago: we love to travel a lot

09/23/2026

Lodovica G.

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IT

Wonderful experience! Thank you Marco until next time!

Wellness, sun, sea and adventure: a weekend full of sailing!

09/23/2026

Francesco G.

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IT

The 3 days of vacation we spent on the [hidden] were a wonderful experience. We saw beautiful places, and we had a very good time. The skippers Daniele and Maria Pia are delightful people, as well as very experienced and competent in the nautical field. And then, Maria Pia's cuisine was really excellent. Super recommended holiday!

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