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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!

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

New

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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4.8

Super!

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

Greece: Ionian Islands

7 days - 7 nights

One departure available

September

€650

Per person

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5.0

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - October

€690

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

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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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4.7

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

Italy: Tuscany

4 days - 4 nights

One departure available

October

€453

Per person

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4.8

Super!

Five days barefoot between Tuscany and Corsica

Italy: Tuscany

5 days - 4 nights

One departure available

September

€490

€440

Per person

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4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

One departure available

September

Starting from

€441

€419

Per person

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4.8

Super!

Come and discover the Egadi Islands! Nature, relaxation and crystal clear waters

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€700

Per person

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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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4.8

Super!

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

Italy: Tuscany

2 days - 2 nights

4 departures available

September - October

Starting from

€230

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

19098 reviews

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Seven days not only on the Amalfi Coast

09/10/2026

antonella a.

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IT

Lovely week on the boat. The organization was impeccable: every detail, from the timing to the activities, was carefully studied and with a professional and welcoming management. The proposed itinerary is exceptional: hidden bays, crystal clear waters, well-selected moorings even when the sea has forced us to change course. This is thanks to the skipper's extraordinary knowledge of the places, who guided us as only those who really live the sea can do. Each stage had a meaning, a rhythm, an emotion. The care for the crew was total, at 360 degrees. Comfort on the boat always at the top thanks to its large size, relaxed but also dynamic atmosphere, never boring. And when you went ashore, the entertainment was always calibrated: the right venue, the right time, the right mood. In short, I didn't take a boat holiday, but I did the boat holiday, the one that also changes the way you look at the sea and experience your land. An experience that stays with you, do it!

Maddalena Archipelago, southern Corsica: wonderful Sardinia

09/10/2026

paola s.

I spent 7 wonderful and unforgettable days on the boat captained by Massimo, a correct, punctual and highly professional person. A great connoisseur of the sea and the winds, who, sailing under full sail, in preserves, was able to lead us to the most fascinating coves of the places included in the program (Sardinia-Corsica) with passion and competence. In addition, Massimo is an excellent cook and together with his skipper Vittoria, he has always delighted us with breakfasts, lunches and dinners, rich in flavors and imagination. The company (8 people in all) delicious and fun, and the memorable places, have made this holiday unique and exclusive, which I absolutely highly recommend!! Excellent verdict

Aeolian Islands on a sailboat: nature, sea and conviviality on Bavaria 46

09/10/2026

Fabio F.

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IT

With Rosario first of all you feel safe. Safety always comes first. In second place is a lot of sailing experience and knowledge of the islands from top to bottom. Rosario took us to fabulous spots for relaxation and snorkeling. Guaranteed fun.

Discovering the Aeolian Islands Between Nature, Relaxation and Fun

09/10/2026

Giovanna E.

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IT

We spent an unforgettable week, an indescribable experience that exceeded my expectations. Davide was a caring captain, attentive to every need that made us feel at home on the boat. With him we discovered all the coves and the most magical corners of the Aeolian Islands. Perfect organization in every detail! Joan

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