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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!

Squid Festival: let's close the season on a 15m boat with a flourish! - 2 boats in company

Italy: Tuscany

3 days - 2 nights

2 departures available

October - November

€280

Per person

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4.8

Super!

Come sail with us in the Cyclades

Greece: Cyclades

6 days - 6 nights

One departure available

September

€600

Per person

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5.0

Super!

Croisière de rêve sous voiles dans les îles de la société 14 Jours

Pacific Ocean: French Polynesia

13 days - 13 nights

One departure available

October - November

€2,090

Per person

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4.8

Super!

A taste of the magnificent Island of Elba

Italy: Tuscany

2 days - 2 nights

2 departures available

September

€300

Per person

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4.7

Amazing Pontine Islands on a sailboat with private bathrooms

Italy: Pontine Islands

3 days - 2 nights

2 departures available

September

Starting from

€312

Per person

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4.8

Super!

Come and discover the Saronic Islands from Poros

Greece: Saronic Islands and Athens area

6 days - 6 nights

One departure available

September

€600

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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5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

5 departures available

September - October

Starting from

€370

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

3 departures available

September - October

€650

Per person

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4.8

Super!

Squid Festival: let's close the season on a high note! - on board a 17mt boat

Italy: Tuscany

2 days - 2 nights

2 departures available

October - November

€280

Per person

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4.9

Super!

NEW YEAR's Eve between sea and land in Norway: chasing the Northern Lights - COTTAGE + SAILBOAT

North Sea: Norway

11 days - 11 nights

One departure available

December - January

€1,300

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

Starting from

€1,000

€750

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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