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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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5.0

Super!

Corfù Paxos Antipaxos

Greece: Ionian Islands

6 days - 6 nights

One departure available

September

€900

Per person

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4.3

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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4.0

New

Lampedusa, Lampione and Linosa among magical colors

Italy: Pantelleria and Lampedusa

7 days - 7 nights

2 departures available

October - November

€500

€348

Per person

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5.0

Super!

Tuscany and North Corsica on a sailing boat

Italy: Tuscany

7 days - 7 nights

One departure available

August

€1,060

€954

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

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5.0

Sailing in the magical Sardinia of the South

Italy: Southern Sardinia

6 days - 7 nights

5 departures available

August - September

Starting from

€790

Per person

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5.0

Super!

Saronic Islands and surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

September

€620

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

18416 reviews

Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/10/2026

Stefano R.

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IT

Perfect experience

Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/10/2026

silvia r.

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IT

A truly beautiful experience in the Aeolian Islands! The catamaran trip allows you to experience the sea and the islands from a special perspective, in a pleasant, informal and very convivial atmosphere. Simone was helpful and competent, certainly contributing to the success of the holiday. It is an experience to be chosen with the right spirit: you have to be willing to party, socialize, meet new people and share spaces and moments of the day with others.  As with any trip, there were a few small aspects that, taken individually, in other circumstances I would probably have indicated as negative. But the experience as a whole was so beautiful and engaging that it largely surpassed them and made them take a back seat. In the end I take with me above all the memory of a wonderful week in the Aeolian Islands and the interesting people I had the pleasure of meeting. An experience that I would gladly do again.

Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/10/2026

Francesca M.

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IT

Little to say, beautiful experience.

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

08/10/2026

Nina D.

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DE

We as a family with 2 children spent a very nice week on Luca's boat. Luca welcomed us very warmly at the port of Portoferraio and took us to his boat. He absolutely adapted to our rhythm throughout the week and showed us many great places. The boat is very lovingly and thoughtfully equipped. Each of us quickly found our favorite place. The children had a lot of fun jumping off the boat and riding SUP. Luca showed us a lot of places on his island and told us a lot about the island and the sea. He is a very uncomplicated, humorous skipper. We enjoyed the week on board very much and went home with many beautiful memories. Dear Luca, thank you very much for a week full of great experiences and unforgettable moments!

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