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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!

Three days of adventure in the Aeolian Islands

Italy: Aeolian Islands

3 days - 3 nights

One departure available

September

€400

Per person

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4.9

Super!

Cyclades from Milos to Milos

Greece: Cyclades

7 days - 7 nights

One departure available

September

€800

Per person - min 2 pax

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4.9

Wind, sea and freedom: a week between Corsica and the Tuscan archipelago

Italy: Tuscany

7 days - 6 nights

2 departures available

August - September

Starting from

€650

Per person

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5.0

Super!

From Mykonos to Athens by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

September - October

€950

Per person

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4.8

Super!

All Inclusive Tour: Capri, Amalfi, Cetara, e Sorrento

Italy: Naples & Amalfi Coast

5 days - 5 nights

One departure available

September

€1,150

Per person

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5.0

Super!

Pula and the enchanting Kvarner islands: special price private cruise

Croatia: Kornati Islands

6 days - 6 nights

One departure available

August

€870

Per person

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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

6 departures available

September - October

Starting from

€370

Per person

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4.8

Midweek on Elba, from Monday to Thursday

Italy: Tuscany

3 days - 3 nights

One departure available

September

€380

€361

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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4.7

Amazing Pontine Islands on a sailboat with private bathrooms

Italy: Pontine Islands

3 days - 2 nights

3 departures available

August - 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

5 departures available

August - September

€600

Per person

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5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

7 departures available

September - October

Starting from

€370

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

18633 reviews

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

08/19/2026

Emanuele Z.

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IT

Nice experience
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Mid-August on the Côte d'Azur!

08/19/2026

Melania Cinzia Z.

-

IT

The cruise was pleasant, without any particular inconvenience. Andrea is very focused on ensuring safety both during travel and during maneuvers for stops. The discordant note that I would like to highlight is that the title of the cruise indicates the Porquerolles which, in fact, are not included in the itinerary, so I would like more aligned information for the user who has to choose.

Pula and the enchanting Kvarner islands: special price private cruise

08/19/2026

Michele R.

Top experience! A week on the boat with my sailor girlfriend, in which everyone did what they felt, and I didn't want to do anything and I didn't do anything. Ilaria and Maurizio were good at respecting my wishes, but I recognize that they behaved very well: we went sailing a lot, they taught those who wanted to learn and managed the stages and movements with the right times. Very spacious boat, we were in the forward cabin which is very nice. For those who want to spend a week on a sailing boat, highly recommended!
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An unforgettable week between Capri, Positano, Amalfi, Ischia, Procida...

08/19/2026

Gloria D.

-

IT

A trip just right to completely take your head off. My husband had a lot of fun being at the helm with Gennaro. All very nice certainly with something to fix. Holiday suitable for those looking for adventure. 😍

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