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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!

Tuscany and North Corsica on a sailing boat

Italy: Tuscany

7 days - 7 nights

2 departures available

August

Starting from

€1,060

Per person

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5.0

Super!

Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

Italy: Aeolian Islands

6 days - 7 nights

10 departures available

June - October

Starting from

€800

€720

Per person

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5.0

Tuscany and Corsica: sailing sun adventure good food energy and well-being

Italy: Tuscany

3 days - 3 nights

2 departures available

July - September

Starting from

€350

Per person

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5.0

New

Weekend of the Pontine Islands to discover Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

2 departures available

June

Starting from

€400

€360

Per person

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5.0

Super!

Four days in Ponza and Palmarola

Italy: Pontine Islands

4 days - 3 nights

2 departures available

June - July

Starting from

€420

Per person

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5.0

Super!

Weekend between Ponza and Palmarola Comfortable - max 4 people

Italy: Pontine Islands

3 days - 2 nights

2 departures available

July

Starting from

€495

€446

Per person

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5.0

Super!

Aeolian Islands in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

3 days - 2 nights

10 departures available

June - August

Starting from

€390

€351

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

10 departures available

June - October

Starting from

€500

Per person

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4.9

Super!

Sailing weekend in Istria

Croatia: Istrian peninsula

3 days - 2 nights

6 departures available

July - October

€260

Per person

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4.9

Super!

Weekend in the Gulf of Alassio and Gallinara Island

Italy: Liguria

2 days - 2 nights

9 departures available

June - August

Starting from

€250

Per person

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4.8

An unforgettable week between Capri, Positano, Amalfi, Ischia, Procida...

Italy: Naples & Amalfi Coast

7 days - 7 nights

2 departures available

August

Starting from

€977

€879

Per person

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4.8

Super!

A sailing trip through history and food and wine to the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

5 departures available

July - August

Starting from

€900

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

17720 reviews

Pontine Islands in 4 days: sailing, caves and crystal clear waters

06/4/2026

Matteo B.

-

IT

The boat was really comfortable, with ample space and private bathroom for each cabin. The downside is that the mainsail was a bit battered and the boat setting was not optimized for sailing. The skipper, Dario, is truly a character with endless stories that will keep you company throughout the trip. If you are lucky, like me, to find fantastic travel companions, you can only enjoy the wonderful Pontine islands!

Long weekend of June 2nd on the Costa Smeralda

06/4/2026

Silvia B.

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IT

Francesco guided us in the world of relaxation and zero stress, lulled by the sea, following the rhythm of the sun and the delicious dinners prepared by him, transmitting his love for sailing and for [hidden]. Removed the watch and forgotten the cell phone, the only commitments are swimming, balancing on. Sup, prepare loaded spritzes and exchange jokes and life anecdotes with those who become your roommates (in this case excellent) for a few days. Thank you Francesco and thank you crew!

June 2nd long weekend: discovering Capri, Ischia and Procida

06/4/2026

Ivana G.

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IT

Very comfortable, spacious and clean sailboat. Gennaro proved to be a nice and helpful skipper, helping to make the experience on board pleasant, and also participating in land trips. Less convincing, however, was the management of the itinerary: the moorings were often far from the coast, even with favorable weather conditions, and the stops did not allow you to explore exclusive places that could only be reached by sea. Furthermore, despite being part of the program, the tender was never used, limiting the possibilities of visiting coves and more hidden areas. Overall, a relaxing and pleasant experience, but below expectations in terms of exploration and itinerary, considering that the context would have allowed it.

June 2 long weekend between Capraia and Corsica - 2 boats

06/4/2026

Rebecca C.

-

IT

It was a beautiful holiday, we sailed between Elba and Capraia and both Matteo and Alessio (the skippers of the two boats) were impeccable, really good and professional. On board I found a wonderful company that made these 4 days truly unforgettable! Super recommended experience

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