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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!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - October

€700

Per person

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4.8

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

6 departures available

August - October

Starting from

€750

€675

Per person

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4.9

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

Italy: Tuscany

7 days - 6 nights

4 departures available

August - September

Starting from

€650

Per person

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4.4

Sailing holiday on the Côte d'Azur: experience the charm of the French Riviera

France: French Riviera and Porquerolles

6 days - 7 nights

6 departures available

August - September

Starting from

€730

€657

Per person

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4.8

Super!

Egadi mon amour: seven days to fall in love, be amazed and relax.

Italy: Aegadian islands

7 days - 7 nights

2 departures available

August - September

Starting from

€600

€540

Per person

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4.6

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

August - September

Starting from

€850

Per person

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4.9

Super!

Long weekend among the wonders of Elba and Capraia

Italy: Tuscany

4 days - 3 nights

4 departures available

August - September

Starting from

€400

€360

Per person

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5.0

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

One departure available

August - September

€1,020

Per person

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4.8

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

12 departures available

August - November

Starting from

€700

€665

Per person

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4.9

Super!

Weekend in the Gulf of Alassio and Gallinara Island

Italy: Liguria

2 days - 2 nights

2 departures available

August

Starting from

€250

Per person

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4.4

Unforgettable adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

10 departures available

August - November

Starting from

€540

€513

Per person

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5.0

Sailing in the magical Sardinia of the South

Italy: Southern Sardinia

6 days - 7 nights

6 departures available

August - September

Starting from

€790

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

18272 reviews

Sailing holiday on the Côte d'Azur: experience the charm of the French Riviera

08/1/2026

Fabrizio S.

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IT

We are Anna and Fabrizio and we want to tell you about our experience, even if we took a long time before being able to write this review. We were partly disappointed and needed to let what we had experienced decant about. It was our first experience on a sailing boat and, above all, our honeymoon: we therefore hoped to keep a very different memory of it. Federico is undoubtedly an experienced skipper and the [hidden] boat allowed us to reach wonderful places. However, from the beginning we felt little involved in navigation, directions were given almost exclusively in English and, when we asked for explanations, we felt ignored or treated with contempt. During the week Federico often appeared tense, not very willing to dialogue and not very empathetic. He was almost always serious and we don't remember moments of real lightness or a shared laugh. In our opinion, a boat holiday should also convey joy, conviviality and the pleasure of living a special experience together; on board, however, we often perceived a tense and unwelcoming atmosphere. Some attitudes and ways of addressing us have also made us feel undervalued and, from our point of view, discriminated against. It is a feeling that accompanied us during the trip and that contributed to increasing our discomfort. Even the comfort on board presented several critical issues: there was a lack of snorkeling equipment, adequate cushions to face the long hours of navigation also when we were stopped in the roadstead we asked if he could take out the Sup or accessories to have fun on the boat or use the tender to reach the beach but we were denied ... We were not even allowed to listen to music, always when the boat was stopped in the roadstead only once after the boys had asked him several times. We are sorry to write all this, because we do not question Federico's technical competence. However, a sailing holiday does not only require experience in navigation: you also need hospitality, availability, communication, respect, empathy and the ability to create a serene atmosphere, so that guests can really feel part of the crew. If it hadn't been for the wonderful places we visited and the wonderful travel companions we met on board, our first experience on a sailing boat would not have been a good memory.

Capri Light Blue - Two boats in company!

08/1/2026

Maria bruna M.

-

IT

As a first experience it was wonderful.

Two days at the Marine Protected Area of the Tremiti Islands

08/1/2026

Elisabetta M.

-

IT

Short and super intense experience. Marco, as a true professional and sea lover, made us live two unforgettable days. To be repeated absolutely 💕
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North Sardinia and Corsica: blue seen from a sailboat

08/1/2026

Gabriele T.

-

IT

Beautiful experience, a week of relaxation between good food baths and some shore excursions. The kitchen service on board was not only good, but also a real convenience... Recommended!

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