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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!

Midweek weekend in Elba: sea, scents, colors

Italy: Tuscany

2 days - 2 nights

2 departures available

September

€200

Per person

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4.7

Week between the Tuscan Islands and Northern Corsica

Italy: Tuscany

7 days - 6 nights

5 departures available

August - September

Starting from

€700

Per person

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5.0

Super!

Sailing Holiday with a Hostess Among the Wonders of Northern Sardinia

Italy: Northern Sardinia

6 days - 6 nights

4 departures available

August - September

Starting from

€1,450

Per person

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5.0

Super!

Vento di Sicilia: from the Aeolian Islands to Trapani

Italy: Aegadian islands

7 days - 7 nights

One departure available

August

€920

Per person

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4.7

Amazing Pontine Islands on a sailboat with private bathrooms

Italy: Pontine Islands

3 days - 2 nights

4 departures available

August - September

Starting from

€312

Per person

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4.8

The gems of the Amalfi Coast: Capri Light Blue, Positano Blue Sky, Amalfi Dreaming History

Italy: Naples & Amalfi Coast

4 days - 3 nights

One departure available

September

€333

Per person

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5.0

Super!

Ibiza & Formentera: one week with cook on board

Spain: The Balearic Islands

6 days - 6 nights

One departure available

September

€750

€675

Per person

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4.7

Whale watching mini-cruise in the Pelagos Sanctuary with WWF guide

Italy: Liguria

4 days - 4 nights

One departure available

September

€609

€579

Per person

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4.5

Ibiza & Formentera: an exclusive journey between sky and sea

Spain: The Balearic Islands

6 days - 6 nights

2 departures available

August - September

Starting from

€1,010

Per person

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5.0

Super!

Long weekend on a sailing boat Cous Cous Festival in San Vito Lo Capo

Italy: Sicily

4 days - 3 nights

2 departures available

September

€345

Per person

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5.0

Super!

Saronic Gulf Cruise: Aegina, Poros, Hydra, Athens Surroundings

Greece: Saronic Islands and Athens area

6 days - 6 nights

One departure available

September

€650

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

4 departures available

August - October

€650

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

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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