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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!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

2 departures available

July - September

€400

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

6 departures available

July - October

Starting from

€650

€585

Per person

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4.7

Week between the Tuscan Islands and Northern Corsica

Italy: Tuscany

7 days - 6 nights

6 departures available

August - September

Starting from

€700

Per person

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4.8

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!

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

Italy: Aegadian islands

7 days - 7 nights

3 departures available

August - September

Starting from

€600

€540

Per person

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4.8

Super!

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

Greece: Ionian Islands

7 days - 7 nights

One departure available

September

€650

Per person

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5.0

Super!

EXPERIENCE THE MAGIC! Sailing and relaxing in a maritime wonderland!

Croatia: Istrian peninsula

7 days - 7 nights

One departure available

August

€649

Per person

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5.0

Sailing in the magical Sardinia of the South

Italy: Southern Sardinia

6 days - 7 nights

7 departures available

August - September

Starting from

€790

Per person

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4.8

Super!

Cast off for a week at sea, a thousand ways to experience it!

Greece: Saronic Islands and Athens area

7 days - 7 nights

5 departures available

September - November

€585

€527

Per person

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5.0

Super!

Educational cruise between Tuscany and Corsica

Italy: Tuscany

14 days - 14 nights

One departure available

August

€1,700

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

2 departures available

September

€950

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

18165 reviews

A week in the Aeolian Islands - 6 islands in seven days

07/23/2026

Deborah T.

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IT

Unforgettable holiday! We managed to tour all the islands included in the itinerary, discovering wonderful corners. Nicola was fantastic: he understood our tastes on the fly, guiding us to magical coves and uncrowded places, away from the chaos. Five well-deserved stars, highly recommended!
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Week end in Costa Azzurra

07/23/2026

Isabella R.

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IT

Beautiful experience. Alessandro turned out to be a skipper with a lot of experience, always attentive to the needs of the participants and available to rediscuss the plans depending on our preferences or weather conditions. The boat is impeccably maintained and is perfect for a weekend of freedom.

The most spectacular islands of the Cyclades: from Athens to Milos

07/23/2026

Frank W.

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DE

The cruise holiday in the Cyclades aboard the beautiful sailing yacht Anemeliá with skipper Alessio was spectacular! A perfect mix of pristine bays, crystal-clear blue waters, charming islands, and sailing whenever the wind allowed. The food on board was excellent, and the company of the other guests made the experience even more enjoyable. We had so much fun! Alessio is an experienced, professional, and friendly skipper who made us feel safe, relaxed, and welcome throughout the trip. Thanks to him, this holiday became a memory that will last a lifetime. We highly recommend this experience to anyone looking for an authentic sailing holiday in the Greek islands.

Authentic Aeolian Islands on a sailboat: between local flavors and crystal clear sea

07/22/2026

chiara a.

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IT

I had contacted the skipper beforehand to warn him that I did not eat fish and he had told me that there were no problems. It was not made WhatApp group before and no one was asked for preferences on breakfast, food, alcohol etc etc. We found ourselves with a galley made without sharing with a charge of 320 of wine, spirits well hidden in the shopping at the supermarket and about 500 euros of fish. I have never been offered any alternative but an egg omelette (with 50 euros spent on eggs) and twice a participant friend of the skipper made me a sauce with great controversy because the skipper imposed himself as a cook denying us to be able to cook. When I represented my need, I was literally pilloried and forced to eat salad that others ate as a side dish after succulent fish dishes. Now I'm wondering if I could get a refund??!! I had already used your platform and I had found it well, this is the reason why I used it again. I represent that we did not have the skipper indicated but there was a switch with his father Andrea who imposed the presence of his partner for two days (I do not know if he contributed to the galley). criticized me continuously because I did not eat fish and in general everyone for everything and in particular those who did not drink as much as he did. The whole group had difficulty communicating with the latter and in the last few days the situation has worsened. If you want further details write to me

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