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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!

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

7 departures available

August - October

Starting from

€1,300

€910

Per person

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4.7

In the blue of Capri and the infinity of the Amalfi Coast

Italy: Naples & Amalfi Coast

2 days - 2 nights

4 departures available

October

Starting from

€275

Per person

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4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

September - October

Starting from

€700

Per person

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4.8

Super!

Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

Italy: Tuscany

6 days - 7 nights

One departure available

August

€1,100

Per person

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4.7

Feast of Santa Candida in Ventotene

Italy: Pontine Islands

3 days - 3 nights

One departure available

September

€420

€378

Per person

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5.0

Super!

Learn to sail in Liguria: First level sailing course

Italy: Liguria

2 days - 1 night

One departure available

October

€220

Per person

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5.0

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

5 departures available

September - October

Starting from

€570

Per person

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4.8

Super!

Week end in Costa Azzurra

Italy: Liguria

2 days - 2 nights

2 departures available

August - September

Starting from

€360

€300

Per person

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5.0

Super!

Sailing week North Sardinia and South Corsica

Italy: Northern Sardinia

6 days - 6 nights

One departure available

August - September

€950

Per person

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5.0

Super!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

6 departures available

September - October

Starting from

€570

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

Starting from

€585

€527

Per person

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4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

September - October

Starting from

€750

€675

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

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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

18716 reviews

On board with the chef at the Egadi Islands

08/23/2026

Stefania C. P.

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IT

What can I say: fantastic week! Max experienced and kind captain, a profound connoisseur of the Egadi both at sea and on land, as well as being an exceptional chef. The sailing from Marettimo to Levanzo with only the sound of the wind and the sea will remain forever in my album of the most beautiful memories. Wonderful group with which harmony was created from the first day thanks to the Neapolitan sympathy of the DJ Lillo who, with the play lists expertly prepared by Alice, cheered all the evenings in the roadstead (memorable the sold out of Cala Rossa with the crews of all the boats on deck dancing). See you soon and fair winds Max!

Different flotilla in Ionian Greece: nature, new friends and fun

08/23/2026

Noemi M.

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IT

Flotilla different - Temptation Boat (15–22 August 2026) Fun week, recommended if you want to party and enjoy the sea from the sea. The tamptation boat of this edition turned out to be the stage for Neapolitan theaters, absolutely appreciated, with gatherings around the evening fire in which some competitors would have liked to burn the sail at the sight of the explosive passion of the partner on duty with other protagonists, while others dived into the aft cabin for savory quickies. In short, between laughter, flirting and lots of sea, fun is guaranteed. Keep in mind: as for the budget, you need to calculate about € 150-200 more than what is communicated (obviously excluding dinners on the ground and personal purchases). In essence, about 500-600 euros are spent per person between the galley and the common fund. As always, boats are pre-composed: so you need luck. There is obviously the risk of meeting the new lawyer (I use the overextended feminine only because it is considered, by most, the most politically correct) on duty who paws at the desire to explain to bystanders in detail the contractual clauses not respected or the sciura who expected a waiter on board devoted if necessary to masseur and palm waver or, again, in need of fresh water for soft and shiny hair in quantities disproportionate to the capacity of the tanks. At the same time, you can be lucky enough to be assisted by an on-board resuscitator who takes your blood pressure without the need for a watch, by an osteopath capable of unblocking your back in 3 moves, etc. In short, a little adaptation is required. Few comments in relation to the organization: the tour is very nice, personally I would have preferred to move more but I understood, talking to the others, that the itinerary as it is organized is optimal. The post-registration emails were unclear, especially for those who are at their first experience and read them overwhelmed by work papers and stress, but it seems to have been a mistake that will not be repeated. Finally, a part of the holiday depends on the skippers and co-skippers: a note of merit goes to Roberto, Claudio, Antonio, Gian and Luca (I apologize if I don't mention the others but these are the people who took care of me!). Thanks also to Alessandro, but with a clarification: he was an excellent fleet leader capable of ensuring everyone's safety; however, I hope that in the future he will be able to better hide his fatigue and a few too many anxiety. Overall: Absolutely recommended experience!
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Corsica as you've never seen it before!

08/23/2026

Marta F.

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IT

A wonderful week! Marco a perfect skipper and Corsica a dream!
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La Dolce Vita on a sailboat: discovering the Côte d'Azur

08/23/2026

MATTIA B.

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IT

A week in excellent company. Very attentive and helpful skipper, we moored both in the port and in the roadstead, when we could for two days we opened the sails. A nice experience

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