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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

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

Greece: Saronic Islands and Athens area

6 days - 7 nights

3 departures available

October

€1,300

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

2 departures available

October - November

€585

Per person

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4.9

Super!

The fantastic Saronic Islands and the surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

2 departures available

October

€750

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

3 departures available

October

€570

Per person

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4.8

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Squid Festival on the Island of Capraia - 2 boats in company (22 seats)!

Italy: Tuscany

3 days - 2 nights

One departure available

October

€280

Per person

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4.7

Voices of the Pelagos: artistic-scientific whale watching expedition with WWF guide

Italy: Tuscany

4 days - 4 nights

One departure available

October

Starting from

€453

Per person

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5.0

Super!

From Mykonos to Athens by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

September - October

€950

€570

Per person

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4.9

Super!

Adventure weekend in the Egadi Islands

Italy: Aegadian islands

3 days - 2 nights

5 departures available

October - November

€350

Per person

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4.8

Super!

Squid Festival on the Island of Capraia - 2 boats in company (22 seats)!

Italy: Tuscany

3 days - 2 nights

One departure available

October

€280

Per person

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5.0

Super!

Barcolana Weekend: experience the largest regatta in the world

Italy: Venice and the Gulf of Trieste

3 days - 2 nights

One departure available

October

€420

Per person

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4.8

Super!

Experience the sea in October!

Italy: Tuscany

2 days - 2 nights

4 departures available

October

€200

Per person

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4.9

Super!

Two days in Elba without worries with a professional skipper

Italy: Tuscany

2 days - 2 nights

One departure available

October

€315

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

19234 reviews

All-Inclusive Sailing: Capri, Positano, Amalfi

09/28/2026

Nathalie P.

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FR

Very nice cruise with our skipper Alessandro who was very knowledgeable and very attentive. Highly recommend.

Let's discover Portofino, Santa Margherita and Sestri Levante together

09/28/2026

Cristina A.

-

IT

Beautiful ride, professionalism and friendliness at the top
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A week sailing in the most beautiful places in the world

09/28/2026

sara s.

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IT

A wonderful experience!! We stayed a week with Piero and Giuseppina booking the whole boat. Despite the adverse weather forecast, the weather was always good. But we have always relied on the wise course decisions of Piero, who in addition to always being attentive and scrupulous, is a very good skipper in all aspects: his daily lessons will not be forgotten! A special mention goes to Giuseppina, with whom I immediately found myself in tune even with just a smile. His cuisine is spatial, better than that of many restaurants in the area! But Piero in the kitchen is not bad either, his spaghetti are excellent! Thank you for this trip and for the company!

Cyclades from Milos to Milos

09/28/2026

Alessio P.

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IT

Fabio is a very precise and professional skipper, thanks to the weather we were able to respect all the descriptions and the boat was really beautiful and comfortable. Although it was not within his competence, we tried some really good Roman dishes. Very skilled with the scientific 😎🤣 scopone It is a thank you to the legendary Irene. Highly recommend the experience

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