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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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4.7

Amazing Pontine Islands on a sailboat with private bathrooms

Italy: Pontine Islands

3 days - 2 nights

2 departures available

September

Starting from

€312

Per person

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4.8

Super!

Come and discover the Saronic Islands from Poros

Greece: Saronic Islands and Athens area

6 days - 6 nights

One departure available

September

€600

Per person

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5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

6 departures available

September - October

Starting from

€370

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

3 departures available

September

€490

€466

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

3 departures available

September - October

€650

Per person

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4.9

Super!

NEW YEAR's Eve between sea and land in Norway: chasing the Northern Lights - COTTAGE + SAILBOAT

North Sea: Norway

11 days - 11 nights

One departure available

December - January

€1,300

Per person

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5.0

Super!

Mykonos and the Western Cyclades by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

2 departures available

September

Starting from

€1,000

€750

Per person

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4.9

Super!

Sail to the edge of the world among the wonders of the North (cottage + sailboat)

North Sea: Norway

7 days - 7 nights

One departure available

October

€1,200

Per person

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5.0

Super!

Pula - Monfalcone

Croatia: Istrian peninsula

6 days - 6 nights

One departure available

August - September

€950

Per person

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4.8

Super!

From Tavolara to Ogliastra, the great emotions of Eastern Sardinia

Italy: Southern Sardinia

5 days - 4 nights

One departure available

September

€1,200

Per person

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4.9

Super!

Baie and fast sailing from Milos to Paros

Greece: Cyclades

6 days - 7 nights

One departure available

September

€940

Per person

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5.0

Super!

Weekend in the Tuscan Archipelago with PROFESSIONAL COOK SKIPPER

Italy: Tuscany

2 days - 2 nights

One departure available

September

€250

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

18934 reviews

Sailing among the Islands of Ulysses. Stewardess on board

08/30/2026

Giovanna Paola C.

-

IT

Nice experience

Southern Corsica & Maddalena - embarkation and disembarkation from Tuscany

08/30/2026

DEBORAH F.

-

IT

It was a great week! ⛵️ We sailed between Elba, Northern Corsica and Capraia. Unfortunately, due to weather conditions, it was not possible to follow exactly the planned itinerary, but this did not detract from the beauty of the holiday. In fact, most of the time we were able to open the sails and fully enjoy the thrill of sailing. Francesco, the Captain, was able to involve the whole crew, transmitting his passion for sailing and making everyone part of the experience. He is a person who is very attentive to everyone's needs, competent and with great experience, but above all capable of instilling safety and harmony on board. The boat is comfortable and spacious. We spent a week between wine, laughter and sea . And there was no shortage of good food either, thanks to the luck of having missed chefs on board! A truly top crew. My experience was super positive; unlike what I read in some reviews, I highly recommend the week aboard [hidden] with Francesco.

Sailing among the Islands of Ulysses. Stewardess on board

08/30/2026

Laura C.

-

IT

A great week! Thanks to the skipper Lionor always attentive and professional and to Ansel best sailor and an excellent cook, they made this boat holiday an unforgettable experience. Highly recommended!

North Corsica & Tuscan Archipelago: we love to travel a lot

08/30/2026

Fiorella F.

-

IT

Lucky experience for time, boat and company, as well as for the competence shown by Marco, an experienced and far-sighted captain who was able to foresee and manage every situation well. Highly recommend to try!!

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