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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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New

Gulf of Noli, bay of the Saracens, cave of the Falsari up to Varigotti

Italy: Liguria

1 day - 0 nights

3 departures available

September

€99

Per person

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5.0

3 days in the wild Aeolian Islands - All inclusive & flexible dates

Italy: Aeolian Islands

2 days - 2 nights

6 departures available

September - November

Starting from

€723

€650

Per person

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4.7

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

6 departures available

September - November

Starting from

€700

€665

Per person

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4.7

Tenerife and La Gomera aboard an 18 m ketch

Atlantic islands: Canary Islands

6 days - 7 nights

10 departures available

January - December

Starting from

€900

Per person

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5.0

New

Basic and advanced sailing courses

Italy: Liguria

2 days - 1 night

4 departures available

October - November

Starting from

€220

€198

Per person

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4.7

Squid Festival- Capraia Island

Italy: Tuscany

2 days - 2 nights

2 departures available

October - November

€250

Per person

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New

Weekend in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

2 departures available

May

€400

Per person

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4.7

From Funchal to Lanzarote: adventure and unforgettable emotions

Atlantic islands: Canary Islands

6 days - 7 nights

One departure available

December

Starting from

€900

Per person

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4.3

The perfect holiday on Europe's hottest and most glamorous island

Malta: Malta

6 days - 6 nights

2 departures available

October

€690

Per person

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4.7

Tuscany and Liguria, we sail between the Apuan Alps and the Gulf of Poets

Italy: Liguria

2 days - 2 nights

One departure available

April - May

€300

Per person

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5.0

New

Weekends immersed in the blue of the sea and the green of the island of Elba

Italy: Tuscany

3 days - 2 nights

One departure available

October

€275

Per person

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4.1

Corso di vela RYA Day Skipper Pratical sailing

Italy: Tuscany

4 days - 4 nights

12 departures available

October - December

€1,400

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

19222 reviews

Fast Sailing Experience between Authentic Islands and Good Food

09/27/2026

Janine E.

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CH

The sailing week was a unique experience. Annalisa & Lorenzo have a lot of experience & we have always felt comfortable. Everything was very well organized & the food was really delicious! Most of the time we spent the night in lonely bays. Thank you very much for these great memories.

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

09/27/2026

Maria luisa G.

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ES

It was a spectacular trip, there was an age difference between us but the guys were great and the skipper Andrea was amazing too. I recommend it.
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North Corsica & Tuscan Archipelago: we love to travel a lot

09/27/2026

Tudor M.

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IT

Super positive feedback for Marco! Beautiful experience.

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

09/27/2026

Anna R.

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DE

I had a fantastic time! The Ionian Islands are really gorgeous, I really didn't expect the impressive beautiful landscape. The villages we visited were also picturesque and Alessandro always had tips on where to get delicious food. The boat is amazing, super clean, the mattresses really comfortable, you really feel comfortable on the boat. Unfortunately, I got sick during our trip and Alessandro took great care of me, I was able to stay on board in the evening and eat with "The Crew", he picked me up earlier from activities and brought me back to the boat. And despite my bronchitis, I really had a fantastic time, a lot of sleeping on and below deck, constant rocking: A dream!! And very important: Our dog Aeros makes the stay for dog people really perfect!!

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