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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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5.0

Raja Ampat: New Year's Eve in the last paradise

Indian Ocean: Indonesia

12 days - 12 nights

One departure available

December - January

€2,070

Per person

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4.8

Offshore and night navigation course on cabin cruisers

Italy: Tuscany

3 days - 2 nights

One departure available

October

€332

€299

Per person

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4.4

Guadalupe to St. Martin via Antigua, Barbuda, St. Barth, and Anguilla

Caribbean: Saint Martin

14 days - 14 nights

One departure available

February

€1,490

€1,341

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

4 departures available

October - November

€723

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

5 departures available

October - November

€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

3 departures available

October - November

Starting from

€220

€198

Per person

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New

Weekend in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

2 departures available

May

€450

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

One departure 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

3 departures available

April - October

Starting from

€250

Per person

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4.1

Corso di vela RYA Day Skipper Pratical sailing

Italy: Tuscany

4 days - 4 nights

11 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

19257 reviews

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Saronic Islands and surroundings of Athens

10/5/2026

Erjon G.

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DE

Andrea is great Captain, we had amazing time even the weather was not our side still we enjoyed a lot.

Aeolian Islands: between sea and authentic flavours

10/5/2026

Giorgia P.

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IT

Wonderful experience!! Well maintained boat; very comfortable to have a bathroom available in each cabin. The tour allowed us to visit enchanting places, swim in crystal clear waters and enjoy excellent fish dishes and exquisite desserts. Carlo, our skipper (Merchant Marine Officer) has put his skills and abilities at our disposal. End of September was a good choice, always sunny without ever sultriness, the right water temperature for wonderful baths. Happy and fun company, with Lorenzo I was able to share culinary secrets in the kitchen. With a bit of luck, we sailed for a stretch in the company of a pod of dolphins. A holiday to be repeated and recommended. Giorgia P.
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

10/5/2026

Aldo B.

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AT

My partner and I had an amazing week at sea, and a big part of that was our crew. Alessandro, our skipper, was highly professional and made us feel safe and well looked after at every moment. Carlo, our steward, was warm, attentive and always ready with a smile. The route between Corfu, Paxos and Antipaxos was stunning, with crystal-clear water and charming harbours. The crew went out of their way to make the trip special. We explored sea caves by dinghy, played an unforgettable volleyball match in the middle of the sea, and got great restaurant recommendations for our evenings ashore. Carlo's lunches on board were delicious, fresh and beautifully prepared. Alessandro and Carlo truly made this trip. We would happily sail with them again and recommend them to anyone looking for a relaxed, fun and well-organized holiday on the water. Thank you both!
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Maddalena Archipelago, southern Corsica: wonderful Sardinia

10/5/2026

Michelle B.

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US

Mossimo and Valentina were superb! Incredible sailing, delicious food, taking us to stunning locations it far exceeded my expectations! I highly recommend sailing with them. Cheers! Michelle

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