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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

Split archipelago, Hvar islands, Brac - with Hostess and full board

Croatia: Split Archipelago

7 days - 7 nights

20 departures available

June - October

Starting from

€1,100

Per person

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New

Cruise between the Maddalena archipelago and South Corsica

Italy: Northern Sardinia

7 days - 7 nights

One departure available

October

€585

Per person

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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

3 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

34 departures available

April - November

Starting from

€650

€618

Per person

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4.7

Tenerife and La Gomera aboard an 18 m ketch - ALL-INCLUSIVE

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

€900

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

2 departures available

April - October

Starting from

€250

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

19267 reviews

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

10/12/2026

Fiona B.

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AU

Andrea was a fantastic skipper and Carol was a great hostess. The week was filled with beautiful beaches, delicious lunches and great conversations and was a perfect way to relax for a week. It was fun sailing along with the second yacht, and we had a great time playing volleyball together. The boat was comfortable and plenty of spots to relax above deck in the sunshine. I highly recommend this trip. Andrea and Alessandro are expert sailors who take the very best care of their customers and always put safety first - but maximize fun and stunning scenery throughout. The hosts on board (Carol and Carlo) were exceptional - making delicious and varied food each day. And little Mattias - the best boat poodle there ever was! What are you waiting for - book this adventure. Thank you Andrea, Carol and Marta for an unforgettable week.

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

10/12/2026

Lee T.

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GB

Wow I had a fantastic week with Alessandro and Carlo, they both were so kind and caring and went out of their way to ensure we had a fantastic trip, even when the weather on the last 2 days meant we had to change the itinerary Ale found a way to ensure we didn’t miss out on visiting new places. Carlo was a fantastic host, his cooking was amazing and so much to eat every day as well as his friendly smile and always there to help. Alessandro, what a great guy, a great skipper, always ensuring we were happy and safe and would go out of his way to take us ashore and find the best restaurants. I have made a new friend for life and will be back next year 🤣 Thanks to you both for a memorable holiday
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Sailing in the magical Sardinia of the South

10/8/2026

Sebastiano F.

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IT

I was looking for a super sea to continue improving my sailing knowledge... With the staff of [hidden] I was able to find all this combined with irony and lightness that never hurt! P.S. Extremely recommended for sailing enthusiasts who want to grow Thank you very much to Gianluca, Valeria and Michela!
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From Mykonos to Athens by sail, with skipper and on-board kitchen

10/7/2026

manuela c.

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IT

Annalisa and Emanuel were professional and nice, we unfortunately had the worst week of wind in sailor's memory and we were forced to always stay still without sailing except for 3 hours on the first day so I can't talk about the cruise destinations except for syros that they propose and that, unlike other islands, it is not crowded and therefore maintains something of the Greek spirit with beautiful villages and has beautiful trekking and beaches (the beaches unfortunately due to wind were not frequentable but I saw them in the treks). Beautiful and spotless boat absolutely comfortable. What can I say? Hope to see you again next year! Maybe with better luck for the climate! Thank you

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