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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

Let's sail in relaxation on Lake Garda - All Inclusive

Italy: Lake Garda

1 day - 0 nights

6 departures available

October

€150

Per person

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New

Premium

All inclusive sailing cruise on Dufour 48 in Ionian Greece with hostess

Greece: Ionian Islands

7 days - 7 nights

One departure available

September - October

Starting from

€1,645

Per person

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5.0

Capraia and Elba Island - Sun, Sea and Fun!

Italy: Tuscany

4 days - 3 nights

One departure available

October

€400

Per person

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5.0

New

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

3 departures available

October - November

€250

Per person

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5.0

EOLIE IN RELAX - Boat with 3 cabins and 3 bathrooms

Italy: Aeolian Islands

6 days - 7 nights

One departure available

October

€607

Per person

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4.9

Relaxing weekend in the Aeolian Islands: Lipari, Vulcano and Salina

Italy: Aeolian Islands

3 days - 2 nights

4 departures available

October

€320

Per person

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4.4

Premium

Cruise to discover Corfu and Ionian Greece - Hostess & Half Board

Greece: Ionian Islands

7 days - 7 nights

One departure available

October

Starting from

€845

€676

Per person - min 2 pax

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4.8

Weekend of emotions in the Blu Pontino

Italy: Pontine Islands

3 days - 2 nights

One departure available

November

€225

Per person

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4.8

Sunny weekend on Elba from Friday to Sunday

Italy: Tuscany

3 days - 2 nights

One departure available

October

€325

€309

Per person

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5.0

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

Croatia: Split Archipelago

7 days - 7 nights

One departure available

October

€1,100

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

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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