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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

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August - September

€1,020

Per person

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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

One departure available

July

€410

Per person

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5.0

Super!

Learn to sail in a week in the Tuscan Archipelago

Italy: Tuscany

6 days - 6 nights

One departure available

August

€849

Per person

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5.0

Super!

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

5 departures available

September - November

€250

Per person

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5.0

Super!

Ibiza & Formentera: one week with cook on board

Spain: The Balearic Islands

6 days - 6 nights

One departure available

September

€750

€675

Per person

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4.8

Super!

A week of sea, volcanoes and fun in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

6 departures available

July - September

Starting from

€690

€621

Per person

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5.0

Super!

Ogliastra to go crazy, mini-cruise among the wonders of Sardinia

Italy: Southern Sardinia

4 days - 3 nights

2 departures available

July - September

€740

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

5 departures available

August - October

€650

Per person

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4.9

Super!

Sailing weekend in Istria

Croatia: Istrian peninsula

3 days - 2 nights

6 departures available

July - October

€260

Per person

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4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

2 departures available

September

€441

Per person

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4.8

Super!

From the Pontine to the Aeolian Islands - Adventure, Navigation, and Relaxation - One Way

Italy: Aeolian Islands

5 days - 6 nights

One departure available

July

€590

Per person

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4.8

Super!

Weekend on Elba, sea, colors and scents.

Italy: Tuscany

2 days - 2 nights

2 departures available

July - September

Starting from

€200

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

17870 reviews

From Piraeus to Mykonos: the Aegean by sail, with skipper and on-board kitchen

06/24/2026

Cesare S.

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IT

Annalisa and Emanuel were fantastic hosts! They made us sail and cooked us excellent meals making us spend a beautiful week discovering the sea of the Cyclades and its beautiful bays, despite the Meltemi

We have known the Aeolian Islands for 20 years, live them with us!

06/24/2026

Alessandro O.

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IT

The Aeolian Islands were a destination that I had wanted to visit for a long time and thanks to this experience, it fulfilled all my expectations by going further with the experience of experiencing the sea from a boat. A crew of nice people with whom I shared laughter, relationships and wonders of the places was fundamental. The skipper Pasquale was fundamental, a great person, who showed professionalism, availability and humanity to those like me who were experiencing this type of adventure for the first time, who made everything simple, pleasant and unforgettable. I recommend everyone to experience the emotions that leave such a holiday made of enchanting views, smells, Mediterranean colors that regenerate the body and mind.

Mini-cruise with WWF guide in the heart of the Tuscan Archipelago

06/24/2026

Giovanni G.

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IT

I would like to express my complete satisfaction with the experience. A special thanks goes to the biologist Elisa: an extremely prepared professional who was able to satisfy all our curiosity with precision and a wealth of details. I really appreciated his competence, professional rigor and his great kindness. I also thank the skipper Niko for the excellent welcome on board his beautiful boat. The navigation was excellent, supported by a constant presence and considerable experience. I was enthusiastic about the activity carried out and the excellent company of the sailing companions.
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Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

06/24/2026

Isla W.

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CA

My mom and I had an amazing time on board Bledar’s boat! I am celiac and was nervous about eating on board but Bledar was so good at making sure I had a lovely gluten free meal without cross contamination. And above all, the trip was awesome; hiking up volcanos, incredible swimming spots, the delicious food and people we met along the way, we will definitely be back! We already miss all the laughs we had at dinner watching the most beautiful sunsets. And his skipper Alessandro was most helpful and kind, highly recommend!!

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