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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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4.6

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

Starting from

€1,260

€1,070

Per person

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4.7

Flotilla Marmaglia Sun & Fun - Croatia - WOMEN SEATS ONLY - BUS INCLUDED!

Croatia: Kornati Islands

7 days - 7 nights

2 departures available

August

Starting from

€1,180

€800

Per person

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4.7

Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

Greece: Cyclades

6 days - 7 nights

One departure available

August

€1,290

€1,190

Per person

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4.8

Super!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

August

Starting from

€920

Per person

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4.7

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August - September

Starting from

€795

Per person

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4.8

Super!

Sardinia and Corsica on a Classic Sailing Ship 4 cabins plus crew

Italy: Northern Sardinia

6 days - 7 nights

2 departures available

August - September

Starting from

€600

Per person

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4.8

Super!

Sailing and Freediving in the sea of Sardinia and Corsica

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August

€870

Per person

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4.8

Super!

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

9 departures available

August - October

Starting from

€1,300

€1,040

Per person

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4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

7 departures available

August - October

Starting from

€590

Per person

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4.7

In the blue of Capri and the infinity of the Amalfi Coast

Italy: Naples & Amalfi Coast

2 days - 2 nights

4 departures available

October

Starting from

€275

Per person

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4.8

Super!

Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

Italy: Tuscany

6 days - 7 nights

2 departures available

August - September

Starting from

€900

Per person

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5.0

Super!

Sailing week North Sardinia and South Corsica

Italy: Northern Sardinia

6 days - 6 nights

One departure available

August - September

€950

Per person

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Reviews - Sailboat holidays & skippered tours

18283 reviews

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Whale watching cruise with WWF guide in the Corfu archipelago

08/2/2026

emanuela f.

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IT

This is my message already shared with the travel group and that I use here too. Thank you Sailsquer! Good morning everyone. This is a message that I feel I can make to close without hesitation or rancour a certainly unique experience. I am a kindergarten teacher where common rules, respect, kindness, knowing how to live civilly and sharing are mainly taught. I left with a load of enthusiasm due to the desire to travel (something I couldn't do for some time for family reasons) and a particularly hard year, so excuse me if I tried to live every single moment with an energy for you, probably, exaggerated. Working to make others feel good, like making a coffee, is an act of kindness that I gladly did but that, evidently, for those like Rocco who has been traveling for days and is perhaps tired of these dynamics, was not always welcoming😩 (dear Rocco, there were several things that upset you, perhaps with clearer indications given at the beginning of the trip you could have avoided several embarrassing situations). Having said that, and to return to the starting point. The review that is often done on the way back from a trip is done first here. Because we shared a journey that everyone chose for different reasons, of course, but all to be respected. I apologize therefore if I have been exaggerated for some, intrusive for others, too noisy at certain times or too silent at others. I just tried to live all the moments and take home as many memories as possible. Overall, for being a group trip with unknown people, it was definitely interesting. You can't please everyone or be friends with everyone but you can learn to recognize and accept diversity. The whale watching experience was the most unifying and exciting part. I thank, therefore, Don for being a prepared guide and extremely helpful and patient even with me and my difficulty in memorizing the names of the children. ceratacei😁 The most beautiful gift that nature has given us, not always forgiving, have certainly been the sightings. Wonderful experience to be surrounded by dozens of common dolphins in the beautiful mare nostrum 😉 Pure emotion!!!! Dear travelers, I appreciated the availability of some of you, the confidentiality of others and the patience of all. Yesterday Anna asked us if we would do this experience again, I immediately said no but, thinking about it, in another context that does not include long days of transfers, such as the Otranto channel, it is not to be excluded because you have less tight schedules it would also help those who have to face several weeks in a row like our skipper and our guide, in order to manage both the uncertainties of the weather and personal fatigue more serenely, to the benefit of a serene and relaxed climate on board. Praise to Rocco for his sailing skills and for sharing his Audace and his time that I know how difficult it can be for those who love boats and the sea. I greet and wish everyone fair winds, on the boat as in life Ad maiora Emanuela F. P.s. I still😉🌬⛵️🌊🐬 sway
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

08/2/2026

Antonella R.

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IT

Kindness:: there is no better word to describe this holiday week. We were literally inundated not only by the beauty of the places, but above all by the infinite care, attention and warmth that the crew reserved for us from the first to the last day. Alessandro the skipper: impeccable from every point of view, a person you can rely on with your eyes closed. He organized wonderful excursions every day, always leaving us maximum freedom of choice. Carlo, the steward: a true guardian angel! He pampered us with delicious dishes and more. Being a great swimmer, he accompanied us on beautiful swims in the most beautiful bays, enriching the trip with fascinating anecdotes about the various areas visited. Eros: the "little dog" of the crew, of infinite sweetness. Added value: sailing together with the boat of Andrea, Alessandro's brother, made the experience even more welcoming and familiar. A journey that leaves you with the memory of wonderful people and the value of small gestures. Super recommended holiday!!
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Sailing cruise to the Pontine: wonders a stone's throw from Rome

08/2/2026

Tiziana L.

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IT

Every experience leaves its mark for better or for worse, it is always an absolutely subjective evaluation. I am an owner and I know how difficult it is to share your boat with others but from here to be jealous so much that it almost puts anxiety in your guests at every step is there. Sailing? A bit of just jib on the way back, sailing with the engine and with the pilot car for about 10/15 minutes on a boat that in any case to move would have had to open jib, staysail and mainsail and have at least 15/20 knots of real wind to move given its weight of 13 tons on 13 meters of boat, bowsprit included. The weather conditions, except during the first transfer to Ponza, have always been favorable for a very quiet sailing because 5 of us were experienced sailors, we would not even have caused damage. Disappointment for those who expected to sail. The boat is uncomfortable for eight people + skipper, there are a few ants everywhere, the kitchen set-up (non-tilting hob) and only one small refrigerator absolutely unsuitable for the number of people, the cabins and the small, unventilated berths are basically uncomfortable except perhaps one that I did not get to see that had already been assigned by the skipper to two friends even before we had all arrived (absolutely incorrect and out of the picture). regulation), Antonio decided everything, from the accommodation in the cabin, to the sleep/wake rhythms, to the daily menu in a nicely dictatorial manner. I am sure that he does his best in sympathy and hospitality but the level is a bit low, (my children, who do not know how to cook, cook better than Antonio). For the rest, the pontine are fantastic, the weather favorable and the travel companions almost all fabulous, We had so much fun and enjoyed the beauty that surrounded us, we were all in the same boat, so! You probably won't publish this review, I understand it and I don't care much but it's right that you know in the end in 6 out of 8 participants we said never again this man and this boat. In short: Beautiful holiday, the islands are a wonder and the company really fabulous, fortunately almost all seafarers! The weather was perfect and we were able to enjoy so much beauty, too bad we didn't sail because the boat itself, in addition to being small and uncomfortable for 8 + 1 adults, is absolutely not suitable for the times of a holiday and then, you know, skippers often reluctantly open the sails. I think Antonio gave the best of himself: he cooked, but he is not a chef, he put up with our presence by filming us nicely every 3/5 minutes for everything, and heroically with a knee out of order he took us around fantastic caves and coves.
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

08/2/2026

Valentina B.

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IT

Alessandro is super nice and helpful. Plan the itinerary and organize the time and excursions by dinghy with great care to give the opportunity to explore the most beautiful places, all beautiful experiences. Carlo's care and cooking are pampering that you don't expect to find on a boat, a real gift! We cannot fail to mention Eros, a four-legged ☺️ skipper of infinite sweetness. Sailing in tandem with Andrea and his boat adds safety and liveliness to the cruise.

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