The whole truth, and nothing but the truth. Reviews by those who have actually been onboard.

Here is what our travellers say about holidaying with Sailsquare.

Only those who have taken part in an experience can leave a review. Reviews based on real experiences lived.

Latest reviews.

We had a fantastic sailing week exploring the Northern Sicily and Eolian Islands Lipari and Volcano with Frizzante. Mark is a competent and professional skipper. The ambience in the shipshape boat is forthcoming and relaxed. We enjoyed good food, music and sailing. Happily recommended!

Excellent sailing trip. I had so much fun!

Great skipper and crew. Obviously highly knowledgeable and experienced about sailing and the sea. Beautiful boat with lost of space - felt as one with nature. The skipper and crew went out of their way to make sure we were comfortable and also had a fun time - trips to shore, nights chatting and singing under the stars, great food. Saw some amazing sealife - dolphins (two types), shark, tuna, turtles. Was great to have a very knowledgeable WWF scientist with us explaining about the sealife and challenges all the way. A magical experience. Very much looking forward to another adventure soon.

two words, fair and professional????

I guess the communication was the biggest issue, despite speaking some English relaying information back was poorly executed by the skipper, which have cost me my flight, some lack of empathy during hiking trips instead of allowing time to rest he was pushing for faster or take the bus. Speaking French round the table despite 2 people not speaking the language out of 4 was little rude, otherwise he was very caring when I was unwell during sailing at times and provided effective medical solution, The trip however was a blast, beautiful islands and locals with packed activities, and amazing memories to remember.

It’s now March and we had our first sailing holiday with Mike last October and not a day has gone by where we’ve not thought about our amazing adventure. Mike is a fantastic teacher, he shared his passion for sailing, made us all feel safe and took us to the most beautiful parts of the islands. We will definitely be back x

Alessandro is an attentive and reliable skipper. His sympathy and availability convinced me immediately to confirm the holiday with him and the choice turned out to be excellent. The navigation was pleasant and flew, Alessandro proved to be reliable, attentive and able to make the group feel at ease. The boat is nice, tidy, comfortable even in winter and very clean. All this, combined with laughter and good shared moments, makes me absolutely recommend a holiday on board with him.

I have said this a couple of times, so please forgive me if I am repeating myself. My experience with Capt. Fabrizio was fantastic. His boat is comfortable and very well appointed, his cooking is of chef quality, and his role as an instructor is phenomenal. He is very clear in his explanations, and gives the crew plenty of opportunity to practice the manouvers without getting stressed or uptight. He is as cool as ice, making small corrections or suggestions for improvement in a relaxed and very effective way. I recommend him without reservations!

Our trip from beginning to end was "plain sailing". Communication with Mike was great and he gave me confidence to book as this was our first time with SailSquare. Mike looked after us like we were family, nothing was too much trouble. He is so relaxed and calm and took so much time to explain how to sail, he's a natural teacher! I would not hesitate to go again. Thanks Mike.

Superb cruise from Capo d'Orlando in Sicily to Nettuno over 8 days on a clean boat, big, easy to maneuver, in the company of Alberto who made us live beautiful experiences: swimming behind the boat in front of Stromboli, dinner at the port of Ischia, unforgettable arrival in Capri at sunrise, walk with a view in Palmarola, paddle in a beautiful bay of Ponza. I learned a lot about sailing and participated with pleasure in the maneuvers, but without ever feeling obliged. The boat is large, clean, well maintained, functional and the atmosphere on board is always good.

We really enjoyed our trip. The boat was nice and spacious though had it been a full trip then it would have been somewhat cramped. The sailing ended up being more challenging than I had expected as winds were quite high but we enjoyed that. Do take a waterproof jacket (we didn’t!). We did have to change the route because of the winds but we really enjoyed the variety of island stops - Places you would be unlikely to get to without your own boat. Rea was a great skipper and had lots of good tips of places to go on the islands .

I joined Alberto on his yacht in Sicily for a 7 day cruise to Nettuno in late September. The 52’ yacht was well maintained and fully functional with many luxuries including paddle board, snorkelling equipment, two fridges and electronically operated heads. Alberto was a very experienced skipper and I felt safe at all times. There was plenty of opportunity to learn as much or as little about sailing as you wanted during the week. We enjoyed many hours of cruising with the sails up and called at a number of beautiful Islands. Alberto found the most sought after anchorages and moorings as well as organising treks ashore which meant we saw the best of the Islands we called at. The crew were all great and I would recommend cruising with Alberto on his beautiful yacht.

It has been a magical week sailing around the Ionians with Andrea! He is very accommodating and welcoming, and despite early age does have some solid sailing experience and knowledge of the sea, navigation and weather conditions. Can't recommend highly enough to anyone looking for a sailing experience, and looking forward to another adventure in the sea! Alessandro was a great hostess during the journey, not only looking after the guests, cooking, cleaning for us but just a fun company to be around, taking us to hidden caves and arranging other fun activities!

We had a wonderful time on board. Great company, great food, manage to visit some really lovely little towns and hike the Path of the Gods. I feel completly zen after the holiday. Would highly recommend and book again.

Thanks to Alberto we had a marvelous week of 6 islands in 6 days, vulcans, grots, caves, increadible lagoons and sails. Alberto is friendly, cooperative and very helpful, he does not speak a lot but if you tell him about your needs, he takes them into consideration at once and adjusts the program. His boat is comfortable and well cared. He is not money oriented at all (some skippers bring you only to the places where they get commissions), on contrary he helped us to economize the money. He knows a lot and loves the sea and navigation. You feel well protected and cared when you are with him on the boat. We'll repeat the experience with pleasure, thanks Alberto!

George is the owner of the sail boats and he has at least 2 skippers that he works with (Eric & Georgios), so your experience can differ really depending on which skipper you get. George is a really cool guy with lots of great tips and local insider tips for taverns, caves and beaches, however, he is not the skipper. Our skipper was Eric. Eric is a polite person, we felt safe with him as he is a experienced sailor. Unfortunately, he preferred speaking French on the boat, which wasn’t so nice for the international crowd. My boyfriend was really curious to learn about sailing, but the English communication was an issue for that. I’d recommend the trip for French speaking tourists. He is also a bit introverted, so if you want to have someone entertaining the crowd, giving proactive advise, then this is not the skipper for you. However, overall Eric is a great person with a good heart. He brought us to some hidden gems for swimming and knows a few nice taverns in the area.

Fantastic week on the Giada. Amazing time and looking forward to sailing with her again in future :)

Highly recommended! Great memories with Riccardo, Giada and the team! Hope to come back soon!

Dears, Highly reccomend Marco as skipper (together with his TEam) ;-) Great experience, relaxing armosphere, clear roles, super food- what else can make you vaccations perfect? Great time!

a beautiful holiday, a very good and experienced crew, Massimo is a good and experienced captain, I was lucky to have wonderful people ????

One of the most beautiful holidays of our lives, with the right mix of notions about sailing, relaxation, and discovery of the natural wonders offered by the marine park of Tavolara. For some of us it was our first time sailing, and I must say that the holiday was above all expectations. Valerio and Ada put anyone at ease and were extremely kind and helpful for the duration of the holiday. A heartfelt thanks! See you next :)

I traveled solo to sail the Istrian Peninsula with Maurizio and other crew. È stato perfetto! In short it was a fantastic trip. A highlight was Maurizio’s thorough knowledge of the places we visited, his boat and sailing. Despite being the only non-Italian speaking member of the crew, all made me feel welcome and included me in conversations and laughter. I look forward to traveling with Maurizio again. Perhaps I’ll also add to my own sailing credentials as Maurizio is an accomplished instructor.

Comfortable and beautiful boat, great food,!top crew,they are lovely father and son! Side to improve the return to the port The last day, too early .. and a few coves visited.

Perfect experience! Sylvain is a really competent skipper and is truly passionate about sharing his knowledge with his crew. The whole crew was involved in all the activities on the boat, from deciding and calculating the route to all types of sailing manoeuvres. We all learnt a lot while also relaxing in beautiful beaches and sharing good Greek food in tavernas in the various choras we visited.

Emmanuel brought us to beautiful places and made sure everyone was experiencing a great week. He adapted to those who wanted to learn and those who wanted to relax. He is quick with a joke in multiple languages. Highly recommended.

We had a fantastic week sailing with Emmanuelle. She is an amazing skipper and as a family we always felt very safe at sail. Emmanuelle was always on hand to help out and is incredibly thoughtful. Sabir is a beautiful boat, but it did get a little hot at times at night, but it was a particularly hot week!

Magical trip…. Just magical!!! Our skipper Nicola was fenomenal in every sense of the word. Gorgeous sites, beautiful navigation routes, great music thanks to our DJ ( Grande Fabrizio) and the crew (meaning us…lol) was incredible. New friends made for ever. Would definitely repeat and recommend this amazing company!!!

Beautiful experience especially for me who have never been in such a boat .. thanks to my skipper I drove sailing???? ... the sea of Greece that I tell you to do .. super easygoing people.. go-go parties.. Dissatisfied????????????

First experience with CrazySail. Certainly, it will be not the last. Marvelous and magical moments throughout the trip. Astonishing locations, beautiful weather and the food on port was amazing. Our skipper Nicola was superb in every sense. He truly lives up to their motto "just crazy about sailing". I had no expectations and I am taking with me memories and new friendships that I will cherish a lifetime. What else can you ask from a holiday trip! My 2 recommendations is more free time at port and A/C on boat. Grande Nicola and the entire CrazySail team.

We were a family with 2 kids Andrea was an amazing skipper who took us for an amazing week across the Islands . This was our first long boat trip and will not be our last.

Beautiful experience, Mario is a very professional and attentive skipper. Excellent also the menus prepared by Stefano, equally kind and professional.

Super sailingholiday. Giuseppe was very kind and in a good mood. He was always taking safe decisions both when sailing and in and around harbours and moorings. He knew the good places to swimm and the good restaurants. Will highly recommend the trip. Henrik, Denmark.

Our family of four (2 adults and two children aged 8 and 10) have just finished an amazing 14-day sailing trip with Francesco. We visited so many beautiful islands, coves and ports including Zakynthos, Kefalonia, Ithica, Lefkada, Kalamos, and Kastos. Francesco was a brilliant captain and we feel so grateful to have selected him. He was wonderful with our children, very relaxed whilst being extremely conscious of safety, and went out of his way to ensure that we had a well-balanced holiday that included sleeping in secluded bays, visiting charming fishing villages, eating in some wonderful tavernas and relaxing as a family. We would highly recommend Francesco for your Greek sailing adventure!

Beautiful holiday with Paolo! He is a reliable and patient person. Attentive to the needs of the whole crew. We sailed between the beautiful islands of the Maddalena archipelago and the coast of Corsica in total safety and relaxation.

Claudio is a fantastic skipper who always manages to create a great atmosphere and who takes care of every person on board making sure of the Well-being of everyone. His sailing experience always makes you feel safe and his passion for the sea is transmissible :) The fact that people like me are coming back for the second time and can't wait to return to the next excursions organized by Claudio is already a review in itself???? Thank you Claudio for this wonderful week!! I also thank the amazing people who have been on board and who have made this week full of laughter, great recipes and stories of life!!!

Such a unique experience! Enrico was really great, he knows the sea like the palm of his hand, we felt secure the whole time, and he’s an amazing cook! Can’t wait to return next year! Grazie mille Enrico!

I spent some relaxing days on the beautiful islands of Ibiza and Formentera on board. Santo and Luisa smoothly sailed us from beach to beach and cook delicious meals. The plan changed slightly due to the winds, but that wasn't a problem at all! We got to know some calmer beaches on the north of the island. I totally recommend spending your vaccation with the company of Luisa and Santo :)

Dario was an exceptional skipper! The boat was spacious and clean. We had a great weekend and Dario was extreamly helpful and hospitable during the whole trip. We learned a lot about sailing, the lake, and the small surrounding towns thanks to Dario’s deep sailing experience. I would really recommend this sailing trip and Dario for everyone!

A truly great experience to go sailing with Alessandro and his girlfriend Sara. The hospitality was through the roof! Super delicious home cooked food morning, lunch, and dinner, and great sailing where you can join in on helping if you like. Unfortunately sailsquare only allows to give 5 stars. They have earned 6 :)

Amazing sailing trip. Alessandro is a great skipper, very experienced. Alessandro and his girlfriend Sara made us feel very comfortable the minute we boarded the boat. It was such a pleasure being in their company for a week. Great local cooking too. I can highly recommend a sailing trip with Alessandro and Sara! You will not regret it.

Behind every memorable sailing holiday is a memorable skipper.

For the skippers on Sailsquare, sailing is much more than work, it's a passion.

Skipper appassionato, mi piace viaggiare, scoprire sempre cose nuove, Adoro anche la montagna, sono socievole,amico di tutti ma pretendo il rispetto . Sono sportivo , maestro nelle arti marziali, e mi piace leggere.

View profile

My fantasy is a true life ... and sailing is my love! Have fun, live & prosper :)

View profile

Buongiorno a tutti! La vela ed il mare sono la mia grande passione, ma mi piace anche camminare, leggere e condividere I pensieri. Dicono che sono un compagno di viaggio sereno ed appassionato, capace di vivere la vela con semplicità e gioia. "Alla via", sali a bordo, issiamo le vele ed il Grande Blu...

View profile

Vivo e lavoro a Milano da circa 10 anni ma la mia grande passione è il mare. Ho imparato ad andare a vela tra la toscana, la mia terra natale, e l'Isola di Capraia. Oramai conosco alla perfezione le isole dell'arcipelago Toscano, la Corsica e il nord della Sardegna. Adoro condividere le mie vacanze e...

View profile

Sono un appassionato del mare e delle barche. Sono nato e cresciuto in questo ambiente grazie alla presenza di mio padre e mio fratello. Mi piace conoscere e stringere nuove amicizie. Ho il piacere di cucinare a bordo per rendere la vostra vacanza completa. Sono molto attento alla pulizia a bordo. Ho...

View profile

Originario della Riviera del Conero, sulla costa Adriatica, sono cresciuto a stretto contatto con il mare sin da ragazzino. A 12 anni un adorato kayak, un po' di pratica sul windsurf, a 16 anni ho avuto la mia prima deriva, un laser, cho ho tenuto per oltre 15 anni. A 19 anni ho conseguito la patente...

View profile

The love for moving around the world is not a choice, but a necessity to satisfy one’s fate. The traveller just has to move, otherwise he’d feel exceedingly unhappy. Simple as that. To me life spent in the same place is worse than just a wasted chance, but a neglected duty that our own judgement, the...

View profile

Vorrei far mia una frase di un uomo che di mare ne sapeva parecchio. “Dopo l'istante magico in cui i miei occhi si sono aperti nel mare, non mi è stato più possibile vedere, pensare, vivere come prima”. Jacques Cousteau.

View profile

La passione per la vela è Iniziata durante il servizio di leva in marina all’Accademia Navale di Livorno. Da allora questa passione è stata sempre condivisa con mia moglie Ada, patentata anche lei dal 1993. Abbiamo iniziato 2 estati fa ad effettuare delle uscite per ripagarci in parte delle spese e...

View profile

Amo volare, navigare, scrivere. La mia vita è dipinta di blu... Ho fatto il giornalista a tempo pieno per 35 anni, e ora continuo a scrivere. Sono anche un pilota d'aeroplano e quando posso prendo il volo. Ma è al mare che posso finalmente dedicare le mie maggiori energie, Salite a bordo del nostro splendido...

View profile

Sono un musicista che ha scoperto il mare, navigo per il Mediterraneo da anni per scoprire rade, città e nuovi orizzonti, prendendo ogni viaggio come occasione per godere del mondo. Ogni persona a bordo è equipaggio e l'obiettivo principale è che tutti siano entusiasti; il mal di mare in caso passa in...

View profile

Sono una persona dinamica che ama la natua, il mare e l'aria aperta. Mi piace condividere la mia passione per la barca e le bellezze che offre il Golfo di Trieste, l'Istria e la Dalmazia. Sono un papà e adoro offire anche ai piccoli marinai il piacere di condurre la mia barca e viverla al meglio scoprendo...

View profile

Sono uno Skipper Professionista dal 2004 e lavoro e vivo per mare la maggior parte dell'anno. La mia passione per la navigazione e la continua voglia di esplorare nuovi orizzonti mi porta a variare spesso le mie mete. L'entusiasmo che metto nel mio lavoro viene trasmesso con ospitalità, gioia e divertimento...

View profile

View profile

Io e mia moglie Agata siamo due amanti del mare e dei viaggi. Dopo anni di percorsi a piedi per il mondo abbiamo deciso di continuare la nostra esperienza per mare. Io sono uno psicologo e mia moglie una ricercatrice universitaria, due professioni distinte ma che hanno in comune la curiosità per la vita...

View profile

Benvenuti a bordo, ciurma! Mi chiamo Lorenzo, vado per mare (la mia grande passione insieme alla musica e lo yoga...che non è quella che si beve ;-)) da quando ho 18 anni. A bordo mi riconoscete facilmente perché sono quello che sta sempre con il naso all'insù in contemplazione delle vele. Volete saperne...

View profile

Amo viaggiare navigare e conoscere pers1 con cui condividere la mia passi1, sono estroverso e di compagnia, chi naviga con me rimane sempre 1 amico e spesso torna a trovarmi... Cucino sempre io a pranzo e cena, per la colazi1 ho tutto il necessario compresa la Nespresso con cui fare il caffe' e il cappuccino!!! La...

View profile

Ciao sono Dario. Le nostre crociere sono delle vacanze in barca a bordo di comodi catamarani con equipaggio. Cabine con bagno privato, servizio di pensione completa e consumi inclusi. Partenze settimanali garantite. Belli e confortevoli i nostri catamarani hanno 6 cabine ospiti, una zona riservata all'equipaggio...

View profile

View profile

Essendo nato davanti al mare questo é diventato subito il mio campo giochi preferito, prima con derive e windsurf, praticato ad ottimo livello e di cui sono istruttore, per poi passare ai cabinati. Ho fatto lo skipper professionista per molti anni navigando in buona parte del Mediterraneo, ai Caraibi...

View profile

View profile

View profile

View profile

View profile

Mi sono appassionato alla vela, conseguito la patente nautica e acquistato il primo Bavaria 40 in società con un amico. Da poco ho acquistato un Bavaria 44 che utilizzerò per gite in Liguria e zone limitrofe noleggiando a privati la mia imbarcazione (con il sottoscritto come skipper). Vi attendo numerosi...

View profile

Caelum, non animum mutant qui trans mare currunt

View profile

Essendo cresciuto in una città costiera ho sempre coltivato l'amore per il mare e fin da piccolo sono stato avvicinato agli sport acquatici quali il nuoto ed in modo particolare la vela. Anche se diverse sono state le presenze sul podio tra il 2005 e il 2015 devo precisare che non sono un "estremista"...

View profile

pratico vela da bambino,vela motore oltre12 dal 1990,per 10 anni conduzione yachts armatoriali in tutto il mediterraneo,sia in gestione continua che trasferimenti e regate,prima collaboravo in scuole vela per base, patenti ,vacanze ,flottiglie,lunga esperienza di cantieristica, nel 1995 realizzazione...

View profile

Join me to a trip of adventure and freedom!

View profile

Vorrei non dire molto anche perche parla il mare per me! Lo rispetto, lo temo e lui mi porta sempre a casa, Eolo e Nett1 hanno il mio tributo ogni volta che ci vediamo, a volte mi ascoltano e a volte mi ignorano ma sempre sono li a darci emozioni! Che tu sia esperto o per la prima volta, io imparo da...

View profile

La voile n'est pas seulement une passion pour moi. C'est mon mode de vie ! Toujours dans la bonne humeur, j'aime partir à l'aventure vers les Baléares la Corse ou même la Sicile. C'est l'avantage de vivre sur un voilier, chaque jour une nouvelle vue et de nouveaux paysages à découvrir... Je serai ravi...

View profile

Mi reputo una persona tranquilla, amo la natura, la vita all'aria aperta, gli animali e naturalmente il mare!

View profile

Ciao sono Gabriele e sono un grande appassionato di vela. Conosco il mondo del mare sin da piccolo avendo cominciato a veleggiare con una deriva al Circolo Tennis e Vela di Milazzo. Sono laureato al Politecnico di Torino in Ingegneria Civile ma nonostante l'età ed il tempo dedicato allo studio ho sempre...

View profile

Dopo anni di attività velica sportiva e ricreativa svolta con famiglia ed amici, ho deciso di fondare un'associazione sportiva per condividere e promuovere la passione per la vela e per il mare ed è in questo ambito mi propongo come skipper per le vostre vacanze. La cosa che più mi piace della vacanza...

View profile

WindArt è passione per la vela, la musica, l'arte, l'avventura e l'adrelina. Siamo prima di tutto sognatori, skipper e appassionati delle cose belle e divertenti. La nostra famiglia ha l'obiettivo di creare e proporre vacanze indimenticabili, mettendo a fattor comune le nostre passioni, attenti a far...

View profile

Chi si bagna con l'acqua salata, non si asciuga più!!! E questo è quello che ci è successo tanti anni fa e che ci continua a succedere. Vivere il mare

View profile

Comincio a navigare da piccolo insieme a mio padre, subito dopo i vent'anni decido di approfondire il lato agonistico e più avventuriero della vela. Frequento il mondo delle barche dai cantieri alla navigazione d' altura, giro dal mediterraneo all' atlantico tra regate, corsi,charter, progetti con disabili...

View profile

View profile

Hello ! I;m Alexandros .My boat is located to Athens. I have more than 10 years of experience and I can get you to the most incredible places around Greek islands! As we are a family business company mostly me and sometimes my father Vasilis ( also captain A' class ,53 years old ) will be your skippers....

View profile

Amo il mare e il vento, mi piace pescare ,cucinare e scoprire posti nuovi.

View profile

View profile

Giovane ma con molta esperienza alle spalle. Andrea ( skipper) è italiano ha sempre passato il periodo estivo lavorando nello Ionio . Vi garantiremo una vacanza stupenda nel segno del relax a bordo con noi cé sempre il nostro piccolo cagnolino (MATHIAS). Un barboncino dolce e socievole( Il barboncino...

View profile

View profile

Ciao, sono la capitana Elvira, vengo dalla Siberia, purtroppo non parlo Italiano ma parlo un po' Inglese. Navigo con il mio compagno francese Nicolas, lui parla italiano. L'anno scorso abbiamo navigato tutto l'estate alle Eolie. Ci siamo innamorati dalla Sicilia e dalla bellezza di queste isole. Siamo...

View profile

Ho imparato ad apprezzare il mare ed il vento, fin da piccolo, con tutti i mezzi possibili. Passando dalle piccole derive, al windsurf e kitesurf; da piccole barche a motore, a vele da regata e crociera di dimensioni ben più importanti. Ho una buona esperienza sia in regate, anche long distance, che...

View profile

My name is George and I have been sailing since childhood and professionally since 2009 on a full time basis. Apart of my homeland Greece I have experienced sailing seasons in France, Italy, Cuba, Burma and Thailand. Now established on Syros island right at the heart of Cyclades, I offer carefully crafted...

View profile

View profile

View profile

La mia passione per il mare inizia nel 1978, data della mia nascita, sulla più remota isola dell'arcipelago toscano: Capraia. Fin da bambino ho potuto apprendere l'arte marinaresca sui pescherecci e su imbarcazioni per il trasporto turistico. Dopo gli studi presso l'Istituto nautico di Livorno è un anno...

View profile

Rui sarted sailing at the age of 6 At the age of 20 he bought his first sailboat a Beneteau first class 8 Crossed the south Atlantic once and the north Atlantic twice and crossed the Pacific ocean as a solitary navigator from Panama to Papua New Guinea. Did a season of chaters as skipper in the Caribbean...

View profile

Since 2013, more than 25,000 travellers have been sailing through Sailsquare.

Since 2013, more than 15,000 sailing holidays have been created by more than 1,950 skippers, in 110 destinations across the world. More than 25,000 travellers have been aboard, leaving more than18,000 reviews. .

Behind the scenes of “the world’s coolest job”

Read the article

“All aboard!” Startup looks to change holiday-making forever

Read the article

How to get the most out of your boat

Read the article

Read all articles