They are always extremely helpful! They take to heart everything you ask them and are always ready with a response. They reply promptly, whether by phone or email, and are patient and knowledgeable in... See more
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I had a contact with Giulia who helped me choose the trip even though I had a limited dates flexibility. Since first contact till the payment the replies were prompt and accurate. I am still about a m... See more
It was a pleasant experience. Letizia is competent, she answered all questions regarding the trip and got in touch immediately. Thanks to her support we finally made the booking.
Company replied
Ringraziamo Roberto e l'armatore, per la loro disponibilità e sensibilità ad aver accettato la ns piccola, dolce Tiffany. Bravi!
Company replied
Company details
- Boat tour agency
- also in
- Boat Hire Service
- Cruise Travel Agency
- Tour Agent
- Travel deals
- Whale watching tour agency
About Sailsquare
Written by the company
Sailsquare is a marketplace that connects local skippers and organisations with travellers keen to live an experience at sea.
Through our platform, people can book individually sailing holidays all over the world.
With over 75.000 available spots onboard 2.000 tours in 110 destinations, and a community made of 150.000+ users, Sailsquare is the biggest marketplace worldwide for sailing tours & experiences.
Contact info
Via Aosta 4, 20155, Milan, Italy
- +39 02 94752565
- hello@sailsquare.com
- sailsquare.com
4.6
Excellent
2k reviews
No recent history of asking for reviews
This company hasn't invited customers recently, so reviews may not be representative
Replied to 80% of negative reviews
Typically replies within 1 week
How this company uses Trustpilot
See how their reviews and ratings are sourced, scored, and moderated.
Reply from Sailsquare
Thank you for your feedback!
We're glad you found our team friendly and helpful. We really appreciate you taking the time to share your experience with us.
Fair winds,
Sailsquare Team
It was a pleasant experience
It was a pleasant experience. Letizia is competent, she answered all questions regarding the trip and got in touch immediately. Thanks to her support we finally made the booking.
4 September 2026
Unprompted review
Reply from Sailsquare
Thank you so much for your kind words 😊️
We’re really happy to hear that Letizia was able to answer all your questions and support you throughout the booking process.
Fair winds,
Sailsquare Team
Great attention by Giulia
Great attention by Giulia, solved me a need I had in one minute.
It is the second time I’m sailing with Sailsquare and I’d always recommend.
7 July 2026
Unprompted review
Reply from Sailsquare
Hello Rodrigo,
thank you for your kind feedback, we’re happy to hear that Giulia was able to assist you quickly and efficiently.
It’s wonderful to have you sailing with Sailsquare again, and we truly appreciate your recommendation.
Fair winds,
Sailsquare team
Easy way to book a unique holiday
Super timely & friendly communication.
24 April 2026
Unprompted review
Reply from Sailsquare
Hi Kim,
thnak you for your feedback, we're delighted to hear that you found the booking process easy and our communication timely and friendly.
Fair winds,
Sailsquare Team
Transfer of a reservation from one to another experience
Competence, Friendliness, Proactive. Cancellation of one reservation, transfer to another.
29 May 2026
Unprompted review
Reply from Sailsquare
Thank you for your feedback. We're pleased to hear that you appreciated the support you received during the reservation change process. We wish you a wonderful sailing experience!
Fair winds,
Sailsquare team
Fast answer
Letizia was super clear on her communication and super fast answers.
27 April 2026
Unprompted review
Reply from Sailsquare
Thank you Pedro for your feedback.
We’re glad to hear that Letizia’s communication was clear and that you appreciated her quick responses. We wish you a great experience ahead.
Fair winds,
Sailsquare team
Helpful support from Sailsquare
I made an error and overpayment when booking a sailing holiday and this was rectified efficiently by Letizia on the Sailsquare support staff. I am looking forward to our sailing trip this summer.
10 April 2026
Unprompted review
Reply from Sailsquare
Hello Heather,
thank you for your feedback. We’re glad Letizia was able to quickly and efficiently help resolve the overpayment issue.
Fair winds,
highly competent staff.
Very active, friendly and helpful staff. My trip will not take place until September 2026; more Information will follow
20 February 2026
Unprompted review
Reply from Sailsquare
Thank you for your feedback! We’re glad to hear that you found our team friendly and helpful. We’ll be happy to support you as your trip approaches.
Fair winds,
Sailsquare Team
Super recommended!
Fast, super polite and wonderful!
Giulia helped me with all instructions for cancelation!
Thank you a lot!!
13 February 2026
Unprompted review
Reply from Sailsquare
Thank you for your kind words. We’re happy to hear that Giulia could assist you promptly and politely with the cancellation instructions. We appreciate your feedback and hope to help you again in the future!
Fair winds,
Sailsquare Team
I LOVE THEM!
They are always extremely helpful! They take to heart everything you ask them and are always ready with a response. They reply promptly, whether by phone or email, and are patient and knowledgeable in guiding you to resolve any questions or concerns.
11 February 2026
Unprompted review
Reply from Sailsquare
Thank you Massimiliano for your wonderful feedback! We’re glad to hear that our team has been helpful, patient, and responsive in addressing all your questions. Your kind words mean a lot, and we look forward to assisting you again in the future!
Fair winds,
Giulia & Sailsquare Team
Great service every time Thank you Sailsqare
Great service every time, thank you Letizia!
I've referred a few friends and family to your website.
Professional, always on time response and really accommodating.
2 February 2026
Unprompted review
Reply from Sailsquare
Thank you so much for your kind feedback!
We’re really happy to hear that you’ve consistently had a great experience and that Letizia’s support has been helpful. We truly appreciate you recommending us to friends and family, it means a lot for us.
Fair winds,
Sailsquare team
Customer Service telephone call with Letizia
Letizia called me back and was very helpful and easy to talk to. She understood the issue I was having and took the time to go back and see past emails to ensure all my queries were answered.
26 January 2026
Unprompted review
Reply from Sailsquare
Dear Assunta,
thank you for your kind words. We’re glad to hear that Letizia was helpful and took the time to ensure all your questions were answered.
We appreciate your feedback and look forward to assisting you again in the future.
Fair winds,
Sailsquare team
Letizia was great in helping me get my…
Letizia was great in helping me get my holiday booked
13 January 2026
Unprompted review
Reply from Sailsquare
Thank you, Katey, for your kind words.
We’re glad Letizia could help you with your holiday booking. We look forward to assisting you again for your next adventure!
Fair winds,
Sailsquare team
Deeply Disappointing Experience
I strongly urge others to think twice before booking with Sailsquare. My trip was plagued by issues that I repeatedly tried to resolve privately, but the company has refused to offer any meaningful support or compensation.
There was no safety briefing, no explanation of emergency procedures, and no guidance on where safety equipment was located. The skipper would also not let us leave without paying him an unexpected 70 euros in cash with no transparency or receipts (which he said was to wash the bed linen...when he actually made me share one old bed sheet with a complete stranger).
Several facilities that were advertised on the website — such as private showers and the kitchen — were suddenly restricted from guest use without prior notice! We couldn't wash ourselves for 4 days... The atmosphere on board was further damaged by unprofessional and inappropriate remarks from the skipper that made multiple guests uncomfortable. He was racist and mysoginistic....not the type of guy you want around when in your bikini all day.
This was not the experience advertised, nor one that felt safe, respectful, or professionally managed. I cannot recommend booking through Sailsquare based on what I encountered. Once again, I have contacted them multiple times privately and they refuse to take any accountability or offer any form of compensation of this expensive disaster of a trip.
5 August 2025
Unprompted review
Reply from Sailsquare
Dear GC,
as already expressed in our private conversations with you, we are very sorry for what you experienced on board, and we appreciate you sharing your feedback publicly as well. Thank you for taking the time to describe your trip in such detail. We regret to read that the situation you encountered fell far below the standards we want every traveller to experience when booking through Sailsquare.
No guest should ever feel unsafe, uncomfortable or subject to conduct that does not reflect respect, transparency, and professionalism on board.
The issues you describe, from the absence of a proper safety briefing to unclear extra charges, restricted use of advertised facilities, and inappropriate remarks, are not compatible with the values we promote, nor with the commitments every Provider accepts under our Code of Conduct (https://www.sailsquare.com/en/code-of-conduct) and Terms and Conditions (https://www.sailsquare.com/en/general-terms).
While Providers operate independently and are fully responsible for the way their experiences are managed, we do take the overall quality of the offer on Sailsquare extremely seriously. Whenever a report touches on safety, behaviour, or the atmosphere on board, we carry out an internal assessment and may take corrective actions when needed, including suspension or removal from the platform.
In this case, the Provider has been active on Sailsquare since 2022, and this was his fourth season on the platform. At the time of your booking, he had an average rating of 4.5 out of 5, with several travellers highlighting his seamanship, professionalism, and attention to the sailing experience. Many past guests appreciated the well-kept boat, the destinations visited, and the atmosphere on board, mentioning his competence, willingness to sail whenever possible, and knowledge of the area. Precisely because of this history, your feedback is particularly important to us, and it is being taken with the utmost seriousness. We truly regret that your experience did not reflect what both you and we expected. Feedback like yours plays a crucial role in helping us intervene when necessary and continue improving the reliability of the experiences available on the platform.
We sincerely hope that your future encounters with sailing will offer the safety, beauty and care that a trip at sea should always provide.
Kind regards,
The Sailsquare Team
Great place to book a vacation cruise
Great place to book a vacation cruise, you can choose by destination, check the skipper, the boat, great experience overall !
1 May 2025
Unprompted review
Reply from Sailsquare
Thank you for your feedback :)
We’re glad to hear that you had a positive experience and that the platform helped you find the right cruise.
We hope to see you again for your next sailing adventure!
Fair winds,
Sailsquare Team
Cancelled four days before departure
The trip was cancelled four days prior to departure in spite of being a confirmed sailing. No reason given .I was refunded the full amount of the holiday and given a £50 voucher towards a future booking. I was however still out of pocket for my airfare , airport parking , and incidentals bought for the holiday not to mention all the business I lost as I imagined I would be away and declined jobs.
So not at all happy and its put me off this kind of experience which is supposed to be built on trust .
29 September 2025
Unprompted review
Reply from Sailsquare
Dear Michael,
we’re truly sorry to read about your experience and completely understand how disappointing it must have been to have your holiday cancelled just a few days before departure. Situations like this are fortunately very rare, but that doesn’t make them any less frustrating, and we sincerely regret that it happened to you.
As soon as we were informed of the skipper’s cancellation, our team did everything within our means to help — searching for and proposing alternative sailing experiences that could allow you to still enjoy your trip and match your original expectations as closely as possible. We’re genuinely sorry that we weren’t able to find a solution that suited you.
As mentioned in our previous communication, all experiences published on Sailsquare are independently created and managed by the skippers, who are the sole organizers and are fully responsible towards their guests. While they operate as independent providers, we nevertheless feel a strong responsibility to ensure that the quality of the offer on our platform remains high — and, whenever possible, continues to improve over time.
Although we cannot guarantee that unpleasant situations will never occur, we do our utmost, when they do, to make things right and prevent similar issues from happening again. Even though this cancellation was beyond our control, we processed a full refund promptly and offered you a goodwill coupon as a small token of our sincere regret for the inconvenience caused.
Once again, we’re truly sorry for the disruption and disappointment this situation caused. We hope you might consider giving Sailsquare another opportunity in the future, to show you the smooth and memorable sailing experience that our community stands for when everything goes as planned.
Kind regards,
The Sailsquare Team
Great assistance
Great assistance! Always available even during holiday periods, kind and ready to help solve any problems.
21 August 2025
Unprompted review
Reply from Sailsquare
Hi Stefano,
thank you for your kind words! We’re really happy to know you felt supported at all times. We’ll be here whenever you need us.
Fair winds,
Giulia & Sailsquare Team
Pre-Departure Injury, Safety Concerns, and Refund Dispute
Might have been a good trip if we actually got to do it, but really doubt it, because the experience appeared to favor Italian guests. We hadn't even left the dock yet, and my boyfriend got injured on their shabby piece of wood that they used for a gangway. No railing, no nothing! He fell into the water, got injured really badly, and almost drowned. Finally, the captain came to help. I think maritime law requires him to at least seek medical attention for his passengers instead of going back to bed. I think the law also states that a report should be filed with the Capitaneria di Porto. I guess that I need to investigate it more, but I know one of the two was not done. In the morning, he hands my boyfriend our two backpacks and stated that we will not be traveling with them. I nicely contacted the company to refund us the €440 cash that we paid on the boat for the charter pack €120 x 2, the deposit (cauzione) €100 x 2, and the €1,197 for the trip (From the Pontine to the Amalfi Coast - 19th-26th July 2025) that I paid for via Sailsquare. Their response to their inadequacies are to place blame on their paying guests. "Unfortunately, it is not our fault that your physical and mental condition was not suitable for traveling." "The trip was carried out regularly; it's not our responsibility if you were unable to depart due to your behavior." (I would actually like to know what behavior. I didn't say two words to anyone after my boyfriend got injured.) "We listened to all the voice messages you sent to the group that night, and it was clear from your voice that you had drunk a lot of alcohol and were not yourself." Had the captain done his job correctly, you wouldn't be able to say any of that. Be warned! Go with a professional company that actually cares about their reputation and business more than retaining funds. One who actually cares for their customers.
Edit: 8/8/25
Please provide me with a copy of your captain's Italian license, the registration of your boat, and the information of your third party liability insurance. I've been asking without response. Future clients, make sure you check these things before sailing with this company.
Edit: 11/19/25 - At least I got some of my money back from the company. They still have the €440 cash that I paid and also have never provided me with the information that I asked for. Hence why I was refunded my money after my credit card investigated. Please be aware! Especially if you are spending a lot of money for a vacation and traveling very far from home.
Edit: 12/18/25
You are all not seeming to understand, but I'm sure you can consult someone who could explain this to you, so these unfortunate things do not happen again with your business.
The captain (master) of a vessel has a legal duty to report an accident to the appropriate maritime or port authority.
This obligation exists regardless of:
-Whether passengers were paying customers or guests
-Whether the captain believes a passenger was sober, intoxicated, at fault, or blameless
Passenger condition does not negate the reporting duty. A captain cannot decide unilaterally that an incident is “not reportable” based on personal judgment. That determination belongs to authorities, not the operator.
A commercial operator is expected to carry insurance precisely because accidents can and do occur during paid operations.
If an accident occurs during a paid trip, the operating company:
-Should provide its insurance information
-Cannot withhold it simply because it believes a passenger caused or contributed to the incident.
15 July 2025
Unprompted review
Reply from Sailsquare
Dear Justuh,
We are truly sorry to read your feedback and understand the frustration of not being able to take part in the sailing holiday as planned.
As a platform that connects travellers with independent organisers of sailing experiences, Sailsquare is committed to ensuring transparency and reliability in the experiences offered, and to fostering fair and responsible relationships between all parties involved. In situations such as this, we collect all available elements – from both sides – and carefully verify every relevant aspect, with the goal of reconstructing what has happened objectively.
In this specific case, the provider informed us that the decision not to proceed with your embarkation was made solely on the basis of safety, which is an essential and non-negotiable priority in any sailing experience. According to the skipper and the other guests on board, your condition at the time of departure was not compatible with the safe and smooth start of the cruise. All other participants clearly confirmed their full understanding and support of the captain’s decision.
In the context of a sailing holiday – where space is limited, collaboration among people is essential, and safety is directly influenced by individual behaviour – the skipper is responsible for making decisions that protect the wellbeing and safety of the entire group.
We understand that this situation caused great disappointment on your side, but it is important to stress that the decision was not based on subjective or discriminatory considerations. It was instead the result of an immediate and responsible assessment of the situation.
This Provider has been working with Sailsquare since 2018, has successfully led numerous experiences with international guests, and has consistently received excellent reviews (score of 4.6/5) highlighting the professionalism, technical skills of the skippers, and their ability to manage group dynamics on board.
Our role is not to interfere with Providers’ operational decisions, but to ensure that the experiences offered through our platform meet high standards of quality and safety. When issues arise, as in this case, we step in promptly to gather information, support dialogue between the parties, and assess any necessary actions, always based on objective evidence. We would also like to clarify that the amounts you mentioned match exactly what was stated in the experience description at the time of booking, including the additional costs clearly communicated in advance and to be paid on board.
We regret that you didn't take part in the holiday as planned. We hope that your future experiences will take place in contexts better suited to your needs and expectations.
Kind regards,
Giulia and Sailsquare Team
Disponibilità ed efficienza da tutto il…
Disponibilità ed efficienza da tutto il team. Complimenti!
23 July 2025
Unprompted review
Reply from Sailsquare
Ciao Silvia,
grazie di cuore per il tuo messaggio! Siamo felici che tu abbia percepito la collaborazione e l’efficacia del nostro team: lavoriamo proprio per offrire un servizio attento e coordinato.
Un caro saluto e speriamo di poterti aiutare presto a scegliere la tua prossima vacanza in barca a vela!
Giulia per il team Sailsquare
Reply from Sailsquare
Hi Liane,
Thank you so much for your message! We're glad to hear that Letizia was able to assist you with kindness and care.
Warm regards, and we hope to help you plan your next sailing holiday very soon!
Giulia for the Sailsquare Team
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