Congratulations on your upcoming proposal plans! We are thrilled to be part of your milestone moment. And you are in very experienced hands as we’ve hosted countless engagements onboard! Around one-third of the private charters we host every year are proposal sails. While we host many special occasions such as birthdays, anniversaries, and even weddings onboard – engagements have truly become our specialty. We were even featured on CBS News NY (view a video of a live proposal!) as well as in a recent Thrillist NYC article for our advice on proposals.

We know you want to make this this perfect moment for your future fiancée. And we are here for it! Here are some details as well as some top tips for the perfect yacht proposal while Sailing Islander.

THE EXPERIENCE: AN INTIMATE OASIS

Step aboard your private yacht and make yourself comfortable! The yacht is all yours during your experience and we want you to feel right at home. The majority of our couples typically enjoy their cruise while lounging on the front bow. The views are magnificent, and we have a comfortable beanbag for you to share and take it all in. Of course you are also welcome to enjoy the back cockpit as well. This is where the helm (“steering wheel”) is and where the Captain will be stationed the entire cruise. There are two long comfy benches with plenty of cushions and a full dining table.

Speaking of dining, you are welcome to BYOB whatever you wish for drinks and food. For proposals, most couples opt to focus on the intimate moment and share views on the front bow, but please know you are welcome to bring onboard whatever you wish and use this cockpit space to dine before or after the big moment!

THE LOCATION: BREATHTAKING FROM ALL ANGLES

We have a special spot in a cove near the Statue of Liberty – with the magnificent Manhattan skyline as a backdrop – that is perfect for proposals. This area is a calm spot (in an otherwise busy harbor) and the views from all angles are truly one of a kind. The majority of our proposals take place on the front bow, where you can take your time, relax and immerse in the moment with your loved one.

See our photo gallery to view many of these romantic proposals for yourself – you can practically feel the moment yourself through the amazing photography of our partner, Electric Love Studios! We highly recommend their service for couples seeking professional photography (view a video of the experience here). Of course, our captain can also always take photos, albeit of course more amateur, but they will always do their best to feature shots from a respectful distance, and can also take photos after the moment.

THE ADVICE: SWEET & SIMPLE MAKES IT STRESS FREE

Hosting as many proposal experiences as we have, you can imagine how many questions we get, and we have seen it all on the water, in terms of various approaches and “set-ups.” Proposals generally in society have become very extravagant, but we would like to impart that when you are proposing on a yacht, you don’t need much more than the setting you’ve already planned. The gorgeous yacht, the serene experience of sailing, the unparalleled views of NYC – you truly don’t need much more.

We welcome you to supplement this as you wish, but we will share that based on our extensive experience – attempts to set up MARRY ME letters literally “fall” short – as on a moving boat, they will indeed fall over 🙂 Some ask to set up rose petals, which is theory are a great touch, but on a moving boat, and with wind, they simply blow away. So, in short, our strong recommendation is to keep it sweet and simple and leverage the unique setting that you have already arranged, together with some thoughtful words from the heart, for the most memorable and stress-free experience possible. Trust us: the recipe for a posh proposal really is as simple as Sailing Islander!

THE PRACTICALS: FREQUENTLY ASKED QUESTIONS

Can I bring champagne? YES, you can bring anything you want aboard for BYOB. Can I bring friends? YES, you can bring up to six guests total, per US Coast Guard. Can I come early to bring flowers and other special touches? YES, we are happy to meet you or your family or friends to retrieve items in advance. Will the Captain take photos? YES, they will do their best and take great pix, but for professional output, we always recommend a photographer – we can recommend one – or you may bring your own.

What if it rains? Is there a bathroom onboard? What if I arrive late? Answers to these and 25+ frequent questions are right here for your reading pleasure. And of course, if you have any further questions, just reach out!

In closing, we couldn’t be more thrilled to help you plan the perfect proposal. As the No. 1 yacht proposal experience in New York City, with hundreds of proposal stories to share from our four years in business, let us ensure an incredibly unique experience and magical moment that your fiancée will always remember – and a proposal love story to share with generations to come!

Interested in planning your perfect yacht proposal? – LEARN MORE AT SAILING ISLANDER.

Looking forward to having you onboard! <3

Jessica (owner)