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A New Shade of Blue(sail)

We’ll let you in on a little secret. We’ve been searching for the perfect name for our business since we conceptualized it.


Many of you refer to us as ‘Bluesail Charters’ - heck, we do too! It rolls off the tongue nicely, it’s memorable, and it includes one of our primary services right there in the name. But that was also part of the problem - it was still missing everything else!


Here’s a little fun Bluesail trivia for you. Did you know there have been THREE iterations of the Bluesail name since 2018? That might seem a little extreme to some of you, however if you’ve been around since the beginning, you’ve likely been a part of the evolution of Bluesail into the company we are today. In fact, YOU are the reason we’re still here, stronger than ever. We’ve combined your needs with our passion for boating and what do you know, we just keep adding services to support you through the boating lifecycle!


So we’ve been searching for a great name for ourselves, but also for you, our clients, guests and students. One that is inclusive of your journey, as well as the evolution of Bluesail. Because with day sails, sunset sails, multi-day charters, documentation consulting, purchase/sale consulting, and sailing education services, we are so much more than just a charter company. And with our latest addition of boat brokerage services - well, it was about time we started looking more globally at our name to be inclusive of our client’s journey.


Take a sail down memory lane with us!


January 5, 2018: Bluesail Group


The early days of finding our footing and still figuring out what we wanted to be when we grew up! (More Bluesail trivia: Captain Tyler hated this name and thought it sounded like a law firm. Looking back, we can agree he was right!)


March, 2018: Bluesail Vacation Yachts


High-end island-style dockside lodging was born at our home base, The Perry Hotel & Marina Key West.


June, 2018: Bluesail Vacation Yachts & Sailing Academy


Yep, that’s a mouthful - but it finally included the educational aspect of our services so we were happy with it (until we weren’t!).


May 2020: Bluesail Charters


The unofficial, yet official (?) nickname we received from locals, students, guests and clients - much easier to remember and it had a nice ring to it! But it still wasn’t right.


April 2021


Something changed this year. Our charter and sailing education services were ‘smooth sailing’, but we ran into multiple experiences with friends and clients who encountered huge obstacles, financial, and legal challenges when buying or selling their boat. It broke our hearts to know they were getting taken advantage of - mostly stemming from a lack of knowledge in the yacht-as-a-business concept, sales tax and insurance world (areas that we know all too well). So we stepped in to help when we could and ended up providing support throughout the entire buying and selling process. And guess what: we loved it! It was then that we realized we wanted to formally offer these services, but it was complicated - red tape, licensure, insurance, and the list goes on and on. We needed partner!


In October 2022 we announced a partnership with the largest privately held yacht brokerage in Florida, Pier One Yacht Sales. While we explored partnerships with several brokerages and new boat dealerships, it wasn't until we met the leadership team of Pier One that it became clear who the right partner was. Our core values have always been integrity, transparency, and flexibility, and the leadership at Pier One not only aligned with this approach to business, but like Bluesail, always put the customer ahead of profitability. A core differentiating factor that made Pier One stand out from the pack. We found a perfect match to close the loop on being able to offer a full lifecycle of services to boat owners and charter guests.


Today: Bluesail Yachting


And it finally feels juuuuust right!


With the addition of yacht brokerage services, Bluesail now offers service and support for each and every part of the boat ownership lifecycle. From a Key West sunset sail or multi-day charter to the Dry Tortugas, to learning how to sail or buying and/or selling a yacht, we are now there to support you at each phase along the boat ownership lifecycle.


Welcome to Bluesail Yachting!





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