Waypoints’ elevated luxury charters are made possible by the exceptional Waypoints team, who are there to help you prepare for a memorable charter experience. We touched base with Chelsea Petraitis, the Charter Sales Manager at the Waypoints Florida base in St. Pete, the Cruising Capital of the Gulf Coast. She shared her favorite things about working with Waypoints Yacht Charters and connecting with new and returning guests.
Can You Tell Us About Your Background and How You Joined the Waypoints Family?
I’ve worked in the charter industry for over eight years, but I grew up dinghy boat sailing and then eventually racing 420s and 470s in New England. I have always loved being on the water, rain or shine. Through my job, I am proud to be able to share my passion with our charter guests every single day. Every summer during college, I worked for a non-profit sailing center in Boston as a US Sailing instructor in the junior and adult programs. After graduation, I entered the workforce with a position at a tech company that was in line with my degree but found myself missing the water and sailing, so I returned to work at the sailing center full-time to develop their STEM program and continue instructing. I am proud to say I gained great experience there and made lifelong connections in the industry, and while I enjoyed my job, I was ready to transition into other work after a few years. That was when I started my first job as a charter sales agent for a worldwide charter company in downtown Boston. I worked at that location for about five years before being offered an amazing opportunity to transfer to their Florida office. In 2021, I was introduced to Kirstie [Palmer, President of Waypoints] and was drawn to her company, Waypoints. I was so impressed with Kirstie’s vision, her plans for growth in the industry, and, most notably, the focus on dedication to their guests. It didn’t take much convincing to join Waypoints!
What Drew You to This Industry and This Career?
I have always loved sailing, especially the technical part of it. I find it really interesting that no two days in this industry are the same. You meet so many different people in many industries from all over the world. Connecting with our charter guests and being able to help them plan for a dream vacation is amazing. Everyone is always having fun, and no one is chained to their desk. We are out there talking about sailing all day with our guests and getting folks on the charter bandwagon.
What Does it Mean to be a Part of the Waypoints Family?
I started with Waypoints in July 2021. Kirstie [Palmer] sold me on Waypoints, and we got along right away. She described the job to me as having a lot of flexibility in terms of establishing my team and the ability to build. It’s amazing being in downtown St. Pete, right on the waterfront, and working at a local charter base rather than an office building far away from the fleet. It is important to be here at the base to get to know our charter guests. I knew this was a great opportunity when Kirstie said, “Stick with me, and we’ll grow.” We have grown so much over the last few years, and we are able to offer elevated charters that stand out among our competitors. We are proud to have a large repeat client base (our Waypoints Wanderers!) who return to charter with us again and again because of the experience that we offer.
I’m so grateful that my journey has brought me here. On my days off, I spend the weekends going to the beach with my fiancé and our dog, Coral. We enjoy boating in our off time and exploring the Florida coast. I love live music, traveling, reading, stand-up paddleboard, and spending as much time as possible with our friends throughout Florida. I was an instructor at the sailing center in Boston, and I am looking to do some coaching and instructing here in Florida again soon. I pride myself on being able to combine my passions with my career and help our charter guests along the way.
What Has You Most Excited for Your Waypoints Charter Guests?
I am truly excited to see how we continue to grow and thrive as a luxury boutique charter company. We now have four beautiful bases, Annapolis, BVI, USVI, and St. Pete, where I am with my team. It is awesome to see our guests return each year. We are expanding our fleet with new boats each season and advancing our ASA Sailing program. Whether you are an expert sailor or you are completely new to sailing, the ASA sailing program has options for all levels. It allows anyone to build confidence in their skills on the water. I always recommend it to our guests who want to eventually sail on their own bareboat charter or even to those who just want a refresher on the boats.
It’s currently powerboat season here in St. Pete, and it’s a great time to charter a power catamaran to cruise around the Florida Gulf Coast. Our newest power-cat in the fleet, the Mojito Breeze, is intercoastal friendly and can go under any bridge, making it super easy and fun to head on down to the barrier islands. Whether you are looking to sail a catamaran or monohull or cruise on a motor yacht, we have it all here, and we can’t wait to see you!
What Makes You Passionate About Sailing and Helping People on Their Charters?
I always want to be as helpful as possible. Sometimes guests are afraid to speak up when they have a question about a certain system, procedure, etc, on charter. They don’t want to risk the opportunity for any judgment based on their experience. I have always made it known to my team and our guests that there is no such thing as a stupid question, and safety is always first. We welcome any and all questions so we can be sure to create an amazing experience for our guests. We want to make you a better sailor and hope you charter with us every year. To me, it is incredible that you can have a job where you are talking about going on vacation and meeting so many different people from all walks of life every day. Truly, it is the adventure that you get to create with your charters year after year. It’s always changing. It is so much fun, and helping people experience memories of a lifetime, and seeing how things continue to grow, is fascinating.
What is Your Favorite Thing About Working at Waypoints?
My favorite thing about my job is my team and watching them blossom. Each and every person on the team brings different strengths to the table. We have a very eclectic bunch from so many different backgrounds and ages. We enjoy coming to work every day, and we are all happy to be here. We laugh quite a bit in this office! It makes it so interesting and fun, no two days are the same. I wouldn’t be able to do my job without their support. My fiancé, Chris, is the base manager here at Waypoints Florida as well, and together we take pride in seeing the growth of the base and the happiness of all of our charter guests.
Ready to book your next charter? Let Waypoints set you out on the adventure of a lifetime. Waypoints Yacht Charters offers you the charter experience you’ve been looking for, managed by charter specialists who know the best sailing waters and hidden gems of their home base. We can’t wait for you to become a part of our Waypoints family.