Employee Spotlight – Jay Pennington
At Waypoints Yacht Charters, our exceptional yacht charters are made possible by dedicated team members who pour their passion into making each charter unforgettable.
Today, we’re shining the spotlight on Jay Pennington, our USA Operations Base Director, who shares more about his journey from the coal mining country of West Virginia to the crystal-clear waters of the Caribbean. We sat down with Jay to learn more about his path to Waypoints, his favorite destinations, and what makes the perfect charter experience.
Can you share a bit about your background and how you came to join Waypoints Yacht Charters?
My wife and I began our journey with chartering and vacationing in the Virgin Islands. Our first trip was in February of 2000. We immediately fell in love with the islands, which set us on a path to planning our escape after several more trips. By January of 2008, we had moved to Saint Thomas. I started working at the Saint Thomas base, which was known as CYOA Yacht Charters at the time. When the owner of CYOA retired and sold the business to Waypoints, I stayed on with the new company.
Are there specific moments or memories from those first few trips that stick with you?
It’s the general atmosphere that sticks with me the most. The place is not only beautiful, but it’s also spectacular. Everywhere you go, every new experience is still a blast. The initial impact for those who haven’t spent any serious time there is just magical—it’s so different from what most of us deal with in the cities or rural areas. Despite not being a big beach person—I grew up inland—the sight of the ocean bottom while sailing, the constant trade winds, and the crystal-clear water are unforgettable.
Unlike Florida and the Bahamas, the islands here are like mountains emerging from the water, offering a totally different landscape. And they’re in the middle of nowhere, 1600 miles from the US mainland and 3600 miles from the continent of Africa. Bordering the Puerto Rican Trench.
What’s something people might be surprised to learn about you?
I am the grandson and great grandson of coal miners from West Virginia on both sides of my family. I was born a long way from the sea.
What does a typical day look like for you as an Operations Manager across multiple locations?
It varies depending on my work location. If I am not at one of the bases then it is much like a “normal” job. Catch up with emails, check billing, talk to the team via phone calls or Teams meetings.
When I am at one of the bases then it includes inspecting boats, meeting with team members, assisting customers and crew members. On the right day you might even catch me cleaning up the heads at the base.
What is your favorite part of your job?
This would be a coin toss. In our industry we get the opportunity to provide a vacation of a lifetime. In many cases we get to do this for clients over and over again. We even have generational clients, both boat owners and charter guests. As a lifelong boat owner assisting boat owners with their new vessels is also a high point. Families work a lifetime in some instances to earn the opportunity to own a boat and share that experience with their friends and family. The impact of those experiences is impossible to quantify.
What does it mean to you to give people the opportunity to spend time on the water?
Providing the opportunity for first-time charter guests to spend time on the water is incredibly impactful. You can’t charter a yacht for a week without it profoundly affecting your view on life and the universe. Travel is the great equalizer. It transcends social and economic differences and challenges what you think about the world.
Many people never venture beyond the few blocks of their neighborhood, so experiencing other cultures and landscapes can be transformative. Knowing that I’m having that kind of impact on people is impressive. It’s moving to see someone return from a trip, someone who works tirelessly in their day-to-day job, and observe how refreshed and changed they are.
With boat owners, some of whom I’ve known for multiple years, it’s rewarding to maintain that contact. I’ve met people who spent years deciding to buy a boat, started with chartering, and are now cruising. Seeing that progression and knowing I had some influence in their decision is really cool. It’s fulfilling to maintain these contacts with owners and be a part of their journey on the water.
How do you ensure a seamless experience for guests across all the Waypoints Yacht Charters bases?
While we don’t want to dilute the individuality of our Boutique Charter bases, the whole team strives to deliver the same quality experience company wide. Our team members are critical to that success. There is nothing better than guests rolling out of their taxi greeting the team like lifelong friends.
What’s a memorable success story from your time at Waypoints?
Just one story would be impossible to single out. We have helped charter clients with weddings, funerals, anniversaries, and I know of at least one child named after the Drake Channel. As for our boat owners, I have had multiple owners fulfill lifetime dreams of cruising, several still are. When one of them checks in from some far away port it is a rewarding feeling. I still have multiple owners that email or text me about their boats from all over the world.
What drew you to the yachting industry?
I would love to say it was some noble calling. The truth of the matter is that I simply wanted to spend more time on the water. Short of a lottery ticket the only way to do that was to work on and around boats.
Do you have a favorite charter destination or personal favorite boating memory?
It is hard to pick just one. My wife and I have been blessed to spend some serious time on the water. I am a little biased but chartering or cruising from the USVI gives you incredible options. The Spanish Virgin Islands to the west. The outlying islands and cays around Saint Thomas. Saint John with national park beaches and the park anchorages. The half Martha’s Vineyard half Reggae vibe of Cruz Bay. The laid-back artsy feel of Coral Bay.
Saint John is the most underappreciated cruising ground in the Caribbean. Then you can reach across to Jost and clear into the BVI with all it has to offer. You’re going to need more than a week.
What’s your favorite local spot in either BVI, USVI, or Annapolis that you’d recommend to visitors?
My favorite local spot has to be Maho Bay on Saint John. It’s what I’d call “That One Particular Harbor” for me. It’s a stunningly beautiful beach, part of the national park in Saint John, with sea turtles everywhere and a picture-postcard white sandy beach. It also offers great sunsets—it’s the whole package.
The bay is easily accessible with plenty of different anchorages nearby. Having traveled all around the Bahamas, the Caribbean, and even Croatia, Maho Bay still stands out as that special spot for me. It’s like an old pair of tennis shoes—it just feels good every time I’m there.
What else do you do while you’re boating?
While boating, I enjoy snorkeling and diving, with a bit of fishing mixed in. However, it’s more about the experience of being in a completely different environment. Being 60 feet under water is the closest thing to outer space that most humans will ever see. It’s a totally different world down there.
If someone new wanted to start yachting, what advice would you give them?
For those new to yachting, I recommend starting with some basic sailing or boating lessons wherever possible. If you have friends who already boat or charter, try to join them and build up some experience. Alternatively, you can charter a boat that includes a captain who can show you the ropes.
One common challenge is that many people want to buy a boat before they have substantial boating experience. If you’re already in your 50s or 60s and have a three or four-year plan to start cruising, the quickest path to learning is to charter a private boat, ideally one similar in size and style to what you envision owning, with a knowledgeable captain.
How do you foster teamwork and morale among your teams across locations?
Communication is important. Sometimes a good old-fashioned sailors’ happy hour can work better than a Teams meeting.
What exciting developments or trends in yachting are you most looking forward to?
I’m particularly excited about the advancements in solar and battery technology in the yachting industry. These improvements are making boats more efficient and user-friendly.
For new yachters who haven’t faced the traditional challenges with boat refrigeration, fans, etc., the difference is night and day—the boats just work more reliably now. Lithium technology, for instance, significantly reduces the need to run a generator off the dock and has greatly improved the efficiency of DC-powered appliances like refrigeration systems.
These advancements are making a big impact and they’re happening quickly. When I started in this industry in 2008, we only had about four boats equipped with air conditioning and generators. Now, it’s unthinkable to put a boat into charter without AC. Boating has become a much more comfortable experience than ever before.
Beyond just lithium batteries, we’re seeing innovations like commonplace water makers that weren’t around eight years ago, and air conditioning became standard about ten years ago. These changes are primarily driven by the vacation market, not the cruiser market.
These advances make yachting more accessible, accommodating needs like CPAP machines, oxygen systems, and making it a better vacation for everyone in the family, no matter their age.
What do you envision for the future of Waypoints Yacht Charters and its operations?
The sky is the limit. The industry shows no signs of slowing down, and as consumers increasingly focus on quality experiences, we are poised to stand shoulder to shoulder with the best in the industry, providing world-class charter experiences for our clients.
What sets Waypoints apart is our staff, our locations, and our commitment to delivering a superior service. From the top down, our attitude is focused on delivering boats in better shape, with better gear than any other bareboat operation. We rival others with the creature comforts we offer—everything from cooking utensils to the general setup of our boats, which are like vacation condos maintained by the best in the business.
Traditional bareboats might provide minimal equipment, whereas our boats are fully equipped to enhance the vacation experience. We don’t turn boats around the same day; we clean them, repair any issues, and take 48 hours to ensure everything is perfect. This is in contrast to operations that might have boats in at 10 AM and out by 4 PM, trying to turn around 20, 30, or even 40 boats in that window—you just can’t do it right that way.
By taking the time to thoroughly inspect and prepare each boat from the order all the way through delivery, sale, refit, and cruising, we maintain control and uphold our high standards, ultimately delivering a better boat and a better experience for everyone involved.
What do you think sets Waypoints Yacht Charters apart from other charter companies?
Our people. Both our core long term professionals brought together under the Waypoints banner and the next generation that we are training up to continue that legacy.
Plan Your Next Adventure
Ready to experience the joys of chartering with Waypoints? From complete novices to experienced sailors, we provide personalized guidance every step of the way. Whether you’re seeking a bareboat adventure or prefer the comfort of an all-inclusive experience, our charter specialists will help craft the perfect vacation for your style.
With bases in Annapolis, the British Virgin Islands, U.S. Virgin Islands, the Bahamas, and now Belize, our team of passionate professionals like Jay can help you discover your perfect sailing destination. Contact our yacht charter specialists today to start planning your unforgettable journey on the water.