Employee Spotlight – Kimmy Cooke

Behind every extraordinary Waypoints charter experience stands a team member with a remarkable story. Our Employee Spotlight series celebrates these individuals whose personal journeys and professional dedication create the foundation of our service excellence.

This month, we’re excited to introduce you to Kimmy Cooke, the heart of our BVII customer service operation. Her path from orthopedic nursing in the United States to becoming an essential part of our Caribbean team reminds us that sometimes the most rewarding paths begin with setting sail toward the unknown.

After being an orthopedic nurse for years in the States, I left that career and moved down here over 15 years ago. I spent a lot of time on my sister-in-law’s boat, which was a day charter—an 80-foot all-wood schooner from the 1950s. It was amazing. Then, I started racing with a group of friends. We formed a core group, participated in different regattas, and had a wonderful time.

I was assisting in running a company in Cane Garden Bay, but when Hurricane Irma hit, it took out the resort. That forced me to reevaluate and figure out my next steps. Amazingly enough, Kirsty Palmer, the President of our company, stumbled across me. She approached me and asked if I wanted to work with her, and I immediately said yes. At the time, I didn’t know much about the industry, but I started working with her and Anthony. It was a steep learning curve—I had to jump into the deep end—but I found out I loved it. I’m a real stickler for details, which helps a lot in this work.

I’m very happy here and love working with this group of people in such an amazing environment. It’s a true community, which is so important when you’re away from home.

What does a typical day look like for you in Customer Service in BVI?

A typical day in customer service starts first thing in the morning with both of my computers going. I’m tapping away, checking time zones to make calls—this morning alone, I called people in Alaska and Ontario.

Then, I prepare for guests arriving that day. By 8:00 AM, they’re often walking in the door, even when I’m thinking, ‘Wait, I need my tea first!’ It’s a very active environment—our guests are here a lot, which is exactly what we love.

Beyond check-ins and paperwork, I make sure guests understand the rules in the BVI and at Waypoints while giving them the best tools for an amazing trip. I love sharing little hidden gems—secret spots they might not have read about. Those unexpected discoveries make a trip even more special.

What is your favorite part of your job?

The fact that our guests become like an extended family. I spend a lot of time with them before they arrive, through emails and phone calls, so when they finally get here, it’s like a grand meeting. They’ll ask, ‘Are you Kimmy?’ and I’ll say, ‘Yes! Are you Danny?’ It’s a lot of fun.”

What does it mean to you to give people the opportunity to spend time on the water?

Helping people experience the BVI by boat is a great reminder of why I’m here. It fills something in me to see that first moment when someone realizes, ‘Oh my gosh, I’ve never seen anything like this.’ Some think places like this only exist in movies.

Hearing their reactions is a gold-star moment for me. I also love when they come back and tell me, ‘This one place you recommended—amazing!’ It helps me build my knowledge, too. I live here and explore, but our guests spend solid time out there, and their feedback is invaluable.

[Curious about what a BVI trip looks like? Check out our BVI Sample Charter Itinerary here.]

How do you ensure a seamless experience for guests across all the Waypoints Yacht Charters bases?

The ‘secret sauce’ to making trips seamless? My background in nursing helps—I’m detail-oriented and I make sure every box is checked.

My goal is for guests to have the best possible time. Some have saved for years to take this trip, planning it for their kids or parents. That’s why we take it seriously—so they can have serious fun and create lasting memories. For me, this isn’t just a job—it’s about giving them the tools to make their experience everything they imagined.

What’s a memorable success story from your time at Waypoints?

One story that stands out was a guest who, before arriving, was very particular—lots of emails, long phone calls, very direct and to the point. As we got closer to his trip, I finally asked, ‘What’s the deal?’ And he told me: his friend was battling cancer, and this was their last trip together.

That changed everything.’ I pulled every string, called in every favor—I was going to make sure they had the most incredible trip possible.

I love what I do. I feel really fortunate to have this job.

Do you have a favorite charter destination or personal favorite boating memory?

A lot of people love going to Jost Van Dyke, and I do too. Many visitors feel like they have to go to Soggy Dollar, and while it’s a great experience, if I’m going, I’m heading to Diamond Cay at the east end of the island.

There’s a hike on the eastern side of Jost Van Dyke to the Bubbly Pool, a natural whirlpool, and it’s amazing. It’s about both the journey and the destination. The walk isn’t very long, but it’s not for babies, that’s for sure.

Along the way, there are painted arrows on the rocks marking the path, and as you go through these rocky hills, little goats pop up around you. The biggest hermit crabs I’ve ever seen are just walking along the pathway—it’s like they’re out for a stroll. Then, you pass a salt pond, which now has ducks in it, something we’d never seen before. And finally, you reach the Bubbly Pool—it looks just like an oasis. It’s a dream day. There’s nothing there except for Mother Nature’s whirlpool, formed by giant rock formations with an opening in the center.

It doesn’t get enough attention, which is actually a good thing because it stays pristine, but people who appreciate nature’s entertainment over man-made attractions should definitely see it.

If someone new wanted to start yachting, what advice would you give them?

For first-time charter guests, my best advice is to communicate with your charter company. It’s surprising how many people will call with questions and then ask, ‘Do you know much about the BVI?’ I just look out my window—yes, I know exactly what it looks like! It’s a sunny day, it’s 87°F, and it’s beautiful.

Talk with your customer service team—that’s what we’re here for. We want to help you plan the best possible trip. So many guests don’t realize all the little extras they can include, like a sleep-aboard the night before, pre-arranged provisions, or even ordering a cake for a special occasion. You won’t always find that kind of information on a Facebook group or in a guidebook, but by reaching out directly, you’ll get the details that can make your trip truly special.

What do you think sets Waypoints Yacht Charters apart from other charter companies?

Customer service is, of course, a big part of what sets Waypoints apart, but equally, if not more important, is the quality and attention given to the boats.

Anthony and his crew are so committed—it’s important to them that every guest has a great experience. They genuinely want to see people smiling.

We don’t just meet expectations—we want to exceed them, whether it’s with the boats, the experience in the office, or even after a guest leaves. I send follow-up emails checking in—asking how a daughter’s graduation went, for example—because we take the time to get to know our charter guests. We want to understand what they want and what will make their trip perfect.

Plan Your Next Adventure

Kimmy’s insider knowledge of the British Virgin Islands, combined with her genuine desire to create personalized experiences, makes her an invaluable resource for anyone planning a charter.

Her reminder that the BVI offers something truly special resonates in her advice: “One thing people often forget is that while the BVI is right next to the USVI, it is a separate country. We’re an international destination, and some visitors don’t realize they need a passport to come here. St. Thomas is so close you can see it, but once you cross over, you’re in a different place. I think once people understand that, they get excited. There’s different food, different culture—it’s an opportunity to try something new.”

Whether you’re a first-time charterer or a seasoned sailor, Kimmy and the entire Waypoints team are dedicated to helping you discover hidden gems and create memories that last a lifetime. Contact our Waypoints Yacht Charter Specialists today to begin planning your unforgettable journey through the crystal-clear waters of the British Virgin Islands.

Can you share a bit about your background and how you came to join Waypoints Yacht Charters?