Story and images by David Kilmer
I’ve sailed with Capt. RJ Portmann on just a handful of trips, but everyone has been unforgettable. He and his wife Jenna run Delana Mae, a Lagoon 50 charter boat in the Caribbean. When RJ’s leading the show, with his infectious grin and globe-spanning connections, the hospitality reaches an epic scale. For my latest book, The Way of the Captain, I asked Capt. RJ about his favorite itinerary, as well as practical advice for running a boat, and here’s what he had to say:
RJ’s Best of BVI Day
My perfect day on the water starts at Norman Island, in the Bight. The night before, we’ve usually tied up at the Willy T, and that always guarantees some fresh memories and good laughs floating around the crew the next morning. I like to anchor in the corner, back to the rocks, where the water glows that perfect turquoise blue. I get up early, cup of coffee in hand, and just soak in that calm before the day begins.
From there, we raise anchor and head toward the Indians. I always save the Indians for the morning. The light is better, the crowds haven’t shown up yet, and the reef is waiting just for us. If I can grab my favorite mooring ball — the one right over the coral garden — I know we’re in for something special. Breakfast is usually just a snack before we get in the water, because everyone’s too excited. I’ve told them already that this is one of my top three snorkels in the world, and when they see it for themselves, they understand why.
It’s even more perfect when Jenna gets in the water. She’s a divemaster, and she loves the sea, but her sense of responsibility on the boat often keeps her in the galley when we’re underway. On the days when she joins the snorkel, guests get to see her as I do: this graceful little mermaid under the surface, pointing out fish, bringing up sea urchins for kids to touch, moving through the water with ease and joy. I get just as much out of watching her as I do from the reef itself.
After the Indians, we set sail. In winter — December through April — the winds are usually just right. Delana Mae needs a strong breeze — about 18 knots — to really stretch her legs, and when she’s got it she sails beautifully. We head up Sir Francis Drake Channel, engines off, usually in a few long tacks. I love it when the course takes us past Peter Island, then almost into Road Town, where the cruise ships are docked, before we ping-pong back across the channel. That’s real sailing, the kind that reminds you why you fell in love with this life.
We make it to Cooper Island for lunch. Cooper has that little beach club vibe — just bougie enough to feel fun, but still relaxed. We get a walk down the boardwalk, a good burger, a stretch of the legs ashore — a nice punctuation mark in the day.
From there, we take another sail north to Virgin Gorda. We usually anchor in St. Thomas Bay, close enough to Coco Maya that you can almost hear the music from the deck. Often, we snorkel the coral heads nearby or just enjoy the view of The Baths with those giant granite boulders rising out of the sea. If the night ends with dinner ashore at Coco Maya, that’s the cherry on top — the vibe there is unlike anywhere else in the islands. But even if we stay on the boat and serve dinner aboard, this is still one of the most picturesque spots to spend an evening.
That’s my perfect day. It has everything: the fun of the night before, the quiet of the morning, a world-class snorkel, a full stretch of sails, good food, and a setting that never loses its magic. Best of all, it’s a day where my guests see Jenna at her best, where I get to share not just the beauty of the islands, but the joy of the life we’ve built together.
RJ’s Habits of the Helm
Tighten all screws. There are three kinds of skippers. The worst sees a loose screw, shrugs, and leaves it. A decent one grabs the screwdriver and tightens the loose screw. The best — the kind I strive to be — fixes the one that’s loose and then finds every other screw that fits that driver and tightens those, too. I want the boat to be better than when I started.
Keep it yachty. Our first rule on board. That means form and function. It’s the way we flake lines with a cow hitch so they’re ready to pull and throw and keep decks clear so guests don’t trip. Keeping it yachty means minor problems never have a chance to grow into big ones.
Don’t be a jerk. This rule is simple, and bears repeating: Don’t be a jerk. You’ll pull into an anchorage where someone swings a little too close, or you’ll get boat boys yelling at you about something. It might be tempting to get hot, but what’s the point? That person is about to be your neighbor, or maybe the guy you need help from tomorrow.
Safety above all. Our third rule covers everything else. From day one, I drill it into everyone: One hand for you, one hand for the boat. Always keep yourself between the fire and the exit. We can replace everything on board except you.
Respect the partnership. Not all captains work with their life partner, but I do, and it takes its own discipline. The habit that saves us is staying in our lanes. I respect her role, and I resist the urge to “fix” something that isn’t mine to fix.
Guard your time. I’m usually the first one awake, but I safeguard my early time in the stateroom. I check the weather, review the route, answer emails, and plan the day. That preparation lets me give my full presence to the guests, which is what they came aboard for in the first place. Once I walk out that door, I’m on.
Captain David Kilmer is a longtime private yacht skipper with decades of experience on the water and a gift for translating real-world experiences into clear, actionable insights, both in fiction and nonfiction.
Captain RJ’s story is excerpted from The Way of the Captain: Habits of the Helm for Boats & Life, which profiles 25 captains of all types of command, and shares their protocols for management and leadership. It’s available now on Amazon (free to Kindle Unlimited subscribers) or directly from the publisher at wayofthecaptainbook.com.
