I am hooked! Completely and totally hooked on flying while on vacation. It started with a flight in Maui back in 2018. I had a little over 280 total hours at that point in my logbook, with 222 hours in our Mooney. What I didn’t have was any time in a Cessna.
Maui - 2018
It wasn’t long after I started flying that I set a goal to land a plane in all 50 states. The most difficult would be Hawaii, followed by Alaska. With the Mooney, Alaska is in reach, but Hawaii was a different matter altogether. So, in 2018 when we had a trip coming up to Maui, I started looking at flight schools that rent planes. Maui Aviators had a Cessna that could be rented, but it would require a 1-hour checkout. Renting it for an hour with a CFI to get checked out and then heading out on my own around Maui—when I had never even sat in a Cessna—sounded like a bad plan.
“How much would it be to rent the plane for two hours and pay the CFI to come along?” I asked.
That is how my wife and I found ourselves standing on the tarmac at Kahului Airport in Maui with a CFI who was amazed that I had never spent any time in a Cessna. Those of you who have flown a 172 know why it is such a great training plane. We soon found ourselves flying clockwise around Maui, past Molokini, across the channel to a couple of shipwrecks off the coast of Lanai, and then across the channel again to Moloka’i.
As we skimmed the plateau and approached the north coast, the CFI told me he would take the controls for a minute so I could look out and down as we crossed the cliffs. It was a rush as we went from a few hundred feet above the ground to it dropping away over 3,000 feet to the ocean below.
I took the controls back and continued the flight around the eastern point of Moloka’i and then approached the airport on Maui from the northwest. The tower was trying to bring us in on Runway 5 before an Airbus that was on a straight-in for Runway 2, and it sure sounded like it wasn’t going to work out.
Sure enough, the squeeze play didn’t work, and we were given a left 360 and told to proceed straight to the numbers coming out of the turn. Remember, I now had about 1.8 hours total time in a Cessna and zero landings. I’d also been flying the plane the entire time, and I think the CFI had possibly forgotten those two little facts. As we approached the end of the runway—at the spot where I would pull power in my Mooney—I pulled the power in the Cessna. The CFI quickly shoved the power back in before the plane started sinking too much, and I apologized for nearly planting it on the runway. “It’s okay, this plane has seen worse,” he replied.
You said this was about St. Thomas
I know—you’re thinking, “Why am I reading about a flight in Maui if the title of the article is ‘Flying in St. Thomas UVI’?” It will all make sense if you don’t give up reading.
Fast forward to the beginning of this year, 2026, and we have a trip coming up to St. Thomas in the US Virgin Islands. I’m well past my goal of flying every week for 52 weeks. In fact, at the time I was passing 70 weeks. While I know it is eventually going to come to an end, I don’t want to see it die at 75 weeks. We would be leaving on a redeye on a Saturday night and returning the following Saturday evening. The only way to keep the streak going would be to either stop by Fullerton on our way home from LAX around 10:30 p.m. after having been awake since about 3 a.m. CA time (bad idea), or find a way to fly in St. Thomas.
It wasn’t as easy as finding flight options in Maui. There were two flight schools listed, and one never responded to my requests. The other had closed the business, but fortunately the guy who had owned it referred me to a CFI who had access to a Piper Warrior. After a little more follow-up, the plan was in place.
As we sat by the pool the morning of our flight, I saw a silver and blue Piper fly by and commented to Kathy, “I wonder if that’s our plane.” That afternoon we caught a taxi to the FBO side of the airport and were dropped off at a hangar that had the address stenciled above it. There was a locked padlock on the door, and locks on all the other access doors to the hangar—just another roadblock. But after a call to Ken the CFI, we found out we were one hangar away from the correct one and walked next door.
We sat down inside the FBO and came up with a plan.
Ken: “Where do you want to fly?”
Me: “I have no idea. Where do you normally take people on sightseeing flights?”
Why try to choose when I have no idea about any of the area, I thought.
Ken: “Have you ever heard of Epstein?”
I tried not to laugh.
Me: “Yeah.”
Ken: “His island is right next to St. Thomas.”
Me: “Really?”
Ken: “Yeah, we can fly over it and then past the British Virgin Islands, up toward a place called Anegada, then back past St. Thomas.”
Me: “Sounds good.”
Ken: “If you want, we can go over to Culebra and do a low approach. We can’t touch wheels down because of Customs, but it’s a really cool approach. Have you ever seen St. Barts?”
I had seen those videos of the planes coming over and dropping down the hill to the runway at St. Barts.
Me: “Yeah, that’s pretty wild.”
Ken: “This is a challenging approach, kind of like that. It’s really fun.”
He went out to pre-flight the plane and then we joined him. I mounted our Insta360 to the left tie-down and hoped the battery would last for the expected 2-hour flight—and that my mount would hold so it wouldn’t end up in the bottom of the Caribbean.
He made all the radio calls as we taxied out and then did the run-up. He talked me through the takeoff, and then we were flying over the incredible blue waters of the Caribbean. He was the ultimate CFI/tour guide. Around the south side of St. Thomas, over Little St. James (Epstein’s island), past St. John, over Norman Island and the infamous Willy T floating restaurant, and then up toward the British Virgin Islands we flew.
We passed a huge yacht off the coast of Virgin Gorda and past Necker Island, the private retreat owned by Sir Richard Branson, on our way to Anegada. As we approached the western tip, Ken pointed to a pink patch just off the coast and said, “Do you see the flamingos down there?”
Sure enough, there was a huge flock of flamingos in the water just off the coast that took off as we approached. We watched them skim the water, and I rolled the plane into a right bank to keep them in sight. It was absolutely stunning. If I published the entire video and you made a drinking game out of every time Kathy or I said “Wow,” “That’s amazing,” or “Beautiful,” you would probably be so drunk by the end of the flight that you wouldn’t remember watching it.
We made our way along the north coast of Tortola, past Jost Van Dyke, and continued east along the north coast of St. Thomas bound for Culebra.
The airport at Culebra is on the south side of the island, and you make your approach from the northwest through a canyon. He talked me through the power, speed, and flap settings as we crossed Flamenco Beach and entered the canyon. Following the road, I could start to see the end of the runway up ahead.
You only have about 1,000 feet after exiting the canyon to get lined up with the runway.
“Just kind of drop it in and slip it a little bit so you don’t accelerate,” he said as we exited the canyon.
“This would be kind of a perfect speed you would want, but you need to be a little more lower there,” he continued as we got closer.
“A good bit lower right now because you want to be on the ground by the windsock.”
Almost to the numbers he said, “So like this, if this was our actual approach…”
I finished the sentence: “We’re going around.”
“Yeah, go around.”
After that low approach, it was back to St. Thomas where I logged a landing at Cyril E. King Airport (STT). It was an unbelievable flight that I will never forget.
How small is the GA community? Small enough that me—a guy from California—can fly in St. Thomas with a CFI who was born and raised in St. Thomas but did all his private pilot training out of Johnston Regional Airport (KJNX) in North Carolina. The exact same airport that was our home base on the east coast when I flew our Mooney coast-to-coast in 2019 to visit my son’s mission areas.
Tips for Vacation Flying
So why did I tell the Maui flight story? Because the things that made the Maui flight a success are the same ones that made St. Thomas a success. When we flew in Maui, I paid the CFI to come along and it was great to let him worry about the radios, talking to ATC, making position calls over places that I didn’t know the names of. All I had to do was fly the airplane and look out the window.
In St. Thomas it was the same thing, and having him make the radio calls was even more beneficial than in Maui. When you are used to ATC here in the states, the accents in the Caribbean made the calls more difficult to understand. Add the fact that I knew none of the landmarks, and my radio calls would have been worthless. Not to mention having all his local knowledge to take us to the most scenic places and tell stories along the way.
So yes, I am hooked on flying while on vacation whenever possible. And I will always take a local CFI along so they can show us all the great places and do all the work while I just enjoy flying the plane and looking out the window.
