First of all, do you need to drive? Yes. What are you gonna do, take taxis everywhere? That may work if you're on a half-day cruise stop, but not for a multi-day stay. We rented a car from Dollar, which you can do over the internet like renting anywhere in the United States. This is the car we got: a Hyundai Getz!
These things are basically junk, but you see them all over the island. They're kind of the standard rental car and I think a lot of locals own them too. They remind me of when Hyundai first sold the Excel in the United States for $4,995... no power anything, no intermittent wipers, no automatic turn signals (you need to turn them off manually after a turn - this hasn't even been *available* on most US cars since the 1970's), and just cheap creaky plastic everywhere. Also, a cassette deck! But they're fine to get around in on St. Maarten's roads.
You can rent better cars if you want. If you do go upmarket, I recommend springing for a Jeep. It's pointless to just get a bigger, more expensive sedan or coupe on this island - you either want as small a car as you can stand, or a 4x4. We saw a few people driving around in rented Mustang convertibles (and Dollar has them), which is actually ridiculously stupid on this island for a whole bunch of reasons. St. Maarten is not California.
We also rented a GPS, even though a bunch of people told us we wouldn't need one. Wrong! We would have been hopelessly lost from day one without it. I think people who say it's not needed just must not go anywhere - we had to drive from the airport all the way to the opposite side of the island for our first trip, and we went to all four corners of the island after that. St. Maarten doesn't have highways - every road is practically a back country road, and they all look the same. Don't count on using your smartphone, either. My phone actually does work in St. Maarten but data roaming costs are ridiculous, and there's no offline Android GPS app (either paid or free) that seems to have decent St. Maarten maps. (All too bad, because the rented Garmin Nuvi did nothing if not make me homesick for Google Navigation.)
I like driving (well, in ideal conditions), but I do get stressed out/annoyed/pissed off if I see other drivers being stupid. I found driving on the island to be incredibly stressful to the point that my wife ended up taking over halfway through the trip and I never touched the wheel again.
For one thing, traffic on St. Maarten is a bitch. Parts of the island are still pretty quiet but other parts are really built up (and seem to be getting moreso), and it seems like you have to drive through those areas to go pretty much anywhere. In the photo above, you see a long line of cars - the car directly in front of us doesn't have his brake lights on because he's actually in park. The tiny single lane roads just can't handle all those cars, and certainly not the idiot drivers on St. Maarten that will think nothing of stopping in the middle of the street to talk to a friend they happen to pass by or read a restaurant menu as they decide where to eat. Because of how small the roads are, there is no way to pass these jackasses. You can get backups for miles caused by somebody who has just decided to stop in the middle of the road for no good reason.
Ditto for parking.
This is Marigot, on the French side. We had to park on the edge of town. In Grand Case, we had to make three trips to the town before we could park at all.
This is Grand Case. There is a parking lot (which was full) and otherwise it's street parking, but you have to find an actual spot, which can be challenging. Here we're - what else? - stuck in traffic. This photo also illustrates another reason why you don't want a convertible - we'd been hit by a sudden and intense rain shower a few minutes before (which seems like it didn't even make it to Grand Case), before things completely cleared up 5 minutes later.
To be fair, the parking problems aren't true everywhere - like anyplace else, St. Maarten has its busy areas and its not so busy areas, and its busy times. This was peak season and it also makes a difference how many cruise ships are in port. When we first got to St. Maarten, there seemed to be four or five large cruise ships in port at the same time, and it was a weekend.
The roads themselves seem like they were built about 50 years ago and then not maintained since. There were several areas we had to drive through on a daily basis that literally looked like the surface of the moon. (This is one reason why a 4x4 isn't a bad idea.) On our road to the hotel, which is actually a private road, we did see some homemade patchwork repairs being made using a trowel and what looked like that concrete stuff you buy in a tub at Home Depot. Better than nothing, but I guess there's no budget on this island for pothole repair crews.
Tailgating is a problem too. Because of the slow speeds that are most common on St. Maarten's roads, drivers have probably gotten used to being stuck to the back bumper of the car in front - even when speeds do pick up. There are some quiet stretches of road where you can get up to 70 or 80kph, and if you happen to have someone behind you, they'll still be so close that you can't see their headlights in your rear view mirror.
You see how close those cars are - it looks like bumper to bumper traffic, but on this stretch of road everybody's doing about 70kph.
You also need to be careful of wildlife. Like this guy:
These goats were also in the road when we first came upon them:
And while I surprisingly have no photos of them, there are tons of stray dogs you need to dodge.
Lastly, there are some monster hills in St. Maarten. This almost never comes through in pictures, but probably the best illustration I captured of it is the pic of our hotel entrance from my last post:
The main road there is actually a steep slope downward, and the hotel entrance is a steep slope upward. If you go to the right into the hotel there, you can also make a quick left to go to the office, which you can't even see because it's another blind hill that goes almost straight down for a second. You can see all the hills around in this pic too, and imagine that they all have similar roads to this. Our car was just barely able to navigate these roads with its little lawnmower engine, and there were definitely a few times I really wondered if we were going to go flipping down the side of a mountain. (There's one particular strange upward curve on a hill by our hotel where I swear, we were only held onto the road by centrifugal force as we drove around it - if we'd have stopped, I feel like our car would have tumbled off.)
Driving's a necessary evil on St. Maarten, but it's probably not going to be the most pleasant part of your trip.
Incidentally, we had no problem with Dollar Rent-a-Car. A lot of horror stories are floating around about various car rental agencies on St. Maarten, but our experience was smooth.
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