Hitching on Saint Martin/Sint Maarten island is certainly possible. Sint Maarten is very small, and doesn't have any real custom to hitchhiking, but in spite of that, hitch-hiking is certainly doable. The Island's nickname is The Friendly Island, and the people are indeed very friendly! So if you hitch-hike on St.Maarten/St.Martin, don't expect to get a ride fast (as people are not used to it), but wait a little, and wait for that one cool person who will take you. The conversations are really nice, and the local experience is very worth it. The major advantage on St.Maarten/Martin is that the island is very small, so once you have a ride, you will cover the most of your distance in one ride
The French side is much friendlier and easier to hitch hike as well as being incredibly scenic.
Unfortunately crime is a problem here as the French police have no jurisdiction over the border and local Dutch police are very lax (the coast guard is very strict however). It is unlikely that you will notice anything while you are there, but drugs are a big problem. Armed robberies of boats increased dramatically in 2014/2015.
Taxis are everywhere on St.Maarten/Martin, and it's really easy to get from one place to another on the island. The distinction between taxi and normal passenger car is very small though, so people will often stop for you and ask money for a ride. Keep this in mind.
Hitchhiking a boat
Boat hitching is best from the Simpson Bay marina, the marina at Lagoonies (other side of Simpson bay - put a notice up) and Marigot marina (French side).
One good option is also to stand at the dinghy dock near the ferry stop in Marigot, and ask everyone.
You also have a radio program on the VHF were you can say that you are looking for a boat. For this, talk to Michael from Shrimpy's (a laundry shop in Marigot). He is the one in charge of the radio program.
St.Maarten/Martin has a population of about 75,000 people, on an area of about 85m2. It means a high population density, and therefore a lot of traffic on the roads. St.Maarten/Martin has a slight problem of overcrowding, but for hitch-hiking, this is a good thing :)
St.Maarten/Martin's population is made of a lot of different peoples and nationalities. Most of them are native creoles, born on the island or on neighbouring islands. But there are also large groups of Dominican, North American (USA), and European (French, Dutch) people. In general, North Americans and Europeans are more familiar with hitch-hiking, so they are a good source of rides too.
Where to start
Although you can start just about everywhere on the island, The best places to start is at transportation hubs, like bus stations, airports (St.Maarten/Martin has 2), and the exit lanes out of the 'cities'. A lot of cars depart from there in the same direction.
Accomodation and Sleep
There are a lot of empty Irma Houses (houses destroyed by the Irma hurricane) where you will find a good spot to sleep. Be careful though that the place you go is not already occupied by someone else.