Try someone like Marine Electronic Services I believe an in line connector kit does exist consisting of an in line plug and socket and a pair of damp-proof rubber seals. It may not be sufficiently waterproof though.
It would be better to disconnect internally and pull the cable out through the deck gland. Or cut it intenally so that the join is not out in the open. Is installing a deck plug an option so that it can easily be disconnected in future.
What VicS says is correct. You can also join coax by using two PL259 plugs and a male-to-male connector type SO239. Check the diameter of the cable: If it is 5mm it will be RG58 cable, 6.5mm will be RG8X cable and 10mm will be RG8U. Get the appropriate connectors - the plugs may all be the same but they need the right adaptor for the size of cable they are to be connected to.
Speaking from personal experience, having very recently spent many hours fiddling with connectors, I would keep the connections to the minimum and where needed the simplest type. These deck plugs, which I have one, has caused me nothing but trouble. My reception is A1 when I bypass it and join the pins direct, but fit it all back in the deck plug and it all goes to cock!!
I would deffinitely keep it internal and use a gland, and then follow js48's connection details.... if only I had thought mine through properly.......
Why use such a large plug as the PL259. and why add another link ?
If you must go PL259 then you can buy a female for one end of the join, but you would be much neater using BNC 50s (male one end, female the other)
If I had to join above deck, I would replace the cable to the mast head (normally the source of 90% of problems, go through a deck gland and then use a BNC joint.
Whatever connector you use, I would try and get one with gold plated contacts as they are less prone to oxidation IMHO, others may disagree and I would be interested in their comments.
I would prefer to not have any connectors in the system other than the SO239 at the radio and the SO239 at the antenna. A continuous run of appropriate cable terminating at each end in a PL259 is the most secure option. I would use a deck gland that allows the entire PL259 to fit through. However, many installations need a connection so you don't have to extract the cable from inside the cabin headlining whenever you drop the mast. It is best to put the connection inside the boat, of course. In that case a bnc connector is fine. For an external connection at the foot of the mast I would always opt for a PL259 - PL259 connection, taped over, for ruggedness and waterproofing. The bnc is not suitable for external use but if it is well taped I'm sure it will be ok in most cases. Deck plugs are based on this principle, and deck plugs usually fail quickly unless meticulously maintained. The bnc is most suited to quick release applications which is why it is always used on test equipment. A TNC connector, the threaded version of the bnc might be a better optoin if you don't like the bulk and size of the PL259.
I think gold pinned connectors are best, but silver is ok because even though it does oxidise the silver oxide is a good conductor!
I had a 'proper' deck gland with a screw on plug and hard wired internal connection that meant that when the mast was unstepped I could unscrew that ariel lead and then reconnect. It was not all that reliable - the actual connectors inside the plug seemed to be a hit and miss. When I installed a new ariel I removed all the internal bits of the deck fitting, just leaving the outer casing which provided a hole in the coach roof with a 3/4" tube sticking up. Then I just cut off the plug on the ariel lead and led the cable through the hole but using the plastic sleeve from the old set up pushed onto the tube to make it waterprof. Inside I just used standard male to female coax connectors to join the ariel lead to the old lead connected to the radio.
When I unstep the mast I cut off the plug and pull the whole cable through. Then when I reconnect I can use the male/female plugs again. I've found this the simplest and most elegant solution. Any worries about the ariel can be checked easily and simply by just checking the plugs, and the through deck connection is as waterproof as the old 'proper' screw in gland was.
I'll probably create a storm of indignation from people using the 'correct' kit, but I buy my coax conectors from Maplins at 99p and always carry spares. They are simple, and screw on tight to the shield and the core cable. They work fine and are cheap and easy to replace.
What you call a gland sounds like a deck plug. You are correct, they are (IMHO) a disaster. But with a proper gland big enough to pas the connector through, you don't need to cut the plug off to pull it all through and you have a single unbroken length of coax from radio to antenna.
Or, as has been said above, if you must have a join, have it inside the boat with a deck gland to pass the connector through when you need to drop the mast.
They are simply tapered rubber plugs, with a hole in the middle and a split to one edge. You push the plug onto the wire via the split and when you tighten down the cover it compresses-up and becomes water tight. As long as a connector will pass through the hole in the cover (and in the deck), you can take the whole thing apart without removing the connector.
I used on a previous boat ... a "Torpedo joint kit" ..... available from most TV / Electrical component shops ....
Its bacially a tube that unscrews into two halfs ... pass each half on to respective cable ends .... strip insulation exposing screen braid .... this is pushed back to expose the inner core and wire - strip a short length ...
There is a double ended screw joint that inner wires puch into ... tighten both screws to grip the inner wires. The braid then is spread over the outer part ... Bring both halves of plastic tube back together and screw up.
If you want to be doubly sure of being watertight .... squirt some silicon into tube ends before screwing together - I just taped the whole thing up and it lasted years. It had positive connection etc.
Another boat - I used BNC male and female as Talbot says .... no problem. Again to keep dry - I taped up.
If anyone wants to - you can get small junction boxs with clip on lids ... that could be fixed to deck or underdeck to have such joints in ... easy to get at etc.