Some like a permanent installation; some like to just plug something in when in a harbor. A lot depends on the boat. Some boats are not well suited for permanent installation. And, you certainly do not want to risk anything getting in the running rigging.
If you want to go full boat (pun intended), such that you could have a permanent installation and provide wireless access to more than one computer, try this out.
1. Antenna permanently mounted on a stanchion, the backstay, radar arch or some other safe place. I would only use Omni antennas so you don't have to worry about where the access point is. I would also try to keep the gain down around 7-9dBi to use a higher gain antenna starts to cause other problems maintaining a signal because of the vertical beam width being so narrow.
2. Using low loss RF cable, run to a Client Bridge. This unit will "talk" to the APs on shore (or other boats as someone suggested). I would suggest an outdoor unit and mount it someplace below deck, such as in a lazaret. The Client Bridge can be connected to power via Power over Ethernet. Given most boats have 12VDC you need to be sure to get a device that uses that power if you want to plug it in directly rather than going from 12VDC to 110VAC and back to whatever voltage.
3. Using CAT5 cable, connect the Client Bridge to a unit set up as an Access Point that will "talk" to all the PCs, Macs and even other wireless devices on board.
I know sailers who have been quite happy with either the EnGenius EUB-362-EXT or the ALFA AWUS036H with just the short rubber duckie that comes with the units. Then there are several who add a higher gain antenna, still just screwed on in place of the short one. Most typically they are upgrading to a 7dBi or 9dBi omni antenna. Every 3dB increase in either transmit power or antenna gain increases the effective radiated power (not to be confused with range which is affected by lots of the things). Then there are folks who add an active USB extension cable (they're about 15 ft.) and then they can move the antenna and unit farther away, some even hoist it up a flag halyard or something similar.
Those USB devices are great for one computer at a time. (The ALFA works with Apple Mac while the EnGenius does not). If you want to hook up two or more computers at the same time, then you'll want to move to a "Client Bridge" approach.
Yeah we use a 9dbi external antenna. There's supposed to be a lot of signal strength lost due to cable length. The cable usually comes in ten foot lengths and was going to need 4 of them for the run I had in mind. So I had a 36 foot one made up to eliminate the connectors along the run. I figured that some of that loss had to be at each connection so I did the best I could by eliminating them. They say that a longer USB is the way to go. I just didn't have that option available to me.
I had a friend with a similar set up but he couldn't pull in half the signals that I could. His cable was only about 5 feet long while mine was 36. So he brought system over to our boat and we interchanged parts to see what the difference was. It turned out that his antenna was killing him. He changed to an 8dbi antenna and he was able to see everything that I could. So it seems the antenna was more important than the cable length.
We also got ours from Amazon. As far as the software goes, when you boot up your system the first thing you do is a scan. Then the software provides a list of hot spots that the booster is seeing. You see signal strength, the hot spots name and if its encrypted or not.
Connectivity just depends on whether there's an unprotected source or not. We've been to Jackson Creek in Deltaville and have been able to connect. We've been in Washington, DC and seen a hundred sources but every single one was password protected. In Miami Beach there are hundreds of hotspot and a few are open for us to "borrow" some wifi.
I would say that we can get free wifi in most places. Once we know an anchorage has an open hot spot we often stop there just for that reason. Even if we have to sign up for a pay per view wifi site at least we can do it from the boat rather than carrying the laptop to shore.
Price the Alpha system as well its the supposedly "the newest and the bestest" but I haven't seen one in person.
Antenna gain. Up to a point, higher gain is a good way to go. Higher gain antennas actually help on the "receive" side. However, if you get above about 9dbi, the vertical beam width is so narrow (6 deg, 3 up, 3 down from horizontal) that rocking due to any wave or wake causes you to lose signal off and on.
Cables The big question is the attenuation of the cable. And you are right that the connectors can introduce some loss, too. If you chose (and can use) the low loss cables you will help a lot. LMR400 only loses about 0.7dB over ten feet while LMR200 loses about 2dB over that same distance. Trouble with LMR400 is that it's pretty stiff.
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