If you have Netflix and Amazon Prime you are able to watch literally all of Star Trek with no cost to you other than the subscriptions you have already. If you only have Hulu for whatever reason, you can watch all the shows but not the movies (who does that anyway?).
Also, keep in mind I'm only listing streaming options that are covered by monthly fees already. For example Star Trek III: The Search for Spock is available on Amazon streaming for $2.99, but I'm not going to list it because it costs extra.
Star Trek Seasons 1-3 (1966)
This is the most obvious place to start. I've seen a few episodes here and there over the years, but never really enough to understand any of it in a grand scale. From what I remember, it is quite campy, but it was the sixties, what was I expecting? I am going to try to start here, but I honestly don't expect it to hold my attention enough. Hopefully it will!
Star Trek: The Original Series on Netflix
Star Trek: The Original Series on Amazon Streaming
Star Trek: The Original Series on Hulu
Star Trek: The Original Series on Amazon Streaming
Star Trek: The Original Series on Hulu
Star Trek: The Animated Series (1973)
Apparently due to fan demand, the crew from the original show re-appeared in animated form in 1973. This seems to be a continuation of the original series. I have read that this was canon at some point, then it was decided it would be longer be canon. I'm going to try to watch it all, but I'm not really sure I'll be able to handle this. I find trouble trying to watch any animated made prior to the late '80s. It just doesn't hold my attention unforunately. I'll certainly try though!
Star Trek: The Animated Series on Netflix
Star Trek: The Motion Picture (1979)
This is where I was told to start watching Star Trek. Apparently the quality really begins to improve and it is much less cheesy. So, if I can't get through the first series, I'll just move to this. Please be aware there is apparently a director's cut, which is probably better, and I don't believe it is streaming anywhere.
Star Trek II: The Wrath of Khan (1982)
I have personally been informed that this is the best Star Trek anything ever. I'm definitely looking forward to watching it, Star Trek: Into Darkness spoilers here...After watching the new one featuring Khan, I'm very interested in the character. I'm also told Into Darkness and this have many similarities, I'm excited to find out what.
Star Trek III: The Search for Spock (1984)
Without reading the synopsis, I'm going to assume Wrath of Khan ends like Into Darkness did but Spock dies? Then they go somewhere to revive him? Apparently Leonard Nimoy, who plays Spock, directed this film and the next one.
Star Trek IV: The Voyage Home (1986)
The Voyage Home is the fourth film in the series and second film directed by Spock. The film is dedicated to the Space Shuttle Challenger. From here on out, I'm probably not going to go over too many plot details, I don't want to find them out myself.
Star Trek V: The Final Frontier (1989)
The fifth film in the series is directed by William Shatner and is apparently terrible. It once had the record for the highest opening weekend of any Star Trek film, but apparently it dropped off right after that and received some very poor reviews. Either way, I'm going to watch it.
Now things are going to get a little tricky. The films and series start interconnecting, so I'm only going to provide links once, but I'll keep listing them in the order you should watch them.
Star Trek: The Next Generation Season 1-4 (1987)
This is an entirely new series. I'm told it is around 100 years after the original, so you could probably start here and easily figure out what is going on. Keep in mind, you are only supposed to watch seasons one through four, then another movie before watching season five. No idea how important that is though.
Star Trek VI: The Undiscovered Country (1991)
This is the final film starring the cast of the original series. I assume there is a reason to watch the first four seasons of the Next Generation first, but I'm not entirely sure. Either way, it was much better received by critics and fans than the last film. Reddit user /u/amendmentforone has informed me this can be watched after the Final Frontier as it has nothing to do with The New Generation. Thank you!
Star Trek: The Next Generation Season 5 (1991)
Now apparently The Next Generation seasons six and seven take place simultaneously to Star Trek: Deep Space Nine seasons one and two. I don't think it is quite as intense as Buffy/Angel simultaneous episodes, but I could be wrong.
Star Trek: The Next Generation Season 6 (1992)
Star Trek: Deep Space Nine Season 1 (1992)
Star Trek: Deep Space Nine is a departure for the series. To my knowledge, everything prior to this has been about journeys or exploration, or trekking perhaps? This show focuses on one specific space station. Apparently things come to them regularly to keep the excitement going. Honestly, it sounds good to me, but apparently gets mixed reviews.
Star Trek: The Next Generation Season 7 (1993)
Star Trek: Deep Space Nine Season 2 (1993)
Star Trek VII: Generations (1994)
Generations is the first film based on The Next Generation. Apparently The Next Generation was scheduled for an eighth season, but at the last minute they decided against it and moved to films. The film got mixed reviews, I won't say much else.
Star Trek: Deep Space Nine Season 3 (1994)
Star Trek: Voyager Season 1 (1994)
I think this series is a spin-off from Deep Space Nine, but I'll find out eventually anyway. The show ran for seven seasons tying it for the longest with The Next Generation. Of course this series doesn't have all the film The Next Generation has.
Star Trek: Deep Space Nine Season 4 (1995)
Star Trek: Voyager Season 2 (1995)
Star Trek VIII: First Contact
First Contact is the eighth Star Trek film and apparently is wonderful. Obviously we all know that famous tagline, "Resistance is Futile". This film introduces a new villain and people seemed to like him. I read one article that said people compared the villain the Cenobites from Hellraiser.
Star Trek: Deep Space Nine Season 5 (1996)
Star Trek: Voyager Season 3 (1996)
Star Trek: Deep Space Nine Season 6 (1997)
Star Trek: Voyager Season 4 (1997)
Star Trek IX: Insurrection (1998)
The ninth Star Trek film was described as "back to it's TV roots", but that wasn't a compliment. Apparently this one just feels like an extended episode of The Next Generation, but if you want more Next Generation, what is the problem?
Star Trek: Deep Space Nine Season 7 (1998)
Star Trek: Voyager Season 5-7 (1998)
Star Trek: Enterprise Season 1 (2001)
This how is a prequel to the original series, taking place about ten years before the Federation is created. I don't know anything other than that. It is the last Star Trek series ending an 18 year run of different shows.
Star Trek X: Nemesis (2002)
The final Star Trek film in this reality was apparently a huge failure. It got some decent reviews, but absolutely tanked at the box office making it a huge financial failure. This movie kind of ended Star Trek as we know it...
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