So I was talking to a friend of mine yesterday and we were on the topic of Christmas and he was like "But you get presents for eight days or something!". Now, since that is a bold-faced lie made by Americans trying to equate Hannukah to Christmas as to not feel like they've got the short end of the stick. For the most part from what I've seen, on Hannukah kids just get Hannukah money a single time (and only kids).
So let's break it down and see what we have. Note that my experiences may differ since I live in Israel and so pretty much everyone celebrates it here (and public transport is shut down on most holidays).
Rosh Hashana - New years. Family dinners for two days. The special dish - an apple with some honey. Whoopie-fucking-doo, why not just get a plum and a packet of sugar while you're at it. At least there's a couple of days off, but it brings about the inexorable onslaught of family dinners. One star.
Yom Kippur - This one widely differs according to your own tradition. Either you go to the synagogue and fast (boring and uncomfortable), just fast (just uncomfortable), or stay at home and play board games. If you're in Israel you can enjoy the fact that there are no cars and go jogging/cycling down the highway (and there's no television if you're into that), which admittedly is pretty awesome. However in recent years with the advent of various electric bikes, this too has become dangerous so this is somewhat nullified. Three stars for that one time I cycled to the beach and it was empty and so it was pretty nice.
Sukkot - Another week-long holiday! Only if you're not a kid you only get two days off. This time it's family dinners in a sukkah! Which is basically a tent. I hope you like bugs in your soup and occasionally leaking water everywhere. Special dish - your ultra-religious uncle inspecting your sukkah and telling you it's not up to his standards and he can't eat there. One star.
Hannukah - Ah! The festival of lights! Get ready to awkwardly sing dumb songs with your coworkers and eat inferior donuts. I don't need a fire-hazard in my house, I've got electric lights. It's eight days but you get none off unless you're a child, which means you're gonna see many of them at work. One star.
Tu Bishvat - Even kids don't get a day off and all you get is you get is dried fruit. Like Halloween if every house gave only raisins. One star.
Purim - Now we're getting somewhere! Three days of people wearing costumes and giving eachother candy (including adults). Sounds like an amazing version of Halloween, and it would be except that there are no days off for adults. Also, because it's three days long (and the previous day it's celebrated in schools) people can't be arsed to wear a costume for that long and so there's never a critical mass of people in costumes. Four stars for candy, folks in skimpy outfits and short-lived cultural references costumes. Best time of the year in the army. Also I fucking love Hamantash. If it were concentrated in one day (that we had off) it'd be five stars.
Passover - We're back to family dinners! Another week of holiday with just two days off (and two family dinners). This time there's no leavened bread anywhere which means food is garbage everywhere unless you're in Tel-Aviv-- but it's definitely garbage at your family dinner in which kids sing loudly and the reading of the Hagada never ends. Prepare for a lot of stomach-ache from Matza. One star.
Lag Ba'Omer - You light a bonfire and there's only time off for kids because the state has gotten sick of everyone skipping it. Do adults even celebrate this? I don't know. Four star as a child, one star as an adult.
Shavu'ut - One day off, you always kinda forget about this holiday. It features eating a lot of dairy products and cakes and shit. I have no idea what vegans do during this time. Family dinner with no meat, hope you're not lactose intolerant. Two stars for cheesecake.
Tu Be'Av - You're not getting two Valentine's, fuck off. One star for consumerism.
I'm sure other religions / cultures have shitty holidays too. But I've always heard good things about Jewish holidays so it's good to put this out there.
Also, if you're thinking "at least you get a lot of time off as a kid"-- this comes at the expense of no winter vacation and a short summer vacation.