Friday, December 23rd
It is preferable to daven Mincha before lighting Chanuka candles, but one should not miss out on a minyan to daven before lighting. The Israel Center has a Mincha minyan at 12:10pm on the Friday, Erev Shabbat Chanuka (December 23rd) to facilitate this. Chanuka candles should be lit BEFORE Shabbat candles – even if different people are lighting each. Count on 5-10 minutes before the posted Shabbat lighting time; adjust according to your household’s experience. Save Ma’oz Tzur for the Shabbat table – it saves some time and helps bring Chanuka to Shabbat Chanuka.
* In Jerusalem, some follow the practice of delaying Shabbat candle lighting for 20 minutes (4:25pm this year, instead of the scheduled 4:05pm) and lighting Chanuka candles right before Shabbat candles. ** For Maale Adumim and Petach Tikva, for those who generally light Shabbat candles at the Jerusalem time, they can delay 15 minutes, since their sunsets are about 5 minutes earlier than Jerusalem’s. Places whose Shabbat candle lighting times are 18-22 minutes before sunset, should keep to their posted times. Care should be taken when lighting early (as on Friday, but even during the week for a variety of reasons) to…  Never light before PLAG mincha – use 3:40pm as the red line; it works for the whole Chanuka this year, In Jerusalem. For elsewhere in Israel, either check your local calendars or pad this time by a few minutes. Outside of Israel, the times are most likely to be different – a local calendar should definitely be consulted.
 Make sure the candles are long/fat enough – or that there is sufficient oil – to last the required amount of time after stars-out, and then some. They should last at least until 5:50-6:00pm (using the later Shabbat-out time as TZEIT), but preferably somewhat longer (as mentioned above).
Motza”Sh, Dec. 24th
Candles for Motza’ei Shabbat should be set up from before Shabbat so as not to delay the Chanuka candle lighting any more than necessitated by Shabbat. (This is not required by halacha, but it is a highly desirable thing to do, which reflects a love for this mitzva.)
Many shuls will daven Maariv on Motza’ei Shabbat Chanuka earlier than usual (13-17 minutes after sunset is an acceptable Tzeit HaKochavim time for the reciting of the Sh’ma – even though Shabbat is not over yet). This allows people to get home closer to “right after Shabbat” and maximize the time that Chanuka candles will be lit during their “prime time”. OBVIOUSLY, one cannot light Chanuka candles – or even set them up – before Shabbat is out. But by having set up for Motza”sh on Friday, and by davening Maariv a little earlier, and by hurrying home, unnecessary delay can be avoided and the prime time for candles can be maximized.
On the note of setting up on Friday for Motza”Sh lighting too: Since on Friday we will light four candles, and we need five for Motza”Sh, you either need a second Chanukiya for the job, or you can set up four of the five candles for Motza”Sh in the blank section of the Chanukiya and then remember to add the fifth candle with minimal additional time. Have your matches and helper candles ready too from before Shabbat.
Which goes first? Havdala or Chanuka candles.
This is a topic that bears yearly review because of how fuzzy our memories can sometimes be. TWO MITZVOT TO PERFORM – Havdala and Chanuka candles. By the rule of TADIR (that which is more frequent should be done first), havdala should be said first. And by logic, one should “finish” with Shabbat and then light candles for the next day of Chanuka, which is Sat. night / Sunday. Many authorities hold that on Motza’ei Shabbat, one should say havdala first and then light Chanuka candles. This opinion is followed by the majority of Chanuka-candle-lighting Jews all over the world. The Maharal (among others) is vehement in his insistence that we cannot possibly consider doing something so “weekday-ish” as lighting candles, unless we have first said havdala. He rejects any contrary arguments. (Even if you want to point to the halachic permission we have on Motza’ei Shabbat to do certain things before havdala (provided, of course, it is after Shabbat time-wise and we’ve either davened Maariv with ATA CHO-NANTANU or at least said BARCH HAMAVDIL… – answer the phone, for example, with Chanuka candles the objection would be based on instituting candle lighting as a permanent task before havdala. This first opinion objects to the formalizing of such a weekday activity before the havdala ceremony.
ON THE OTHER HAND… there is a strong argument for lighting Chanuka candles before havdala. First of all, Shabbat is over when it is 5:21pm (to use Jerusalem time as an example – substitute your location’s Shabbat out time) AND one has said Havdala in davening (ATA CHONANTANU in the Maariv Amida) OR at least said BARUCH HAMAVDIL BEIN KODESH L’CHOL. The Havdala with wine, spices, candle, is NOT what ends Shabbat – it is what honors the departing Shabbat (and permits eating and drinking). Even so, havdala should go first, except for one very important factor: The prime time (and according to some opinions, the only time) for Chanuka candles is ticking away – namely, the first half-hour after dark. We cannot, of course, light Chanuka candles when it is still Shabbat. But we should maximize the portion of time of the “half-hour after” once we are allowed to light. Havdala will wait; Chanuka candles will not.