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Answer: There are two main issues to deal with: whether they are considered doing work on your behalf; whether there is a problem of marit ayin.
In this case, UPS is doing melacha on your behalf, at least in regard to driving to the pick-up point and perhaps other matters. (It might be somewhat of a lenient case since you do not interact with the person who is doing the work – see Mishna Berura 307:24.) It is generally permitted to have a non-Jew do work for you on Shabbat if they are doing it for their own purposes. When one pays the non-Jew to do work that the Jew wants, the major distinction is as follows. If the non-Jew is paid by time, it is considered doing work for the Jew; if he is paid per the job, it is considered that he is working on his own behalf (for the pay) (Shulchan Aruch, Orach Chayim 247:1). UPS obviously gets paid for the job, which is good. On the other hand, even in that case, if one instructs him, explicitly or implicitly, to do the work specifically on Shabbat or Yom Tov, it is forbidden (ibid.).
Therefore, you would have to give them a time for pick-up that would not necessarily be on Shabbat or Yom Tov (i.e., they have time before or after). From a look at their site, it seems that one’s request can be made for anytime (24/7). On the other hand, in a response to my written question (I cannot gauge the expertise of the specific customer service worker), pickups are generally done from 9 AM to 7 PM. Accordingly, during some of the year, if you allowed them to come all day, it would not necessarily be on Shabbat/Yom Tov and at other times, it would be on the same halachic day. The halacha is that it is not enough to provide them a theoretical alternative to work on Shabbat, but it must be practical (Mishna Berura 307:15). (You could ostensibly give them a two-day window to come on, but your question implies that you have a reason for it to be on one specific day and not the day after. The day before would also be fine.)
An interesting consideration arises with two days of Yom Tov. Is it permitted to tell them to come, say, anytime on Monday, when Monday is the first day of Yom Tov and Monday evening starts the second? This should be fine for any Yom Tov other than Rosh Hashana. That is because we treat each day as a mutually exclusive doubt. Namely, if the first day is holy, the second is not. If the second is holy, the first is not (Shulchan Aruch, OC 513:5). So if they have all day and part of the night of Monday, they have the opportunity to pick up on chol. Rosh Hashana, in contrast, is treated as two definite days of Yom Tov (ibid.).
There is still a problem, due to the halacha that one is not allowed to have a non-Jew take an object from a Jew’s home on Shabbat, unless he took it unexpectedly (Shabbat 19a). All explain that it has to do with marit ayin, but differ as to what people will think. The Shulchan Aruch (246:2) says that one will think that the Jew told him to carry it out for the Jew’s benefit into the public domain. If that is the case, then if the non-Jew lives within the same eiruv as the Jew’s home, there would be no problem, and it is possible that the same would be true of at least some cases on Yom Tov even without an eiruv (Taz 246:3). The Rambam (Shabbat 6:19) says that people will think that the Jew improperly sold or the like to the non-Jew on Shabbat. In that case, it applies even within an eiruv (Magen Avraham 246:6; see Sha’ar Hatziyun 246:7). In this case, it would seem that according to everyone there should be marit ayin because one who sees the non-Jew taking it on Shabbat or Yom Tov will not realize that he did not tell him to come specifically on the holy day (see Mishna Berura 252:17). Therefore, if you want the pick-up, in addition to including a possibility of chol pick up, you should also have it picked up from a non-Jewish neighbor’s house.
Bemare Habazak - Rabbis Questions (654)
Rabbi Daniel Mann
261 - Whose Minhag About Being Chazan Should an Avel Follow?
262 - Sending Packages on Shabbat or Yom Tov
263 - Animal Experimentation
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Kuzari -Rabbi Ari Shvat Kuzari class 8- "Answering Questions on the Kuzari's Proof from Mass Revelation
Rabbis in Midrash
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Kuzari -Rabbi Ari Shvat Kuzari class 9 - "Seeing is Believing" (parag. 21-30)
These paragraphs elaborate on the theme that seeing and knowing is better than any attempt to prove logically, and begins explaining the difference between Israel and gentiles.
Ein Aya Various Universal Stages of the Geula Process
Rav Kook examines the various stages of redemption, explaining how (in addition to the obvious oft-mentioned stages of ingathering the exiles, reviving the Hebrew language, army, state etc.) the messianic dream of world prosperity, the State of Israel and world unity can and are realistically and logically gradually coming true.
Kuzari -Rabbi Ari Shvat Kuzari class 8- "Answering Questions on the Kuzari's Proof from Mass Revelation
How do we know that the "claim" of mass revelation to 2,000,000 witnesses at Mt. Sinai is really true? This important class answers all of the questions skeptics ask about this claim of the Kuzari.
Ein Aya Armies Still Necessary for Balance & the War Against Wars
Rav Kook explains why the world was originally divided into the various seemingly contradicting ideologies and cultures, in order to develop each one respectively. Swords or armies symbolize how each respective ideology defends themselves, as well as deters their opposing ideologies and cultures. On the other hand, the messianic era will be one of peace, and Rav Kook explains the transition to that stage, which mankind is already undergoing.
The Land of Israel LGBT'S IN ISRAEL
The question was asked, how can one make Aliyah with the LGBT parades?
Kuzari -Rabbi Ari Shvat Kuzari class 7 - Five Accumulative Proofs of G-d
As a preparation for the Kuzari's classic proof of G-d from the mass-revelation at Sinai, we start here with 5 other directions to strengthen our belief which also contribute to what the Kuzari will present as well.
Ein Aya Muscle & Meaning: The Dual Nature of Gevurah (Physical Strength)
Is physical strength and fitness a necessity or an ideal? Although it if often totally overlooked among topics of Judaism, Rav Kook writes that it clearly is also a necessity to deter the many enemies of Israel, but even in Y'mot HaMashiach, in the Messianic era, to a certain extent, it's ideal continues even after our enemies will have been finished off.
