KAA

I cannot answer but I will be on the Anthem too! I have an Universal Annual Pass so we are going to a Universal for the day. I am hoping someone has experience with this!

I've been on a few Christmas/New Years cruises! It's not going to be the same as being home for Christmas, but they do really go all out. I am speaking more from an adult perspective, so there was definitely big trees on every ship, but I think different ships do different things. I have seen cookie decorating, getting presents from Santa, plenty of activities. However, we are mostly taking in the sun and the nice weather being from New England :) 

I'm a "no quote" on Bermuda, have not been there, will be on my 2019 Anthem cruise.

I will be on anthem for the Holidays this year. I have been on all three ships. They are are very good ships. I am doing the 9 day Bermuda on Grandeur in June 2018.

The real issue with Bermuda is, it's bigger than you think ..... once you fall in love with the island, which you will, you will want to see the whole thing (with a Rum Swizzle in hand).
Horseshoe Bay is as stunning as they say, there's tons to see and do around dock area.  That one picture of the building with the two clock towers is the Clock Tower Mall.
When we go back in October, we're dedicating the full day there to St. George....it's the one part of the island we haven't made it to.
Bermuda is incredibly easy to get around in .... especially with the famous Pink Buses

We Love, Love, Love Bermuda ....... And, as you look at my signature, Grandeur ..... in fact, we'll be going back again in October for the 7-nighter (3 Days in Bermuda).
Instead of going into something wordy, here are a few pictures ....

Me personally, I would choose #1 

All are good options and I actually have 1 and 3 booked myself.
I would do 1 for the ship, but 3 for the itinerary. We may actually cancel our Anthem cruise simply because 1 day in Bermuda simply isn't enough. I really wish they'd overnight there a skip the Bahamas.
Option 2 is good for a classic ship and ease of boarding/convenience of port, but I still think 3 is the best of the 3.
 

Well, I'm only sailing there for the first time in October, can't really say if no overnight is a problem. I know that @coneyraven has been a few times and loves it there. He regularly sails Grandeur on the 5- or 7-night single-port itinerary, as it's a favorite of his. Hopefully when he sees the mention he can chime in with some more advice about whether no overnight could be a deal-breaker.

I would say that if you're doing a Bahamas itinerary in just a few weeks, which presumably will already be stopping at Nassau and Coco Cay, then the Grandeur itinerary might be the least interesting unless you just want to experience Bermuda and what it's like on Grandeur. Certainly, an overnight in Bermuda is a big plus if you've never been; I'm finding out how much there actually is to do there and glad I have an overnight for my trip there in October on Anthem.
Apart from that, I can't really be much help. The Freedom itinerary sounds the most interesting to me personally, as I'm more of a "ports matter more than ship" guy, so I'd go with that one myself. But I'm not you.  How many times have you been to those ports, and how eager are you to see them again? Same with the Anthem itinerary, which also sounds pretty good to me even without an overnight in Bermuda.

If it's purely based on ports, go with #3. We did that exact itinerary about a month ago and it was INCREDIBLE. The islands are gorgeous, and the Freedom class is a great class of ship. 

Haven't been on 1 or 2 yet, but 3 I have and that will be my vote, love that itinerary and ship.
I will be on Freedom in October out of San Juan, going to Aruba and Curacao, have Anthem picked for July 2019 may be same itinerary and no plans for Grandeur yet.
I'm also Diamond and have Grand Suite picked on freedom.
Welcome to the form BTW.

It does, but it is only for GS and above & Pinnacles.  So if OP went to a JS, that wouldn't apply.

My first cruise was on Enchantment and at the time it was so disorientating just for the fact that it was our first cruise. But then we started to go bigger and bigger and bigger. We had recently went on a Jewel and Rhapsody and realized how being on a smaller ship was actually so nice too. With that being said, I still love all the ships (Anthem is probably my favorite), mostly because we tend to stay on board a lot, so its quiet when everyone leaves, but its always nice to have the small ship feel too. I think there are perks to both and you should definitely try it out too :)