Nay

@Nay I think arriving the day before, no matter what time, is a great idea. You have plenty of time if there are issues. People arrive that day, especially for a late sail away. No worries.

I would not hesitate to sail on Freedom. Fabulous ship.

Thank you all SO much for your replies, this is a great weight off my mind.
This blog site is brilliant by the way. I've asked "dumb" questions on it previously and everyone is so helpful and nice! 
My husband often posts questions on a DIY site and the responses he often gets are rude and nasty. 
Well done everyone on here, you're a great help to us novice cruisers

Crown Bay aka "downtown"
Nope. You can walk to downtown Charlotte Amalie, but the rest require a taxi
Very easy. Taxis are plentiful and all over the place.  

LOL.  On November 3rd, 2019, New Jersey will "fall back" and be on Eastern Standard Time. 
When you fly to San Juan to board Freedom, San Juan will be one hour ahead.  They'll probably tell you on the plane when you land in San Juan to set your watches ahead one hour.  
From that moment forward the time will never change at any of your ports or on the ship.    

We did the Northbound Radiance and 3 night cruise tour at the end and we did Denali. The cruise tour thru Royal Caribbean was awesome.  It was a perfect ending to a perfect Bucket List vacation.  They have longer cruise tours if you can stay longer.

I lived in AK for almost 4 yrs right outside of AK.  I do believe the ship does not matter, but I would say the time of the year matters just as much, and maybe more if the itenary s port intensive.  In Anchorage we call May the SPIT month.  It basically does not rain, but it is not unusual for it to spit...mist, light showers all day.  Plus, a TON of big arse mosquitos.  By early June the mosquitos and spit is gone.  June and July are the best months. I would book 3rd week of June prior to summer solstice.  Believe it or not Denali is warm, than again I lived in AK for yrs.  If it is sunny, you can expect a dry air 80 degrees.  August, you are getting back into iffy weather.  Still slightly warm during the days, but chilly at night.  Depending on how cold August gets you might see more bears and moose....going into hibernation.  I would say that no matter when you go, if you dock in Anchorage, you need to book Simon and Seaforts.  It is an amazing restaurant (pricey), but the service, the ambience and if you can get a window table it is worth the cost.  Try the prime rib and the crab/artichoke dip.   I would stay at the Hilton over Captain Cook Hotel.  You can easily walk to Simon and Seaforts.  The Hilton has an amazing roof top restaurant/bar when we lived there.  They are north of Captain Cook.  
If you are in Anchorage I would suggest Eagle River Rafting.  http://rafting.allaboutrivers.com/Alaska_river_rafting/Eagle_River_(AK)_rafting-riv265.html 
We lived in Eagle River.  It is about 25 mins from Anchorage.  It is a mild ride, but still a lot of fun.
I would also suggest that if you are staying in Anchorage to contact Simon and Seaforts and book asap if you want a window over looking the bay.  I cannot tell you how amazing this restaurant is regarding food and service. 

https://secure.royalcaribbean.com/cruises/?dates_maxDate=09%2F30%2F2020&dates_minDate=05%2F01%2F2020&destinationRegionCode_ALCAN=true&durationCode_12plus=true&durationCode_9to11=true&icid=hpnvbr_pagehe_fnd_hm_awaren_938

Cheapest.  
I always get a kick out of people who are convinced one side is better.  99% of the time you have land on both sides.  For a few hours before entering the inside passage land might be more visible on port but more marine life might be visible on starboard.  
I did a suite with large balcony once Southbound  Hardly used it - too cold.  Having done interior cabins twice in Alaska I’d rather splurge on excursions which are expensive in Alaska rather than on a balcony or a bigger balcony.  Hint - sitting on an excursion I was lifted up higher compared to the guy with a balcony next to me because my wallet was fatter .
Helicopter to a glacier I’ll never forget.  I can barely remember using my balcony.  Consider a location close to stairwells so you have quick access to outer decks on either side of the ship.
Where ever you are, go to the outer decks outside to see both sides   You never know what side a whale might appear on, or what side has a better view at any given moment   Staying in your cabin is a terrible idea because you miss half of it especially at a glacier.
Most of the time you will be in channels with land on both sides so ship motion isn’t a big thing.  You can encounter some waves during the open ocean sprint into the inside passage for a few hours. Or you might have no motion.   If you or your SO is sensitive to motion and the thought of being anywhere but midship is a source of stress, stay midship but the potential for motion is greater in the Caribbean.

Yes... Atlantic Time Zone = San Juan Time = Ship Time = Port Time, which just happens to also be my favourite time ... MIMOSA TIME !!??

Hey JasonL, I feel your pain by not being close to cruise ports that go to the caribbean. We are going on our first ever cruise in Feb, flying to San Juan from TN, doing a southern caribbean cruise on Freedom OTS. Plane tickets certainly aren't cheap, I guess if we had a family of 5 as you do, it would be put on the back burner. Save & plan to make it happen!!

We are also 1st time cruisers. Will be on Freedom in Feb for our 44th anniversary. Cannot wait, but not sleeping worrying about packing, planning ect.Was hoping Freedom wouldnt be too large to enjoy. We will have 2 sea days which sounds like that will be nice. We have a balcony on 9th deck. Any advice, do's donts?
Happy BD

The only ship that has had nasty drinking water was Navigator on our Thanksgiving Cruise.  After the second day it tasted fine.  Usually the ships water is very good.

I am far from being a water snob but I will have to say that it is actually pretty good to me.  The wife did not want to go the YETI route the last few cruises but after she saw the ease of it all, she quickly became a fan.  

They will allow you to bring water onboard. They have an official policy about it. And I did it as recently as this past July.
I would not count on being allowed to bring any plug in power strips. Not many cruise lines allow it due to fire hazards. You can bring a USB hub without any problem usually. 
I copied this from Royal Caribbean’s website.
 
One of the best things about cruising is the food! And there will be many dining options available to suit most tastes and preferences. However you are free to bring non-perishable prepackaged food in limited quantities.
While we have many drink offerings onboard, you are welcomed to bring select beverages onboard.
On boarding day, each stateroom may bring up to two 750 ml bottles of wine or champagne, as long as one guest is of legal drinking age. Corkscrews will be provided for guests to enjoy their drinks in their stateroom. If guests wish to enjoy their wine or champagne in our dining or bar venues, there will be a corkage fee applied.
Guests may also bring non-alcoholic beverages as carry-on items on boarding day. Non-alcoholic beverages may not exceed 12 standard (17 oz.) cans, bottles or cartons per stateroom. Milk and distilled water brought on for infant, medical, or dietary use are permitted. 
Guests who purchase alcohol bottles onboard, in a port-of-call, or bring more than the two permitted bottles on boarding day, will have their items safely stored by the ship. These bottles will be returned on the last day onboard for enjoyment once home.

Well, they stopped letting people put luggage tags on massive amounts of water and getting it delivered to their room.  This was actually always against the rules but was ignored by most port personnel.  (You weren't allowed to bring any water or soda on board, just 2 bottles of wine per stateroom).  Now they have an actual policy that allows a limited amount of water or soda to be carried on by you and they enforce no water/soda in checked luggage.  So perhaps that is the source of the conflicting information you're seeing.

Board Allure of the seas a week ago from Miami , carried with me 4 bottles of water and two bottles of wine , no issues at all.

Must admit i sometimes have difficulty sleeping even in my own bed due to bad back pains however on this trip i had no issues what so ever. 
This was probably down to a number of factors, Being tired at the end of a long day, having had a few beers and the bed not being uncomfortable all helped.
 

2020 for sure, back to Caribbean to do the ABC Islands if possible 

I am from Denmark and the government recommend Hepatitis A and B when travelling to the Caribbean. 
I did however not get those vaccines when I travelled there. #livingontheedge

Not coming into San Juan, but going out, regardless where you are going, you have to go through agriculture 

I think Freedom is an awesome ship for a first-time cruiser to experience. She was mine and my family's first ship, and my wife and I thought she was great!

It’s where the ship anchors out from the port and you take a “tender” (smaller boat) into the port. There will be several coming and going from ship to shore all day. 

We were just on Liberty this summer with our Grandson, and even though we didn't have to we paid for Voom and used Whatsapp so that my Grandson could talk with his Mom each night  and video chatted with her a couple of nights. Otherwise I leave the below information for family.
Emergency Contact Number, 1888-724-7447                        
Ship Name, Liberty OTS                        
Reservation ID, xxxxxxx, under the name, ????                        
Room number, 1286           
 

Just ask a crew member where the free wifi is.  They always know.