UkuleleCruiser

I'm leaning towards voyager class ships. They have most of the amenities that a large class has (including promenade) but has less people and the feel of a small ship. I think of them as 'medium class', with the pros of both large and small classes.
 
I haven't tried radiance class (will in sept) but it may be a contender aswell with it famous multiple views of the ocean.
 
That said the ship I'm most sentimental about is the Enchantment, she's in a class of her own after being stretched. First ship and fell in love with cruising on her.

I love Serenade, Freedom, Grandeur, Allure, Liberty or any other Celebrity or Rccl ships.

We have only sailed with Celebrity, so I cant comment on any of the RCL ships. In January we will be on Freedom, and I can say we are really excited about it! We have a family panoramic room, which I cant wait to see!

Since its Christmas Day there won't be much open. If the weather is nice, go for a stroll along the seawall. You might enjoy the history display in the basement of the Galvez. It only takes a few minutes but is interesting and tells about some of the famous people who have stayed there and the ties to the entertainment, organized crime, and political figures of the last century.

I am not sure. As I recall, they would have something at the gangway you could get your picture taken with. But not at sites other then the dock or tender.

Based on everyone's feedback, I do see the value at $250 or $300, but I think I will still pester people to take our picture and spend that money on drinks, food, and other non-essentials.

In Old San Juan we did La Casita Rones which is a rum bar and 'Puerto Rican Rum Embassy' located right at the pier downtown.
 
St. Maarten we went to Topper's Rhum Distillery
 
I skipped St Kitts; the group went to Brinley's, I took a catamaran to Nevis and had a "Killer Bee" at Sunshines.
 
On Antigua we toured Antigua Distilleries and had a tasting.  One was a bottle that was distilled in 1981 for their independence and aged 25 years.  Fabulous!  That bottle came home with me - the kids really don't need to go to college after all...
 
While in St. Lucia we toured St. Lucia Distilleries and partook of many rare rums the management set out for us.  They really went out of their way to educate us on the whole process, from cane field (or molasses tanker, depending on the brand) to barrel to bottle.  It was a fantastic experience.
 
On our last stop in Barbados, we toured St. Nicholas Abbey where they owners make an artisanal rum, and then off to Mount Gay's production facility at the north end of the island (not the visitors center near the port).  They gave us the V-V-VIP tour of the plant, followed by a session where we got to mix our own blend of rum (and take home a small bottle with our names on it), and finally we went into the aging facility where they gave us chalk and we were able to write our names on a barrel.  On the way back to the ship we stopped at the Visitor's Center and a bottle marking Barbados' 50th Independence Anniversary managed to make it home with me.
 
It was a fabulous experience for a rum enthusiast like myself!
 
Rob Burr is a rum expert and he and his wife Robin organized the tours.  
http://www.robsrum.com/2016/06/16/caribbean-rum-cruise-announces-vip-distillery-tours/
 
It was a fabulous experience for a rum enthusiast like myself, and I highly recommend it if you are interested in the spirit.

33 drinks goes quick....at least on my cruises it does...
 
I always get the drink package....and usually break  even for the cruise on the first day.....everything else after that is "free".....haha

This approach makes tons of sense in our case...I may do something like it!

that's a lot of drinking on the first day of the cruise.

You're still my hero. :)
 
I've had the drink package on my two last cruises, and the most recent one was a rum tour where we visited distilleries and had tastings, etc., so wound up drinking on shore rather than staying onboard.  Even so, the drink package was worth it to me to try new drinks, have everything prepaid, etc.  
 
My wife on the other hand doesn't drink as much as me onboard so the package doesn't work for her.  Because she's paying for each drink, she'll have maybe one drink a day.  I wish they would offer the 10 Drink Card at the beginning of the cruise so I could pick one up for her and tell her to have fun with it.

I'm in! For me, it's the Navigator. But probably after Christmas -- All my funds are going to my Liberty cruise right now! Live like a pauper now, cruise like a king!

I do like the option to just buy guacamole and chips with a la carte, but if I want to sit down for a meal, the cover charge model makes way more sense (plus I like the ambiance/experience of Freedom/Voyager class Sabor over Oasis class).

Matt, I saw it on either day 3 or 4 of the 7 day.

They offered it on the Nov. 19th Adventure sailing as well, day 3 or 4 of the 7 day.  I don't recall the exact day as I had the drink package.  (that didn't come out the way I meant it)

My avi is not an indicator of current consumption patterns...

Not sure if anyone is still interested but I just got off the Oasis and they had the 10 drink card for $79.

They key is for you to stop and take a lot of photos during your cruise. 

And don't forget to use your C&A Gold 2-for-1 milkshake offers!

Booked May 20th!!!! :D 

That wasn't nice to call those other two bartenders names....
 
 
:P

It took me a moment, but THAT was FUNNY

This is a little bit like asking which wine is best. Ask five people that like wine what their favourite wine is and you'll get five different answers, and I suspect the same for cruising.
 
But for me personally, if flights weren't an issue, my preference would be a southern itinerary out of San Juan, Puerto Rico. Old San Juan is a very cool place to spend a day or two pre- or post-cruise. I'd prefer Freedom Adventure over Jewel because it has a few extras like the FlowRider, but I wouldn't hesitate to cruise Jewel again.
 
Of course if some people wanted to do Walt Disney World or Universal Studios (i.e. Harry Potter World), then Orlando might make more sense. If New York City appeals to the crowd, then cruising out of Cape Liberty (which is right around the corner from the Statue of Liberty) on Anthem might offer the greatest amount of overall awesomeness for the group as a whole, but would require a 9 to 12 day cruise to get farther than the Bahamas.
 
Given you've got folks coming from different directions, the cost and convenience of the flights for everyone involved might tilt the scales to one cruise over another. You might want to begin on Google Flights and compare how the flights will look for various ports of departure. Also consider whether or not the amenities of an Oasis or Quantum Class ship are make or break to your party. 
 
Not sure that helps, but I'm sure it will be great whatever you choose.

Last couple of cruises I have booked the Next Cruise onboard. I have paid a $100 deposit, but then get a $100 OBC for the current cruise, so it's pretty much like booking without a deposit and then getting $100 off the next cruise (because I would have otherwise had to pay that $100 to my bar bill on the current cruise).

Yes. On our next cruise (19 days!) we took advantage of that. We were upgraded from an Inside cabin to a Promenade View cabin. And we had to forfeit the $100 OBC we received from the original booking. Glad this doesn't work the other way, because the prices are now going up. We might be moved to a broom closet! :-)