First - it will depend on the length of your cruise. Buying the Cheers package at $59.95 plus gratuity for a 12 night cruise PER PERSON can be breathtakingly expensive. However - for us - it it always 100% worth it. I build it into the "cost of the cruise" - and it's still usually cheaper than a Disney or Celebrity cruise.
I start with some Baileys in my cappuccino (both included in cheers) . . . . . maybe two.
I usually have my first cocktail around 10 or 11am as I'm starting to think about lunch.
Rum and Diet Pepsi (meh) with lunch . . . maybe two
Something fruity or margarita-y on the pool deck or at the casino on sea days mid afternoon.
When they kick in - I'm always up for an espresso martini. (I get a double espresso from Java Blue and bring it to the Alchemy Bar if they're open.)
Vodka martini just before dinner.
Glass of wine with dinner
After dinner aperitif (Drambuie, Frangelico, Amaretto, etc.) with coffee
Nightcap cocktail in the casino or at the production or comedy show.
Plus all the soda, premium coffee, bottled water and milkshakes I can drink throughout the day. π
If that's not your typical(ish) day - don't get the Cheers package.