Free Dining vs. Annual Pass

Is there ever a scenario where Free Dining while staying at CBR for 4 adults is NOT a better deal than Annual Pass discounts with TIW? DH and I are leaving next week to take our toddler for 6 night stay. We could upgrade our 6 day hopper tickets to annual pass and get TIW at the beginning of our trip assuming we know that it is worth for later in the year. We are planning to go back again in Nov or Dec with grandma and sis to see Christmas party etc. We have booked Free dining trip for 4 nights at CBR. Grandma and sis will need tickets but if we do free dining it doesn’t seem to make sense to upgrade now to annual pass since we also will be forced to get tickets. Thoughts? Any suggestions or recommendations on whether it makes sense to upgrade to annual pass now or not? Thanks so much!!

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Free dining is very frequently not the cheapest option. Saving on not having to buy two sets of tickets, TiW for 20% off including alcohol and free valet parking sounds like a great option.

Ap would already save you $300 on buying tickets. Add in a room only discount (plus the extra at least 15% you can save booking through Orbitz) and unless you guys are big eaters doing a lot of expensive signature meals I can’t see how free dining would work out to be cheaper for you.

I second @Outer1.

I’ve been running the math lately, and FD is pretty good if you’re staying at a moderate, but I did the math this week.
RO discount on Orbitz + marginal AP cost + TiW + food
Full-price rack rate room + Full-price tickets

RO comes out ahead most of the time… UNLESS you’re going to have 4 adults in a room at CBR, in which case you pretty much make out like a bandit on FD.
AN ALTERNATIVE would be to upgrade to AP, STILL get the FD package, then SAVE the tickets from the FD package for a future year’s trip after your AP has expired (Others have talked about that on here, but you could confirm with WDW).

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