How do I make sure I get the best deal when planning ahead?

[mommymanda]

I am planning our next Disney trip for August 2016. I already know the best deal for my family is during free dining. We always book holidays the last week of August, which so far has a pattern of also being a free dining deal time.

Now history shows Disney releases this deal in May.

Airlines offer me the best prices in February. So what do I do? Book flights and hope the pattern continues? Book a room at full price in February with flights, and hope changing things won't be to hard?

Just looking for tips, I'd love to surprise the family next year by flying since normally we drive the 20 hour trip.

 

[sam_gordon]

What would your response be if you weren't offered free dining? Would you not take the trip? If the lack of free dining would mean no trip, then I wouldn't book airfare until I knew there was free dining.

However, also factoring in is what airfare would do between Feb & May. Airfare might increase enough that the money you save by booking in Feb might pay for your dining (if a free dining pkg isn't offered).

Personally, I would book the flights when I see an acceptable price, and book the full price room. I don't think changing is hard.

One tip on airfare, start looking in September 2015. You might be surprised and be able to get a good rate earlier than February.

Another option if the free dining doesn't work out is do a "non Disney" vacation. I know that's blasphemy, but there's Universal, Sea World, Tampa, Cocoa Beach, cruises, etc.

 

[mommymanda]

What would your response be if you weren't offered free dining? Would you not take the trip? If the lack of free dining would mean no trip, then I wouldn't book airfare until I knew there was free dining.

However, also factoring in is what airfare would do between Feb & May. Airfare might increase enough that the money you save by booking in Feb might pay for your dining (if a free dining pkg isn't offered).

Personally, I would book the flights when I see an acceptable price, and book the full price room. I don't think changing is hard.

One tip on airfare, start looking in September 2015. You might be surprised and be able to get a good rate earlier than February.

Another option if the free dining doesn't work out is do a "non Disney" vacation. I know that's blasphemy, but there's Universal, Sea World, Tampa, Cocoa Beach, cruises, etc.

I've been trying to figure the same. How badly do we want to take this trip, what is my final budget.

I have priced this trip monthly for the past 10months to see what deals work best for us. The only fixed is the travel date...but through it all it worked out that booking during free dining is definitely the only time that works for our budget.

Flying from Canada, watching prices they range from $220-$350 depending on the month (lol same flight just different time of year booking). If the flights are not under $250 than flying is not an option.

So I think to answer the first question. If we can't get free dining than we wouldn't go...if we can't get affordable flights we would just drive again.

 

[sam_gordon]

If a non-Disney vacation isn't an option AND no free dining = no vacation, then I think you have to wait to confirm free dining before you book airfare.

Seriously though, start watching airfare as soon as it comes out. You might be able to get a decent price that would allow you to go even without the free dining.