Booking DCL Sept 2027 tips please.

So thanks to you all, we already put a dep on a 5 night Fantasy for the 3 of us (daughter will be 4 yrs old). We wanted a 4 night but 5 was the only way to get both islands, with Nassau being first. 9/5/27; floor 9, 2 below the pools, like recommended (8 was slightly cheaper); interior like I wanted but only a couple doors from my group's balcony room for 5, a short walk, across from elevators. It was roughly $3700, which I have sticker shock even with expensive expectations, since this doesn't include flights. 1st dinner. I think there is a pirate day with optional dress up.

We're leaning towards buying the insurance, roughly $200, not just because of hurricane season, but if someone gets sick/hurt. What do you guys think on that?
Any reason not to prepay gratuity?
If we do stick with a WDW stay beforehand, and buy a Mears Connect bus from MCO to motel. Is it best to Uber from resort to port or use a shuttle?
Does it make sense to get a later Port apmt. like close to 3pm, to try to go to MK until like 11/12pm? With the 5 night, we'd only be looking at a 1 or 2 night stay so potentially only 2 park days without anything on the Port day (and first day being a partial flight day).
 
Being cost sensitive, I would not bother with the park visit at all. Park tickets for 1 or 2 days is the most expensive per day ticket you can get. Trying to go to the parks for a few hours, then heading to the port would not only be very rushed, but a waste of a day's ticket. You would miss the activities and lunch on the ship.

Perhaps stay at Animal Kingdom Lodge and enjoy the resort and animals. Get the earliest port arrival time and head out after breakfast to enjoy those extra hours getting to know the ship.

If magic kingdom is a must do, then I would stay 2 nights at WDW, preferably at a MK resort and get started early at MK on your full day. Take a break in the middle of the day and head back in the evening.

The least costly would be to get a hotel near the port. Enjoy the day at Jetty Park. There's a beach and park area where you can watch the Disney ships sail in and out. Disney Treasure should be in port on 9/4/26.

Can't help with insurance since I live locally and never buy it. But just make sure if you buy that it covers what you think it covers. I'm sure others can chime in as you would probably want to protect your airfare as well.
 
If you plan to go to a park on embarkation morning, you will need to check out of your room, store your luggage, return to the hotel, get your luggage, and get transportation to the port. As cigarboo mentioned above, you would spend a few hours in the park and pay for a full day. I agree that you would be better off getting a character or other nice breakfast (my family likes to do Boma, even if we are not staying at Animal Kingdom Lodge) or going to Downtown Disney if you want to spend more time in the Walt Disney World area.

I would not recommend planning to arrive at the port much later than 2 pm. There could be traffic issues or other delays. If you are at a Disney resort, the Disney shuttle would be the most convenient, but may leave earlier than you would prefer. There are many private companies that book travel between WDW and the port in advance. I would be nervous planning an Uber that morning, because it is a good distance to the port.

If you don't mind giving Disney money in advance, there is no reason not to pre-pay gratuities. I have never had service so poor that it caused me to reduce my gratuity rate -- I usually end up adding to the amount.

Insurance is a personal decision. Think about what might happen that could cause you to miss the cruise (illness, injury, travel problems, bad weather, etc.) and what could cause unexpected expenses while on board (primarily illness or injury). Then look at whether the insurance Disney offers would cover those issues. Insurance purchased through Disney covers will not cover airline cancellations and rebookings unless the airfare is booked through Disney, and will not cover medical costs before or after the cruise. If you have other insurance that covers flights and/or medical care in the US, that may not be an issue. If you do want insurance, you should look into other companies that may offer lower rates for more coverage.
 

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