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I booked my next HAL cruise while still on a cruise.

I understand I can shop for the best deal from a TA and have the booking transferred to the TA with the best deal.

What prevents me from continuing to shop it?

If I transfer to an TA, then find a better deal later,

can I have the booking transferred again from the 1st TA to the later TA?

When does this window stop?

Up till first payment?

(Deposit was only $2 dollars)

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there is a time window to transfer to a TA and once that transfer is done it will be difficult to change again. It's best to build a relationship with your TA. Most will work WITH you to get you the best experience, they do not work for you. There comes a time when "shopping" around looking for a better deal will result in the loss of the best deal you already had in hand.

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Transferring from HAL to a T/A, yes easy to do, shop around and dish it to your preferred T/A. Swapping from T/A to T/A, not so easy. You will need to cancel with one, which will usually lose your onboard booking bonuses in the process of rebooking with another.

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