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I will be traveling alone round trip from Philadelphia to Orlando in December using my Amtrak Guest Reward Points. I was hoping someone could give me some feedback if the insurance is a good purchase since I'll be using my points and not paying out of pocket.
 
My opinion is no.

The only thing that the "insurance" you purchase from Amtrak covers is the train portion itself. It is a direct train from Philadelphia to Orlando, so once you're on the train, there's no chance of missing your connection. And if there was a connection involved, if it's a guaranteed connection, Amtrak is responsible and will take care of you. If you have to cancel, you can get a 90% refund in cash or a 100% voucher for future travel on Amtrak.

As I see it, the "insurance" is just a money maker for the insurance company in this case.

If you want travel insurance for any other reason (hotels, medical evacuation, etc...), it's up to you. Your credit card may even provide this at no charge!
 
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I have no idea whether travel insurance would cover a trip "purchased" using reward points. Maybe someone else would know.

Below are guidelines regarding cancellations of rewards trips (from Amtrak website).

REWARD TICKET MODIFICATIONS & CANCELATIONS
  • For modifications on one-way, round-trip or multi-segment reward travel, the following will apply:points difference (to new prevailing fare) will apply in all cases with a 10% points penalty withheld on any fare difference returned to member
  • If modifying a non-sleeper ticket within 24 hours prior to departure, or a sleeper ticket within 14 days prior to departure, an additional "close-in" penalty of 10% of the points redeemed will be collected (waived for Select Executive).

[*]For modifications to reward travel on a multi-ride ticket, the following will apply:
  • Before first ride, a full exchange in point value will be issued without penalty
  • No exchange value in points after first ride or after expiry—whichever comes first

[*]For modifications to reward travel on a monthly pass, the following will apply:
  • Full exchange value in points prior to valid month
  • No exchange value in points on or after first day of valid month

[*]For cancelations on one-way, round-trip or multi-segment reward travel, the following will apply:
  • A 10% points penalty is assessed for any refund (redeposit) back to the member account.
  • If canceling a non-sleeper ticket within 24 hours prior to departure, or a sleeper ticket within 14 days prior to departure, an additional "close-in" penalty of 10% of the points redeemed will be collected (waived for Select Executive)

[*]For cancelations to reward travel on a multi-ride ticket, the following will apply:
  • Points are refunded minus 10% point penalty if unused and unexpired
  • Redemption non-refundable if first trip used or if ticket expired

[*]For cancelations to reward travel on a monthly pass, the following will apply:
  • Points are refunded—minus 10% point penalty—prior to first day of valid month
  • Redemption is non-refundable on or after first day of valid month

[*]A "no-show" for any segment will result in forfeiture of points and travel for that segment, as well as all subsequent segments in the itinerary. A "no-show" is defined as a passenger's failure to travel on a segment from its origin without first canceling that portion of the itinerary.
https://amtrakguestrewards.com/info/2016redemptionguidelines
 
Insurance covers the cash portion of your trip, not the free portion. I never purchase travel insurance when traveling Amtrak since I can get a refund or voucher. Also, I do not pay in advance for hotels or rentals cars since those reservations are non refundable nor changeable. The cost of insurance is worth the price for a cruise since reservations have to be made so far in advance.
 
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