Welcome to the forum.
Actually you are looking at a "multi city" or "open jaw" ticket, not two one-way tickets.
The only answer to your question is, "Buy the ticket when it is cheapest." Obviously neither the question nor the answer are realistic.
Monitor fares, know what a "decent" fare is so that when you see a "good" fare you can jump on it.
The correct answer is to buy your ticket when you are comfortable with the price. That way, after you buy your ticket if the price goes down you are satisfied since you bought the ticket at a price you were comfortable with. If the price subsequently goes up, you are even happier.
Welcome to the forum, Pat.......when we travel to Orlando, I often find better prices by taking Alaska Air (our only airline from Juneau) to Seattle and then connecting with Southwest to Orlando......SW has some great fares for some weekday flights......you may be able to work out better rates either returning from Anchorage to Orlando, or arriving in Seattle and taking the ship transfer to Vancouver......
Thank you fti and Mombear!
I appreciate the response. Right now am when I check the travel sites the multi city is coming up to 650 (to 800 if shortest time) per person. So am not sure whether it is too early to book the ticket. But observing the trend for the last one month looks like it is the standard price.
>>>Any specific local things to do which are not listed on common websites?<<<
Not sure what the common websites are, but you won't get any better "real" advice as what you will find here on Trip Advisor. I'd encourage you to read some of the trip reports to learn a little about what others have found of interest throughout Alaska. (There is a "search" feature you can key in "Trip Reports" to find them.)
As for your ticket price, $650 to $800 is about the norm based on a R/T ticket purchase from Milwaukee, so I'd say it's a reasonable price range.
I'd buy at $650 personally. By the way, if you book Alaska Airlines they have a best price guarantee. If you later see a lower fare on the same flight, they will issue a credit for the difference. I've used it a few times and it seems to work well.
Enjoy your cruise and don't forget to spend more than a few hours in and around Anchorage afterwards!
On December 22nd we arrive in Galveston after a 32-day cruise. From there we needed a flight to Milwaukee from Houston Hobby. Had kept an eye on prices for several months and they appeared to go up. But, my point is are you more interested in getting a deal or guarenteed flights for your cruise?
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