Where did you want to travel to @fenwaypark? Fenway Park?
I stayed a night there. Didnāt seem the greatest. Prince Rupert was a bit more quaint.
Drove through some redneck town in BC before where I stopped for food in a bar. Twas like a scene from the Blues Brothers. Good ribs though.
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I lived in Boston for a couple of years after College. Also spent every summer working as a painter for Dad.
I would like to visit Alaska and Cuba.
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I was shocked at the obvious levels of opioid addiction in Canada. I had seen it in San Fran but I just didnāt associate it with Canada, which was naive of me. Yes in Vancouver you could walk one block from the main tourist drag and next thing you know youāre surrounded by pitiful addicts.
As regards Rocky Mountaineer they refused to compensate passengers for the loss of a day on the train. Their only offer was a discount on your next booking which was a bit shit given that for nearly all the passengers it was a once in a lifetime experience. Thankfully I booked with Trailfinders who gave me a full refund. Decent skins.
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Bring a raincoat to Alaska.
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Thatās the one bit of advice Iād give fellas is pay off the mortgage as soon as you can. If you come into a few bob donāt bother buying a fancy car, pay down the mortgage instead. There is great freedom in late middle age in knowing that come what may you have a roof over your head and to be able to give the two fingers to the rat race when you are no longer able for it. Nothing sadder than watching a lad cling on in a hostile work environment because he canāt afford to retire.
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They get tons of complaints but like you say itās not like they expect any repeat business lost. And itās often part of a bigger trip usually to Alaska so gets lost in the overall experience. A lot of the passangers are older brits and aussies and while they might quietly give out they usually take it in their stride. The yanks raise hell and threaten to sue almost weekly! But the company doesnāt care. Mind you business is down so the message might be getting through but they have a monopoly on that train line and the scenery is probably what people remember in time.
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what time of year where you in Alaska? heard the mossies are fucking savage in some areas
September
Clear the mortgage if you can at all in your 40s. I know it is easy say it, but do that.
As my cuz says above you get a great sense of freedom from it.
Work to a stepped retirement if you can figure a pathway. I moved from a high stress job that was underpaid for the work delivered to owning 50% of a business and have never been as content to get up and go to work in the morning, having worked full time for over 35 years.
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That always seemed the wisest move to me too, but TFK financial gurus like @briantinnion & @gilgamboa firmly recommend putting additional money into your pension over clearing off the mortgage.
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Apart from working in Mordor it sounds great!
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Youl be mortgage free in your 60s either way ā¦the only variable is how much money youl have coming in
Wouldnāt put anyone off paying off the mortgage all the same. If I won a small lotto itās the first thing Iād do
Mordor could be easy on Monday and tough on Monday week. We will take our chances
Iām 51, mortgage finished at 60, have a decent pension pot built up, youngest finished her masters next year and will have a state job like the eldest once she finishes, riddle me this we had our kids young, college etc beyond expensive, we had our 2 in the prime of our working careers going through it, but yet from both sets of friends between both of us by the time weāre retiring they will have 18 year olds starting out. Itās a young manās game as Greavesie used to say to the Saint.
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Humblebrag much?
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Were you able to understand that post? I couldnāt make head nor tail of it 
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ā Iām alright Jack ā
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Il have the kids through college by 60 after that its all the wan
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No, just outlining our circumstances versus our friend group, each to their own.