How do I get myself to spend a bit more

All great ideas. I reviewed our plans in Savannah, Ga and Charleston, SC and spent a couple of hours on various booking sites. In Savannah, I canceled our 2 nights in a Quality Inn that was a couple miles out of the city and off an Interstate to a highly rated old Inn (built 1823) right in the historic district (with a hot breakfast and a free drink voucher for the bar) for $47 more a night. In Charleston, I went from a Econolodge (again outside the city off an Interstate) to a B&B in the historic district (hot breakfast vs stale bagels and cereal) for $63 more/night.

I think my bride will be happy for the extra $220 I spent.

I think I have moved 3 or 4 steps along the way . . .

I was talking to DW last night about a road trip that is coming together for us, to Florida, in November. We can make it in 2 long days, or bust it up into 3 shorter days. I've always been a "let's get there as fast as we can" kind of traveler, but we are going to try to break it into 3 days. One strategy I have is to book nicer places with gyms and pools so we do something besides spending all of those extra hours in a musty room waiting to fall asleep.

Small step for mankind, big step for me.
 
I think it's a good idea to tell us after you've decided, since clearly you're not asking for input. If you disclosed what you're considering, I imagine you'd hear lots of opinions on it.
Yes, you understand! I just would rather wait at least until I complete the test drive phase, or maybe until after I buy the SUV, before revealing the model. Yesterday it thunderstormed so no test drive, and it may be a few days, weeks, or months before I complete the test drive.
 
I was talking to DW last night about a road trip that is coming together for us, to Florida, in November. We can make it in 2 long days, or bust it up into 3 shorter days. I've always been a "let's get there as fast as we can" kind of traveler, but we are going to try to break it into 3 days.

This is something I've started trying to do, as well. Previously, when mapping out long road trips, I've tried to maximize the distance I can cover each day, carefully choosing the cities in which to book hotels in order to split the entire trip up evenly and efficiently. But recently, I've gotten a bit more philosophical and am taking the "It's not the destination, it's the journey" approach. Adding an extra day or two seems to make each (shorter) day of driving much less stressful.

And on a related note, I've been telling myself it's OK to spend more on higher quality hotels or B&B's when I'm travelling. After all, it's not like I take so many trips a year (usually 2 or 3) that spending an extra $50/night would have a noticeable effect on my budget. Same goes for airfare and dining out when I'm travelling. For my next trip, I'm going to try a mental "hack" when I'm searching for hotels or airfare. I plan to identify a "budget" option that makes my cheapskate self happy and then actually purchase the next higher priced one that's more convenient and/or more luxurious.
 
Yes, you understand! I just would rather wait at least until I complete the test drive phase, or maybe until after I buy the SUV, before revealing the model. Yesterday it thunderstormed so no test drive, and it may be a few days, weeks, or months before I complete the test drive.



Sounds like you're in no hurry so you can enjoy the process at your own pace. Have fun! One time a high pressure salesman was trying to push us into buying a car when we had just started looking. He asked DH "what would I have to do to get you to buy this car today?" This was after we had repeatedly said we were just starting to look. DH said "sell it to me for $10". The guy left us alone after that. First and only time I've ever seen a speechless car salesman! [emoji23]
 
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