How am I going to Vegas twice this summer?

I've been going to Vegas since January 1997. Most years I've made at least one trip, but there were a few years when I never made it.

I didn't keep detailed trip reports of my visits. The Internet was barely a thing in 1997, nobody was thinking about blogging or posting trip reports. I'd love to have a list of the trips, travel companions, nights spent, hotel(s) occupied and fortunes lost over the past 21+ years.

By my calculations, I've been to Vegas more than 30 times. My first solo trip was 27 hours. I spent less than 24 hours in Sin City during a trip to Laughlin several years ago. I tend to go at least five nights when I travel these days.

I started traveling solo to Vegas circa 2004, before I knew that was a thing. I figured if I couldn't find a friend who could commit to a trip, why should I forgo a visit? I've done the solo trip at least a handful of times, including Halloween 2011. My first Halloween in Vegas. I loved it so much that I've spent five of the past seven Halloweens in Vegas.

For a few years I was averaging two trips to Vegas per year, but that is no longer the norm. My girlfriend and I started dating in early 2012. She went to Vegas with me for Halloween that year. She doesn't love it like I do, but she loves the cheap vacation, and knows it's one of the few places I want to go. So for most of the past six years we've split our vacation time between Vegas and a destination of her choosing. I won't go to Nashville with her, but in recent years we've been to San Antonio, Puerto Vallarta, Mexico, New Orleans and, as of a month ago, Key West. I had been to three of those places and liked them well enough that I was willing to return, but they're not places I plan to visit annually.

I was in Vegas last Halloween, and I expected my next visit to Sin City to be this coming Halloween. That changed a few weeks ago.

For the past several years I've been getting together during the summer with one or two college friends and attending a Major League Baseball game at a ballpark I've never been to. In 2012 I was in Boston. In 2013 I was in Dallas and Houston. In 2014 I went to Pittsburgh. In 2016 I was in Tampa and Miami. Last year I went to St. Louis, Atlanta and Cincinnati.

This year the trip was supposed to be to San Francisco and Oakland. Actually, it was supposed to be to happen last year, but it was postponed. A few weeks ago it was postponed again.

That's because it's not cheap to get to San Fran when you want to go by train from Chicago, and that's part of the San Fran itinerary. One of my buddies, Woody, has been saving Amtrak points via his Amtrak credit card for about five years, but it's not cheap, or easy, to convert the points into the train ticket we want. So three or four weeks ago we postponed the train yet again and considered other destinations. Woody has been to all 30 current ballparks as of last year, so now he's doubling back to previous destinations, in part because I'm going to try to get to all 30. I've been to 18 of the current ballparks as of today.

We considered three cities as options for our 2018 trip after we aborted San Fran for the second consecutive summer. There were a few cities we ruled out this year for various reasons. Our options were San Diego and Anaheim, Kansas City or Arizona.

Kansas City is easy to visit any year I want. It's about six hours from Minnesota. And it's not far from Woody in Milwaukee. Our third friend, Roast Beef, lives in Boston and doesn't always make it on our baseball trips. He has family in Kansas City, so I thought that might have appeal to him, but he preferred to go somewhere that would feel more like vacation this year. He found great rates on weekly timeshare rentals, and soon we were booking seven night in Vegas during that same early August week we had blocked off for San Fran.

Why Vegas? Woody hasn't been there since 2000, and is curious to see how different it is. He doesn't love it, but he had been there a few times during the 1990s. I'm pretty sure he made his first trip to Sin City before I did.

Woody also knows that I have long wanted to see a minor league baseball game in Vegas. So the idea was that we'd go to Vegas for part of a trip and drive over to Phoenix for an Arizona Diamondbacks game. And that's what we're doing in two months.

Fun fact: Beef has only been to Vegas once, to the best of my knowledge, and that was with Woody and me in April 2000. So the three of us will return together more than 18 years later, and it will be the first return visit for both of these guys. I've been there at least 25 times since then, and probably 30. Needless to say I'm the driver and tour guide for this trip.

The thought of hot summer nights in Vegas never crossed my mind a month ago when I was in Key West. I was sure I'd be going to San Francisco this summer. And within days of returning from Florida: Boom, a bonus visit to Vegas.

I still intend to go to Vegas for Halloween, so this is most definitely a bonus trip.

And then a funny thing happened late last week.

My girlfriend and I have stayed at The Orleans a handful of times, although not since 2015, as we stopped getting good offers from our favorite Vegas casino. We're not high rollers, but we'd get decent offers that would entice us to stay and spend money there, as opposed to downtown.

Although I put in more time gambling at Orleans than my girlfriend does, she was the only person to get an email offer last week. She priced a five-night hotel stay over Fourth of July week and found that we could stay there for $257, resort fee included. (It's waived for this offer.)

Obviously the Fourth of July week isn't a super busy week, and reservations are light, otherwise she wouldn't be receiving a $50/night offer. Although Vegas isn't her first choice for a vacation destination, she knows how cheap it can be, and she wants an excuse to travel this summer if at all possible.

Last year we jumped through the necessary hoops to score a great deal from Southwest Airlines. She signed up for two credit cards and we used them to charge the minimum required on each within three months. We earned bonus miles for both cards, and my girlfriend earned a companion pass from Southwest for the remainder of 2017 and all of 2018. We have only used it thus far to go to Vegas last fall and Florida this spring, but my girlfriend has plenty of points left in her account and wanted to go somewhere this summer and fall. So with free airfare for both of us to Vegas and a $250 room for five nights, she offered to go to Vegas in less than four weeks.

Needless to say, she didn't have to twist my arm.

I have yet to tell my buddies I have booked a pre-Vegas trip for our August Vegas trip. I'm still in awe of the fact that five days ago I was tickled by the fact I'd get to go to Vegas once this summer. And now I'm going twice.

And yes, Halloween in Vegas remains on my to-do list this fall. Wish me luck!