Booking my first trip — much to learn!

I recently took a weeks vacation to the great Pacific Northwest. It was a last minute booking, but the vacation days were there for the taking! This was my first true vacation focused around points and miles. While I didn’t get to fly in a First Class suite, I got a lot out of the trip — from learning about the hobby to exploring new terrain. In classic millennial fashion, I would have loved to book some sort of business class award ticket across the world. But with such a small window my options were limited. So without depleting all of my miles, the PNW was a great option — as I had heard great things about the scenery, and it is one of the few places in America I have yet to travel.


2 tickets DAL-SEA on Delta for 30,000 points each – Upgraded to First Class on 3 of 4 flights

For some, maybe you are saving up for some extravagant trip, like a honeymoon. Or you just want to be able to fly around the globe in all the best first class products. But for some, it is about saving money on travel you would already have done. So flying economy on a less than average carrier won’t affect you as much, because you’ll still have plenty of points to play with after.

I can’t say I’ve decided exactly how I want to use my points. I have a points strategy , but in my everyday life I am incredibly frugal. My millennial inclinations definitely draw me to all of these wonderful new business class products that airlines are releasing– but I also worry about the withdrawals I will go through after, when all the points are gone.

I am somewhat lucky in that I accumulate miles and hotel points on a daily basis for business, and still was able to cash in on the 100,000 point sign-up bonus for Chase (no longer available). The well documented benefits of Chase Ultimate Rewards points has me salivating at a possible trip in the future, but for now I


want to hold those points as much as possible, and build my cache for an even grander trip in the future.

For this trip I decided to take advantage of the 70,000 points sign-up bonus I was targeted for through the Delta Gold American Express.  It is well known that SkyMiles have lost their value tremendously, but I have remained loyal to Delta and the things that make them succeed. I was able to cash-in that sign-up bonus for two round-trip tickets from DFW- SEA, each 30,000 miles. With Dallas not being a hub city fo

r the airline I knew I would have to connect, a cardinal sin in the world of travel experts, but for me a chance to visit the infamous LAX, a Priority Pass lounge and hopefully higher chances at getting an upgrade.

It did all that and more. We took 4 flights, connecting through LAX both ways. I knew that flying off business hours would give me pretty good odds at getting upgraded to first, but then again it was two people instead of one. Nevertheless, I got upgraded to first on 3 of the 4 flights! Rounding up, I basically redeemed a first class ticket for the price of an economy.

My early flight from DFW-LAX we were treated with a breakfast service, much to my surprise.

The three flights in first got me meal service — saving a pretty substantial amount of money on airport meals. I have flown first class before, but never received meal service–so I was pretty excited to get the full treatment. Overall, I was pleasantly surprised by the quality of food. Got a breakfast, lunch and dinner, and the only one that really fell short was the dinner on the return LAX-DFW. It was a chicken and quinoa salad that was not heated up by design, but honestly should have been. Too make up for that though was an excellent clam chowder to go with a salmon fettuccine.

Lunch: salmon fettuccine with a stellar clam chowder.

With only one complaint aside, I was thoroughly impressed with the first class experience. Unfortunately my three first class flights were on Embraer Jets, so nothing too fancy, but the service was really impeccable and the food was better than expected.

Millennial Musts

Make sure you read my article on Delta upgrades policy to ensure that if you have a chance to get upgraded, you do! With that you have the opportunity to enjoy the First Class experience too!


4 nights at the Hyatt House Downtown for 12,000 points a night at a total of 48,000 Hyatt/Chase points

2 nights at the Delta by Marriott Resort – Victoria Inner Harbor for $102/night at my corporate rate for a total of  $204


1 night at the Four Points by Sheraton – Seattle Airport for 21,000 Marriott points transferred to SPG (7,000 SPG points)

First stop was the new Hyatt House-Seattle Downtown, quite literally right across from the Space Needle. To begin, I am a huge fan of Hyatt, but have since moved to Marriott/SPG. I accumulated a decent amount of Hyatt points through business travel, but this trip basically ran me dry. I will eventually get the Hyatt credit card which will probably bring me back to Hyatt properties (luckily), but for now I

IMG_0973.jpgam focusing on SPG/Marriott. Where I work is basically Hilton or Marriott market, so I chose Marriott.

I booked with 30,000 points I had left over from business travel, then transferred 18,000 Chase Ultimate Rewards points to my Hyatt account.

This booking was a bit of whirlwind, and I talked about it previously.

First, I am only a Discoverist with Hyatt but the last two times I have stayed at a Hyatt property I have been upgraded to a room with a better view. See my view of the Needle! >>>

As mentioned, I have begun staying at Marriott properties. In comparison, it wasn’t until I got to Gold status with Marriott that I would be considered for room upgrades. At this Hyatt House they also took care of me with giveaways — 2 bottles of water a day and drink coupons at the hotel bar.

We weren’t given the largest room in the hotel, but we really didn’t need any more. The staff was all very friendly, and the complimentary breakfast buffet was easily the best I have had at a hotel. While not the highest category Hyatt in the Seattle area, the fact that this hotel was so new brought with it so many great amenities. I would definitely recommend this hotel to anyone that is looking for a slightly cheaper (in terms of points!) option in downtown Seattle.

I next had the option of booking a hotel in Victoria, BC with points, but found a far cheaper option.

For the most part, I have had a ton of success booking through the Chase Ultimate Rewards portal. It takes a bit of patience, but there are usually great deals if you look hard enough.

Millennial Must’s

When booking through the Ultimate Rewards portal, always compare against the value (in points) on the company website. If value is better through the company, either transfer as a 1:1 transfer partner, or consider paying for the booking and saving the points for later use.

For this particular booking, I scoured the UR Portal in hopes that I could develop some sort of benchmark and eventually see a price drop. I did not have a specific hotel in mind, but I knew that I needed something close to downtown Victoria/Inner Harbor. We planned on walking everywhere so I was hoping for a deal in what I imagined as the more sought-after area.


The Delta Marriott – Victoria Inner Harbor caught my eye, but while I had seen a price in the 12,000 UR points range, I didn’t act on it and that price quickly rose. Being the millennial I am, I procrastinated, thinking that the price would most definitely find its way back down. It never did, and the price through Marriott is even more ridiculous. So at this point I was looking at other options, possibly staying at an Air B&B, maybe a smaller inn or hotel.

All of my prayers were answered when I tried the price at my corporate discount. Now many companies differ when it comes to using corporate discounts with personal travel, but luckily I work for a company that allows it. And much to my surprise, the corporate rate brought the cash price down about 60% !! I was shocked. I had gone into the trip not planning to pay for any hotels, but this was just too good of a deal to waste my points.

Millennial Musts

Always consider every option when booking with points. While it may seem “free” booking any kind of travel, you don’t want to waste your hard earned rewards on an inflated redemption. 

So I ultimately paid $205 USD for a two night stay, that would cost the normal traveler over $500. It was one of the nicest hotels (actually a resort) I’ve stayed at, and I can’t say enough about the staff– but hey, I guess it’s what to expect in Canada (eh?). Sure, points would make it free, but think about the savings I can get elsewhere — and $300 savings is nothing to laugh at!


There was one more hotel I needed to book, and while this may have seemed like the opportunity to use cash and not waste points, I had used that excuse up in Canada.

We were coming in late to the Seattle port, but with an early flight the next day I decided to stay somewhere close to the airport. I knew hotels would be cheaper out there, and for the most part we were worn out from the entire week, so it was definitely the right call.

Transferred 21,000 Marriott Points to SPG, at least felt like a good deal — but i’m interested to hear where others draw the line? Same with my Delta/Marriott Victoria booking, what is your cutoff for paying with points?

Travel once we got there

This definitely equates to the largest out-of-pocket expense I incurred on the trip. Includes getting to and from Seattle and Victoria, then a rental car to explore the mountains of the GREAT Pacific Northwest.

There weren’t many options when getting from Seattle-Victoria, but the easiest and most efficient option is definitely the Victoria Clipper. For two round trip tickets, it came out to $165. 

Not a terrible option getting across the border, but there is definitely some sort of monopoly on this specific of a route. From downtown Seattle to the inner harbor, this is really your only option besides a float plane. I could have rented a car, but the overall experience was very easy — so I would definitely recommend it.


A large attraction in the Seattle area is the national parks and mountains all across the area. I knew we’d need a rental car, and luckily I had gained two free days with National through my business travel. Paid for being a millennial (under 25), but all in $60 for two days of a full size car out of downtown Seattle was pretty remarkable

All IN

60,000 Delta SkyMiles for the RT tickets

30,000 Hyatt points

18,000 Chase UR Points

$205 for the stay in Victoria, BC

21,000 Marriott points

$225 for excess travel

All in, about $430 out of pocket for travel. I am one who loves to save as much as possible on food during the week at home, but ultimately, no matter where you are you’re going to have to eat. So while it doesn’t exactly cancel out, we’ll say $430 for a trip for two –which I’d say is pretty remarkable in my book.

The final leg…

While this was an awesome trip, and I had a lot of fun playing around with the different options for travel, I am really looking to take my next trip to the next level. This game is constantly about learning — best ways to redeem airline miles, best hotels to utilize, etc. And I am continually reading up on all of it, now hoping that my next trip is even better. Stay on the lookout.


Tucker is an avid points and miles enthusiast. Being fully involved in the world of credit cards and frequent flying for only a few years now, he brings a very fresh and unique perspective to the world of travel.


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