Have you ever wondered what it’s like to live the high life? Like, walk into a place and have everyone at your beck and call, falling hand over foot to serve you? I’ve always been fascinated by those that spend tens of thousands on extravagant vacations, and throw away money faster than a Justin Bieber album just to have people pretend to like them for a few days and give them whatever they want. I could not IMAGINE blowing that kind of money (wait, yes I could. AND I DID!) in less than a week. But I’ve always wondered what it would be like to be THAT GUY. You know, roll up in my Porsche, tip the chauffer a Benji, and walk inside with my shades on, because I’m just cool like that.
Well, I finally made it happen (minus the Porsche), but I DIDN’T PAY A DIME!
Enter: Credit Card Churning
To my regular readers, this is nothing new. You’ve already read through the biggest post ever on this blog, my credit card churning plan for 2013. Well, we finally took our first trip using some of our easy-earned credit card points. Since I blew through most of my vacation earlier in the year on a sweet cruise, we decided to take a fun weekend trip down to Portland to enjoy some fine dining and Willamette Valley’s selection of Pinot.
Being moderate “winos”, we are very familiar with the area, Michelle went to school just outside of Portland for 4 years. We enjoyed bouncing around to the free wine tastings back when we were living on only $14 an hour, but now that our palates have matured (lol, makes me sound rich when I talk like this), we wanted to taste the finest that Oregon had to offer. Michelle reached out to a winemaker friend from the area and got some suggestions for the best wineries around. We mapped out 5 wineries, some with tasting fees up to $15 per person, and bottles starting at $40, and even had to make reservations at a few of them. FANCY PANTS!
Now it was time to book the hotel.
Fancy Hotel Booking
Before even thinking about this trip, we had picked up the Amex Starwood Preferred Guest card (you can find the card here) to take advantage of the amazing redemption values and higher end hotels around the country. We had just reached 30,000 points (25,000 bonus + 5,000 spend on the card in 6 months), so we were eager to enjoy vacation on the credit card companies for once! One day, my wife was talking to me about her favorite hotel in Oregon, The Nines, in Portland. As usual, I was chatting to her about points and our plans to take over the world a sweet vacation, and she asked if her fav. hotel was a Starwood property. Good question! I open up my Google machine, searched out the hotel, and low and behold, the friendly little Starwood icon in the lower left corner of the screen. W00t W00t!! Winner winner chicken dinner! (with asparagus, pilaf and an ’07 Pinot Noir).
I quickly logged on to my SPG account, looked up the hotel and was shocked that I could book a room for only 10,000 points a night! Normally hotels in this price range (about $450 a night after taxes/fees) go for 16,000, so this was a SWEET FRICKIN DEAL! I called the SPG concierge (yes, we’re getting REAL FANCY now) and the kind lady helped find me a city-facing room for 2 nights for Michelle’s birthday weekend. I was really hoping for an upgrade to a corner room, but nothing was available. Sensing that I was a little bummed, the kind lady on the phone searched a bit more and offered me an upgrade to the “Club Level” for a measly 1,500 points per night. What benefits come with club level? I’M GLAD YOU ASKED! Free breakfast in the lounge, free WiFi, free beer and wine all day, free cocktails in the evening, snacks all day, hors d’oeuvres in the evening and dessert until closing after that. HOLY SNAPPLESAUSE YES PLEASE!
We booked that faster than Taylor Swift’s boyfriends get dumped, and were getting pretty excited for our FREE vacation! But, being the KING OF FREEBIES, I decided to go one step further. I found a traveler’s forum, and found a thread for The Nines hotel. I reached out to others on their successes/failures in getting a room upgrade to a corner room. Soon after, the Assistant GM of the hotel contacted me directly, and wanted me to give him a call. WIN! I gave him a jingle, and expressed to him my desire for a corner room in the hotel. He was unable book the corner room for me, but assured me that we would get the BIGGEST ROOM AVAILABLE on the floor. Done and done. Even better, when we arrived, they had a nice little platter of chocolates signed “Happy Birthday” in chocolate syrup for Michelle. Check out the pics!
Baller room on the 12th floor!
Wine & Fine Dining For Free
We drove down to Oregon and arrived around 4pm on Friday, just in time to check in. After checking in, we headed over to the lounge for a free glass of wine and some hors d’oeuvres before meeting some friends for a fancy dinner. Michelle had booked an exclusive dinner at a place where only people who listen to bands that you’ve never heard of go to (The Gilt Club). We felt young again (wait…we’re in our mid-twenties), ordered up some fun drinks, and enjoyed catching up with friends. The menu was unique and fun. We ordered asparagus with elderflower vinegar, Nettle gnudi and grilled hangar steak with friend oysters, and topped it off with an amazing butterscotch brule’ with honeycomb and vanilla ice cream! We ate until we were near food-coma levels and slapped down over $100 for the AMAZING meal and experience. Totally worth it.
Awesome eats! Photo Credit: Mikaela Ovenell
The next day, we scooped up our free breakfast, met up with our friends, and headed out on our winery tour. As the DD, I just shared my tastings with Michelle, and we hit up one of the wineries we had visited before, Rex Hill. Mostly, because their reserve wine is taken from “Jacob’s Vineyard”, and well, that’s just cool. After that, it was lunch time, so we stopped by a coffee shop near Michelle’s old school. They make AMAZING sandwiches, so we sat down for a fun meal with friends, ate our fill, and were out. Only $30 for the pleasure, and the nostalgia was priceless! Then it was off to more wineries.
Drinking “Jacob’s” finest with friends!
We dropped by Hip Chicks Do Wine in Newberg, because it was within walking distance of the coffee shop. We grabbed a bottle of white, and headed out to the fanciest place of the day, Bergstrom Winery. The tasting fee was $15 per person, the place was a bit snooty, and us hoodlum kids had no place in a fine establishment such as this. PALEASE!!! We drank our wine and headed out to Arbor Brook Winery. This place was awesome, and had some cheese and fruit samples out. We dug in, and planted ourselves outside as the sunshine finally came out to greet us. We tasted through their flight, was impressed with their service and delicious and affordable wines, and walked out with 3 bottles (I finally got my bottle of Pinot Noir!) and a $70 bill. The last place we hit was a small winery called Aramenta Cellars. The place was owned by a fun old man whom everyone wished was their grandpa. After tasting through the flight, we picked up a bottle of Pinot Gris, and were on our way back to get ready for dinner. Only out about $150 for a day of wine tasting and 5 bottles of wine. Not bad at all!
Awesome view from smug-pants winery.
5 bottles of wine (and a bottle of non-alcoholic, carbonated Pinot)
We got back to the hotel, and got ready for the fanciest dinner of all, on the rooftop restaurant in our hotel. The place was called “Departure”, and featured fine Asian cuisine. It was a la carte’ style, and our group just kept ordering and ordering because the food was so amazing! We started with steak and pork belly sushi, which really set the meal off right. We all ordered some AMAZING drinks, and they brought on a round of…well, I honestly can’t even remember, but I DO remember that ALL the food was marvelous. We were able to really enjoy the meal here, tipped generously, and spent more here than any of the previous locations.
Our absolutely gorgeous guests! Especially the one on the right 
The next morning, we grabbed our usual breakfast, and walked the town a bit before heading back north. We actually sat down at one point in a restaurant, but being in downtown Portland during lunch hour, all I could think about was the food trucks. We left the restaurant and walked across the street to pick up some yummy! I got the Yakisoba, while Michelle opted for the Gyro. We were a bit cold, so we ended up eating our meal in the car before shipping off back home. Only another $25, but the memories made were worth every penny!
I love Portland food SO MUCH!
But Wait, I Thought You Said Free?
I did say that, didn’t I? Well, in comes the magic of the Chase Sapphire Preferred credit card. The other card we brought along with us was this fancy little blue card, and we had previous put $3k on this card in the past 3 months to get our 40,000 bonus points. By the time we reached Portland, we had about 45,000 points, which equaled a $450 statement credit. Which is funny, because that’s about EXACTLY what we paid for our food and wine for the duration of our stay. So, yes, we partied it up FOR FREE, feeling like a celebrity fresh outta rehab (wait, no…that’s a really bad metaphor…ummm…you know what I mean…right?). We were able to enjoy a great weekend with friends, good food, good wine, and great accommodations for the price of exactly $0*.
For a weekend that could have cost us upwards of $1,300, it was definitely much more enjoyable for free. No worries about penny pinching or overspending. We had a set budget (you knew I’d bring it back to this, right?) for our variable expenditures and were able to book a sweet hotel on credit card points. This isn’t something only a super smart genius can figure out, it’s actually pretty simple. You plan a trip, get some rewards credit cards, get the bonuses, book your stuff, and enjoy yourself knowing that it’s all comp’d by the “evil credit card companies.”
We’ve got big plans for a trip in the next year, and I’ll be filling you all in on the details soon. For now, start stacking those points and go hit a beach on behalf of the “generous” credit card companies and their bonuses 
*We did spend money on gas and a gift for our son, but the food, wine and hotel were completely free. Also, as a disclaimer, enjoying a vacation isn’t all about spending thousands of dollars. We have had just as much fun spending VERY little money on a road trip to Newberg to stay with friends, or camping for $25 a night. I just wanted to try something different using our points, and this was the perfect opportunity for it. As always, NEVER spend money you don’t have to buy crap you don’t need. And don’t blow money on pointless stuff, let the credit card companies do it for you. If you have ANY credit card debt, do not use this strategy, and if you can’t pay your card of every month, you should not being worrying about rewards.
Comments: Anyone use their credit card rewards for some fancy traveling? Doesn’t it feel great to have someone else pay for your vacation? If anyone wants some advice on a trip or needs some help putting together a list of cards and rewards for their traveling goals, feel free to contact me
