At 30 years old, true surprises in life come few and far between. This April I was lucky enough to get an incredible gift from my best friend Sam that included an amazing surprise. For my birthday gift, she got me a freaking VACATION ya’ll. And here’s the best part–I didn’t find out where we were going until we got to the airport! So at 4am, after staying up way later than planned chatting and doing our nails, we drove to O’Hare Airport in Chicago, Illinois where I finally found out we were going to ——> PORTLAND, OREGON!!!!

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Getting There

Sam and I are currently based out of the Midwest so we flew into Portland since we only had 4 days of freedom. It was an easy flight out of O’Hare and we both loved the opportunity to catch up on our reading! Our plan was to arrive in Oregon as early as possible so we could take full advantage of day 1. Once we arrived, an Uber took us to our hotel and from there we stowed our bags and took off to explore! Portland International Airport is an awesome airport — small with fast and friendly security and lots of great food options.

Fun Fact: Due to a law in Oregon, businesses are not allowed to increase their cost of food in the airport just because it is in an airport!

Where to Stay

We stayed at a fantastic hotel called The Benson which is right down town. There are a variety of different neighborhoods in Portland and I truly feel any of them would be great to stay in as the city is super easy to navigate. Uber and Lyft services are plenty and the walk-ability of the area is high [as long as it isn’t pouring rain]. There are a decent amount of homeless people downtown but they seem to be harmless for the most part. The people of Portland [and Oregon in general] are so wonderfully friendly and more than willing to point you in the right direction or offer their recommendations. The Benson is older, classy and historic; I highly recommend it!

Day 1

As soon as Sam and I got into Portland, our stomachs were rumbling and breakfast was a MUST! One theme of our trip was INSANE breakfast experiences! Our first stop was Bijou Cafe where I had the most amazing oyster mushroom omelette [I know it sounds weird but they were fried with a super flavorful breading…plus oysters are my FAVORITE food!] with a refreshing side salad. I also enjoyed a Bloody Mary garnished with a pickled green bean.

Next up: Portland Saturday market in the historical Old Town! This is a very popular attraction and a must visit while you’re here. The standards to be able to sell anything at this market are very stringent so the quality of all products are top notch. Over 1 million people visit every year! The flower stands were my favorite and almost all the booths offer free samples of whatever they are selling.

Since it was raining [a common trend here], we headed over to another Portland gem: Powell’s City of Books in the Pearl District! This is the largest independent book store in the entire world so as an avid reader and lover of book stores, this place was everything I hoped it would be! Sam and I spent a long time walking through the aisles of this GINORMOUS haven! There are a variety of areas color coded so you know where you’re going. This store is so huge they offer maps to customers. The selection was incredible and the prices were very competitive. Powell’s also offers used books at varying prices depending on the condition of the book. I highly recommend checking this place out!

Fun Fact: No sales tax in Oregon!!

Before long we were ready to fill our bellies again so we headed to Von Ebert Brewing for dinner where we met up with my aunt and cousin who happened to also be in Portland [small world!!] I had bone marrow for an appetizer along with a ginger lemon fizzy wine that I greatly enjoyed. For dinner Sam and I each got something different and split both dishes — steak salad with blue cheese dressing and a double cheeseburger with pimento cheese…both were delicious. The beers here were mostly IPAs which is not my preference but overall I really liked this place!

Finally, we ended our first day with drinks at Vault Cocktail Lounge. This place is dark and sexy and the bar tenders make a show of mixing cocktails including a little pyrotechnics! If I lived here, this would likely be my go-to spot!

Fun Fact: Recreational marijuana is legal in Oregon

Day 2

Day 2 started off with another incredible breakfast, this time at Cheryl’s on 12th where I had the most decadent crab omelette with a cheesy hash brown bake. The food was to die for and the service was impeccable. We arrived right as they opened and were one of the first seated–expect long [but so worth it!] waits if you go later in the morning.

The plan for our day included a waterfall and wine tour with a company called Evergreen Escapes. This trip along the Columbia River Gorge provided tons of breath-taking views along with a vast array of information about the area provided by our guide [who was ironically originally from Illinois!] We were picked up at our hotel and headed off on our adventure.

FUN FACT: Oregon has an Urban Growth Line law that prohibits the spread of urban areas past a certain point in order to preserve wildlife.

Our first stop down the Historic Columbia River Highway was at the Chanticleer Point which overlooks Rooster Rock State Park as well as offers a view of Crown Point/Vista House, a blunted cliff created by lava flow 14-17 million years ago. Crown Point officially became a National Natural Landmark in 1971.

The next stop was our first waterfall– Latourell Falls. We were fortunate enough to be the only people at this one and therefore got some great pictures! This waterfall is 249 feet and is located in Corbett, OR.

As we continued our adventure down the Columbia River Highway, we stopped at a tiny post office in Bridal Veil, OR where brides-to-be flock just to have its stamp on their wedding invitations.

Next up we stopped at the second largest year-round waterfall in the United States: Multnomah Falls. This waterfall was gorgeous and is a very popular stop for tourists. This waterfall includes a restaurant, nice[ish] restrooms and a gift shop at the base of the walking path to get to the fall.

At this point we were treated to some DELICIOUS coffee that our guide made for us! Oregon is known for their coffee and unique coffee shops can be found all over Portland. If you are a coffee drinker, this is for sure the place for you. Don’t be caught with a Starbucks coffee in your hand!

The 3rd and final waterfall we stopped at was called Starvation Creek Falls. This one is tucked away where most tourists do not stop; it also serves as a trail head for many walking/hiking paths. This stop was gorgeous and offered many photo ops.

After taking in the sights, it was time to get to the wine portion of our tour! We visited 2 wineries: Wy’East Vineyards and Cathedral Ridge Winery. Wy’East offered a phenomenal pinot noir flight tasting as well as a general one; I highly recommend the pinot noir flight! This area of the gorge has a very similar climate/soil/etc as France which is why they are largely the only 2 regions that produce the grape used to make pinot noir. Cathedral Ridge offered a wonderful flight complete with multiple tastings of their reserve wines. The woman conducting the tasting was delightful and gave us as many tastings as we wanted! We bought several bottles to take home!

After getting back from our tour we headed over to Jake’s Famous Crawfish where we met up with my aunt and cousin again for drinks and dinner! I had the most delicious raw oysters and a fantastic cocktail. Later on I ordered an entree of crab and shrimp stuffed Alaskan Halibut which was a bit pricey but so worth it. Our bartender Mike was AWESOME and the service was fantastic!

We actually ended up staying out so late that some of us wanted a second dinner so we made our way to Backwoods Brewing Company where I snacked on a Caesar salad while everyone else enjoyed burgers and nachos. We had actually originally gone into a diner called The Roxy which has awesome reviews online but the waitress was SO incredibly rude to us as soon as we walked in the door that we turned around and left. It seemed like a really cool place so I’m hoping we just caught her on a bad night but based on other reviews online specific to the service, that doesn’t seem to be the case. Regardless, we had a fantastic day full of all things Oregon!

Day 3

Day 3 started with THE SECOND BEST BREAKFAST I’VE EVER HAD GUYS!!! It was so freaking good and came very highly recommended. May I introduce to you– Screen Door Restaurant, an absolute MUST TRY if you’re ever in Portland. Sam and I decided to split 2 meals; chicken and sweet potato waffles and lemon blueberry pancakes. Both were insanely delicious and we finished all of it. I also got a side of cheesy grits because I haven’t had good cheesy grits since I lived in Memphis, Tennessee–they did NOT disappoint!! We only waited about 20 minutes for a seat on a Monday morning, however, we were told wait times can get upwards of an hour or more.

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After filling our bellies, we headed to the Portland Aerial Tram to get a high up view of the city! This tram goes between the Oregon Health and Science University at the top [where there is a coffee shop!] and the South Waterfront neighborhood at the bottom. If you ride the tram from the top down, there’s no cost! We were even lucky enough to have a clear day where we could see Mount Hood and a little bit of Mount St Helens!

Sam and I then enjoyed a leisurely afternoon walking around Nob Hill doing a ton of shopping at all the cute boutiques! Of course we had to stop at Salt and Straw, the most adorable ice cream shop with very unique flavors! They offer as many samples as you would like and encourage you to try every flavor! Sam and I both ended up getting a flight of four different flavors for $9…you read that right, a FLIGHT OF ICE CREAM!! Mind blown. My flavors were: sea salt with caramel ribbons, lavender honey, pear and blue cheese and strawberry honey balsamic with black pepper. I KNOW, the last two sound kind of gross, right? They were, hand to God, my absolute favorites…and I’m not even a big blue cheese fan.

Once we had our fill of shopping, we headed back to the hotel to get ready for a fancy dinner at Portland City Grill, famous for its views of the city as it sits on the 30th floor of the US Bancorp Tower. We hit up the happy hour and enjoyed sharing several tapas plates, a drink or two, and live piano music. The food was mediocre but the view was beautiful!

Instead of staying for dinner, we decided to hit up a food truck and go back to our hotel to eat and lounge around. Food trucks are a huge scene in Portland so we couldn’t leave without trying at least one. It was the perfect ending to a long, fun day exploring Portland!

Day 4

Our plan to fly out of Portland at 11am meant we had a limited amount of time to round out our perfect girls trip. Obviously perfection can be found in a box of specialty doughnuts so…off to Voodoo Doughnut we go!! This is technically a chain but a limited one so we were very excited to check it out! We each tried two different doughnuts — my choices were The Homer (pink frosting with sprinkles) and Dirt (vanilla frosting with huge chunks of oreo). Both were, as expected, heavenly.

Sam and I have been best friends for 30 years now and this trip was the perfect way to celebrate that! Portland has so much to offer and the people we met were incredibly kind and more than willing to make suggestions of how to make the most of our time in the area. With over 100 people moving to Portland daily, this city is sure to become even more popular than it already is in the near future. I highly recommend a visit ASAP!!

Best friend travels <3