I'm 25 & This Is How Much I Spent On A Trip To Portland With My Roommate

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Welcome to Travel Diaries, a Refinery29 series where we tag along as real women embark on trips around the world and track their travel expenses down to the last cent. Here, we offer a detailed, intimate account of when, where, and how our peers spend their vacation days and disposable income: all the meals, adventures, indulgences, setbacks, and surprises.
This week's travel diary: A 25-year-old digital account executive goes to Portland, Oregon while her family celebrates her 25th birthday, without her.
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Age: 25
Occupation: Digital Account Executive, Public Relations
Salary: $48,000
Travel Companion: My roommate
Hometown: Chicago, IL
Trip Location: Portland, OR
Trip Length: 4.5 days
Annual # Of Vacation Days: 15
Costs: We booked round-trip flights on Southwest. Even though the initial price of Southwest’s flights might be just a tad more expensive than, say, Spirit Airlines, it makes the most sense to fly with them since there are no baggage or seat fees! We each paid for our own ticket.
Total: $321.96
Costs: Nowadays, I hardly ever travel without staying in a cute, local Airbnb! I feel like staying in an Airbnb provides such an authentic experience of the local scene and I love it. We scored a super trendy private guest house in the Hollywood district near downtown. It included a private deck with a hammock, an outdoor life-sized checkerboard, a full kitchen, and plenty of makeup remover wipes (WHAT?!). Coffee was also provided and was definitely taken advantage of.
Quick tip: When selecting an Airbnb, be sure to check the amenities the spaces offer. Oftentimes you can save money on small things that add up quickly, such as coffee, tea, etc. Having a small kitchen is also beneficial to make breakfasts in the morning to cut costs down. The total cost of the place was $711.47 and we split it evenly.
Total: $355.73
Miscellaneous pre-vacation spending:
$42The day before our flight, I got a fresh mani/pedi at my favorite local nail salon, something I try to do before any vacation.
$56.64 – I also did some shopping for the trip which included a new belt, a cropped black tank top and a swimsuit from Target.
$33.24 – My new favorite Lancôme foundation from Ulta.
Total: $131.88

Day One

4:30 p.m. – Laptop closed, OOO message turned on! My roommate and I take the L-train (re: Chicago’s amazing transportation system) straight to Midway Airport. This technically did not cost anything since my Ventra pass was loaded with pre-tax dollars taken out of my paycheck.
5:45 p.m. – Security was a breeze, so, naturally, we try to locate the best airport bar to grab a drink. We see Midway now has an HVAC pub (Chicagoans: if you know, you know) so we stop there and I order a very overpriced glass of Kim Crawford Sauvignon Blanc. $15.02 with tip
6:45 p.m. – Board our flight and dinner is served. I eat one of the blueberry RxBars I packed in my carry-on backpack. I mostly nap on the flight and also read a bit of Daisy Jones and The Six, by Taylor Jenkins. Highly recommend!
10:05 p.m. – Arrive at our Airbnb and promptly zonk out after looking at a few Portland influencer feeds on Instagram.
Daily Total: $15.02

Day Two

5:30 a.m. – I’m naturally an early bird, but wasn’t expecting to be awake this early after a long night! Oh well. I brew a pot of coffee using Allegro grounds and add in a scoop of vanilla protein powder I brought from home. Oh, it’s also my 25th birthday! I respond to some text messages from overnight and like a few Facebook posts.
7:00 a.m – My friend wakes up and we decide on a few things to do today. We decide to go to Trader Joe’s down the street and pick up some breakfast and snack essentials. My grocery cart includes gum, baby carrots, asiago cheese, cashew and almond nut mix, greek yogurt, and apples. My friend on the other hand picks up organic red wine, a small ciabatta baguette, blueberries, spinach greek yogurt dip, and a beef jerky stick for her (I’m pescatarian). She spends around $20 and we call it even. $19.25
8:30 a.m – Notice a cute farmers' market on the walk to our Airbnb and make a note to hit that up before going downtown for the day.
9:30 a.m – After getting ready, we head on over to the farmers' market, which is just as nice as we expected. Beautiful peony bouquets, lavender plants, succulents, fresh breads, wine, beer, and so much more! We sample some pita and tabouleh, then try a cold brew CBD-infused beer. Not too shabby. We walk away without purchasing anything.
10:00 a.m – We head into the city for the day! There is a transport center within walking distance of our Airbnb. I always love figuring out the public transport systems in new cities! Portland’s seems pretty easy. My roommate purchases my day pass for me but I promise to buy her something later.
11:30 a.m. – After walking around downtown for awhile and hitting up some famous spots, like Powell’s Books, we head on over to Chinatown to explore the Lan Su Chinese Garden. The tickets cost $12.95 to get in and we each pay for our own. $12.95
12:30 p.m. – This garden is beautiful! Such a nice gem in the middle of a city. We head to the onsite authentic Chinese teahouse. My friend and I each order a green herbal tea that promises to cure any ailments. It tastes not the best (I’m really not a tea person) but I drink it anyway and relax for the experience. We sit at the teahouse for awhile and realize we’re getting “overly zen,” so we grab the check and get ready to leave. I pay $11.50 (with tip) for the both of us since my roommate covered my transit pass earlier. $11.50
2:00 p.m. – After walking around the city some more and hitting up some downtown Saturday markets, we go on a mission to locate an ATM for our goods. We finally find one in a sketchy gas station and each take out $20 but the ATM fee tacks on an additional $3. Back to Serra! $3.00
2:45 p.m. – We decide we’re hungry for lunch. Head to a casual poke place called JoyPoke near downtown before our next stop: the SE neighborhood. I buy a small bowl ($10.99) with spicy tuna, spice crab, shrimp, seaweed salad, and a few other toppings. So yummy! $23.99
3:00 p.m. – We hop on the #2 bus from downtown and head to the SE District! There is a free tasting from 4 to 6 p.m. at SE Wine Collective (found out about this on Facebook), so until then, we walk around the neighborhood and stop at a cute plant/gift shop called Gone West. I buy a Millennial Pink-colored scrunchie. Apparently Portland has no sales tax, so I pay the exact amount. Weird coming from Chicago where our sales tax is through the roof. $8.00
3:15 p.m. – There’s a brewery called Little Beast Brewing with outdoor seating next to the store, so we decide to make a pitstop before the wine tasting. The brewmaster is super knowledgeable and makes me and my friend flights based on our alcohol preferences. I tell him I like a little hoppy, not sour, white IPAs and he puts together a custom flight for me! I love them all. $14.16
4:10 p.m. – We head to SE Wine Collective and try three sample wines: Prosecco, a dry rose, and pinot noir. Yum. Then, we chat up the owner and she gives us plenty of recommendations for lunch and dinner spots in different neighborhoods.
4:45 p.m. – Decide to stay here for happy hour. The chef is from France and apparently her hors d’oeuvres are to die for. We each order a glass of Viognier, plus french onion dip, and crunchy kale salad to share. It’s to die for. $14.00
8:30 p.m. – After SE Wine Collective, we go back to our Airbnb and munch on some baby carrots, cheese, and the baguette from Trader Joe’s and then take much-needed naps before dinner. Apparently a lot of restaurants in Portland close at 10:00 p.m. but we finally find a spot called Wilder Bar Cafe that’s close-ish and open until 11:00 p.m. Uber there and split the cost ($8.70). At dinner, my friend and I each get a cocktail (mezcal with orange bitters for me), share fried broccoli as our starter, and split two entrees: mussels and frites, and a quinoa veggie burger with a polenta “bun." It also comes with a side of balsamic kale salad. We eat about ¾ of the meal and tap out. The check comes and it’s $30 for my half including tip. We’re so full we decide to call it a night and head home! $38.70
11:00 p.m.I notice my family back home hosted a birthday party for me… sans me? The photos included a cake, beer and flowers. We are a group of extremely sarcastic individuals so I text my parents to say thanks for the party.
Daily Total: $145.55

Day Three

5:45 a.m. – Sleep in slightly later than yesterday. Make more coffee in our kitchenette coffee maker and add half a scoop of my vanilla protein powder. For the people in the comments, yes, doing this does make the powder curdle slightly on the top of the coffee, but a girl’s gotta get in her protein somehow on vacation!
6:45 a.m. – I do some yoga poses to stretch out, and a few squats (Bulgarian, sumo) using the living room couch. At home workouts are not nearly as effective or motivating as the gym but this’ll do. Background: I typically lift weights 5-6 times per week and have 1-3 cardio sessions, so whenever I go on vacation I need to remind myself to just relax about it and give my body a break.
9:00 a.m. – We shower and get ready for the day in “cute casual” athleisure since we’ll be walking around the city again today. What I’ve learned about PDX so far is that it’s much, much more laid back than Chicago. I don’t mind it one bit.
9:30 a.m. – The day’s tentative plans have been made and we’re out the door! Today we’re heading to Washington Park to hike and check out the scenery. We take public transit directly to the park (we buy a transit day pass) and take a shuttle bus to the Rose Test Garden. Some guy who’s off his wacker gets on the shuttle and promptly asks the driver to drive him to downtown Portland. Ummm? Good news is that the park is free admission! $5.00
12:30 p.m. – Even though the roses aren’t in full bloom until early June, we still get some amazing views (and Insta Stories) of the nature that’s right in the heart of the city. We hike on the trails for ~1.55 miles and explore the Hoyt Arboretum. I love nature and this is exactly what I need to start the day off right. We head back into the city for our next stop: lunch.
2:00 p.m. – We make it to the other side of Portland via public transport and are walking into Harlow, a super cute gluten-free and vegan café. I’ve been perusing the menu all day and at this point my friend and I are famished. I order the Farmer’s Skillet, which has tempeh, roasted root vegetables, steamed kale, and brown rice. There’s some sort of vegan curry sauce as well. This is amazing. I also order a cold brew coffee and chug about five glasses of water. $15.00
3:30 p.m. – We had plans to go to an improv comedy show at 4:00 p.m., but we’re really diggin’ the vibes in the neighborhood we’re already in, so decide to stay here. Head over to a brewery called Imperial Bottle Shop and my friend and I each get a flight ($11.50 with tip). Feeling a bit tipsy all of a sudden (maybe from not eating for 8 hours?) so we head into a very unique clothing shop called Maripol right next to the brewery. I buy a badass jean jacket with blue and yellow plaid accents ($64.00). Worth it. $75.50
6:30 p.m. – Back at our Airbnb. We pour two glasses of wine, and have a giggle festival. I start waxing poetic on a variety of things and then we decide we need to get up and ready for our dinner reservation at 9:00 p.m.
8:30 p.m. – We’re early for our reservation so we grab a seat at the bar and each order a glass of red wine. Mine is a French wine called Domaine de Durban, Beaumes-de-Venis. I feel fancy ordering. $14.50
8:45 p.m. – We’re seated! The restaurant we’re at is called Mediterranean Exploration Company; we’ve heard amazing things about this place and decide this will be our one “splurge” dinner. It’s small plate shareable style, so we start off with homemade Labneh and pita bread, and then share warm freekeh salad and grilled salmon, plus share a Challah bread pudding for dessert. Everything is cooked to perfection and we’re very satisfied but not overly full, which honestly is the best feeling. Order another glass of wine and relax at our table until it’s time to head home. We split the bill and my half with tip ends up being $52.00.
11:00 p.m. – Back at our Airbnb (we took public transport home) and we can’t stop raving about how flavorful the food was and how much we loved the restaurant. 10/10 recommend. Do my nighttime routine and fall asleep almost immediately after laying down.
Daily Total: $161.50

Day Four

7:00 a.m. – Slept in! Same routine as yesterday: wake up, make coffee with protein powder, and eat a small breakfast of Greek yogurt with blueberries and an apple. We’re hiking Mount Tabor this morning so we head out fairly early and purchase our daily transit pass then hop on the bus to the park. It’s pretty overcast today, but we don’t mind one bit. $5.00
11:45 p.m. – That hike was amazing and much needed! We ended up hiking around five miles total. The views of the cityscape and volcano were incredible. Decide we’re exhausted and need to get caffeine in our systems ASAP. Lucky for us, Portland is very walkable so we decide to continue “hiking” and head to Stumptown coffee in the Hawthorne District.
12:30 p.m. – Make it to Stumptown coffee! I’m so excited to be at one of their brick-and-mortars (Whole Foods in Chicago sells their cold brew, but nothing beats the real deal). I order a drip coffee and add in a splash of soy milk. I pay in cash. $2.10
1:15 p.m. – We’ve arrived to our next destination: ¿Por Qué No? Taqueria. This place lives up to the hype and the vibe here was just what we needed. I order a mezcal margarita no salt, one veggie taco and one pescada taco with red cabbage slaw. My friend and I also split a side of chips and fresh guac. She pays for the two of us and I Venmo her for my half. Everything is so tasty! We both tap out after one and a half taco, lol. We’ve been total foodies on this trip (something I never do at home; Plain Jane meals over here) and I’m lovin’ it. $20.00
3:00 p.m. – After lunch, we get on the bus and go back to our Airbnb to relax and plan the rest of the day/night. On the walk home we also stop at the Trader Joe’s to get a bottle of white wine. My friend pays.
4:30 p.m. – Wake up from our naps and start getting ready for leaving the Airbnb again. I could honestly nap for another hour but we must prevail! We get ready, drink a glass of the Trader Joe’s wine and throw some laundry in the in-unit washer.
6:00 p.m. – On the way to Enso Winery, a super cute winery and urban tasting lounge in the SE district. I order a glass of their L'American which is a red blend of petite sirah, zinfandel, and mourvèdre. My friend also orders a glass of wine and we pay separately. $10.00
8:00 p.m. – It’s time for our dinner reservation at Kachka – an authentic Russian restaurant. It’s also located in the SE district so we walk there from the winery. Neither of us have ever tried traditional Russian food, so we’re pumped! It’s shareable style as well. We order the following (all split): Zucchini Buterbrod (wheat sourdough), Herring “Under a Fur Coat,” Sauerkraut, Brindza Pashtet (sheep's milk dip), Halibut Shashlik (fish skewer) with Lepyoshka bread. Everything is AMAZING and I’m so glad we ventured out of our comfort zones for this experience. This place is a must for anyone traveling to Portland. The plates are small so you can split with your friends – the waitress (surprisingly based on the above list) told us we barely ordered anything at the end of the meal but we were full and satisfied! We also each drink two glasses of red wine during dinner and shared a strawberry shortcake style Russian dessert. The total bill comes to $96.60 and we split evenly. $54.00
11:00 p.m. – Take the bus back to the Airbnb. Makeup off, teeth brushed and in bed. We walked 29,000 steps according to my Apple Watch and I am so exhausted that I fall asleep almost immediately. What a day!
Daily Total: $91.10

Day Five

7:00 a.m. – Rise n’ shine! I’m feeling stiff so I stretch and do some yoga poses, make coffee with protein powder, and eat my last Greek yogurt.
9:15 a.m – We each made appointments to get 60-minute massages at a foot spa in Chinatown. Hop on the MAX rail ($5.00 day pass) and arrive right around 9:45 a.m. We notice we’re right next to the Lan Su Chinese Garden from day one. $5.00
11:00 a.m. – I refuse to go anywhere other than Chinese foot spas for massages. Those ladies and gents really know how to get the kinks out, plus it’s super affordable. I pay $35 for the massage and use cash (that I got out from the ATM) to tip $12. Both my friend and I feel like we’re in a trance from how relaxed we feel. Mmmm. $47.00
12:30 p.m. – Realize some work-related expenses came through on my checking account, so I pay off my company AMEX ($443.59). That way it won’t appear that I have more money than I actually do and I love paying these right away as soon as my expenses go through.
1:15 p.m. – After getting ready at the Airbnb, we head out again for lunchtime at Cheese and Crack, a specialty charcuterie spot. My friend and I split a delicious cheese board that comes with oatmeal crackers, wheat crackers, a small baguette, honey, apple butter, olives, cheddar, and brulée brie cheese. We also each get a small side salad. She pays for the both of us and I Venmo her $11.00 for my half. $11.00
2:00 p.m. – There’s a vintage shop right across the street and I’m a sucker for local vintage shops. We head inside and each purchase T-shirts. Mine is a W.A.S.P. band tee and I snap a photo of it to my boyfriend who loves '80s hair metal, lol. $20.00
2:30 p.m. – Feeling tired, we head across the street to a local coffee shop to get some much-needed caffeine. I buy a cold brew using my cash and my friend gets a fancy looking honey latte. $3.00
2:50 p.m. – Hastily check into our Southwest flights! Somehow score B1 and B3 for our seating order. :)
3:15 p.m. – There’s a brew pub right next to the coffee shop and we’re feelin’ boozy, so we head over! We’re the first ones there and the bartender is super chill and lets us taste test all of the beers. I decide on an IPA and my friend gets a sour. After drinking our beers for a bit, the bartender comes to our table and asks if we eat bacon (?). I say no, and then he brings out a free plate of roasted Brussel sprouts! Apparently there was a ticket left on the counter from the day before and the chef made them. They taste so good after our minuscule lunch from earlier. $5.00
4:45 p.m. – We head across the street as there’s another brewery! Are we on a bar crawl? This place is called Coalition and they are known for their CBD-infused beers. Curious, I end up talking with the brewmaster about it and he shares a ton of information about what the beer can do for you, how they infuse it, etc. I love learning from local craftsman! I order a CBD-infused IPA for $7.00 and I tip $1.00 with the last of my cash. $8.00
4:45 p.m. – We head across the street as there’s another brewery! Are we on a bar crawl? This place is called Coalition and they are known for their CBD-infused beers. Curious, I end up talking with the brewmaster about it and he shares a ton of information about what the beer can do for you, how they infuse it, etc. I love learning from local craftsman! I order a CBD-infused IPA for $7.00 and I tip $1.00 with the last of my cash. $8.00
6:30 p.m. – Craving Mexican food, we decide to go to Taqueria Nueve as our last foodie stop of the trip. It’s still happy hour, so we order margs and chips and guac to start. For the main course, we split fish enchiladas, rice and beans, pico de gallo and some Mexican beet dish which is amazing. Split the bill evenly and my portion is $38.09. My friend ends up tipping more than I do because her margs were $2 more expensive than mine. $44.09 with tip.
8:30 p.m. – Realize I’m decently tipsy, so by the time we’re back at the Airbnb, it’s makeup off and lights out almost immediately.
Daily Total: $138.09

Day Six

10:30 a.m. – Check out of the Airbnb after a slow morning of coffee, yoga stretches, and packing up. We have some time to kill before our flight at 2:50 p.m., so we head for brunch at a local cafe. I order a farmer’s skillet with a side salad. $10.00
12:45 p.m. – At the airport with a Starbucks cold brew in hand. I use a reward so this costs me nothing.
9:15 p.m. – Landed back in Chicago and catch a ride home with my dad (my hometown is super close to Midway airport,) as my mom and I are headed to Door County, Wisconsin tomorrow morning for some R&R.
Daily Total: $0
How did you prepare for this trip?
My friend had visited Portland last year and already had some ideas up her sleeve. I also looked to influencers in the area such as @themoptop and @alisonwu to see what their top recommendations were. One of my old coworkers also moved to Portland from Chicago a few years ago, so she was able to give a ton of ideas for things to eat, drink, and do like a local.
Did you use credit card points or miles to pay for parts of this trip? If so, please explain further: Nope!
When did you book your flight? Do you think you got a good deal?
We booked our flights on a whim one day in early March when we decided a joint birthday/girls trip was absolutely needed (my roommate's birthday is the day before mine and we both turned 25) and we agreed that Portland was a place we both were interested in exploring. I do believe we got a good deal since we were flying halfway across the country!
Do you have credit card debt as a result of booking this vacation? If so, how much? Nope! I pay off my credit cards in full each month and this trip was no different. Since we booked flights in March and the Airbnb was paid in two increments, I was able to budget my funds appropriately. Money spent during the trip was mostly funded by my last paycheck(s) from my old part-time job at Ulta; which I recently left in mid-April.
What was the best meal or food you ate while you were there?
Kachka by far. I had never experienced anything like it before and now I can say I’ve eaten traditional Russian fare which included that interesting seven layer Harring “cake.” Seriously, look up photos of it on Instagram. Unreal.
Is there a tourist trap you wish you had avoided?
Luckily, the day we went to the Lan Su Chinese garden it was pretty empty and we were able to enjoy the grounds and the teahouse in peace, but when we were back in Chinatown on Tuesday for our massages, the gardens were completely filled with kids on field trips! This was probably the most “touristy” activity we did.
What advice would you give someone who is traveling to the same location?
Follow Alison Wu and The Mop Top on Instagram. Ha! But seriously, I always recommend looking to Instagram influencers who are local to the area you’re traveling to. Oftentimes they are hitting up the cool spots like niche coffee shops, hole-in-the-wall restaurants and the best dive bars around.
Is there anything about your trip you would do differently in retrospect?
This came down to affordability, but I would definitely rent a car next time to be able to drive out to the Oregon beaches and wineries and orchards. It was a bit far out from the city to get to some of these spots sans car.
Would you stay at your Airbnb again?
I would, yes! It was quaint, quiet, and secluded from the main area of the home. There was also a hammock and nice outdoor seating area for our recreational activities. It was pretty small, though, and there was only one bed with the bathroom right next to it. Luckily my friend and I are comfortable enough with each other that we made it work, ha.
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