Portland Bucket List: Your Guide to the Perfect Valentine’s Weekend

The key to a perfect couple’s getaway: Part planning, part spontaneity. Our professional (and personal) experience has taught us that having a few solid goals gives structure to your time together and leaving some space in your schedule allows for room to play and discover new things. Fun!   

To strike the perfect balance of romance and playfulness, try crafting a Valentine’s Day bucket list together, using this guide as a jumping-off point.    

Pre-Dinner Drinks 

Begin your evening close to home at your hotel bar. If you’re staying at the Woodlark Hotel, that means Abigail Hall, the reigning queen of old-school Portland cool. This intimate bar is as much a destination for locals as it is for guests—be sure to stop by for a seasonal cocktail and romantic, soft-focus vibes. 

Keep things sophisticated at the Driftwood Room, a dreamy 1950s-inspired lounge. Offering legendary drinking experiences like Champagne cocktails and flights of Manhattans paired with expertly curated bar bites, the Driftwood is truly a vintage-inspired experience. 

Other great places to imbibe: Stem Wine Bar PDX; Hale Pele; Bar West   

Dinner Date 

Ahhh Laurelhurst Market…where do we begin? Our love for this stalwart dinner spot goes deep, with its commitment to bold flavors and high-quality ingredients and grounded, no-nonsense sensibility that lets you know you’ve landed in the Pacific Northwest. Enjoy choice cuts from their in-house butcher shop, rich sides and a charcuterie board for the books.   

Another amazing option: Find something for both of you at the Bullard Tavern, where Texas hospitality meets Oregon’s bountiful food landscape. Set conveniently in downtown Portland, this cozy establishment brings you high booths and original, in-season fare that’ll fill you up without putting you out. Think fresh oysters and upscale takes on classic bar eats like steak nachos and wood fire burgers, just to name a few.   

If a casual vibe is what you seek, check out Pacific Crust Pizza for their outdoor-infused ambiance and fresh, foldable pizza. Stick with a classic or go expert level with something more adventurous like Spicy Veg or the beloved Bear Spray—a soppressata, olive and chili oil-covered affair. Not up for dining in? Grab a pie to share and bring it back to your room, then plan your next move.    

What To Do 

Whether dinner’s the main event or not, consider seeing a show with your main squeeze. See Pink Martini—a Portland favorite since 1994—for their Valentine’s Day weekend performance (February 12, 13, 14) or check out Helium Comedy Club for some laughs. Bonus points if you stumble onto live music. 

Hot Tip: Get to Helium early for the best seats.   

Night Cap  

Round out your night with something lucky to sip on. Play your odds at fun-loving Fortune, home to high-energy vibes and elevated takes on your classic cocktails. Located in Sentinel yet a destination unto itself, this bar is a winner. 

Still have more on your list to check off? Visit the Vault Cocktail Lounge for high-brow beverages without the attitude usually reserved for cocktail culture. 

If you’re more of a sweet tooth than a bar fly, hit up 1927 S’mores Company, a cozy spot serving up gourmet versions of this classic campfire treat, plus coffee. Perfect for late dates, 1927 is more like a cabin in the city than a restaurant or bar, so come and get comfy. 

Speaking of bucket lists, make sure to get a scoop from an original Salt and Straw location. This cult-favorite ice cream will have you dreaming of potato chip cupcakes, lavender honey and more. Walk or get a lift to one of the several locations throughout the city to finish out your night. 

Hot tip: Skip the line and head straight to the front for pints to-go. Grab a few and bring back to the hotel room for a delicious way to unwind. 

Where to Stay 

Our Portland hotels are located perfectly in reach of all the bars, restaurants and shopping you’ll need, should you want to venture out for a gift. Stay at one of our inspired PDX locations for world-class service and design: Choose from Hotel deLuxe, Dossier, Hotel Lucia or Sentinel, all staples in the downtown Stumptown scene. 

Don’t forget to bring: This list; Extra room in your suitcase for your Powell’s Books purchases 

Eat Brunch 

It’s morning time and you’re feeling fine. Order breakfast-in-bed with your sweetheart or head out for brunch if you’re feeling adventurous. Head to Hotel deLuxe for a gourmet take on your classic benedict and French Toast at Gracie's, or try Screen Door for the best Southern brunch west of the Mississippi. (Fried chicken and waffles included). 

Round out your weekend with a couple relaxing hours together at Knot Springs spa. The perfect weekend completed. 

Hot Tip: Lines looking long? Skip standing around and order Pine State Biscuits online. Be sure to ask for Texas Pete on the side.