Looking for a getaway for Valentine’s Day, or a couple’s weekend any time of year, to snuggle up by a fire, sip wine and fall asleep to the sound of the ocean? Traditionally a haven for families in search of Skee-Ball and saltwater taffy, Seaside has also grown into a modern-day sweet spot for wine aficionados, foodies, art lovers and, well, lovers. This two-day itinerary — which you can even do without a car — will reignite your passion for the quirky beachside town less than 90 miles from Portland. Here’s how to spend your next dreamy getaway.
Checking in: Boutique rooms, wine flights and homestyle Italian
Enjoy a friendly Oregon-Coast welcome at Gilbert Inn, an ideal adults-only basecamp for your romantic escape (so book your babysitter now). Located just a block from the beach and steps from Seaside’s compact city center, the historic 1880s-era Gilbert Inn has been recently renovated into a cozy hideaway — retaining its original Queen Anne-style charm as well as all the comforts of home.
After checking in, walk a block over to the Naked Winery Tasting Room and unwind from your drive with one of their lauded, regional wine flights. Next, wander a half-block to Seaside’s iconic Broadway Street and peruse the impressive lineup of good eats. Finns Fish House serves up tasty seafood, salads and burgers in a sophisticated atmosphere. If you’re in the mood for Italian, cross the bridge to Nonni’s Bistro for the best risotto in town, not to mention standout cioppino. After a delectable meal, it’s a leisurely stroll back to your warm bed.
Day One: Shopping, games and beachfront dining
Wake up to the sound of waves crashing and the aroma of fresh scones baking — Gilbert Inn serves a complimentary breakfast you don’t want to miss. Delish baked goods, homemade granola, savory bites and locally-roasted coffee in the cheery sunroom are a wonderful way to start your first day. Fuel up and head out for a walk along Seaside’s 1.5-mile Promenade, gazing out at the beachgrass-covered dunes and the Tillamook Head promontory.
Walk north past the historic Lewis and Clark Monument marking the official end of the Corp of Discovery, up to the city’s playful murals and then circle back to Broadway for some shopping, Seaside-style. Fairweather House and Gallery specializes in glass, iron and wood artwork by local artisans and Molly Morgan Jewelry offers unique sterling-silver jewelry. Wander into Rust and Dust Vintage for old-school lunchboxes and other kitsch treasures, and then venture upstairs to Seaside Massage and Spa for a rejuvenating “Mermaiden” and “Merman” facial. Afterwards, float around the corner to Holladay Street and into Dough Dough. This new bakery is all the buzz and the chocolate-tahini rolls and signature “Cool Kid” blend of Coast-based Sleepy Monk Coffee Roasters will satisfy the most discerning palette. Plus, the illustrious Beach Books is one door over — bonus!
Next, go head-to-head at air hockey or bumper cars inside Seaside’s classic Funland and walk down to Broadway’s carnival-style shooting gallery and win a stuffed penguin for your love. Penguins aside, the winter sun is likely starting to set and your stomachs starting to rumble.
It’s time for Maggie’s on the Prom, the quintessential spot for a romantic ocean-view dinner, where the steamer clams and sautéed foraged mushrooms are divine. Later, see what’s playing on the big screen at the newly reopened Times Theater and Pub. Be sure to grab a bottle of regional red at The Whet Spot on your way back and cork it beside the Gilbert Inn’s outdoor fire pit.
Day Two: Trails, waterways and happy hour
Fill up on the Gilbert Inn’s flaky scones and layer on the fleece because your second day is all about exploring the breathtaking North Coast. Wheel Fun Rentals, next door to Gilbert Inn, offers cruiser bikes and surrey (four-wheeled) bikes; Cleanline Surf rents kayaks for a peaceful Necanicum River paddle; or just lace up the sneaks and hit one of the area’s scenic hiking trails. The moderate 6-mile Tillamook Head Trail winds through lush Sitka spruce and the 8-mile Neahkahnie Mountain Hike is arguably the most scenic on the Oregon Coast.
At the south end of Seaside, Indian Beach in stunning Ecola State Park has several short trails as well, plus jagged black rocks and tidepools galore. After your cheeks are flushed and mind refreshed, return to Seaside and hit up the town’s happy-hour scene. Seaside Brewery and Times Theater and Pub both brew their own beer and the pub fare is excellent. Across the street from the brewery, the new family-owned Westport Winery tasting room is a lovely spot to sip a flight as well as sample the lineup of oils, vinegars and gourmet snacks.
Warm up, fill up, and then slip into one of the souvenir shops along Broadway to get your matching Seaside sweatshirts. Last stop? Grab a snack and a pick-me-up at Beach Day Coffee before heading home with sand in your shoes and memories in your hearts.
If you go:
All year round, Gilbert Inn offers a romance package that includes fresh flowers, sparkling cider, chocolate and two wine glasses to start your escape off right. If you love Gilbert Inn, also check out the recently renovated Inn at the Prom (across the street from Gilbert Inn) and Inn at Haystack Rock, a short drive south in Cannon Beach.
Leave the hassle of driving at home and consider making it a car-free getaway (it’s more romantic that way, too). NorthWest POINT, an Amtrak thruway bus service, offers daily bus service from Portland to Seaside. The trip takes just over two hours and tickets are $17 apiece.
