9 Dreamy Date Ideas for Valentine's Day in Portland

We set the mood for a handful of adventures for you and yours to enjoy on this most romantic of holidays.

By Larisa Owechko February 4, 2015

Get pampered at Hotel Monaco with theAt Your Service” special.
Hotel Monaco, Feb 14—More Info

Experience luxury for a night as butlers meet your every need (and then some). In addition to the hotel’s normal hosted wine hour (5–6pm every day), Monaco’s butlers will serve you local sparkling wine with oysters and caviar, draw the perfect bath, provide grooming services, and drive you to any destination within 30 miles of Portland. In the morning, they’ll deliver espresso to your room before brunch at the hotel’s Red Star Tavern, and you’ll be granted late checkout—frolic about in your room until 2pm! Book one week in advance.

Go to a sausage fest in Mt. Angel.
Festhalle, 500 S Wilco Hwy, Feb 13-14—More info

The annual Mt. Angel Wurstfest is just an hour south of Portland—far enough to feel like you’re getting away for a bit, but without the slog of a long drive. There will be local microbrews. There will be German beer. There will be traditional German music, complete with accordion. There will be handmade sausage varieties with delightfully unpronounceable names like the frickadelwurst. Best of all, it’s just $5 per person, and all proceeds go towards community improvement for Mt. Angel. Sehr gut!

Pair wine with chocolate in the Columbia River Gorge.
Feb 14–16—More info

Make it a long weekend and head out to the Columbia Gorge Wine & Chocolate Weekend, where 20-plus wineries are partnering to create a uniquely Oregonian Valentine’s Day excursion. Highlights along the 40-mile swath of Gorge wine country include new reds, local bubblies, and sweet pairings, as well as the debut of Mt. Hood Winery’s much-anticipated 2013 pinot noir. Partner hotels (like Columbia Cliff Villa and Skamania Lodge) are also offering special discounts for the weekend—so stay awhile! 

Watch an award-winning Nigerian film.
Moriarty Arts and Humanities Building, Room 104; Feb 14 at 7 pm—More info

Director Chika Anadu explores the damaging effects of traditional social expectations on a Nigerian woman in the 2014 African Academy Award winning B is for Boy. The director will be present to answer questions about the film after the viewing. Bring your glasses to read the English subtitles: the movie won Best Film in an African Language and was filmed in Igbo. B is for Boy is part of Portland’s 25th volunteer-run, non-profit African Film Festival, which runs February 12 through March 8. All viewings are free and open to the public.

Stay at the 50 Shades of Grey hotel.
Heathman Hotel, Restaurant and Bar; Feb 13-28—more info

If EL James’ scandalous series gets your heart racing, take your significant other to the hotel that plays host to Anastasia Steele and Christian Grey’s first of many trysts. The Heathman embraces its role as setting to the fictional pair this Valentine’s Day, offering a package that includes tickets to see the movie at a nearby theatre, a 50 Shades of Gin cocktail, and a dinner menu with items mentioned in the series. And if you want the night to last a little longer, you can also reserve a two-night stay (complete with tie toolkit and a bottle of wine).

Explore Seattle’s underworld.
Pioneer Square, Seattle; Feb 14—More info

Take a short road trip up to the other Pioneer Square (did you know that Seattle has one, too?) and learn about the city’s underground history with Bill Speidel’s Underground Tour. This one’s not for the claustrophobic or faint of heart, as the tour will explore the rugged, subterranean remains of old downtown Seattle. After emerging from the underworld, the tour will take you over to Doc Maynard’s, a restored saloon from the 1890s, to warm up with some bourbon and dessert.

Watch Breakfast at Tiffany’s on a big screen at Portland’s Hotel deLuxe.
Hotel deLuxe; Feb 13–15—More info

Delight your inner Audrey Hepburn superfan by booking Hotel deLuxe’s Breakfast at Tiffany’s overnight package. Watch the romantic 1961 classic on a 16-foot screen as you sit back in cushy VIP seats and enjoy complimentary champagne and popcorn in the hotel’s beautiful, gold-leafed screening room. Cocktails and additional snacks will also be available for purchase. The two-night package also includes coffee and doughnuts in the morning.

Scope for orcas in the San Juans.
Friday Harbor; Feb 14—More info

Embark on a three-hour tour off the Washington coast, where you’ll be charmed by sea lions, seals, seabirds, and orca whales. Sure, it’ll be chilly, but the San Juan Safari boat has a warm cabin with huge windows, so you can seek refuge from the invigorating wind of the spacious walk-around deck. Marine naturalists will be on hand to answer questions, and binoculars will be available to help you see wildlife.

Go to the Northwest Flower & Garden Show.
Washington State Convention Center; Feb 11–15—More info

Let your romance blossom at the premier gardening event in the PNW. There will be a dazzling array of intricate display gardens and the most free horticulture seminars offered by any garden show in the world, on topics like sustainability practices, edible gardening, urban farming, among many others. The five-day event will also include more than 80 book signings and a wine garden overlooking the exhibitions. 

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