The Perfect Getaway: A romantic weekend in Portland, Oregon
Whether you are reveling in a budding romance or new parents in desperate need of a romantic reset, Portland’s gardens, bike trails, intimate restaurants, and wine bars make it an ideal setting for some time together with your love.
By Tanvi Chheda | August 16, 2022 (Updated October 9, 2025)
From Portland’s chic Pearl District to the city’s more bohemian Eastside neighborhoods, there’s plenty of outdoor spaces, food, and art to discover with your love.
Friday
Morning
Settle into your room at Canopy by Hilton Portland Pearl District. The modern and minimalist hotel sits in the heart of downtown Portland, making it an ideal base for a long weekend of exploration. Once you’ve dropped your bags, ease into your stay by heading around the corner to Nuvrei. Aside from offering a feast for the eyes (trust us, your grid will love these photos), the minimalist coffee shop creates artful drinks and delicious twists on classic pastries — croissant with rosewater glaze, anyone?
Afternoon
Head back to the hotel and borrow complimentary Canopy Bikes to explore the Pearl District and downtown Portland, or the nearby waterfront trail with public art and city- and river-views to take in along the way. You can even ride to the Portland Japanese Garden, just 2 miles away from downtown and located within Washington Park. Set on 12 acres with meandering streams, waterfalls and tree-lined paths, Portland Japanese Garden is among the most authentic Japanese-style gardens outside of the archipelago itself and comprises eight individual gardens. Here you can connect with nature and one another, while gazing at the incredible views of Mt. Hood in the distance. Park your Canopy Bikes, grab each other's hand and explore the rest of Washington Park at your leisure, including the International Rose Test Garden, where more than 10,000 individual rose bushes bloom, and the Oregon Zoo, home to both exotic and native animals of all sorts. Hop back on your bikes and head back to the hotel to freshen up for dinner.
Evening
Portland’s foodie reputation precedes itself. For dinner, head to Republica. Located just a few blocks from the iconic Willamette River, the chef’s farm-to-table tasting menu was made for sharing and draws as much from Mexico as it does the local bounty. Think diver scallops, spring turnip, and Oregon wild rice with nixtamalized corn and mole blanco or purple sweet potato and amaranth alegria. A 20-minute walk away is bakery Papa Haydn, where a slice of apricot white velvet, cherry bomb, or German chocolate cake await. After a sweet treat, head next door to Jo Bar & Rotisserie for cocktails and live jazz.
Saturday
Morning
Add a splash of culture to your romantic getaway with via free docent-led tour at the Portland Art Museum, where the impressive 50,000-plus piece collection includes Native American art, Japanese prints, photography, and American landscapes as well as works by Vincent van Gogh and Claude Monet. Off set the more serious morning activities with a reminder of what it’s like to be a kid again. That’s right — ice cream for breakfast! Head to Salt & Straw where you can taste such inventive flavors as goat cheese marionberry habanero, Arbequina olive oil, and salted, malted chocolate chip cookie dough.
Afternoon
Remember the simple pleasure of wandering through a bookstore? Opened in 1971, Powell’s Books is practically synonymous with Portland. Browse new and old titles, pick up a souvenir, or join an evening author reading. (The children’s section makes for fantastic presents so you don’t feel too guilty for leaving the kids at home.) Just across the river, the Oregon Museum of Science and Industry (OMSI) offers a unique afternoon date locale for science-loving partners. What could be more romantic than taking a trip through the cosmos in the Kendall Planetarium with your favorite person?
Evening
It would be remiss to visit Portland and not step into a wine bar. Pint-sized Bar Diane specializes in natural wines from near and far. Best of all, the selection is constantly changing, so there’s always the chance to try something new. One night you might find an orange wine from Slovenia or sparkling rose from France’s Loire Valley, which can be paired with oysters, almonds, or a cheese plate for a light bite before an evening symphony concert.
Sunday
Morning
With a tagline like “It’s all about the love,” can you think of a better breakfast spot for the last morning of your romantic weekend away than Mother’s Bistro? Cozy up to each other and some delicious comfort food — fresh-baked buttermilk biscuits, frittatas, or French toast — at this downtown Portland fixture known for its brunch. From here’s it’s a short walk to Portland’s iconic White Stag neon sign for a photo-op to remember your trip by. If your carb-filled breakfast has you raring to go, take a half- or full-day trip to the Columbia River Gorge. About 25 minutes from Portland, this breathtaking river canyon is the epitome of Oregon splendor and a must-see stop on any Pacific Northwest itinerary.
Afternoon
Browse ceramics, tea towels, staplers, and leather wallets at Portland’s design shops Canoe and Woonwinkel. When you’ve got some room, detour to Voodoo Doughnut, a no-frills doughnut shop, before some rejuvenation and relaxation at the city’s most trendy wellness spot, Knot Springs. Featuring a yoga studio, soaking pools, and spa, this wellness center in the Central Eastside neighborhood was inspired by hot springs in southeastern Oregon’s Alvord Desert and bills itself as a social club. Soak up as much time as you can together during a visit to the Springs, before indulging in a foot rub or facial treatment. The latter uses organic, whole-plant, and locally sourced products from skincare brand, Laurel.
Evening
Close out your romantic West Coast getaway with a delicious meal at Mediterranean-inflected Tusk. Feast on falafel, labneh, and roasted king trumpet mushrooms with zhoug and hemp seed puree, all washed down with delicious craft cocktails. Our pick? The Sugar Kisses, combining vodka, pistachio milk, yuzu and aromatic bay leaf.
Tanvi Chheda
Formerly an assistant editor at Travel + Leisure, Los Angeles-based Tanvi Chheda has been freelancing for 15 years now. She writes mostly about lifestyle and travel, which often spills into arts & culture, food, design, and more. With two young children, family travel is also a passion of hers. Given her South Asian heritage, she writes about India quite frequently as well (she was born in India and speaks three Indian languages). When not traveling or writing, she enjoys reading, cooking, and spending time outdoors. Her work has appeared in the New York Times, the Wall Street Journal, AFAR, Virtuoso Life, Four Seasons magazine, Qantas, Inspirato, Invited, Pasadena magazine, OLTRE, and Ciao Bambino, among others.
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