Romantic Getaways in Portland, Oregon: Tax-Free Vacations for Two 

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Romantic Getaway in Portland, OregonSipping Coffee and Enjoying a Cool Autumn Morning Along the Portland, OR Waterfront

By: Greg Mattson, ERV Editor - Updated Mar 29, 2019

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Almost everyone agrees: Portland, OR is one of the most romantic places for a weekend getaway in the entire Pacific Northwest. (The fact that there's no sales tax in Portland or the state of Oregon helps too!) A few words that start with W describe it well: wonderfulwild, and even a little weird...

Here's a quick guide to some romantic places, things to do, and hotels in Portland, OR. You'll also find some ideas for scenic spots and day trips to nearby Oregon attractions.

The Best Time to Travel to Portland: The best part of the year for romantic getaways in Portland usually runs from about late April to mid October. Autumn brings vivid fall foliage, and the rains don't usually set in until November.

10 Romantic Places & Things to Do in Portland:

Visiting Portland Rose Garden

1. Rose Gardens - take the time to stop and smell the roses at Portland's beautiful International Rose Test Garden. May to October is the best time to visit when everything's in bloom, but the nice views of downtown Portland are year-round. (400 SW Kingston Ave, Portland, OR)

Powell's Books, Portland

2. Powell's Books - you may not ever come across a more awesome bookstore in your life than Powells. As huge as it is, the great thing about Powell's is that it's not big box - it's still got that corner book store atmosphere. Grab a coffee at the cafe inside and soak it all up. (1005 W Burnside St, Portland, OR)    

Multnomah Falls, Oregon

3. Day trip to Multnomah Falls - an easy day trip just 30 miles east of Portland along I-84 (about 45 min drive). With 600+ ft of falling water in a spectacular setting on the Columbia River, Multnomah is easily one of the most scenic waterfalls in the USA.   

Eating at a Food Cart, Portland OR

4. Lunch at a Food Cart - not all of Portland's great dining takes place inside. Their world-famous food carts are easy to get to in the downtown core, and the variety of ethnic choices is astounding. If you enjoy the occasional "eat on the street", don't miss this!

5. Portland Saturday Market - check out all the crafts, the art, the food and the trinkets. (West Burnside St, Portland)

6. Forest Park or Mt. Tabor Park - great places to get out and fill your lungs with that sweet Pacific Northwest air...

7. Tom McCall Waterfront Park - no.1 place for watching Portland's interesting people! (SW Naito Pkwy, Portland)

8. Portland Streetcars - try a "diy tour" of the city from inside one of these, especially if it's raining.

9. Crave Bake Shop - you have arrived at cinnamon roll heaven...(460 5th St, Lake Oswego, OR)

10. Portland Pedicabs - try a fresh-air bicycle tour with someone else doing the peddling! (360-510-1818)

Portland's Most Romantic Hotels:

Kimpton Hotel Monaco Portland

Hotel Monaco Portland OR - BedroomRomantic Queen Room with City View at the Kimpton Hotel Monaco Portland
  • Kimpton Hotel Monaco Portland - the 4-star Hotel Monaco (part of the Kimpton Hotels chain) is located deep into downtown Portland and within easy walking distance to shopping, transit, food carts and theaters. Very friendly people at this hotel, and of all the hotels we've stayed at in this chain, this Monaco had the best wine evening! Members of their InTouch loyalty program (free) get complimentary WiFi. What Other Couples Liked: Very Romantic...Great Mix of Boutique and Hip...Witty and Posh Decor. 2019 ERV Rating* for Romantic Portland, OR Hotels: 94% Excellent. (506 SW Washington St, Portland, OR  503-222-0001)

Kimpton RiverPlace Hotel

RiverPlace Hotel, Portland, ORThe RiverPlace Hotel, Perfect for Romantic Accommodation in Portland OR
  • The RiverPlace Hotel - another romantic Portland Inn that's just recently joined the Kimpton chain. Rooms are big, recently renovated and decked out with the latest high-tech flat-screens and Wi-Fi (unlike some other places, we've never had poor Wi-Fi at a Kimpton!) River and City View rooms are recommended, and in the evening you'll appreciate the little extras like their plush robes and turn down service. What Other Couples Liked: Clean and Serene...Staff Go the Extra Mile...Evening Wine Hour . 2019 ERV Rating* for Portland Honeymoon Hotels: 95% - Excellent. (1510 SW Harbor Way, Portland, OR 888-869-3108)  

Romantic Getaways in Portland - This Week's Best Deals on Places to Stay: Hotel Monaco, RiverPlace, Modera and Heathman Hotels 

Romantic Portland, Oregon B&B's:

Lion and the Rose B&B

Lion & the Rose Romantic B&B, Portland, ORLion and the Rose Victorian Guesthouse in Portland, OR
  • Lion and the Rose Romantic Portland B&B this romantic bed and breakfast is in Portland's Irvington neighborhood, just across the river and northeast of the downtown. The 8 King and Queen rooms vary in size and character, and some are outfitted with claw tubs or a JACUZZI® tub. You can choose your stay and pricing with/without breakfast, and they offer packages for wedding receptions and bridal showers as well.  What Other Couples Liked: 5 Minute Walk to Trams and Restaurants...Terrific Hosts...Early 1900's Victorian Decor. 2019 ERV Rating* for Portland Romantic B&B's: 97% - Excellent. (1810 NE 15th Ave, Portland, OR  503-287-9245)

Portland, OR Honeymoons & Romance Packages

Many of the honeymoon packages you find in Oregon are located on the coast by some of the luxury inns and resorts in places like Cannon Beach and Astoria. But if you're getting married in Portland and would like a few days in the city before heading off elsewhere, here's a few after-the-wedding packages you might like:   

  • Romantic Hotel Packages in Portland - the Hotel Monaco (listed above) has a couple of special offers that sound ideal for a special vacation or anniversary in Portland. They include champagne, roses, chocolates, valet parking and late check out.
  • Portland's Most Romantic Honeymoon Suites - the Hotel Monaco's Grand Suite comes to mind here with it's 2-person jetted tub, separate living & dining areas and deluxe Italian linen. Still with Kimpton Hotels, the Hotel Vintage Plaza has ten very romantic King Spa Suites which also give you a whirlpool tub for 2, views of the city and 750 square feet of living space.    

More Romantic Oregon on ERV:

Romantic Dining in Portland, Oregon

Here's three romantic restaurants in Portland worth seeking out:

Portland City Grill - dining for two with a 30th floor view is always nice, and they have excellent steak, seafood and sushi. (111 SW 5th ave, 503-450-0030) 

Higgins Restaurant & Bar - romantic and organic bistro, fresh seasonal specials, good selection of wine and brews. Considered one of the best restaurants in Portland, Oregon. (1239 SW Broadway, 503-222-9070) 

Paley's Place - voted no.1 recently for most romantic place to eat in Portland. They do an amazing ribeye, and an equally terrific vanilla Crème Brûlée. (1204 NW 21st Ave, Portland, OR)

*ERV Rating: our unique, non-scientific ratings for romantic accommodation include:

  • Amenities: including Whirlpool bath or JACUZZI® Tub, scenic view, fireplace, lounge, etc
  • Location: proximity of hotel to restaurants, pubs, downtown, etc
  • Clientele: demographic the hotel attracts (couples, families, business travelers, etc)
  • Popularity: based social media & crowd-sourced reviews 
  • Value: product offered compared to room rate 
  • Please Note: percentage ratings are not absolute but for comparative use only  

√ COVID Safety Plan: identifies hotels and inns that clearly indicate they are taking measures to prevent the spread of COVID-19.

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