Things To Do

Gabbiano's

This is one of our favorite date night spots with great Italian food and fun cocktails. You'll be talking about the fried Mozzarella on your flight home, we guarantee it.

Take Two

Victoria Bar

Great selection of cocktails and all sorts of vegan/gf food options. Lovely outdoor patio as well!

International Rose Test Garden

A frequent setting for an impromptu date in the spring and summer, we have spent many hours enjoying the sights and scents of the hundreds of different varieties of roses on offer here. We ain't called the Rose City for no reason!

Powell's City of Books

A whole city block of books - if you're a reader, or know one in your life, this is a great place to spend a few hours browsing.

Cornet Custard

Josi's favorite ice cream in town, Jonathan's by proxy.

Flying Fish Company LLC

Really quirky little fish shop. The chowder is incredible, really.

No Saint

Excellent selections of wood-fired pizza and wine close to our venue. Expect a wait!

Mt. Tabor Park

One of the more delightful parks in east-side Portland. Meander your way to the top and reward yourself with lovely views of downtown to the West, and Mt. Hood to the east.

Aalto Lounge

Our first date location. We drank a few too many cocktails and only ate olives, but remember it well.

Radio Room

A staple of Alberta Street, this is a great bar and rooftop!

Beacon Rock State Park

If you're feeling a little adventurous, this is an incredibly rewarding short climb up a fascinating rock formation in the Columbia River Gorge. You'll be rewarded with an amazing view!

Vista House at Crown Point

Really unique historical building in the Columbia River Gorge. As you head east from Portland, you'll find yourself driving the same historical highway that many Oregonians made in their Model T's!

Lower Macleay Park

Sprawling semi-wild semi-urban forest in Portland's west side. We recommend hiking Lower Macleay park to the Pittock Mansion as a fun and easy way to experience this special place.

Pittock Mansion

Drive or hike here (from Lower Macleay park) for an impressive view of the Portland skyline!

Cannon Beach

Beautiful coastal town that will give you an idea of what life is like on the Pacific side of the country.

Haystack Rock

If you time the tides right, get ready to see some really cool sea creatures!

Tillamook Creamery

A quintessential stop on any Oregon coast day trip! Enjoy a free-to-the-public museum where you can see the famous Tillamook products being made and packaged. We're big fans of the Octopus cheese packaging machine.

Grant High School

Where it all started.

Gado Gado

Great restaurant, but we would be remiss if we didn't acknowledge that this was technically the first date we went on when it was My Canh, a family-run Vietnamese restaurant that offered $1 spring rolls and $3 fried rice lunch specials to the high schoolers. There just happened to be a little shy of a decade pause in between the first and second date.

Marchesi Vineyards & Winery

We really enjoyed a visit to this winery a few summers ago, and recommend if you're touring the Hood River area.

Trillium Lake

If you're making a day trip to Mt. Hood, this is a lovely lake to visit along your way.

Timberline Lodge

A legendary ski destination for the Pacific Northwest, but also an excellent place to take in the panoramic views and have a cup of cocoa, or hot toddy of choice.

Crystal Springs Rhododendron Garden

This is a lovely public garden near J+J's house in SE Portland. If the tiny parking lot is full, you may be forced to park in the neighborhood which requires a little walk, but it is worth it!

Fort Stevens State Park

This is one of Jonathan's favorite places in Oregon. Check out easily accessible WWII bunkers, (what remains) of the wreck of the Peter Iredale, or make your way out to the Jetty to look at the Columbia River bar, one of the most dangerous passages on the West Coast.

Astoria

The oldest town in Oregon, this is a really interesting place to eat, wander, or pass through on your way to the coast.

Silver Falls State Park

You'll be amazed how many waterfalls they jammed into one state park!

Painted Hills

The name gives it away, beautiful place. You will definitely need a rental car to access this!

Bend

Very neat town in Central Oregon. This is a great stepping off point for accessing the high desert of Oregon.