Despite being one of the largest neighborhoods in the city, it’s sometimes hard to decide where to go for a date in downtown Portland. It’s not that there are a lack of options -- rather, there are too many! And you’re not interested in taking the easy route: Stop A. Dinner. Stop B. Bar.

Well, you’ve come to the right place. Here we have curated a list for you that is nice and easy to read, complete with “Cassanova pro tips” (AKA our version of how to be romantic), to let your sweetheart know that this is, in fact, a date.


Urban Wine With Ur Bae

downtown date ideas
downtown portland
wine tasting

We all know that the areas surrounding Portland make for killer wine country, but who says you have to go all the way to the vineyard for a wine tasting?

Portland has several wineries right here in the city! What makes this a great downtown date idea is the fact that you get to learn about Portland’s wine scene from the cozy throes of Portland’s hip, urban, boutique wineries. Nothing gets those endorphins rolling like a slight buzz and a healthy flight of learning new things.

Casanova Pro Tip: Write down the wines/tasting notes your date enjoyed the most so that you get a sense of what they like. This will come in handy when you’re looking for the perfect, meaningful gift on a later day!

Find out more Wildwood Adventures

A Streetcar Named Caffeine

downtown date ideas

This is no ordinary Streetcar Tour. The objective: Caffeine. The terrain: 5 of Portland’s top cafes, and a hot set of earth-friendly wheels. Sounds like a great date idea to us!

This is a unique downtown date because it allows you to explore not only the city, but many of the cafes and coffee traditions within. You’ll get a chance to try samples at each stop, deciding on your favorite so that you and your sweetheart will know exactly where your new fave cafe is by the end of the trip.

Casanova Pro Tip: After all of that caffeine, you and bae are going to want to do something to spend your energy. Ahem… We just might know a place for active date ideas!

Find out more Third Wave Coffee Tours

Beers, Bikes, and Boo

downtown date ideas

Did someone say active date ideas? Well, look no further. This beers, bikes, and brew tour is perfect for the guy or gal who likes to push those pedals to the metal!

Visit several microbreweries around town, visiting downtown, The Pearl District, and NW Portland along the way. Enjoy sampling freshly-brewed beers and burn those calories faster than you can ingest them!

Casanova Pro Tip: At one of the stops, leave a small gift, such as few flowers, or a dinner menu to hint at where you’re going afterwards, waiting in the bike’s bottle holder. No bottle holder? Even better! Gift bae a new bike bottle holder! It’s the little things that count.

Find out more Brewery Bike Tour

Ghostin' in the Red Light District

downtown date ideas
ghost tours
ghost stories

Get a fun scary view of East Portland’s Red Light District. This downtown date idea is perfect for exciting storytelling and a good reason to cuddle close.

If the weather permits, this tour will actually attempt to make contact with “the hereafter” -- fingers crossed for sunny skies!

Casanova Pro Tip: Plan on going to a fun, social place afterwards so that you’re not spooked the whole night -- unless your date is into that, of course!

Find out more Hawthorne Ghost Tour

The Downtown Downlow

downtown date ideas
city tour
portlandia tour
funny activities

This is the tour to take for the couple that likes to laugh. Whether you’re new to the city or you’ve been here all of your life, there’s always plenty more to learn -- and this tour aims to amuse.

Laugh as you learn about voodoo doughnuts, the world naked bride ride, Shanghai Tunnel ghost stories, and more. This will be the perfect trip to finally bring out that cute laugh-snort of yours!

Casanova Pro Tip: Tell your sweetie that you’re going to surprise them later this week with something fun, but that for now you just wanna “Netflix and chill.” When you turn on Portlandia, tell bae it’s a hint for your date night plan! It will be fun for both of you as he/she tries to guess what you have in store.

Find out more Secrets of Portlandia