Naughty Travel Guide to Portland

Sienna Sinclaire Naughty Portland 4

Your Naughty Travel Guide to Portland, Oregon

Decided to get out of town for the weekend and visit Portland, Oregon. Boarded a train at Union Station in Los Angeles, as I love train travel…so relaxing and stress free as compared to flying. Plus if you’re not in a hurry, then what’s the rush? The train schedule started from Los Angeles and ended in Seattle before turning around and heading back. Instead of going all the way to Seattle, I decided to get off at Portland so I could have more time to visit.

Little did I know that Portland was such a naughty city, and it was recently designated the most promiscuous city in the US. I should have notice this right away when I asked my waiter, “What’s there to do on a Sunday night?” And he responds with, “Well, how liberal are you?” That’s not usually the response you get from a waiter when asking them that question, but in Portland you never know what kind of naughtiness you’ll get into if you just know where to look.

If you find yourself in Portland for a day or an entire weekend then try out my naughty itinerary below. And if you have any suggestions to share please do in the comment section…thanks in advance.

Pack For Your Naughty Trip to Portland

Travel Bag for all your sex toys

Bags for your dildos and vibrators

Travel-size sex toys 

Carry-on sex toy bags

Discreet carry-on sex toys

Naughty By Day in Portland:

Sienna Sinclaire Naughty Portland 5

  • Powell’s Bookstore – Make sure to make a stop here…Powell’s City of Books is an independent bookstore in Portland, Oregon, that fills a whole city block with more than a million new, used, and out of print books. It’s the largest used and new bookstore in the world and a great place for naughty lover’s to visit who are looking for erotica, sex in history, sex education or any naughty subject. I could have easily spent an entire day browsing all their naughty books but had to discover other naughty places of Portland. Luckily I was able to find some new books to add to my naughty collection…can’t wait to read them. Check out the books I bought below along with browsing Powell’s bookstore for more naughty titles.

The Myth of Monogamy: Fidelity and Infidelity in Animals and People

The Science of Kissing: What Our Lips Are Telling Us

The Soul of Sex: Cultivating Life as an Act of Love

History of Orgies

View More Books on Sexuality Here

  • Underground Portland Tour – Expose the sins of Portland’s past on this tour through Old Town and Chinatown! We walk through the remains of the physical underground as well as exploring the underground subcultures, political underground and immoral underground of the city’s sordid history, and expose the myths behind the legends of the so-called “Shanghai Tunnels.”

“We’ve revamped this tour based on new investigations into the worst of the illicit, naughty, bawdy, corrupt and shady activities of Portland’s not-so-proud past. This walk is a treat for lovers of all things sinister – crime, scandal and controversial characters – a no-holds-barred excursion into the worst Portland has to offer.

After walking the streets for about ¾ of the tour, we’ll hand out flashlights and delve into the subterranean levels under Old Town Pizza in an area which once led to the legendary “Portland Shanghai Tunnels.” If you want to discover the true, inside stories behind ‘crimping’ (the real name of what is now called shanghaiing), you’ve come to the right place. Even though shanghaiing is what makes it on TV, we’ll surprise you with an unscripted commentary of all of the other screwed up and scandalous things that have happened in Portland – both socially underground and physically underground.

We explore other underground topics besides kidnapping. While everyone loves journeying into the bowels of the city to view entrances that once led to the legendary “Shanghai Tunnels”, we also delve into dozens of other somber monuments to the our shameful past of sex, ethnic crimes, gambling, corruption, and more.

This tour is rated PG-13 and is certainly not for the faint of heart.”  Tours are daily at 11am, 2pm and 4:30pm.

Buy tickets for this tour here.


  • Portland Boat Tour – Not the naughtiest tour out there, like the Underground Portland tour, but very interesting if you want to visit the floating brothel. But I’m sure if you ask nicely your captain will share some naughty history with you. Plus if it’s a nice sunny day in Portland, a relaxing way to see the city.

Buy tickets for this tour here


  • Naughty Shopping – No trip is complete without a little shopping…buying sexy lingerie and sex toys to complete your naughty trip that is. Below are some places worth visiting while walking around Portland. Just as you need a sexy dress for out on the town, whats underneath it is just as important! Plus you’ll need some naughty toys to complete your naughty visit to Portland.

Lingerie Stores

Lillie Boutique 

1007 E Burnside St.

Oh Baby 

722 NW 23rd Ave.

Jane’s Vanity

521 SW Broadway

Sex Toy Stores

She Bop

909 N Beech St.


300 SW 12th Ave.


Can’t find what you’re looking for at these stores? Then you can always visit my sex store before visiting Portland to stock up on goodies at


  • Voodoo Doughnuts – – A visit to Portland is not complete without a trip to Voodoo Doughnuts. Yes, the line may be long (up to 30 mins or more) but well worth it for their delicious, naughty donuts. Nor are they discreet with their naughty slogans (“The Magic is in the Hole” or “Good Things Come in Pink Boxes”), bumper stickers (I got VD in Portland), apparel and donut names (Cock & Balls) even though there are kids who line up outside. Which just shows how liberal this city is, as no one seems to care. And why should they? Naughty is good!

Sienna Sinclaire Naughty Portland 2

Voodoo Donuts Portland

I walked away with 2 “pink boxes”! Of course I bought the “Cock & Balls” which you can customized as I did with my name. It ended up being my favorite with a creamy surprise filling in the middle. And make sure to get their voodoo donut which they are famous for and feel free to “poke” away.

Voodoo Doughnut Portland

Plus these donuts are great for when you have late night munchies from a naughty night out in Portland. I enjoyed my “Cock & Balls” late that night. Only ate the cock and saved the balls for breakfast!

Sienna Sinclaire Naughty Portland 3


Naughty By Night in Portland:

  • Sexy Hotels – Here’s a list of the sexiest hotels in Portland. This city may be more hipster, but if you’re like me you can still find glamour and sex appeal in this city. These are my two favorite glamour hotels in Portland.

The Nines

Nines Hotel

Hotel Deluxe

Hotel Deluxe Portland

  • Sexy Restaurants – Want to feel sexy and naughty, along with being around sexy people, before a wild night out on the town? Then these two restaurants are the sexiest in Portland.

Departure at Nines Hotel 

Tapas style eating and amazing food. Order as much as you want so you can taste all the different flavors they offer. My favorites were the Curry Noodles and Carrot and Avocado Salad. Dinner for 2 people (6 dishes) plus two drinks came to about $90. Very inexpensive when you live in Los Angeles.

Departure Patio Portland

Departure Portland

Departure Porland food

Gracie’s at Hotel Deluxe

Gracie's Hotel Deluxe Portland

  • Burlesque Shows – Looking for a strip tease without all the nudity? Who doesn’t like to be teased! You can start your night off with a burlesque show before heading to the main attraction at a strip club or live sex show. Visit this burlesque website for all things burlesque in Portland along with showtimes.


  • Stripclubs – I was very impressed with Portland strip clubs, not just because they have full nudity while selling liquor, but they had no cover and drinks were only about $8. Normally drinks at strip clubs cost around $15-$25 depending on the city you’re in. I was a little shocked, not that many things shock me, that they allowed full nudity and the sell of liquor because most strips clubs in the US don’t which just shows you again how liberal this town is. Not only do the girls get fully nude while sipping your favorite cocktail but at some strip clubs they come down from the stage and straddle you naked. (Of course there is no touching). This is great as you don’t have to go to the “back room” for them to get fully naked. Plus the strippers seemed fine with patrons only tipping a dollar or two.

Depending on what day of the week you visit the strip clubs also determines how wild they get. Some places, such as Casa Diablo, can have girl on girl action on stage along with girls playing with themselves anally or vaginally. And I’m sure the more you tip the naughtier they get. I didn’t make it to the “back room” when I visited because I couldn’t find a girl I liked but I’m sure more goes on in the back room 😉

Casa Diablo is about 10-15 minutes outside of downtown but worth the visit as it’s suppose to be the best, as many people have commented, and gets pretty wild depending on which night you visit. I’m going to guess the weekends. There are tons of strip clubs in downtown Portland where you can have just as much fun and the girls are prettier. All depends on what you’re looking for and your taste.

Visit here for a list of Portland strip clubs


Sienna Sinclaire Naughty Portland

  • Live Sex Shows – I was pleasantly surprised to find that they offer live sex shows in Portland! They are close to being brothels but no sex (or so they say as everyone knows it all depends on how much money you’re willing to spend). You don’t have to go far to find one or seedy areas in the city as they are located in downtown Portland right next to any trendy bars. The one I visited was Pussycats, the one in the photo. They don’t sell alcohol but you can easily visit a bar or strip club then head next door to one. Here are some of the services they offer; sensual rubdowns, shower shows, pole dancing, fetishes, S&M, poly, dominatrix, dungeons, 2-girls shows, masturbation, toy shows. Some even offer escort services to your hotel room.

For Pussycats, next to Dante’s, you walk up 3 flights of stairs to a door where you ring a buzzer. They talk to you through the intercom and tell you right away how much it costs per person to come inside, $130pp. They only want serious people. You are not allowed to just walk in and take a free look so make sure to visit their website first to see the girls and contact them with any questions.


  • Male Revue Shows –  These are great places to visit with your girlfriends if you’re looking to see sexy guys (and penises). Ok they may be classified as gay strip clubs, but who cares! Some of these men are sexy and many girls visit them for some naughty fun. Plus how many places can you visit a male strip and see penises? Not many that I know of…and I would know. So try something different on your next trip to Portland. Darcelle XV even offers great drag shows on certain nights so visit their website for a schedule.

Darcelle XV 



-Naughty Travel Guide to Naughty Cities

About siennasinclaire

Author - Sex Coach - Model - Naughty Lifestyle Expert
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