The City of Books Portland, Oregon

Chapter 1

Get lost in the legendary aisles of the Pacific Northwest. Our Portland itinerary explores the quirky, rain-kissed soul of the city through its massive book landmarks and hidden neighborhood gems.

With each trip Stay by the Book presents, we invite our travelers to read a novel set in the city we are exploring, prior to attending. Our first night together we will hold an informal book discussion and your guides will point out memorable elements from the novels throughout your adventure.

We have selected the following two novels, feel free to choose which sounds most like you or to read both!

  • After helping a lost elderly woman, Bob starts volunteering at her senior center, where he meets a cast of quirky characters and is forced to revisit his own history, including a painful complication from his youth. 

    The Portland Connection: The novel is deeply rooted in the geography of the city, mainly the East Side (please note this is not the area we will be exploring this trip - we will be West Side). It captures the quiet, rainy, intellectual atmosphere of Portland.

  • Mika, feeling like a disappointment, is contacted by her 16-year-old daughter, Penny. To impress her, Mika fabricates a successful life, but the deception grows, especially as she develops a relationship with Penny's adoptive father, Thomas. It’s vibrant and modern, much like the neighborhood food scene we will be exploring.

    The Portland Connection: Mika lives in Portland, and the book is peppered with specific local energy. It captures the modern "indie" spirit—the art galleries, the specific coffee culture, and the feeling of navigating the city’s unique creative social circles.

The Paperbacks

Only 2 Spots Remaining!

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Only 2 Spots Remaining! 〰️

August 28 - August 30

Starting at $650 per person

Vibe: Community, Creativity, and Local Flavor.

The Paperback experience is designed for the reader who loves the pulse of a city’s creative heart. This weekend is a celebration of Portland’s "Indie Spirit," focusing on community-focused bookshops, shared stories, and the legendary food truck scene that makes the PNW so unique.

Exploring together means plenty of strolling throughout the day! Comfortable walking shoes are highly encouraged so you can wander, browse, and explore with ease.

  • Dive deep into the neighborhood culture at the world’s largest independent bookstore, followed by a playful white-elephant book swap, and plenty of "reading in the wild" sessions in historic city blocks and sun-drenched parks. We will visit multiple local, independent bookstores and shopping boutiques.

  • Savor the city's most authentic flavors, from award-winning wood-fired pizza in a vibrant, industrial-chic setting to a festive gathering at a famous open-air food-truck garden.

    Your journey concludes with a farewell brunch featuring iconic, soul-food-inspired comfort classics in the heart of the Pearl District.

  • Includes a curated boutique stay at the most bookish 4 star hotel in Portland and a welcome swag bag filled with local literary treats to fuel your weekend adventure.

  • Check in: Friday, August 28, between 2:00 and 3:00 p.m. Make your way from the Portland International Airport to the 4 Star hotel where one of our tour guides will be waiting in the lobby to check you in and help you get settled before the adventure begins!

    Check out: Sunday, August 30, brunch will be at 9:00, then you can choose to join us for one last reading session by the river, which we will conclude at noon.

Portland Paperbacks Portland Paperbacks Portland Paperbacks Portland Paperbacks
Portland Paperbacks
from $650.00

$950 - Single Occupancy

Luxuriate in your own room with a king-size bed and private bathroom.

$850 - Double Occupancy (per person)

Bring a friend to share in the adventure - or be paired with a new one! Two queen beds and a shared bathroom.

$750 - Triple Occupancy (per person).

Are you a bestie trio? No problem, we are too! We understand how hard it is to find tours that allow up to three in a room! Two queen beds and a shared bathroom. Please note that this pricing is only available to people traveling together in a group of three.

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The Hardcovers

Only 4 Spots Remaining

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Only 4 Spots Remaining 〰️

August 29 - August 31

Starting at $1500 per person

Vibe: Exclusivity, Historic Luxury, and Fine Curation.

For the traveler who wants an elevated, all-access pass to the city’s literary soul, the Hardcover retreat offers a "Collector’s Edition" experience. This tier is defined by its premium pace, private sanctuary, and high-end indulgences.

Exploring together means plenty of strolling throughout the day! Comfortable walking shoes are highly encouraged so you can wander, browse, and explore with ease.

  • The Experience: Enjoy the city through a lens of exclusivity. You’ll join a private culinary and literary walking tour led by a local expert, exploring historic sites while enjoying a multi-stop gourmet lunch. There will be plenty of "reading in the wild" sessions in historic city blocks and sun-drenched parks, as well as visits to multiple local, independent bookstores and shopping boutiques!

  • Elevated Dining: Experience the pinnacle of Portland’s culinary scene, featuring a sophisticated Italian dining experience and a stunning farewell dinner at a high-rise restaurant with panoramic skyline views.

  • Privacy & Lodging: Every Hardcover guest is guaranteed a private room at the most bookish 4-star hotel in Portland, providing a quiet, upscale sanctuary to retreat to after a day of city exploration.

    Exclusive Indulgences: Receive our most premium Collector’s Swag Bag and a special highlight of the trip: a surprise, personally curated bookish treat selected specifically for you as a permanent memento of your journey.

  • Check in: Saturday, August 29, between 2:00 and 3:00 p.m. Make your way from the Portland International Airport to the 4 Star hotel where one of our tour guides will be waiting in the lobby to check you in and help you get settled before the adventure begins!

    Check out: Monday, August 31, brunch will be at 9:00, then you can choose to join us for one last reading session by the river, which we will conclude at noon.

Portland Hardcovers Portland Hardcovers
Portland Hardcovers
$1,500.00

$1,600- Single Occupancy

If you are traveling with a friend, you will still get your own room, but we can put you in nearby or even adjoining rooms if you’d like! Please drop us a note after booking to let us know you’d like to be near your bestie!

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The Duology

Only 2 Spots Remaining!

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Only 2 Spots Remaining! 〰️

August 28 - August 31

Starting at $1200 per person

Vibe: The Ultimate Anthology. Why choose one when you can have both?

Can’t decide between the indie energy of the Paperback retreat and the refined luxury of the Hardcover experience? The Duology is your all-access pass to the complete Portland story. Designed for the traveler who wants a longer stay and a full-spectrum adventure, this four-day journey blends the best of both worlds into one seamless itinerary.

Exploring together means plenty of strolling throughout the day! Comfortable walking shoes are highly encouraged so you can wander, browse, and explore with ease.

  • The Best of Both Editions: You’ll kick off your weekend with the Paperback crew, diving into the vibrant neighborhood energy and community book swaps.

    The Luxury Transition: On Sunday, your experience "levels up." You’ll transition into the Hardcover tier, for exclusive group activities and fine a dining experience.

  • While with the your Paperback crew you enjoy Portland’s famous local pizza and food-truck scenes.

    On Sunday you’ll transition into the Hardcover tier, joining an exclusive private culinary and literary walking tour and enjoying a high-end farewell dinner with a skyline view.

  • A Room of Your Own: Like our Hardcover guests, the Duology tier includes a guaranteed private room - unless you are traveling with a friend - for the duration of your stay, ensuring you have a consistent, upscale sanctuary to recharge between adventures.

    Premium Perks: You’ll receive the Collector’s Swag Bag and the signature surprise, personally curated bookish treat, ensuring you head home with a library’s worth of memories.

  • Check in: Friday, August 28, between 2:00 and 3:00 p.m. Make your way from the Portland International Airport to the 4 Star hotel where one of our tour guides will be waiting in the lobby to check you in and help you get settled before the adventure begins!

    Check out: Monday, August 31, brunch will be at 9:00, then you can choose to join us for one last reading session by the river, which we will conclude at noon.

Portland Duology Portland Duology Portland Duology Portland Duology
Portland Duology
from $1,200.00

$1,800- Single Occupancy

Luxuriate in your own room with a king-size bed and private bathroom.

$1,450 - Double Occupancy (per person)

Bring a friend to share in the adventure! Two queen beds and a shared bathroom.

$1,300 - Triple Occupancy (per person)

Are you a bestie trio? No problem, we are too! We understand how hard it is to find tours that allow up to three in a room! Two queen beds and a shared bathroom. Please note that this pricing is only available to people traveling together in a group of three.

View Options
Three white rectangular plates on a wooden table with various dishes. The top left plate has broccoli, shredded cheese, and a dollop of sour cream. The top right plate has black beans with cheese, scrambled eggs with vegetables, and lime wedges. The bottom plate contains fried rice with vegetables and eggs, and lime wedges. There are forks and knives on napkins next to the plates.

  • Boutique Accommodations: A stay in a historic hotel revered for its literary atmosphere and library-themed mezzanine.

  • Curated Dining: All meals are included, ranging from casual local favorites like artisanal donuts and wood-fired pizza to sophisticated multi-course fine dining and private gourmet food tours. All non-alcoholic drinks are included, and at select stops, a set number of alcoholic drinks will be covered.

  • Expert Curation: Guided pilgrimages to a world-famous, multi-story bookstore and neighborhood crawls to hidden stationery gems and independent boutiques.

  • Thoughtful Extras: A welcome swag bag of local goods and—for our Hardcover and Duology guests—a personally curated surprise and guaranteed private lodging.

  • The Logistics: We handle every reservation, tour fee, and tip so you can simply focus on the next page.

  • An Instant Reader Community: "We clung to books and to our friends; they reminded us that we had another part to us" - The Guernsey Literary and Potato Peel Pie Society. Beyond the books and the city, you are joining a small, curated group of fellow bibliophiles. From our "First Chapter" icebreakers to shared evening novel discussions, you’ll find a welcoming space to connect with others who value a good story as much as you do.

What’s Included:

Three white serving dishes on a wooden table filled with various dishes: the first dish contains a broccoli salad with shredded cheese and a serving of sour cream, the second dish appears to be black beans with shredded cheese, and the third dish is
A peaceful park scene with a paved walkway, surrounded by green foliage, tall trees, black benches, and street lamps, with buildings in the background.
Breakfast with scrambled eggs, mixed berries, pancakes with bacon, fried eggs, toast, and coffee.
A person walking on a brick sidewalk lined with trees in an urban setting, with office buildings and a parking garage visible in the background.
A hand holding a piece of cake with chocolate and vanilla layers inside, topped with a graham cracker cracker crust, in a paper wrapper with black and white text.
A riverfront park with a flower bed, trees, a bridge over water, and suburban houses in the background under a cloudy sky.
City street scene with tall modern glass buildings on the right, older architecture on the left, and a pedestrian area in the center. The sky is partly cloudy with patches of blue. There are signs for nearby establishments, streetlights, trees, outdo
Join Stay By The Book for shopping in the heart of Portland where you will find charming stores filled with vibrant art, unique merchandise, and memorable souvenirs.
Plate of small sandwiches, French fries, coleslaw, and pickles with a small cup of barbecue sauce, alongside a plate of fruit salad with pineapple, grapes, orange slices, and a piece of cornbread.
Join Stay By the Book on a visiting to the famous local bookstore Powells!
Interior of a cafe or restaurant with a wooden beam ceiling, large windows, and a black menu board showing coffee options. People are seated and a barista is working behind the counter. Bottles of sauces and drinks are visible on the counter.
Empty city street lined with trees and multi-story buildings on both sides, with tram tracks and traffic lights, in the daytime with a partly cloudy sky.