The Five On It • Portland Guide

Five Portland guide plans, already made.

Stop comparing options and building your own itinerary. We have already done it, every pick includes the full plan, insider tips, reservation advice, maps, backups, and the exact order to do it in.

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Full itineraryMaps for every stopInsider tipsBackups & budget options
What's inside

Five guides, planned down to the minute

Every one runs start to finish, the spots, the timing, the order to do them in, plus reservations, maps, budgets, and a backup for each.

01
DowntownCentral and walkable, transit at your door.
02
The Pearl DistrictGalleries, boutiques, and polished loft-living.
03
The Central EastsideWhere Portland's food-and-drink soul lives.
04
Nob Hill (NW 23rd)Leafy, charming, and village-like.
05
The WaterfrontRiverside, with the bridges and the views.
The first of five · a first taste
The Walkable, Connected Core

Downtown puts you within a walk of Powell's, the waterfront, the food carts, and the MAX and streetcar, and a straight ride from the airport.

Revealed inside

A grand, art-filled hotel in the heart of downtown, topped by the Departure rooftop bar and restaurant with skyline views. It's a stylish, perfectly central base with a great perch built in.

Revealed inside

Downtown is central and convenient but can feel uneven block to block, so pick a hotel in the lively retail-and-Pearl-adjacent core. For sheer convenience, it's the easy call.

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Revealed inside

Add the lack of sales tax, and a car-free, central Portland trip is both the easiest and the cheapest way to do the city.

Planning a guide like this yourself can take 4–6 hours. Here, it's already done, yours to download in seconds.

5 complete guides, every one chosen and mapped, yours for $5.

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A note from us

From us to you

We've done every one of these guides ourselves.

Some are where we celebrate birthdays. Some are where we take friends visiting Portland. Some have just become our favorite “we don't even need to think about it” go-tos.

These are the guides we recommend to the people we care about most.

Now go enjoy it,

The Five On It
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Five guides in Portland, ready tonight.

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