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.

Get instant access, $5 Instant digital access. Yours forever.
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
Where to StayBase centrally and graze across the districts.
02
Getting AroundWalk, bike, and ride, skip the car in town.
03
The IconsThe three that capture the city.
04
Eat & DrinkCarts, coffee, beer, and a doughnut.
05
Parks & DistrictsThe urban forest and the neighborhoods.
The first of five · a first taste
Downtown & the Pearl District

Downtown and the adjacent Pearl District are the most convenient first-trip base, walkable, central, and connected by the free-flowing MAX and streetcar, with Powell's, the waterfront, and good hotels right there.

Revealed inside

Across the river, the eastside (around Burnside, Hawthorne, and Division) is where Portland's food-and-drink soul lives, carts, breweries, and indie shops.

Revealed inside

The leafy Alphabet District around NW 23rd Avenue is charming and residential, tree-lined streets, boutiques, and cafes, an easy streetcar ride from downtown.

+ 1 more
Revealed inside

It costs nothing, and it's Portland at its most beautiful.

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.

Unlock all five, $5

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
Stop planning. Start going.

Five guides in Portland, ready tonight.

Pick one, make the reservation, and go - the hard part is already done.

Unlock all five guides

Instant access to your web guide, printable PDF, and map.

Or get it inside the Portland, All Guides Bundle, $15 →