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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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
The Columbia GorgeA canyon of waterfalls, thirty minutes east.
02
Mount HoodOregon's iconic volcano, an hour and a half out.
03
Willamette ValleyWorld-class Pinot Noir, under an hour south.
04
The Oregon CoastSea stacks and a historic port, ninety minutes west.
05
Hood RiverA windsurf town of orchards and breweries.
The first of five · a first taste
Multnomah Falls & the Waterfall Corridor

Just thirty minutes east, the Columbia River Gorge is a dramatic river canyon lined with waterfalls, crowned by the 620-foot Multnomah Falls.

Revealed inside

Beyond the roadside falls, the Gorge has superb hikes for every level and grand viewpoints over the river. Even short walks reach waterfalls and vistas; bigger trails climb to panoramic bluffs.

Revealed inside

It's close and hugely popular, so go early, and note Multnomah Falls and some corridor access can require timed-use permits in peak season. Check before you drive out.

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Revealed inside

The building and the overlook are free, it's only thirty minutes from the city, and it's the most dramatic, no-cost sunset in the region.

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

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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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