Itinerary Types - which is yours?

TL;DR No one travel itinerary perfectly works for every traveler. Let us help you formulate an itinerary that will work best for you to see the real Oregon of your own, not 'one' that worked great for some random travel blogger.

Given the size of the state of Oregon, it's practically impossible to see all key travel destinations within one trip. So our first question to you is, what is your travel style? Most travelers look for one of the three itinerary types: a road trip, a deep-dive into one or two regions, or multiple day trips centered around a single home base. While each has pros and cons, all of them can be planned out effectively to cover both the well-known gems and hidden gems so you get what you want out of the real Oregon.

#1 Road trip style: by avoiding out-and-back driving, it's a very efficient way to enjoy various destinations scattered all over the state. This would be ideal for travelers who (1) don't mind the frequent lodging switches and (2) have a pretty long total travel duration (say, a week-ish or more). This is of course a generalized comment since one could adapt a partial road trip loop to accommodate for a shorter travel length.

#2 Deep-dive style: you came, you saw, you conquered. If you'd rather pick a region of your top interest and fully experience it with no room for skimming, this would be for you. It's most resemblant to how locals would plan a weekend getaway. A bonus is you repack/unpack only once.

#3 Day trip style: this will be a great sampling tour especially for travelers with a limited time in Oregon or those who don't want to put all their 'weather eggs' in one basket. You can wake up, check which region has the best weather today, and simply head there. While multiple out-and-back drives make it less time-efficient than the other two styles, the flexibility it offers shouldn't be overlooked.

As Oregon locals, we can confidently say all of the above styles (and any mix-and-match mash of them) work great as long as you acknowledge their pros/cons in advance. So please, don't stress about which style offers the highest objective value - pick what you can imagine yourself enjoying the most.

Now I invite you to browse our flexible road trip itineraries, deep-dive itineraries, and day trip itineraries. Pick a destination that genuinely sparks the wanderlust inside your gut, not what has become the most famous on social media. Don't hesitate to reach out if any help is needed. We formulated these itinerary examples from our own experiences living and traveling in Oregon, and our singular goal is for you to enjoy the real version of this mad beautiful state.