Here's a sample itinerary for a drive from Portland to Skagway. If you're planning a road trip to Skagway, you can research locations to stop along the way. Traveling with a dog or cat? View pet-friendly stops between Portland and Skagway. Find the best hotels, restaurants, and attractions based on the most talked about places recommended by Trippy members.
Your starting point is Portland, Oregon.
You can enter an exact street address if you want to get precise directions, but this is optional.
Since there are only 2 travelers, we assume you're driving 1 car. You can adjust the number of people traveling at the top. We assume a maximum of 4 passengers per car, but you can change the number of cars to fit your situation.
Seattle (248 answers)
Pike Place Market (113 mentions)
Space Needle (54 mentions)
Experience Music Project (25 mentions)
Pioneer Square (25 mentions)
Kerry Park (24 mentions)
restaurants around Seattle:
Matt's in The Market
hotels around Seattle:
Inn at the Market
questions about Seattle:
Is the Space Needle worth seeing?
Best free things to do in Seattle?
2-day solo trip to Seattle - What to do?
Where are the most photogenic areas in Seattle?
What are the best restaurants in Seattle?
108 Mile Ranch
Your final destination is Skagway, Alaska.
You can enter the exact street address of your destination, but this is optional.
This section could be endless, so rather than trying to suggest every local activity or attraction, we'll leave it open-ended.
These are some of the places people talk about on Trippy:
Of course, Trippy is the perfect place to ask questions because there's an entire community of travelers talking to each other and sharing tips and advice. Trippy is where you can get answers personalized for your tastes, budgets, trip dates & more!
Click the button below to explore more questions and answers related to Skagway.
Yes, even this step is optional, because if you're on vacation who wants the trip to end? It's okay, you can start planning your next trip!
Don't forget about exploring your own hometown with a staycation. You can also find some cool day trips or get away for a weekend. Maybe try typing in a faraway location like London, Hong Kong, or Sydney, and get inspired for your dream trip around the world.
And if you know Portland well, please help your fellow travelers and answer their questions about Portland!