Guide to Dramatic Cliffs, Tide Pools, and the Best Seafood You’ll Find
There’s something magical about the Oregon Coast. The jagged rock formations rising from the Pacific, the charming coastal towns, the fresh seafood. Living in Texas, this feels a bit like stepping into another world. And the best part?
This is the trip that made us realize the Pacific Northwest deserved way more of our travel calendar than it was getting. Five days. One incredible road trip. And a masterclass in why coastal exploration beats resort-sitting every single time.
Quick Trip Overview
When: Late May (May 27–31)
Where: Portland, Cannon Beach, Lincoln City, Newport
Who: Just us two <3
How Long: 5 days / 4 nights
Vibe: Relaxed road trip with plenty of hiking, beach exploration, and small-town charm
Day-by-Day Breakdown
Day 1: Portland Arrival & NW 23rd Exploration
We flew into Portland on Southwest (booked through the Chase Ultimate Rewards portal), and I have to say—the Duniway Portland made the perfect first stop. This is where our Fine Hotel & Resort (FHR) credit came in handy, covering one night and unlocking premium perks like room upgrades and hotel credits.
Pro tip for families: Use that FHR night strategically on your arrival city. You get more than just a room; you get a reset point before hitting the road.
The hotel itself is beautiful—downtown Portland location, excellent lobby bar, and we made full use of the $100 dining credit. There happened to be a jazz band playing in the lobby.
Where we ate:
- Lunch: LucLac Vietnamese Restaurant (excellent pho and rice bowls)
- Dinner: Tusk (a bit upscale but worth it; we made reservations and used our Open Table credit from my Chase Reserve card)
- Happy Hour: At the hotel bar using that $100 credit (seriously, don’t leave hotel credits on the table)
Before dinner we spent the afternoon exploring NW 23rd Avenue on e-bikes—a tree-lined neighborhood full of boutiques, coffee shops, and local vibes. It’s the kind of place where you feel like a local, not a tourist.
Day 2: Cannon Beach & Ecola State Park
The drive from Portland to Cannon Beach is only 1.5 hours. This is when the Oregon Coast really starts revealing itself.
Cannon Beach is the postcard-perfect coastal town. It has that small-town charm, excellent restaurants, and a long, sandy beach that feels less crowded than you’d expect.
Where we ate:
- Lunch: Ecola Seafoods — get the clam chowder!
- Dinner: The Wayfarer – our table had a view of the big rock. Funny how a giant rock can be so beautiful.
What we did:
We spent the afternoon at Ecola State Park, specifically the Indian Beach Trail. This is a moderate hike with incredible payoff—you get dramatic coastal views, sea stacks, and if you’re a Goonies fan, you’ll recognize the beach where they filmed those iconic scenes.
Pro tip: Go early if you can. We arrived mid-afternoon and had stretches of trail nearly to ourselves. The reward at the end? Standing on the actual Goonies beach with the rock formations looming above.
After the hike, we grabbed fresh seafood at Ecola Seafood and settled into The Wayside Inn for the night.
Happy hour stop: Pelican Brewing Company (local craft beer, food options, casual vibe)
Day 3: Neahkahnie Mountain & Tillamook Cheese
This day was a gem. We started early with breakfast at Sea Level, then headed to Neahkahnie Mountain—one of the highest points in Oregon at 1,680 feet.
Important note: There are multiple trails up Neahkahnie. We took the South Trail, which is 3 miles round trip, and absolutely worth it. We parked at the trailhead listed on AllTrails and went for it.
Here’s the honest truth: this hike was stunning, and we nearly had it entirely to ourselves. We only saw one couple at the summit, and they left as we arrived. For a family looking for a relatively easy hike with massive payoff, this is it.
The views from the top stretch for miles—you can see the entire coastline, and on a clear day, the perspective is humbling.
Where we ate:
- Stop on the way back: Pacific Seafood in Bay City (grab fresh crab, shrimp, oysters to take with you or eat there)
- Afternoon: Tillamook Cheese Factory (yes, it’s touristy, but the cheese is legitimately good, and kids find the factory tour engaging)
What worked: Starting early meant smaller crowds on the trail. Bringing snacks and water kept energy levels up. The combination of hiking + cheese factory + fresh seafood made for a perfect day.
What we’d do differently: The Tillamook Cheese Factory can get crowded in peak season. If you go in summer, aim for early morning or late afternoon.
Day 4: Lincoln City
We moved south to Lincoln City for the night, but this day belonged to a spontaneous detour that became the highlight of the trip.
We’d planned to stay in Lincoln City and grab happy hour at a local spot (Kyllos), but then we decided to drive to Tidal Raves in Depoe Bay instead. It was about a 30-minute drive, and it was absolutely worth it.
Tidal Raves sits right on the water with floor-to-ceiling windows overlooking the ocean. We watched the waves crash against the rocks while eating fish and chips and fresh seafood. The vibe is casual (it’s not fancy), the food is excellent, and the setting is unbeatable. This is the kind of restaurant that reminds you why you came to the coast in the first place.
On the way: We stopped at Boiler Bay State Scenic Viewpoint—a short pull-off with dramatic ocean views and churning white water. Perfect for photos and a quick stretch.
The following morning: We found a secret beach that is only reachable at low tide. This was at 7am the day we were there and it was about a mile walk on the beach from the closest parking spot. When we got there, we had the entire beach to ourselves. It felt like another planet. Make sure to give yourself enough time to get back before the tide rises!
Day 5: Devil’s Punchbowl, Yaquina Head Lighthouse & Drive Home
Our last full day was less about hiking and more about exploring the quirky, beautiful spots that make the Oregon Coast special.
We debated doing Drift Creek Falls, but made the strategic decision to skip it. It would’ve been an hour inland and an hour back, and we’d already hiked significantly the day before. Sometimes the best travel decision is knowing when to slow down and not overcommit.
Instead, we explored Devil’s Punchbowl State Natural Area—a collapsed sea cave that fills and empties with the tide. It’s genuinely cool, and there are several good spots to explore without being overly strenuous. There’s also a small town nearby with a MO’s restaurant (classic Oregon coast chain), a winery (Flying Dutchman), and a coffee shop—perfect for a low-key afternoon.
We then drove to Yaquina Head Lighthouse, where the America the Beautiful Pass ($80 for a year-long national parks pass) got us access without per-vehicle fees. The lighthouse is stunning, the trails around it are easy, and it’s a perfect short stop on your way down the coast.
Where we stayed: Allred Hotel in Newport
Dinner: Clearwater Restaurant in Newport—a multi-level seafood restaurant with incredible views, packed but worth the wait.
What worked: Building in a slower day allowed us to enjoy the remaining spots without rushing. The lighthouse was a perfect way to end our coastal exploration.
What we’d do differently: Nothing, honestly. This day hit the right balance.
Day 6: Return to Portland & Departure
We drove back to Portland, a comfortable drive with time to grab lunch on the way. Our flight was at 3:00 PM on Southwest.
Pro tip: We arrived at the airport super early and used our Priority Pass to access one of Portland’s airport lounges. We spent a couple of hours there (free snacks, comfortable seating, bathrooms that don’t feel like airport bathrooms), and it made the wait to board feel less like a grind.
Points & Miles Strategy: How We Booked This Trip
Here’s the exact breakdown of how we kept costs down:
Flights
Southwest Airlines via Chase Ultimate Rewards Portal. I redeemed our two round trip flights for 59k points. I was able to use points boost at 1.5x and saved 29k points. Not my best redemption, but still good!
Night 1 – Duniway Portland (FHR Benefit)
Our American Express card comes with a Fine Hotel & Resort credit covering one night annually. We strategically used this on our arrival night in Portland, getting both the night covered and a $100 dining credit.
Cost: $0 (covered by FHR credit) + $100 dining credit used at the bar + free breakfast
Nights 2–4: Various boutique hotels along the coast. There are very few chain hotels along the coast. I wanted a room with an ocean view each night. The weather was perfect to sleep with the doors to the balcony open each night.
Why we paid cash for some hotels: Not every hotel stay needs to be a points redemption. Sometimes the cash price is reasonable, and it makes sense to preserve points for higher-value redemptions (like flights).
FAQ
Q: What’s the best time to visit?
A: Late May through early September is ideal. Weather is more stable, and you avoid the rainy season. That said, the coast is beautiful year-round, and spring and fall offer fewer crowds. Just pack for variable weather.
Q: How many days do we need on the Oregon Coast?
A: Four to five days minimum to feel like you’ve actually explored. Our five days were good but felt slightly compressed. Six to seven would be ideal if you can swing it.
Q: Is the Oregon Coast expensive?
A: Not compared to many beach destinations. Food is reasonable (especially fresh seafood), hotels range from budget-friendly to upscale, and activities are mostly free (state parks, beaches, lighthouses). It’s actually one of the more affordable coastal trips we’ve taken.
Q: Are the restaurants kid-friendly?
A: Generally yes. We ate at upscale spots (Tusk, Clearwater, The Wayfarer) and everything else we tried was casual. Most places have kids menus or can accommodate dietary needs. Seafood shacks and casual restaurants dominate the coast, which suits families well.
Q: What should we pack?
A: Layers, comfortable hiking shoes, swimsuits, light jackets, and windbreakers. Sunscreen is essential. We’d also recommend bringing snacks and water for hikes, even short ones.
Q: Is it worth doing a side trip to Tillamook Cheese Factory?
A: If you like cheese and your family enjoys factory tours, yes. It’s somewhat touristy, but the cheese is genuinely good, and kids find the process interesting. Budget 1–2 hours including the gift shop. Go early or late to avoid peak crowds.
Q: Can we use points to book hotels on the Oregon Coast?
A: Not easily, unless you’re staying at a major chain (some Hiltons, Marriotts, etc.). Most coastal Oregon hotels are independent or small chains. This is why we mixed cash payments with points-booked flights. Focus your points on flights, which offer better value.
Q: What about rainy weather?
A: The Oregon Coast is rainy October–April. Late May is generally good weather, though drizzle isn’t uncommon. Pack a light rain jacket. On our trip, we had perfect weather, but we also happened to get caught in a downpour while eating dinner at Kenko in Costa Rica—the point is, bring layers and don’t let a little rain stop you.
Ready to plan your own Oregon Coast adventure? Start by calculating how many points you’d need for flights, then build out your hotel and activity plan. Need help understanding points and miles? Check out our Beginner’s Guide to get started.
Have you visited the Oregon Coast? Share your favorite spots in the comments—we’d love to hear where your family went and what you discovered!
