Cannon Beach

Drive Time: 1.5 hours

Arrive in Cannon Beach with an empty stomach. You’re going to need it. Just when you think you’ve sampled all of this culinary hub’s edible offerings, more will bloom: Castaways Tiki, Irish Table, and new sushi spot Fishes, to name three within the past few years. Even the Cannon Beach Hardware Store’s getting in on the trend, pouring six taps of regional micros (although we can’t vouch for the wisdom of mixing hammers and hefeweizen). One thing we do advise: saving room for the s’mores in the Surfsand Resort’s bonfire package. 

Anchor Point To celebrate its 20th year, the elegant Stephanie Inn gave itself a face-lift with a new entry, floors, and fireplace fronts. The plate-scraping breakfasts, wine hour, and warm cookies haven’t changed. From $379 
nibbles The perfectly charred hand-tossed creations from Pizza A’ Fetta never get old. 
Dive In Tucked between Hemlock and Spruce Streets, 10-month-old Cannon Beach Distillery, founded by CB native Mike Selberg, is worth seeking out.  

Coos Bay & Charleston

Drive Time: 4 hours

“Idyllic” isn’t a word often used to describe the once-booming mill town of Coos Bay. But then again, most visitors don’t know where to look. Like on the Coos Bay Boardwalk, where the floating Fisherman’s Seafood Market doles out the day’s fresh catch. Or at *Lighthouse Beach, a hidden stretch of sand whose unmarked entrance—a surfer path between two houses—keeps the masses confined to nearby Sunset Bay State Park. Or floating atop a kayak on one of the South Slough Estuary’s guided tours, where if you squint hard enough into the federally protected waters, you might spy an otter staring back. 

Anchor Point A set of stairs is your private path to Lighthouse Beach when you stay at the Loft by the Lighthouse. From $175
nibbles The big-as-your-face fish tacos at Sharkbite’s come with a side of advice about where to catch waves.
Dive In Score your crabbing cage, rings, and license at Charleston’s Davey Jones Locker. Then take a few steps outside and toss it all right off the dock.  

*Directions to Lighthouse Beach
From Charleston, follow the Cape Arago Highway. About 3/4 of a mile past Bastendorff Beach, you'll see a sign for Lighthouse Way on the right. Park on the side of highway, and walk in, staying left at the fork. Between two houses on the right, you’ll see a steep surfer's trail (with a rope to help you balance) that will take you down to Lighthouse Beach.

Florence

Drive Time: 3 hours

In the early 20th century, Eugene weekenders white-knuckled their Model Ts along stomach-churning switchbacks for the pleasure of a weekend on Florence’s shores. Today, the death defying happens a few miles south, in the Oregon Dunes National Recreation Area, where places like Sandland Adventures and Sand Master Park sell adrenaline by the hour with dune buggies and sandboard (surfboards for dunes) rentals. But downtown Florence hasn’t forgotten its legacy. Many of the boutiques and galleries in Old Town proudly call out their history in bronzed plaques (or through proud bartenders). And when it opens this summer, the new interpretive center garden will join 38-year-old Siuslaw Pioneer Museum in commemorating Florence’s adventurous tradition.

Anchor Point Save money (and shoe leather) by staying at the clean, comfortable River House Inn, newly remodeled and within paces of Old Town. From $119
NIBBLES No reservations at perennially packed Waterfront Depot? Try the globe-trotting menu at Spice, helmed by the Depot’s owners. 
Dive In Mix history with adventure on the Mapleton Hill Pioneer Trail, an easy half-mile hike that traces the once dangerous route to Florence.  

Oceanside & Tillamook

Drive Time: 1.5 hours

The sunsets are so stunning at Oceanside Beach that even the seagulls stand still to watch. If you come armed with a good action plan, your kids will, too. First maneuver: bypass the frenzy at the Tillamook Cheese Factory for Blue Heron French Cheese Company, where kids can fuel up on free samples before they feed the llamas, goats, and emus at the on-site petting zoo. Then tap the energy reserves with a kayak trip along the newly designated Tillamook County Water Trail. If a tour of the artisan goodies at Tillamook’s Second Street Public Market hasn’t worn down their defenses, reveal your secret weapon: Oceanside’s four miles of surf-friendly beach. 

Anchor Point Simple but sufficient, Three Arch Inn’s huge picture windows frame the perfect sunset. From $105 

nibbles There’s only one place to eat in Oceanside: Roseanna’s. Fortunately, its made-from-scratch pies rival just about anything in Oregon anyway.

Dive In Big and little kids will love the foray to Tunnel Beach, a pretty patch of sand accessed through a hole blasted in stone at the north side of Oceanside Beach.   

Port Orford

Drive Time: 5 hours

Highway 101’s dogleg in Port Orford is about the only thing that keeps it from being a blink-and-you-miss-it town. Case in point: you’ll need just an hour to peruse Port Orford’s hub of eight or so galleries and shops. That’s a good thing, because you’ll want hours, if not days, to explore this area’s natural masterpieces, like Cape Blanco’s sheer basalt bluffs and the sandstone sentinels lining the Pacific at Blacklock Point, a scene so un-Oregon-y you’ll wonder if you didn’t fall into a wormhole and end up in the Mediterranean. A blast of the area’s notorious winds—they’ve been clocked at more than 100 miles per hour—will quickly return you home.

Anchor Point  You’d need a plane to get a better perspective on the Pacific than the one beyond the sleek, modern Muse Guest House’s walls of glass. From $175 
Nibbles  For fresh fish and chips and a close-up look at one of the country’s only dolly docks—where ships are lowered into the water by crane each day—visit Griff’s on the Dock. 
Dive In  Set on the grounds of a former Coast Guard post, Port Orford Lifeboat Station’s museum and hiking trails present a historic and panoramic perspective on this piece of sand and sea.