An Epic 3-Day Portland, Oregon Itinerary

This post contains affiliate links which means that I will make a small commission if you purchase a product after clicking on any of them, at no extra cost to you.

My 3 days in Portland completely stole my heart—almost as much as my 4-day Seattle trip, which says a lot! This city has everything—amazing food, a quirky and laid-back vibe, and some of the most breathtaking nature the Pacific Northwest has to offer. Seriously, I love that you go from sipping artisanal coffee in a cozy cafe to chasing waterfalls in the same day.

If you’re planning a trip, I’ve got you covered with an epic 3-day Portland itinerary that’ll take you to the best food spots, coolest neighborhoods, and, of course, those stunning waterfalls. Let’s get into it!

3-Day Portland, Oregon Itinerary

Day 1: Explore Portland

Check Into Your Hotel

First things first—time to check into your hotel and get settled before diving into all the amazing things these next 3 days in Portland have in store for you! We stayed at the Dossier Hotel, and I was obsessed. The stylish vibes, cozy rooms, and little thoughtful touches made it such a dreamy stay.

I’ll spill all the details in the “Where to Stay in Portland” section, so stay tuned!

Grab Lunch at Urban Farmer

If you’re anything like me, traveling = instant hunger. After a long morning, we were starving and headed straight to Urban Farmer for lunch. Located inside The Nines Hotel, this spot has a sleek, modern feel and some seriously good food.

We went for their grilled chicken sandwich, and WOW—bacon, gruyere, apricot jam, and sofrito aioli? Absolute flavor bomb. We also grabbed a refreshing salad to balance things out. If you’re feeling fancy, their craft cocktails are also chef’s kiss.

Visit the Crystal Springs Rhododendron Garden

Now that you’re fueled up, it’s time to soak in some of Portland’s natural beauty—and trust me, Crystal Springs Rhododendron Garden is a must. This place is a total dream for flower lovers, with winding paths, peaceful ponds, and the most stunning bursts of color.

The best time to visit is late April to early May, when the rhododendrons are in full bloom! But even if you’re visiting in another season, the garden is still beautiful, with azaleas, magnolias, and camellias adding their own colorful touch.

Entrance costs $5 (but it’s free on Mondays!) and is open daily from 10 AM to 6 PM during the spring and summer seasons.

Want even more flower magic? Check out Schreiner’s Iris Gardens or Wooden Shoe Tulip Farm—just make sure it’s bloom season!

Grab a Mid-Day Pick-Me-Up

After all that exploring, a caffeine boost is definitely in order. We spotted a Dutch Bros Coffee nearby, and if you’ve ever been, you know it’s impossible to resist. We first fell in love with Dutch Bros during our Arizona road trip, so finding one in Portland was a sign.

Our go-to order? A vanilla cold brew with half and half and a Snickerdoodle frost (basically dessert in a cup). But honestly, Portland’s coffee scene is top-tier, so if there’s a cute local shop nearby—go for it! You really can’t go wrong with coffee in this city.

Explore Washington Park

Next up—Washington Park! This massive urban park has so much to see, but we focused on two must-visit spots: the International Rose Test Garden and the Portland Japanese Garden.

The Rose Garden is free and absolutely stunning when in bloom (late spring to early summer is the best time to visit). Even off-season, it’s still a peaceful place to wander.

Right next door, the Japanese Garden is one of the most authentic outside of Japan. Think serene ponds, manicured landscapes, and traditional architecture—total Zen vibes. Admission is around $21 per person, but worth it.

Parking Tip: There’s hourly parking nearby, but if you want to explore more, take the free park shuttle to spots like the Oregon Zoo, Hoyt Arboretum, and several hiking trails.

We loved this area so much that we came back the next morning for more exploring!

Have Dinner at Bistro Alder

After a full day, Bistro Alder (inside the Dossier Hotel) was exactly what we needed—amazing food without having to go far.

The menu is packed with Pacific Northwest flavors, and everything we tried was so good. We started with the endive “Caesar” salad and goat cheese deviled eggs, but the kabocha squash soup stole the show—rich, velvety, and perfectly spiced.

For the main course, the pork loin chop was next-level tender, and the raisin and honey sweet-and-sour sauce made it even better.

We also couldn’t resist trying a couple of their craft cocktails—each one unique and perfectly made. Whether you’re staying at the hotel or not, this spot is a must for your 3-day Portland itinerary!

Day 2: Day Trip to Cannon Beach

Grab Breakfast

We were up early (like 7:30 AM early), and surprisingly, a lot of nearby coffee shops weren’t open yet. Thankfully, Bistro Alder serves breakfast Monday–Friday from 7–11 AM—a total lifesaver.

If you’re in the mood for something sweet, go for the French toast. Prefer savory? The breakfast sandwich is a solid choice. They also serve Stumptown Coffee, a Portland favorite—trust me, it’s worth the hype!

Head to the Largest Bookstore in the World— Powell’s Books

Book lovers, this one’s for you! Powell’s Books isn’t just any bookstore—it’s the largest independently owned bookstore in the world.

The second we walked in, we were hit with that new book smell (aka heaven). Four floors of endless books—bestsellers, rare editions, local authors—you name it. The staff is super helpful if you need recommendations, or you can just wander and soak it all in.

They also host author readings, book signings, and literary events, making it so much more than just a bookstore.

Visit the Pittock Mansion

Sitting atop a scenic hill in Washington Park, Pittock Mansion gives you a peek into Portland’s history and some seriously gorgeous architecture. There’s a fee to tour the mansion, but honestly? The lookout point is the real star—and it’s totally free.

From up here, you get sweeping views of Portland, Mount Hood, and the Willamette River. Even if you don’t go inside the mansion, stopping by for the views alone is 100% worth it!

Explore Forest Park

Right in the heart of Portland, Forest Park is a massive 5,000-acre escape packed with lush trails and endless nature vibes. Whether you’re up for a leisurely stroll or a solid hike, there’s a trail for you.

I can never get Remi to commit to long hikes, so we stuck to the shorter ones—like the trail to Witch’s Castle! This 1.5-mile hike leads to some seriously cool moss-covered stone ruins that give off total enchanted forest vibes.

Heads up—parking is free but fills up fast! Try to go early, and as always, follow Leave No Trace to keep this place looking beautiful.

Check out some of the best trails in Forest Park!

Grab Lunch

By the time lunch rolled around, we were starving, so we headed straight to Red Onion Thai—and wow, did it deliver! Their $10 lunch special is a steal. We split the red curry and pad kee mao (drunken noodles), and not only were the flavors incredible, but the portions were huge—we even had leftovers. 10/10 recommend!

Take a Day Trip

A day trip to Cannon Beach is an absolute must. From the iconic Haystack Rock to the jaw-dropping views at Ecola State Park, this stretch of the Oregon coast is pure magic!

We kicked things off with a coffee stop in Seaside, a charming little coastal town. If you have extra time, take a walk along the promenade, visit the aquarium, or just chill on the beach—it’s such a vibe.

State Parks

The best part about Cannon Beach is all the incredible state parks are super close to each other, so you can hit them all in one go.

• Hug Point – A secluded beach with cool rock formations and hidden tidal caves.
• Arcadia Beach – Perfect for tidepooling—we saw so many colorful sea creatures!
• Ecola State Park – Insane coastal views, scenic hikes, and rugged cliffs that make for epic photos.

And of course, you can’t leave without seeing Haystack Rock. It’s not just a cool landmark—it’s actually a National Wildlife Refuge, home to all kinds of marine life. We even spotted starfish in the tidepools!

Downtown Cannon Beach

When you’re ready to explore the heart of Cannon Beach, downtown is the place to be. Charming shops, cozy cafes, and incredible local art galleries line the streets. Visit Pelican Brewing—their coastal-inspired cuisine and refreshing craft brews totally capture the laid-back vibe of the Oregon coast.

I won’t pretend to be an expert since we only had a short time here, but if you have more than a day, be sure to check out this full Cannon Beach guide for even more recommendations!

Come Back and Enjoy Dinner With a View

After a day of exploring, there’s no better way to wrap up your second day in Portland than with an unforgettable dinner high above the city at Portland City Grill. Perched on the 30th floor of the U.S. Bancorp Tower, this spot is all about breathtaking views, incredible food, and a warm, upscale atmosphere.

As soon as we walked in, the floor-to-ceiling windows stole the show—Portland’s city lights sparkled below, and Mount Hood stood proudly in the distance. But let’s talk about the real star of the night—the best salmon of our lives.

I’m not exaggerating. The blackened salmon was absolute perfection—a gorgeous sear on the outside, flaky and tender on the inside, with a flavor that was rich yet delicate. Sometimes, simplicity is what makes a dish amazing, and this one was a true masterpiece. If you’re planning a 3-day Portland itinerary, do yourself a favor and add this dinner to your plans!

Day 3: Waterfalls + Hikes

Grab Breakfast

I saw Gravy recommended in nearly every Portland blog post, and it lived up to the hype. This cozy breakfast spot nails both quick, friendly service and insanely good food.

Now, let’s get to the important part: the French toast. Made with fluffy challah bread, it was absolute breakfast perfection—light, golden, and just the right amount of sweetness. I savored every single bite.

If you’re mapping out your 3 days in Portland, Gravy needs to be on your itinerary. It’s the kind of place that fuels you up for a day of adventure, and honestly, I’d go back in a heartbeat.

Chase Waterfalls

If you love waterfalls and scenic drives, then the Columbia River Gorge Scenic Highway needs to be at the top of your 3-day Portland itinerary! This route is packed with breathtaking Oregon waterfalls, making it perfect whether you’re down for a challenging hike or just want an easy stop to soak in the views.

First stop—Multnomah Falls. You can’t come to Portland and not see this beauty! Just a short drive from the city, it’s easily the most famous waterfall in Oregon—and for good reason.

We hiked the 2-mile out-and-back trail to the top, and wow—it was so worth it. The views from the top were unreal, and the sense of accomplishment made it even better. But if hiking isn’t your thing, don’t worry! You can still get that classic bridge-and-waterfall shot from the lower viewing area—no hiking required.

Beyond Multnomah, we checked out Latourell Falls and Bridal Veil Falls, and each one had its own unique charm. Latourell’s towering basalt columns were straight-up mesmerizing, while Bridal Veil Falls had this dreamy, fairy-tale-like cascade that felt straight out of a movie.

Pro tip: Parking fills up fast, especially at Multnomah Falls, so get there early! We arrived at 8:30 AM and had a peaceful experience, but by the time we left, the crowds were rolling in.

🚗 No rental car? No problem! This half-day Columbia River Gorge and waterfall tour covers all these stunning spots plus a couple of extra hidden gems.

Check Out Some Other Nearby Hikes

If you’re craving even more outdoor adventure, Powell Butte Nature Park is a must-visit. Just outside Portland, this spot has stunning views of Mount Hood and a mix of easy and moderate trails—perfect for a laid-back hike. We stuck to the shorter trails, which still gave us epic views of the open landscapes.

Heads up: Some trails don’t have much shade, so bring sunscreen and bug spray to keep things comfy.

And if you’re up for another incredible hiking spot, check out Tom McCall Preserve—just 30 minutes from the waterfalls and Portland. While we didn’t make it there this time, everyone raves about the panoramic views and wildflower-covered trails. It’s officially on my list for next time!

🚗 Want a combo tour that includes waterfalls and Mount Hood hikes? This epic 8-hour adventure has you covered!’

Treat Yourself to a Locally Crafted Brew

No trip to Portland is complete without diving into its legendary craft beer scene. This city is packed with breweries, and we made it our mission to check out a few of the best. First up—Ecliptic Brewing.

Ecliptic Brewing blends creativity with bold flavors. Every sip felt like a perfect reward after a day of hiking!

The vibe is super laid-back and welcoming—exactly what you want when you’re kicking back with a cold one. The staff knows their stuff and is more than happy to walk you through the menu, so if you’re indecisive (like me), they’ll help you find your perfect match.

If you have time for more breweries, check out Deschutes Brewery and Cascade Brewing Barrel House as well!

After a few rounds, you might need a break—we sure did. We headed back to freshen up, took a quick 30-minute power nap, and got ready for round two of exploring.

Pregame Dinner with a Donut

Let’s talk Portland’s donut game—because, wow. We had to do a little taste test between two of the city’s most famous spots: Voodoo Doughnut and Blue Star Donuts. Here’s our thoughts:

• Voodoo Doughnut – Wild, over-the-top, and full of personality. Think crazy toppings, funky flavors, and a neon pink aesthetic that screams Portland. Definitely a fun experience, and their classic Bacon Maple Bar is a must-try.
• Blue Star Donuts – The more elevated, gourmet option. Their brioche-based dough makes for the fluffiest donuts, and the flavors? Next level. Blueberry Bourbon Basil and Passion Fruit Cocoa Nib were our favorites.

Honestly? Both were so good—it just depends if you’re in the mood for fun and funky or refined and fancy.

Check Out a Speakeasy

You know I can’t resist a hidden speakeasy, and Portland delivered. We stumbled upon Bible Club, and it felt like stepping straight into the Prohibition era.

Tucked away in what looks like a regular house, this spot is all about vintage charm and expertly crafted cocktails. The mixologists are total artists. Whether you’re into the classics or want something totally unique, they’ll whip up something magical.

No password needed—just step inside and let yourself be transported back in time. With dim lighting, antique decor, and cozy seating, it’s the perfect place to wind down after a long day of adventures.

Enjoy Dinner

For dinner in Portland, Clark Lewis really stood out. Known for using fresh, locally sourced ingredients, this spot celebrates the best of the Pacific Northwest’s flavors.

The menu changes often, depending on what’s fresh, so you’ll always have something new to try. Our meal started with a delicious Caesar salad, crisp and light with a crave-worthy dressing. The carrots were a surprising hit—simple but elevated to a whole new level.

For the main course, we had the salmon, cooked perfectly. While it was tasty, it was tough to top the incredible salmon we had at Portland City Grill the night before. Still, Clark Lewis delivered a solid dinner.

Where to Stay in Portland, Oregon

Portland is full of unique neighborhoods, each offering something special. Here’s a breakdown of some great places to stay:

• Downtown – If you want to be close to everything, Downtown is the spot. It’s buzzing with shops, restaurants, and plenty of entertainment.
• Pearl District – This trendy area is packed with art galleries, stylish shops, and a killer food scene.
• Nob Hill (Northwest) – Think cozy cafes, Victorian houses, and boutique shopping. Nob Hill feels more residential and relaxed but is still close to parks like Forest Park and Washington Park.
• Hawthorne – For a quirky, bohemian atmosphere, Hawthorne has it all. With vintage shops, cool cafes, and eclectic dining, this neighborhood is perfect if you’re looking for something laid-back and artsy.

Each of these neighborhoods gives you a different slice of Portland, depending on what vibe you’re after!

Dossier Hotel

We stayed at the Dossier Hotel in Downtown Portland, and it was perfect! The location made it easy to walk to everything, and the service was amazing. The hotel’s on-site restaurant was a great bonus, too!

Our corner room had stunning views of the city and mountains, and the bathroom’s huge windows let in so much light. The hotel also had local art everywhere, which gave it a really cool vibe.

They even offer free bike rentals to explore the city, plus umbrellas if it rains. If you want a comfy spot with great views and a prime location, Dossier is the way to go!

Getting Around Portland, Oregon

Portland’s public transportation is solid, but honestly, I’d recommend getting a rental car. It gives you the freedom to explore beyond the city—think awesome day trips without being tied to a schedule.

Quick travel hack: If you’re worried about pricey overnight parking, I feel you! Remi and I always use Spot Hero to find cheaper parking nearby. For example, we found parking at the City Center Parking Garage, just a few blocks from our hotel. It cost us $21 a night, compared to the $55 at our hotel.

Just a heads-up: if you rent a car, don’t leave valuables in it. Break-ins can happen, so keep everything out of sight!

Ready for an epic weekend in Portland?

Portland is one of those cities that has so much to offer! Whether you’re hiking to waterfalls, exploring quirky neighborhoods, or enjoying a cold brew at a local brewery, there’s no shortage of adventures in this 3-day Portland itinerary. I hope this guide helps you make the most of your time in the city! Let me know what you’re most excited to check out in Portland!

Before you go, be sure to follow me on Insta @guidedbydestiny and check out some of my other West Coast blog posts:

One day in Joshua Tree

Day trip to Palm Springs

Los Angeles to Joshua Tree road trip