Top Portland Romantic Tours

Escape the hustle and bustle of the city for the day on this guided tour to Multnomah Falls and the Columbia River Gorge Waterfalls. Travel along the historic Columbia River Highway National Scenic Byway and stop at the magnificent falls of Multnomah, Latourell, and Bridal Veil.

Escape the city for an afternoon exploring some of greater Portland's most scenic falls. Travel along the Columbia River Gorge, home to the largest concentration of waterfalls in the country, stopping at the epic Latourell Falls and Multnomah Falls. Enjoy panoramic views from the Crown Point Vista House and hear about the local legends and natural history of the area from your guide.

Get out of the big city and explore the stunning beaches and beautiful towns along Oregon’s northern coast on this full-day, small-group tour from Portland. Visit the charming towns of Manzanita and Cannon Beach—home of the famous Haystack Rock—browse antique shops and art galleries, and stop at several beaches to maximize your time at the Oregon Coast.

Immerse yourself in the beauty of Columbia River Gorge on this full-day trip from Portland to Mount Hood! With your small group, take a guided tour of such iconic Oregon destinations as Multnomah Falls and the famous Timberline Lodge, and enjoy lunch in the charming city of Hood River. Your tour also includes pickup from over 60 hotels in Portland and a private or small-group option.

Whether you want to relax after a long day of sightseeing or need to unwind at the end of your workweek, a sunset dinner cruise along the Willamette River is sure to do the trick. The journey offers spectacular views of the Portland skyline and city’s main landmarks. Listen to live music while you enjoy a freshly cooked Pacific Northwest meal.

Portland takes pizza seriously—and this tour is the easiest, most fun way to taste the scene in one walk. You’ll hit four pizzerias on a relaxed route with short walks in between (about ~1 mile total), tasting a curated progression of styles and signatures. This is a full-meal experience: each guest gets a full slice at each stop (four slices total). Your guide keeps it laid-back and social while sharing quick, useful pizza insight—what makes a great slice, what to order, and where to go next depending on what you loved most. Pizza and drinks are included. Rain or shine, come hungry and ready to eat like a local.

Get stellar views of downtown Portland from inside an airplane with this aerial experience for up to three passengers. You'll fly over iconic sights such as the Portland, Oregon sign, the Moda Center, the Rose Quarter, and Providence Park, with the chance to take aerial photos of downtown Portland, the Willamette River, and the city's many bridges. This small-group airplane tour is available in English and Spanish to accommodate more travelers.

Visit the top attractions in the Columbia River Gorge National Scenic Area and Mt. Hood National Forest on this day trip from Portland. After spending the morning chasing waterfalls and marveling at 500-pound fish at Bonneville Fish Hatchery, enjoy free time for lunch in historic downtown Hood River. After lunch, we will visit a vineyard in the region for a wine tasting and drive more than halfway up the side of Mt. Hood to explore Timberline Lodge

Soar over the Columbia River Gorge on a sightseeing flight that takes you from Portland to the scenic gorge. Ideal for visitors who are short on time but don’t want to miss any of the highlights, these 20 minutes of flying time show you more than you could see on a full-day ground excursion. Plus, the aerial view provides great photo opportunities.

Fly over Portland and the nearby Columbia River Gorge with this private flight experience. You’ll see the Portland Sign, fly over ancient rock formations, and soar past multiple waterfalls (including Multnomah Falls) all the way to the Bridge of the Gods in the Cascade Locks before heading back into Portland.

Experience Oregon from the sky with this aerial tour above some of the state’s most dramatic scenery. This small-group flight takes you above the Columbia River Gorge, over the Mt. Hood National Forest, past Multnomah Falls, and back to the city. Note: depending on the weather, the pilot may have to alternate the route.

This is Portland’s elevated sushi night out: a small-group, omakase-style progressive dinner across three top sushi spots downtown. Instead of tiny samples, you’ll sit down at each stop for chef-selected dishes—crafted to highlight different styles, cuts, and techniques—so you leave genuinely full and seriously impressed. Over 2–3 hours, you’ll enjoy a curated progression that can include nigiri, sashimi, specialty rolls, and seasonal plates (selection varies by night). Your guide keeps it fun and approachable while explaining what you’re eating, how to spot quality, and how to order with confidence the next time you’re at a sushi bar. All food is included, and group size is capped so the experience stays personal and high-touch. —and if you have dietary needs (gluten-free or vegan), message us after booking so we can plan your best possible menu. Why this is worth it: you’re getting a guided, chef-curated sushi progression at three restaurants in one night—without the guesswork.