Top Oregon Cruises & Sailing

Hop aboard the Portland Spirit for a trip along the Willamette River with this sightseeing tour of Portland. Your captain will ferry you under some of the city's famous bridges and waterfront sights, and you'll have plenty of chances to take photos of the city right from the water. You'll also have the option to buy snacks and drinks from the onboard bistro.

Enjoy lunch along the Willamette River on a 2-hour cruise in Portland. Great for newcomers and locals alike, the leisurely cruise presents an expansive vista of Portland from the water. In addition to exceptional views and food, the afternoon tour also includes commentary from your captain and live entertainment. Prepared with local ingredients, your meal can be upgraded to include an appetizer and dessert.

Start your day off right with a 2-hour brunch cruise along the Willamette River. Board the boat in the late morning and soak in the scenery of northern Oregon as your boat glides away from Portland. When you’re ready, help yourself to a buffet brunch accompanied by sparkling wine or apple cider. You can walk around the deck or sit near the cabin windows to view the stunning landscape.

This day trip is a tour along a section of rugged coastline along Oregon's northern coast. There will be one or two town stops, and multiple stops at headlands and beaches. The trip will include a short hike through oldgrowth Sitka spruce forest, beach time, tide pools (if tides allow), sea stacks, viewpoint stops, and a lunch stop in a charming coastal town. If group interest allows, stops with a more technological history focus may be made, such as the Tillamook Air Museum and/or Tillamook Cheese Factory.

Explore Portland from a unique vantage point on the water, cruising beneath its iconic bridges while spotting bald eagles, ospreys, sea lions, and other Pacific Northwest wildlife. Led by a US Coast Guard–licensed captain and a Oregon-certified professional guide, each tour blends natural beauty with Portland’s rich 200-year maritime history. Guests may reserve a premium private charter for up to six people for an intimate luxury experience, or join a shared cruise with up to 18 passengers—available daily—for a lively and accessible way to discover the city’s scenic waterways.

Portland River Tours delivers a premier river experience through carefully curated routes featuring iconic landmarks such as the Steel Bridge and the White Stag now the Portland Oregon neon sign, paired with engaging commentary on the city’s history, architecture, and culture. Enjoy our spacious, well-appointed boats designed for comfort, supported by eco-conscious operations and a strong commitment to exceptional service. Choose a premium private charter for up to six guests for an intimate luxury experience, or join a shared cruise with up to 18 passengers—offered daily—for a vibrant and social outing on Portland’s scenic waterways.

Experience the ultimate buggy excursion with Oregon Buggy Excursions. Drive your own buggy and explore Oregon’s breathtaking landscapes at your own pace. Unlike crowded group tours or rushed guided trips, you’ll enjoy the freedom to set your own schedule. We’ll guide you via text message, suggesting unique stops—from hidden local gems to scenic viewpoints—while you decide how long to linger at each. Embark on a personalized adventure, soaking in fresh air and stunning sights. No experience? No worries. Your clear instructions ensure most guests feel confident within minutes. Your unforgettable day includes foldable chairs for comfort. You'll have the option to visit Astoria's rich local history of Maritime shipping and film history, or choose from lakes, rivers, and coastal beaches (just bring your own towels).

Visit the northwestern Oregon Coast without renting a car by booking this small-group tour from Portland. Your local guide will be on hand to provide commentary as you make your way along the Pacific Coast, and can help you and the other members of the group decide on what stops you want to make along the way.

The Columbia River Gorge is known for its dramatic waterfalls and impressive vistas—but if you don't have car, planning a trip from Portland can be tricky. Instead, enjoy a hassle-free way to check off many top attractions in just half a day, all thanks to this small-group sightseeing tour. Visit the historic Vista House, admire Latourell Falls, stop at Multnomah Falls, and more, all while your guide shares insider stories.

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.

This immersive 7-hour tour takes you through Seaside, Gearhart, Astoria, and Cannon Beach, blending iconic landmarks, rich history, and stunning natural scenery. Explore the Peter Iredale shipwreck, view the mighty Columbia River Bar from the South Jetty, and walk through historic Fort Clatsop. You'll also enjoy Astoria’s waterfront charm and, if tides allow, stroll the tide pools at Haystack Rock. Led by a local guide with deep regional knowledge, this small-group tour offers a relaxed pace with engaging stops and scenic drives. Includes bottled water and a $10 meal credit toward clam chowder or another local favorite. Highlights: • Small-group tour of 4 coastal towns • Fort Clatsop, Fort Stevens & South Jetty • Peter Iredale shipwreck & Haystack Rock • Astoria’s history, Column, and viewpoints

Jeff Davies has 30+ years of guiding Willamette Valley Wine Tours. I have top reviews on TripAdvisor, Google and Yelp for Private Tours & Group Tours. My commentary will give guests insider knowledge and our winery visits will give guests memorable encounters with winery staff. I can specialize the tour to suit your taste. I prefer wineries with amazing wine and beautiful views but, it's your choice. You can choose your wineries and can also pick them . Also, there are lunch choices to be made.

The Oregon coast is one of the most majestic geologic formations that was formed by lava flows millions of years ago. We depart to the coast and have lunch in the charming town of Cannon Beach and do hiking and exploring on the coast. Explore the majestic Oregon coast, view the amazing Haystack Rock formation, and during low tide gaze at starfish and clams. We will also explore Oswald State Park for lite trail walking and see the stunning cliffs of Manzanita point. This is a joinable small group tour for 2 persons or more, door to door service. Please dress for the season, expect a full day beginning 10am and back to Portland by 6pm.

Explore Oregon’s rocky northern coastline, dotted with beaches and sea cliffs, on a scenic full-day trip from Portland. Travel the picturesque US Highway 101 through quaint beach towns, stopping in Cannon Beach, Ecola State Park, and Oswald West State Park. Enjoy panoramic coastal views, geological wonders, and wind-swept beaches without the hassle of self-driving, and learn more from your guide than you would going alone.

Visit Mt. Hood and the Columbia Gorge, with a couple of stops for wine tasting along the way, with this full-day tour. You'll visit Multnomah Falls, the Columbia Gorge's most famous attraction, hang out at Mt. Hood's historic Timberline Lodge, and pay a visit to two different wineries to taste Gorge-produced wine. There will be a hosted lunch on tour and a glass of wine at one of the wineries included. You will also be able to purchase beverages at your leisure during winery visits.

City Lights & Tiki Nights Cruise - An Hour of Tiki, Tunes, and Waterfront City Views. Step aboard for Portland’s most unique evening escape: the City Lights & Tiki Nights Cruise. This 21+ 1-hour journey along the Willamette River combines the laid-back fun of a floating tiki lounge with unbeatable views of the city skyline sparkling against the night sky. Sip your favorite drink as you glide past glowing bridges and the illuminated waterfront, all while island-inspired décor, tropical music, and tiki lounge vibes set the perfect mood. Each week brings a different theme, from masquerade parties to neon nights and other festive celebrations, so every cruise is a one-of-a-kind experience. Check our social media to see the upcoming theme schedule and plan your night out. Whether you’re looking for a fun date idea, a gathering with friends, or just a new way to enjoy Portland after dark, this cruise blends scenic views with lively, island-style energy you won’t find anywhere else.

Experience the best of Oregon's nature in a small-group tour. The adventure begins with hotel pickup from your Portland accommodation to Silver Falls State Park. Here, you’ll follow your guide on a moderate 5.7-mile (9.2-kilometer) hike along the Trail of Ten Falls. Then, enjoy tastings and a freshly prepared picnic lunch.

Explore the Oregon coast on your own terms, with this private, customizable tour led by a local guide. You'll have three hours of guide and driver service at your disposal. You’ll be able to either explore areas that you've researched ahead of time or simply get recommendations from your guide, depending on your interests.

Enjoy Portland from the water on this relaxed, island-style sunset cruise along the Willamette River. This 2-hour experience blends scenic views, tropical vibes, and a welcoming atmosphere for a memorable evening on the river. Cruise past floating homes, historic riverside properties, Waverly Country Club, and glide under 10 iconic bridges as the sky shifts with sunset colors and the city reflects on the water. The route includes a unique stretch behind Ross Island, offering a quieter, more scenic perspective you won’t see from shore. Settle into flexible seating aboard our tiki-styled boat, featuring both open-air areas and a covered palapa rooftop with wind protection screening for added comfort in cooler weather. Snacks and drinks are available for purchase onboard, including cocktails, beer, wine and cider. Whether you’re sightseeing, celebrating, or simply unwinding, this sunset cruise offers a fun, social way to connect and experience Portland from a whole new angle.

Jeff Davies has 30+ years of guiding the Multnomah Falls / Mt. Hood "Loop" Tour with Columbia River Gorge Waterfalls. I have top reviews on TripAdvisor, Google and Yelp for Private Tours & Group Tours. My commentary will give guests insider knowledge. I can specialize the tour to suit your taste.

Being short on time doesn’t mean you can’t see the best of Portland. This morning tour showcases some of the city’s most popular attractions in just half a day, including Pioneer Courthouse Square, shopping areas such as the Pearl District and NW 23rd, the Lan Su Chinese Garden, and more. Seasonal stops at the International Rose Test Garden and the World Forestry Center add to the fun.

Enjoy superb views of the Portland riverfront on a 90-minute sailing cruise along the Willamette. Set out from Portland on a small-group tour up the river, stopping to view Portland's floating homes as well as uninhabited Ross Island. Savor the surrounding scenery―including placid Holgate Channel and the Oaks Bottom Wildlife Refuge―as you go. Bring your own snacks, refreshments and spirits to satisfy both hunger and thirst throughout.

Discover lava tube caves, old-growth forests, waterfalls, and more on a guided tour of Mt. St. Helens. The park’s vastness and variety of attractions can be overwhelming on your own, but by visiting with a guide you don’t miss any of the highlights. Plus, you can learn about the area’s geology, ecology, and history—much of which you might miss if visiting the park on your own.