Top Oregon Cruises & Sailing

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.

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.

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.

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.

A cruise down the scenic Williamette River lets you take in top Portland sights such as the Steel Bridge or the white stag neon sign—but standard boat rides are often crowded and include tired audio guide commentary. Treat yourself to a more elevated experience on this sunset river cruise, which includes narration from a live guide and space to spread out, plus plenty of photo opportunities.

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.

Capture the views of the Columbia Gorge without having to keep your eyes on the tour. Travel in the comfort of the private vehicle. Guide will provide you live commentary about the tour. Make space in your phone because all the views are worth capturing.

Escape the city for half a day—and explore the scenic highlights of the popular Columbia River Gorge—on this private tour. Pick between morning and afternoon start times, set off in a luxury Mercedes, and head into nature. You’ll discover stretches of the 74-mile (119-kilometer) highway, and immerse yourself in the Pacific Northwest scenery. Discover waterfalls like Latourell Falls and Multnomah Falls, admire Beacon Rock, stop at scenic viewpoints, and more.

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.

Escape to an island paradise without leaving PDX on this tropical happy hour cruise! Sip a delicious drink, take in the city sights, and catch up with old friends or meet new ones aboard Portland's only tiki-style river boat. Depending on the day, crew and crowd, vibes vary from lively and energetic to chill and relaxing. Come connect, take in the fresh air and celebrate a special occasion—or just life itself! At Island Style Charters, every day is a party. **Perfect for:** Happy hour • Celebrations • Work Groups • Travelers • Afternoon Dates • "Just because" **Highlights:** Tropical tiki boat • Downtown river views • Music, drinks & snacks available for purchase **Cruise Duration:** 1 hour **August:** 4:30 PM check-in, 5:00–6:00 PM cruise. **September & October times vary** Please review all booking details and communications carefully before your cruise.

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.

One of Portland's many nicknames is Bridgetown, not much of a surprise given that the city is split by a river crossed by 10 bridges. With this tour, you'll hop aboard a pontoon and head from the southernmost of the city's bridges, the Sellwood Bridge, making your way north. You'll pass through downtown, eventually coming to the last bridge within the inner city: the towering Freemont Bridge, before heading back south.

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.

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.

Journey along Oregon’s breathtaking coastline stopping for viewing wildlife, pristine beaches and rocky cliff headlands. Learn about natural, Native American and regional history. Northern Oregon Coast Tour options include beach or ancient forest walks, shopping, wine tasting or cheese factory visits. Note: Although Astoria is historic, we think this part of the Oregon Coast is more beautiful and majestic.

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 northern stretches of the Oregon Coast with a local guide on this private, customizable tour from Portland. You'll get to ride along the Pacific Coast Scenic Byway, take a hike through old-growth forest, and stop at one or two local towns or attractions of your choosing along the way.

Discover the nature, history, and tastes of the Columbia Gorge in a single day on a small-group tour from Portland. Highlights include a hike through Columbia River Gorge National Scenic Area, a visit to the Columbia Gorge Discovery Center & Museum (admission included), and a stop at Multnomah Falls. The excursion concludes with a tour of the historic Sunshine Mill Winery (tasting at own expense). Hotel pickup is included for added convenience.

There's no better way to explore Portland than on bicycle, and with this private electric bike tour, you'll get to see the best of what this city has to offer, like a local! This tour is led by a former city spokesperson who knows the city inside and out. There will be plenty of stops along the way for photos and snacks, and special requests can be made in advance.

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.

**City Lights & Tiki Nights Cruise – Tiki, Tunes & Waterfront Views** Step aboard for Portland's most unique evening escape: the City Lights & Tiki Nights Cruise. This 21+ one-hour cruise along the Willamette River combines the fun of a floating lounge with views of the city skyline sparkling against the night sky. Sip your favorite drink as you glide past glowing bridges and the illuminated waterfront while music and social vibes set the mood. Every cruise is unique as the vibe tends to align with the energy of the group onboard, often ending in one big dance party. Whether you're planning a date, celebrating a special occasion, simply gathering with friends, or looking for a new way to enjoy Portland after dark, this cruise blends scenic views with lively island-style energy. **August:** 9:30 PM check-in, 10–11 PM cruise. **September & October:** Usually 8:00 PM check-in, 8:30–9:30 PM cruise. Please review all booking details and communications carefully before your cruise.

Book your Private Transfer from Astoria Cruise Port to Portland International Airport (PDX). Don't go through all the hassle of waiting in a long taxi or shared shuttles queues and use our private, door to door airport/port transfer. Your driver will be waiting for you at a scheduled time and you will travel comfortably to your destination. • Meeting with a Nameplate • We track your Flight • Door-to-door Service • No Hidden Charges • Clean cars & Professional drivers

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.