Top Portland On the Water

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.

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.

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.

Experience the sights of the Columbia River Gorge from a unique vantage point on the water during this adventurous river cruise. From your seat onboard a Explorer Jetboat, snap photos of the Willamette River and Columbia River, including Cape Horn, Multnomah Falls, Crown Point, Rooster Rock, Beacon Rock, and Mount Hood. Listen as your guide provides insightful live commentary as you enjoy the exhilarating ride along the water.

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 Event start time is the check-in time. No need to come earlier. The cruise leaves the dock when all passengers are checked in. October cruise times vary** Please review all booking details and communications carefully before your cruise.

Experience the unrivaled beauty of the Columbia River Gorge, Cascade Mountain Range, and Mount Hood—and see them all in one hassle-free, time-saving excursion—on this full-day tour from Portland. In the comfort of a luxury vehicle, travel with just your guide and a small group for company. Enjoy a guided tour of the Gorge’s top destinations, including Vista House, Multnomah Falls, Timberline Lodge, Hood River, and more.

The Upper Clackamas River awaits with a thrilling half-day rafting excursion that promises unforgettable fun. Nestled just a short drive from Portland, this trip offers a mix of roaring rapids and tranquil stretches, all framed by lush old-growth forests. As you navigate the river's exciting twists and turns, there are plenty of chances to splash around and cool off in the crystal-clear waters. With experienced guides leading the way, safety is paramount, ensuring you can focus on enjoying the ride. Prepare for an adventure packed with adrenaline and stunning scenery.

Step aboard Portland's only tiki boat for a 1.5-hour river cruise blending laid-back island vibes, scenic city views, and playful onboard fun. Relax and take in downtown landmarks and iconic bridges, sip a drink, and enjoy the breeze as we cruise the Willamette. A lively host keeps the atmosphere fun with games like trivia and cornhole, plus chances to win prizes. Whether you're here to unwind, connect with family, meet new friends, or rediscover the city from the water, this cruise is designed to flow with the moment—a perfect mix of relaxation, socializing, and river adventure, all with unforgettable island style. This event is 2 hours in full with 1.5-hours guaranteed time underway, cruising along the Willamette. The first 30 minutes of the 2-hour event window is for check-in and boarding. Once all passengers are checked in, the boat departs. Please feel free to email directly with questions or to confirm your scheduled departure time.

Our Sips & Sights Tasting Cruises pair local wine tasting with a 2-hour sightseeing and social cruise on the Willamette River! Featured wineries: • Oct 4: Love & Squalor • Oct 11: Hip Chicks Do Wine • Oct 25: Stoller Family Estate Your ticket includes: • 2 hours cruising time • Three 1-oz wine tastings from the featured winery host • One full glass of select wine from our onboard bar • Charcuterie snack • Hawaiian lei + grand prize raffle entry • Onboard game, prize + Portland sightseeing tidbits Hear from the featured winery while enjoying Portland's bridges, city views and river scenery. Our onboard bar is also open for additional purchases. All ages welcome. Alcohol is for guests 21+ with valid ID. Sail, sip & see Portland in Island Style! Note: Listed time is check-in time. Cruise departs once all passengers are checked in, no later than 30 minutes after check-in.

**City Lights & Tiki Nights Cruise – Tiki, Tunes & Waterfront Views** Step aboard for Portland's most unique evening escape! 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. For October, we're having Halloween fun so feel free to come in costume! 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. Note: Listed time is check-in time. Cruise departs once all passengers are checked in, no later than 30 minutes after check-in.

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

Head out to the Columbia River Gorge for half a day of visiting cascading waterfalls and scenic overlooks with this tour from Portland. You'll visit Multnomah Falls, the highest waterfall in the state, as well as lesser-known falls throughout the region. You'll also have the chance to take mini-hikes in the area to get better views of waterfalls and the surrounding scenery.

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.

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.

Upon arriving in Portland International Airport, avoid lugging around your baggage and waiting in line for a taxi. Book this private airport transfer and get to your destination quickly and in comfort. Transfer is available to your hotel in Portland, Beaverton, Lake Oswago, or Tigard.

Immerse yourself in the beauty and bounty of Willamette Valley's renowned wine country on this full-day, small-group tour from Portland. Perfect for all levels of wine enthusiasts—from newcomers to connoisseurs—this tour whisks you to three or four top-rated vineyards. Sample a range of varietals (tasting fees own expense), enjoy a picnic lunch, and benefit from door-to-door service.

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.

Forget the stress of booking a (sometimes unreliable) taxi or shuttle to Portland International Airport. Reserve this private transfer for a quick and comfortable ride to the airport from your hotel in downtown Portland, Beaverton, Lake Oswago, or Tigard. Arrive at the airport relaxed with time to spare!

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.

Paddle through the calm, winding waterways of Scappoose Bay, one of the most serene and wildlife-rich kayaking areas in the region. This guided experience takes you into quiet tidal channels surrounded by wetlands and forest, where it’s common to spot birds, river otters, fish, and other native wildlife. The tour follows a relaxed pace, with time to float, observe nature, and take photos rather than rushing. With stable kayaks and attentive guidance, it’s well suited for both first-time paddlers and those seeking an easy, enjoyable outing on the water. What truly sets this experience apart is its private and unrushed format. The route and rhythm are adapted to the group and conditions, creating a more personal connection with the landscape. To keep things seamless, private transportation from a location chosen by the traveler is included, along with fresh snacks and water—so you can focus entirely on the experience.

Enjoy Portland from the water on this relaxed, island-style sunset cruise along the Willamette River. This 1.5 to 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 under iconic bridges as the sky glows with sunset colors and the city reflects on the water. The route includes a unique stretch behind Ross Island for a quieter perspective rarely seen from shore. Enjoy open-air seating plus a covered palapa rooftop with wind screens for comfort in colder weather. Snacks and drinks, including cocktails, mocktails, beer, wine, and cider, are available for purchase. Whether sightseeing, celebrating, or simply unwinding, this sunset cruise is a fun, social way to experience Portland from a whole new view. Note: Listed time is check-in time. Cruise departs once all passengers are checked in, no later than 30 minutes after check-in.

Experience highlights of the Portland area on this full-day sightseeing tour, including the blossoming food cart culture, diverse neighborhoods, Pioneer Courthouse Square, and the unspoiled beauty of the Columbia River Gorge. Immerse yourself in a guided tour of Portland’s fascinating history and quirky contemporary culture. Explore with a small group or upgrade for a private tour.