Top Portland 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.

Sailors will enjoy a two hour sunset sail aboard a beautiful yacht in the heart of the Columbia River Gorge. Sailors can interact with the captain, learn to sail, steer the boat, winch in the jib sheets, or just relax on the deck as we navigate up and down the mighty Columbia in the wake of Lewis and Clark.

Get an up-close look at the Columbia River Gorge on a sightseeing cruise that takes you under the Bridge of the Gods and past sights such as the Bonneville Dam, Native American fishing platforms, and locations where kite surfers and wind surfers show off their skills. Snacks and drinks are available for purchase on board the boat.

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 evening on the Columbia River on a dinner cruise that provides views of the Columbia River Gorge National Scenic Area from a historical sternwheeler. A seasonal menu features local ingredients for the 3-course dinner with bread, salad, main course, and dessert. Along the way, listen to stories and history about the river from the captain. Drinks are available for purchase.

Take in the sights of Portland from a different perspective. Enjoy the sights and Captain's narration with a bistro menu and full beverage service for purchase during the cruise.

Escape to the Columbia Gorge on this 2-hour cruise through the "heart of the Columbia Gorge." Enjoy a delicious Northwestern Brunch Buffet with complimentary champagne. Travel through history on an authentic sternwheeler. See the sights and listen to live captain's narration of Oregon's rich history. Sit back, relax and go with the rivers flow. We will take care of the rest. - Features - Two-hour brunch cruise from Cascade Locks, Oregon - Bottomless champagne, mimosas, or sparkling cider included - Enjoy a delicious Northwest buffet prepared onboard - Live historical narration played throughout the vessel - Access to all three decks as well as captain's wheelhouse Boarding 9:30am Cruising 10:00am - 12:00pm

Enjoy a private tour of Portland waters on an up to 90-minute sailing cruise. Bring up to five others on a leisurely meander along the Willamette River, choosing between an up river journey to the forested Elk Rock Island or a ride taking in the city skyline and bridges. Relax, unwind and simply savor postcard views as well as time with your friends and loved ones. You can enjoy BYO snacks, beer and wine to savor while soaking in the surrounding atmosphere.

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.

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.

This day trip is a customized 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. After your pickup in Portland, we'll discuss the interests of people in the group, and your guide will customize the itinerary to those interests. Regardless of interests, the trip will include driving the Pacific Coast Scenic Byway with a short hike through oldgrowth Sitka spruce forest, beach time, tide pools, 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, Tillamook Creamery (currently closed due to COVID-19), or Camp 18. - Please be prepared for whatever the weather may be when your tour runs (e.g. rain gear, sunglasses, hat, extra layers, sunscreen). - Wear shoes that you don't mind getting sandy and wet.

The 85-mile (137-km) long Columbia Gorge NSA would be a national park if it weren't a critical transportation corridor. It features waterfalls, mountains, monoliths, terraces, resort towns, vineyards, orchards, and The River, harboring a plethora of fish and birds, and unique plants and invertebrates. In the early 1900s, Portlanders would drive their Model T cars along the Columbia River Highway to gaze at waterfalls. It was the first scenic highway built in America. There is said to be over 4000 waterfalls; many are hidden away, but many are just a short hike off the Historic Highway. On this tour you'll explore the western, rainforested, southern side of the Gorge, dubbed "waterfall alley" where we'll have you getting wet under a waterfall, peering over cliffs, and learning stories of the area only the locals know.

Want to check out Portland's hot thrift shop scene? You just have to know where to go! Come along with me for a tour of shops that include everything from items plucked out of the dump to high-end Prada at a second hand boutique! Portland's thrifting culture is rooted in our respect for the environment and a commitment to re-use and recycle useable goods rather than send them to the landfill. Consequently, we have many thrift shops of every kind and category! There's no place better to begin than SE Hawthorne Ave., a vibrant street of secondhand shops, as well as a food carts, coffee shops, and small businesses selling made-in-portland goods. It's my treat for coffee or cocktails as we meet to get acquainted and caffeinated! This is a team experience so we can share what we're looking for and act as scouts for each other (me: Frye boots, color brown, size 10). I look forward to going thrifting with you in Portland!

Mt. Hood is the highest summit in Oregon, and the fourth highest in the Cascades. It features waterfalls, glaciers, and historic Timberline Lodge, built by local artisans during the Great Depression, and featuring the longest ski season in the US. To the north of Mt. Hood is the Hood River Valley and Columbia Gorge American Viticultural Area (AVA), the lovechild of the Columbia Valley and Willamette Valley AVAs. You will get intimate with this area through a visit to Timberline Lodge on Mt. Hood, wine tasting, and a stop at Multnomah Falls, the tallest waterfall in Oregon. Your expert guide, with formal background in ecology, natural resources, and wine, will teach you about the natural history, cultural history, and wine background of the area, as you drive the Mt. Hood and Historic Columbia River Highway Scenic Byways. You'll visit 2 wineries. We cover lunch, you cover tasting fees.

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.

On this 3.5-hour tour, you'll get a broad overview of the Central City. We'll make stops at Pittock Mansion and the International Rose Test Gardens. At Pittock Mansion, you'll get pictures of the best views of the city, and the five stratovolcanoes that are visible on a clear day. You'll have plenty of time to smell the roses at the Rose City's most famous garden. Your expert guide will provide background on the sites and city history, while navigating through city traffic, so you don't have to. You'll meander through all of the major neighborhoods of inner Portland on both sides of the river while gaining views of 14 of Bridgetown's 27 notable bridges. Your guide will return you to your departure location at the end of the tour.

If the Oregon Coast is known for anything, it's the majestic views, rugged cliffs, and charming towns. On this private tour from Portland, enjoy the best of what the coast has to offer. You're whisked off on a scenic drive, stop at a local vineyard for a wine tasting (own expense), and stretch your legs with a walk on the beach.

Mt. Hood is the highest summit in Oregon, and the fourth highest in the Cascades. It features waterfalls, glaciers, and historic Timberline Lodge, built by local artisans during the Great Depression, and featuring the longest ski season in the US. To the north of Mt. Hood is the Hood River Valley. You will get intimate with this area through a visit to Timberline Lodge on Mt. Hood, fruit stands in the Hood River Valley, downtown Hood River (your opportunity for lunch and/or alcoholic beverages), and breathtaking stops in the eastern and western Columbia River Gorge (Multnomah Falls included). Your expert guide, with formal background in ecology and natural resources, will teach you about the natural and cultural history of the area, as you drive the Mt. Hood and Historic Columbia River Highway Scenic Byways. Maximum group size of 11. Pickup and drop-off at your hotel.

Visit the lush trails of Portland's gargantuan Forest Park, the only urban wilderness park in the U.S. Your guide will take you along forested trails, telling you about the plants, animals, and history of the park—and the region—as you walk. And if you feel like turning back, there's no pressure. The hike is a moderate 3–5 miles (5–8 kilometers) long, but can be shortened or adjusted to meet your needs.

Mt. Hood is the highest summit in Oregon, and the fourth highest in the Cascades. It features waterfalls, glaciers, and historic Timberline Lodge, built by local artisans during the Great Depression, and featuring the longest ski season in the US. To the north of Mt. Hood is the Hood River Valley and Columbia Gorge American Viticultural Area (AVA), the lovechild of the Columbia Valley and Willamette Valley AVAs. You will get intimate with this area through a visit to Timberline Lodge on Mt. Hood, wine tasting, and a stop at Multnomah Falls, the tallest waterfall in Oregon. Your expert guide, with formal background in ecology, natural resources, and wine, will teach you about the natural history, cultural history, and wine background of the area, as you drive the Mt. Hood and Historic Columbia River Highway Scenic Byways. You'll visit 2 wineries. We cover lunch, you cover tasting fees.