Top Portland Cruises & Sailing

Sailors will enjoy a private two hour sail aboard a beautiful yacht in the heart of the Columbia River Gorge. Each person 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.

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.

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.

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!

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.

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.

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.