Top Portland Sailing Tours

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.

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.

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.

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.

Day or night, experience a private adventure for your party of 2 to 12 people with a lot of lesser know wild stories of the Portland area. Includes the oldest and most expensive yacht club, my favorite peaceful spot on the Willamette and some great views of the city. There are stories no other tour boats tell and places that only our unique vessel can take you, so welcome aboard!