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The Portland Christmas Ship Parade Is Back For 2021

Ho ho ho Oregon, one of the largest and most beautiful Christmas parades ever has started for 2021. This classic parade goes clear back to 1954 and started with only one decorated sailboat gliding down the river. In the years following, more and more ships began to join the parade, becoming increasingly popular and magical over the years. This year makes for the 66th year of the Portland Christmas Ships tradition.

Everything you need to know about the Portland Christmas Ship Parade

If you plan on going to Portland to see the event, you can make reservations at one of the great places to eat at any restaurants on the river, or even book a hotel room overlooking the water. You could also take a cruise on the Portland Spirit and book your ride on the Willamette Shore Trolley's Christmas Ships excursion.

Watch The Parade For Free

If you aren't looking to spend a lot, you can just as easily bundle up with friends and family and watch from the waterfront as the parade itself is free of charge.

Length of Christmas Ship Parade

The Portland Christmas Ship Parade on average lasts about 2 hours and features around 55-650 boats between the two fleets.

Expect The Parade To Be Cold

As temperatures will expect to dip during the winter in Oregon, you will want to dress accordingly. While the weather can have a significant impact on the safety of the performance, there is a chance the parade can be canceled up to 30 minutes before the scheduled start time.

Schedule for the Christmas Ship Parade

The parade started December 3, 2021, and will go all the way through to the 21st of December. For a detailed route description and a list of places to see the Christmas Ships see the Columbia route schedule here and the Willamette route schedule here .

You can also check via  Twitter or  Facebook for updates to the route.

Where to Park

There are plenty of places to park, with spots available at all of the waterfront parks along the routes and at the waterfront restaurants for those with reservations. Here are a few ideas for viewing locations:

• Vancouver Landing Amphitheater
• Warehouse 23
• Beaches Restaurant
• McMenamins on the Columbia
• Vancouver Waterfront
• Tom McCall Waterfront Park
• The Old Spaghetti Factory
• Cathedral Park

Before heading out, make sure to check weather conditions. Hot chocolate is a must! Learn about other great places to see Christmas lights this year in Oregon here .

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Your Insider’s Guide to Portland’s Christmas Ships Is Here

Whether you’re a newbie or a seasoned ship watcher, here’s how to enjoy every minute of this Portland tradition

This year marks the 68th anniversary of a beloved Portland and Vancouver holiday tradition—the Christmas Ship Parade. Just like heading out to chop down your own Christmas tree right after Thanksgiving, this area tradition kickstarts the holiday season earlier than you think. These ships start rolling December 2, showing off their spectacular lights against the backdrop of Portland’s rivers. So make your plans now to start your own family tradition. Head down to the waterfront to watch dozens of lighted boats show off their love of all things yuletide this year.

Portland Christmas Ships: A City Tradition

It all started in 1954 when one single boat departed from the Portland Yacht Club ready to share some Christmas cheer. Over the years other spirited ships have joined in the fun, turning the Christmas Ship Parade into a must-see holiday event. These days fleets of up to 60 brightly lit and decorated ships can be viewed floating down the Willamette and Columbia Rivers throughout December. 

The first Christmas Ship Parade of the season sets sail from the North Portland Harbor on Dec. 2. Parades continue at various locations and times along the Columbia and Wilamette Rivers until Dec. 21. For the full parade schedule, times, and assembly points jump to the end of this article or visit the official Christmas Ship Parade website . Fleets are usually out for about two hours, depending on weather and water conditions.

Related: Holiday Light Shows You Don't Want to Miss

Where to Watch Along the Columbia & Willamette Rivers

Watch From a Waterfront Restaurant

Sitting down to dinner at a restaurant with a view is always in season, but it’s extra fun when you have your own personal parade sailing by. Watching the Columbia River route? Pick a primo viewing location at one of these nearby waterfront restaurants and take it all in. Salty’s Restaurant and Sextant Bar and Galley are great options on the Portland side of the river, while The Cove, Beaches , Who Song and Larry’s , and McMenamins on the Columbia are great choices, if you’re hanging out on the Vancouver side. 

Watching the Willamette fleets? The Old Spaghetti Factory not only has something for everyone on their extensive menu, but it also has great views of the river. Upstream Coffee is also known for its delicious (and warm) beverages and views.

Take in the Show from the Shore

Put on your warmest coat (it is winter in the PNW after all) and watch all the action from the waterfront. Check out the parade schedule for recommendations on the best vantage points depending on the day, time, and route.

Related: Our Top Spots for Holiday Shopping in Portland

View this post on Instagram A post shared by Laura Onizuka | Flamenco Made Simple (@flamencomadesimple)

Unique Ways to Watch from the Water

The Christmas ships aren’t the only ones having fun out on the water. These river cruise options also offer prime opportunities to see everything up close and personal. The Portland Spirit hosts dinner cruises all year. The boat departs at 6:30 p.m., giving you plenty of time to enjoy a meal and take in the parade. Tickets start at around $96 per person. 

Want to really soak in the experience–literally? Yacht Tubs are essentially floating hot tubs that you can rent to go up and down the river. Rentals are available at 6 p.m. and 7 p.m. most weekdays and weekends.

Super serious about watching from the water? Scovare Expeditions offers a special Christmas Ships Cruise , starting at $59. Enjoy panoramic views, hot chocolate, cider, and cookies as you enjoy this unique experience. Really want to get into the spirit? Rent out the entire ship for your friends and family.

Related: Magical Christmas Day Activities for Portland Families

Christmas Ships Parade Sailing Schedules

View this post on Instagram A post shared by Portland Winter Light Festival (@portlandwinterlightfestival)

Columbia River Sailing Schedule

Dec. 2: M. James Gleason Boat Ramp (Opening Night/First Sail/Combined Fleet) Parade start: 7 p.m. Destination: North Portland Harbor

Dec. 3: Camas/Washougal (First Sail/Combined Fleet) Parade start: 6 p.m. Destination: Camas/Washougal

Dec. 5: M. James Gleason Boat Ramp (Second Sail) Parade start: 7 p.m. Destination: Vancouver Waterfront / Hayden Bay

Dec. 6: M. James Gleason Boat Ramp (Third Sail) Parade start: 7 p.m. Destination: Washington Shores/Wintler Park

Dec. 7: M. James Gleason Boat Ramp (Fourth Sail) Parade start: 7 p.m. Destination: Vancouver Waterfront/Hayden Bay

Dec. 9: M. James Gleason Boat Ramp (Fifth Sail) Parade start: 7 p.m. Destination: I-205 Bridge/164th

Dec. 10: St. Helens City Docks (First Sail/Combined Fleet) Parade start: 6 p.m. Destination: St. Helens/Columbia City/Woodland

Dec. 11: JJ Collins Memorial Park (First Sail/Combined Fleet) Parade start: 4:30 p.m. Destination: Scappoose/Multnomah Channel

Dec. 14: M. James Gleason Boat Ramp (Sixth Sail) Parade start: 7 p.m. Destination: Washington Shores/Wintler Park

Dec. 15: M. James Gleason Boat Ramp (Seventh Sail) Parade start: 7 p.m. Destination: Vancouver Waterfront/Hayden Bay

Dec. 16: M. James Gleason Boat Ramp (Eighth Sail) Parade start: 7 p.m. Destination: North Portland Harbor

Dec. 17: Riverplace Marina (First Sail/Combined Fleet) Parade starts: 4:30 p.m Meet & Greet from 8-10 p.m. Destination: Lake Oswego

Dec. 18: Riverplace Marina  (Second SailCombined Fleet) Parade start: 5 p.m. Meet & Greet from 2-4:30 p.m. Destination: St. Johns Bridge/Cathedral Park

Dec. 20: M. James Gleason Boat Ramp (Ninth Sail) Parade start: 7 p.m. Destination: Vancouver Waterfront/Hayden Bay

Dec. 21: M. James Gleason Boat Ramp (Tenth Sail) Parade start: 7 p.m. Destination: North Portland Harbor

View this post on Instagram A post shared by Mike Warner (@photosbymikewarner)

Willamette River Sailing Schedule

Dec. 5: Riverplace Marina (First Sail) Parade start: 7 p.m. Destination: Fremont Bridge

Dec. 6: Riverplace Marina (Second Sail) Parade start: 7 p.m. Destination: Milwaukie

Dec. 7: Riverplace Marina (Third Sail) Parade start: 7 p.m. Destination: Fremont Bridge

Dec. 9: Riverplace Marina (Fourth Sail) Parade start: 7 p.m. Destination: Milwaukie/Oregon Yacht Club

Dec. 14: Riverplace Marina (Fifth Sail) Parade start: 7 p.m. Destination: Milwaukie

Dec. 15: Riverplace Marina (Sixth Sail) Parade start: 7 p.m. Destination:  Fremont Bridge

Dec. 16: Riverplace Marina (Seventh Sail) Parade start: 7 p.m. Destination: Milwaukie

Dec. 17: Riverplace Marina (Eighth Sail/Combined fleet) Parade starts at 4:30 p.m. Meet & Greet from 8-10 p.m. Destination: Lake Oswego

Dec. 18: Riverplace Marina (Ninth Sail/Combined fleet) Parade start: 5 p.m. Meet & Greet from 2-4:30 p.m. Destination: St. Johns Bridge / Cathedral Park

Dec. 20: Riverplace Marina (Tenth Sail) Parade start: 7 p.m. Destination: Milwaukie

Dec. 21: Riverplace Marina (Eleventh Sail) Parade start: 7 p.m. Destination: Fremont Bridge

Online: christmasships.org

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2023 Portland Christmas Ships Parade Schedule

Photo courtesy of Christmas Ships Parade

One of my favorite views of Portland is at night when the city lights reflect off of the glassy surface of the Willamette River. This sight becomes even more enchanting every holiday season during the annual Christmas Ships Parade.

The annual tradition of Christmas Ships gathering in fleets to parade up and down the Willamette and Columbia Rivers is celebrating its 69th year in 2023. Are you a first timer to this event or looking for this year’s schedule? Here’s what you can expect.

Now that we’ve found each other, stay up-to-date on everything that’s happening this holiday season by signing up for my free daily newsletter . 

2023 Portland Christmas Ships Parade

During the holiday season, up to 60 boats, 14 to 65 feet long, make up two fleets each brightly decorated in lights and displays. The privately owned vessels come from Portland, Vancouver, McMinnville, Salem and Hood River areas. Some of the ships owners have been part of Christmas tradition for more than 30 years.

The Christmas Ships Parade are viewable on select nights in and around Portland. The parade can be seen from Portland, Milwaukie, Lake Oswego, Scappoose, Vancouver, Camas, Washougal and St. Helens.

Viewing the Parade

The Christmas Ships Parade is free to attend from multiple outdoor viewing spots.

If you want to make the night extra special, consider making a reservation at a restaurant along the Willamette or Columbia Rivers. I’ve included a list of restaurants and hotels for each event. Ask for a table by the window, or if they have outdoor covered and heated dining options.

Meet and Greet Nights

If you want an extra special experience, attend one of the Meet & Greet nights. Meet the Christmas Ships skippers and see some of the boats up close. If you’re interested in joining the parade, the skippers can answer your questions. These events happen on select nights before and after the fleet heads out on the water for the light show. These events are held at RiverPlace Marina, 1510 SW Harbor Way in Portland.

“ Christmas Ship Parade ” by Visitor7 is licensed under CC BY 3.0 .

The Christmas Ships schedule has 13 select viewing nights from December 1-17, 2023. The fleets run their route for two to three hours. 

View the full schedule and choose what night you’ll take in the sights and sounds of one of Portland’s best holiday light displays. The list is organized by locations and the multiple Christmas Ship nights at those locations. 

Keep in mind that on some nights, events may be cancelled due to weather conditions.

North Portland Harbor

December 1 and December 14 at 7 p.m.

The fleet assembles heading upriver in front of Salty’s Restaurant, 38th/NE Marine Drive and heads to the Tidewater Cove area on the Washington side before heading toward North Portland Harbor. North Portland Harbor is located on the Oregon side of Hayden Island. 

Outdoor viewing

M. James Gleason Boat Ramp, Large Parking Lot (Multnomah County Sheriff River Patrol’s Office) NE 42nd/Marine Drive, Portland     Parking is $5.

Restaurants and hotels

Salty’s on the Columbia 3839 NE Marine Dr., Portland

The Sextant Bar & Galley 4035 NE Marine Dr., Portland

Courtyard Marriott North Portland Harbour 1231 N Anchor Way, Portland

Camas/Washougal

December 2 at 6 p.m.

The fleet assembles in front of Port of Camas/Washougal and parades in the area for about an hour. The fleet will return to the docks and then parade back to Portland along the Washington side arriving in the Portland/Vancouver area around 8:30 p.m. The boats will commence near the James M Gleason boat ramp.

Port of Camas-Washougal 24 South A Street, Washougal

Best Western Plus Port of Camas-Washougal Convention Center 121 Port St., Washougal

Puffin Cafe 24 S. A St., Washougal

John’s Landing to Fremont Bridge

December 4, December 6 and December 14 at 7 p.m. 

The fleet assembles in front of Riverplace Marina, 1750 SW Harbor Way, Portland. The fleet will make their way upriver, past the Old Spaghetti Factory, to the John’s Landing area. The boats then turn and travel downriver to area of the Fremont Bridge  Then they’ll will go under the bridge past the waterfront condos and turn around to Riverplace Marina. The fleet will be out for about two hours.

Tom McCall Waterfront Park 98 SW Naito Pkwy., Portland

Riverplace Esplanade 0300 Block SW Montgomery, Portland

South Waterfront Greenway 838 S Curry St., Portland

The Old Spaghetti Factory 0715 S.W. Bancroft St., Portland

Upstream Coffee 315 S Montgomery St #200, Portland

M. James Gleason/I-5 Bridge/Washington Shoreline

December 4, December 6 and December 15 at 7 p.m. includes Hayden Bay

December 5 and December 13 at 7 p.m. includes Wintler Park

The fleet assembles in front of M. James Gleason Boat Ramp, 43rd/NE Marine Drive. The fleet circles the boat ramp then heads across to the Washington side and then downriver to the I-5 bridge and restaurants and can be seen from both sides of the river. The parade will return to the Oregon side below the I-5 bridge. Note that some dates listed above travel to Wintler Park and Hayden Bay. 

Viewing spots available along NE Marine Drive from NE 29th to 42nd St.

Marine Park SE Marine Park & Columbia Way, Vancouver

Vancouver Landing at Terminal One 100 Columbia St., Vancouver

Beaches Restaurant and Bar 1919 SE Columbia River Dr., Vancouver

The Cove 5731 SE Columbia Way, Vancouver

Holiday Inn Portland – Columbia Riverfront 909 N Hayden Island Dr, Portland

McMenamins on the Columbia 1801 S.E. Columbia River Dr., Vancouver

Who Song and Larry’s 111 Southeast Columbia Way, Vancouver

Red Lion on the River 909 N Hayden Island Dr., Portland

December 5, December 13 and December 15 at 7 p.m.

December 8 at 7 p.m. includes Milwaukie Yacht Club

The fleet assembles in front of RiverPlace Marina, 1750 SW Harbor Way, Portland, and travels upriver to the area of the Milwaukie Boat Ramp. At the boat ramp, the fleet turns and returns to RiverPlace Marina. The fleet should arrive at Milwaukie Bay Riverfront Park around 8 p.m. and then will work its way back to RiverPlace Marina. The boats are out for approximately two hours.

Outdoor viewing areas

Milwaukie Bay Park 11211 SE McLoughlin Blvd., Milwaukie

South Waterfront Park 2001 S River Dr., Portland

Riverplace Espanade 0300 Block SW Montgomery, Portland

Willamette Park 6500 S Macadam Ave., Portland

Sellwood Riverfront Park 1221 SE Oaks Park Way, Portland

Powers Marine Park SW Macadam Avenue south of the Sellwood Bridge, Portland

I-205 Bridge/Steamboat Landing

December 8 at 7 p.m.

The fleet assembles in front of M. James Gleason Boat Ramp, 43rd/NE Marine Drive and continues upriver to the I-205 bridge area and Steamboat Landing. The boats continue upriver to the area of SE 164th in Vancouver. The fleet stays on the Washington side and is out for about two hours.

NE Marine Drive from NE 43rd to I-205 Bridge

Salty’s on the Columbia 3839 NE Marine Dr, Portland 

St. Helens/Columbia City/Woodland

December 9 at 6 p.m.

The fleet assembles at the St. Helens City Docks and heads downriver to Columbia City, and weather/river conditions permitting crosses to the Washington side near Woodland, then returns to St. Helens City Docks. The fleet is out about two hours. Ships remain overnight at St. Helens City Docks and leave Sunday for the trip up Multnomah Channel.

Columbia View Park 3 Strand St., St. Helens South of courthouse parking lot.

Columbia Courthouse 230 Strand St. Above the St. Helens City Docks

Caples House Museum 1925 First St., Columbia City 6-8 p.m. Cookies and hot chocolate with donation

Pixie Park 1816 The Strand, Columbia City

The Roof 31 Cowlitz St., St. Helens, OR

Big River Taproom 313 The Strand, St. Helens, OR

Roy Thai 295 Strand St., St. Helens, OR

Dockside Steak & Pasta 343 S 1st St., St. Helens, OR

Kozy Korner Restaurant 371 Columbia Blvd., St. Helens, OR

Dari Delish 1680 Columbia Blvd., St. Helens, OR

The Village Inn 535 S. Columbia River Hwy., St. Helens, OR

Sunshine Pizza 2124 Columbia Blvd., St. Helens, OR

Scappoose/Multnomah Channel

December 10 at 4:30 p.m.

The fleet meets in the afternoon at Coon Island and leave for Scappoose arriving approximately 5 p.m. then continue up the Multnomah Channel to the Willamette River. This is a long night and arrival at the Willamette River is usually between 8-9 p.m. 

The parade will be visible in the Linnton area at the end. The Willamette Fleet will be seen returning to RiverPlace Marina.

McCuddy’s Landing 34326 Johnson’s Landing Rd, Scappoose

Hadley’s Landing NW Sauvie Island Rd., Sauvie Island

Highway 30 viewpoints

Sauvie Island viewpoints Ferry Street Boat Launch Area

Freds Marina 12800 NW Marina Way, Portland

Rocky Pointe 23586 NW St. Helens Hwy., Portland

Lake Oswego

December 16 at 4:30 p.m.

Meet and Greet

After the parade, the crews are hosting a meet and greet at RiverPlace Marina, 1510 SW Harbor Way, from 8 to 10 p.m.

The fleet will leave RiverPlace Marina headed to Lake Oswego, arriving about 6 p.m., subject to weather and river conditions. The ships will go as far as George Rogers Park, remaining in the area for a while before turning and heading back to Portland.  

The parade will be seen from the Milwaukie Bay Riverfront Park on the way to Lake Oswego and again on the return to RiverPlace Marina. If time permits, the fleet will spend time in Milwaukie Bay on our way back to Portland. The fleet is parading for 3.5 hours. 

Foothills Park 199 Foothills Dr., Lake Oswego

Roehr Park 350 Oswego Pointe Dr., Lake Oswego

Milwaukie Bay Park 11001 SE McLoughlin Blvd., Milwaukie

St. Johns Bridge

December 17 at 5 p.m.

Before the parade, the crews are hosting a meet and greet at RiverPlace Marina from 2 to 4:45 p.m.

The fleet assembles in front of RiverPlace Marina, 1750 SW Harbor Way, Portland. The boats make their way upriver, past the Old Spaghetti Factory, to the John’s Landing area. The fleet turns and travels downriver to the St. Johns Bridge/Cathedral Park area, arriving approximately 6:45 p.m. The ships will remain in the St. John’s area for about 30 minutes (weather and river conditions permitting).

Cathedral Park N Edison Street and Pittsburg Ave., Portland

Liberty Ship Memorial Park 1270 SW Naito Parkway, Portland

For more information about the Christmas Ships and maps of the routes, visit the Christmas Ships Parade website . 

Want more Portland freebies, events and deals?  Subscribe to  my newsletter  (only one email a day), and follow me on  Facebook  and  Twitter !

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Cathedral Park

N Edison St. and Pittsburg Ave. Portland , OR 97203

Visit Website Get Directions

Tom McCall Waterfront Park

Naito Parkway between SW Harrison Street and NW Glisan Street Portland , OR 97204

M. James Gleason Memorial Boat Ramp

4325 NE Marine Dr Portland , OR 97211

Port of Camas-Washougal

24 South A St. Washougal , WA 98671

Milwaukie Bay Park

11211 SE McLoughlin Blvd. Milwaukie , OR 97222

Columbia View Park

3 Strand St. St. Helens , OR 97051

McCuddy’s Landing

34326 Johnson's Landing Rd. Scappoose , OR 97056

Foothills Park

199 Foothills Drive Lake Oswego, OR Lake Oswego , OR 97034

Riverplace Marina

0315 SW Montgomery St. Portland , OR 97201

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[…] 2021 Portland Christmas Ships Parade Schedule […]

[…] from December 3–21. Each night, the ships sail for 2 to 3 hours. Check the schedule on this link. You might join one of the Meet & Greet Nights, where you can meet some of the skippers and […]

[…] 2022 Portland Christmas Ships Parade Schedule […]

[…] Portland Christmas Ships Parade Schedule […]

[…]  It is one of the only free holiday light displays in the Portland area. Another free holiday favorite is the annual Portland Christmas Ships Parade. […]

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Portland Spirit Christmas Ship Dinners

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Cinnamon Bear Breakfast Nov. 30 & Dec. 1, 7-8, 14-15, 21-24, 26-27

Youth (0-12) From $50

Prices may change based on demand and do not include tax, fees or optional upgrades. Proceed to booking to view the current rate — book early for the best price. Group discounts available for 10+ persons; please contact 503-224-3900 or [email protected].  

• Wheelchair Accessible
• Vegan & GF by Request
• Non-Smoking Vessel
• Festive Attire Encouraged

Wheelchairs are able to come aboard the enclosed lower deck — please notify us when booking. Stairs are required to venture to the upper decks where some performances take place.

Join Cinnamon Bear and his friends from Maybeland as they return to spread holiday cheer. The whole family will enjoy reserved seating and a plated breakfast while a cast of fanciful characters entertains the kids with storytelling, music and magic. Tickets include a printed souvenir picture with Cinnamon Bear atop his magical throne, and much more.  You won’t want to miss Jack Frost’s magic show this year, performed by Scott Anderson from America’s Got Talent !  Cinnamon Bear has been a holiday tradition for generations and you’re invited to make this season one your child will remember forever.

Reviews from previous guests

“We took our 4yr old Granddaughter on the cruise. I couldn’t believe how exceptional all of the characters were on the cruise. She had so much fun that by the end of the cruise when the characters lined up to say good bye with hugs, my Granddaughter went through the line 4 times. We are already planning on this being a regular Christmas event that we do every Christmas. Any one that wants to put some happiness in a child’s life you have to take your child on this cruise.” – James

“What an enjoyable way to spend a day. It gets you right into the Christmas spirit. Whoever is under the Cinnamon Bear outfit is just adorable. The Cinnamon Bear made our kids feel so special. The food is very good, for both adults and children. While it may seem to be geared toward kids, groups of adults can enjoy the cruise just as much.” – John

“Again, another wonderful year on the Cinnamon Bear Cruise … this is our fourth year in a row. Am so impressed with the service on board. Every employee goes up and beyond for each child. I am so amazed. Thank you again Portland Spirit! See you next year!!!!!” – Kim

What's Included

Upgrade Options

Add to cart during checkout – Subject to availability • Window Table – $15 per person • Boarding Photo – $15

Departure Information

Cinnamon Bear Cruise Dates: Saturday, 11/30 Sunday, 12/1 Saturday, 12/7 Sunday, 12/8 Saturday, 12/14 Sunday, 12/15 Saturday, 12/21 Sunday, 12/22 Monday, 12/23 Tuesday, 12/24 Thursday, 12/26 Firday, 12/27

Boarding: 9:00 am

Cruising: 9:30 am – 11:30 am Departure Point: Salmon Springs Dock at  1010 SW Naito Pkwy, Portland, OR 97204

Return Details:  Returns to original departure point.

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The Portland Spirit Turns 30 Years Old

The iconic vessel will celebrate three decades by floating the willamette with a ’90s-themed cruise..

The first thing to know about taking a lunch cruise on the Portland Spirit is that the commemorative photo is not optional.

“It’s mandatory—joke’s on you,” said the staffer, as he snapped the photo required by U.S. Coast Guard regulations. (It’s not all official business—the souvenir photo was later available for purchase for $15.)

Once aboard the cruise last Friday, about two dozen passengers sat at window seats on the Willamette deck as a live pianist with impeccable posture played a crowd-pleasing and occasionally surprising set list. Is that “Black Hole Sun” by Soundgarden? The other passengers who had ponied up $67 for the two-hour ride were celebrating birthdays and college reunions and entertaining friends from out of town. One couple had won tickets through an Instagram contest for Travel Portland; another was on vacation from Florida.

The Portland Spirit has been sailing up and down the Willamette River entertaining tourists and locals alike since May 1994. She is showing her age in places—peeling paint here, drab flooring there—despite major renovations every few years.

But what she lacks in radiance she makes up for in nostalgia. Some people might remember taking a Cinnamon Bear cruise at Christmas time, or attending a floating corporate retreat. Others may recall boarding the Portland Spirit around 3 am after high school graduation, singing some Britney Spears karaoke then falling asleep on the shoulder of an ex-boyfriend as the sun rose. You know, hypothetically.

On the occasion of its 30th anniversary, the staff of the 150-foot yacht is hosting two $30 “Best of Portland Anniversary Cruises” on May 9 and 23. Nineties attire is encouraged. Local food and drink vendors will offer samples, including Blue Star and Voodoo doughnuts, Creo Chocolate, Rogue Ales & Spirits, and more.

Characters such as the Unipiper, Una the Mermaid, Korny the Chicken and the Portland Pickles mascot Dillon will be on board. But how will the unipiping work on a moving vessel?

“He absolutely cannot have fire on the boat,” says Mandy Morgan, the Portland Spirit ’s director of sales and marketing who came up with the idea for the cruise. “I made that very clear with him.” (For those already worried—the leisurely 8-knot pace of the Spirit likely won’t throw the Unipiper off his unicycle.)

When Dan Yates and his uncle Wayne Kingsley bought the boat in 1995, Portland was the last major seaport in the country that did not have a dinner cruise—a nightlife tourism trend that swept the rest of the country in the mid-’80s. A U.S. Navy man from upstate New York, Yates is also known in town for his involvement in organizations such as the Central Eastside Industrial Council, the Broadway Rose Theatre Company and the Human Access Project, which advocates for swimming in the Willamette. In 2019, he made news for writing an earnest letter to Mayor Ted Wheeler suggesting he buy a 370-foot ship and convert it into a floating homeless shelter.

Back in the mid-’90s, it was considered revolutionary to prep, cook and plate fresh food on board for passengers, let alone offer four entrée choices. On the lunch cruise last week, diners chose from mushroom ravioli, Parmesan-crusted chicken, baked Columbia River steelhead and herb-marinated beef shoulder.

The fare hasn’t impressed Portland foodies, based on a borderline-vicious Reddit thread on the topic where diners compared it to conference food. But consumed while passing under the Tilikum Crossing Bridge, sunlight glinting off the Old Spaghetti Factory’s iconic purple roof up ahead, with a strawberry lemonade zinger ($13) in hand? There are worse ways to spend an afternoon.

Specialty events like the upcoming Best of Portland Anniversary Cruises are a bit of a financial gamble, according to Portland Spirit general manager Dennis Corwin. On one hand there is the somewhat improbable success of the family-friendly Cinnamon Bear Christmas cruise, given that it is based on a plush character from a 1937 radio program. (December is now the Spirit ’s second-busiest month, after July.) But there have been flops, too, like the mid-2000s cabaret series that Corwin calls “artistically successful but financially horrible.”

Up next: booze cruises, though staff resists calling them that.

“We’ve had that term used.…We have largely taken a lot of those off the schedule because we don’t necessarily care for the clientele it attracts,” Corwin says diplomatically.

The Portland Spirit is rolling the dice anyway and debuting a new happy-hour cruise this summer: a 3:30–to–5 pm cruise for only $29. (The short duration and cash bar should, theoretically, keep the clientele behavior classy.) Related: The boat has never had a genuine “man overboard” situation, but at least one college kid has jumped to be funny. It’s actually illegal, and subject to a possible $25,000 fine, Corwin says.

Corwin joined the staff of the Portland Spirit at age 23 as a singing waiter. Three decades later, he is now part owner of the company and has leaned into the maritime field, as evidenced by his abundant use of nautical lingo. Aboard his workplace are heads, not restrooms. Ladders, not stairs. Galleys, not kitchens.

“I do love the theatrics of what we do,” Corwin says. “It’s not a standard restaurant. We are entertaining people.”

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