Oregon Sailing trips & boat tours

Our most recommended Oregon Sailing trips & boat tours

Portland: 2.5 Hour Dinner Cruise Through Downtown

1. Portland: 2.5 Hour Dinner Cruise Through Downtown

Try out the best way to dine in Portland on the Willamette River enhanced by dazzling city sights and lights. You'll enjoy an evening featuring a 2.5 hour cruise, Northwest cuisine (locally sourced and prepared fresh on board), live piano music and narration of the sights on the outer decks. Partake in freshly baked bread, house salad, your choice of entrée (poultry, beef, seafood or vegetarian) and New York cheesecake dessert. After dinner, head out onto the observation deck to admire the city’s skyline lit up at night. Cruise along the scenic Willamette River, then pass by the impressive Steel Bridge. Along the way, learn about the landmarks from the onboard narration. 

Portland: 2 Hour Lunch Cruise Through Downtown

2. Portland: 2 Hour Lunch Cruise Through Downtown

Hop onboard the vessel and be escorted to your private table. Start off with some freshly baked bread, followed by your choice of entrée (poultry, beef, seafood, or vegetarian). Salad and dessert options are available for additional purchase on board. After lunch, head out onto the observation deck to admire the city’s impressive skyline. Cruise along the scenic Willamette River to Milwaukie and back through Downtown Portland under several bridges. Along the way, learn about the landmarks from the historical narration on the outer decks.

Portland: 2 Hour Champagne Brunch Cruise Through Downtown

3. Portland: 2 Hour Champagne Brunch Cruise Through Downtown

Hop onboard the vessel and be escorted to your private table. Start off with a refreshing glass of champagne, sparkling cider, or an orange juice. Then enjoy a delicious plated brunch made up of breakfast and lunch favorites, accompanied by a dessert buffet. After brunch, head out onto the observation deck to admire the city’s impressive skyline. Cruise along the scenic Willamette River, then pass by the Steel Bridge. Along the way, learn about the landmarks from the onboard narration while sipping on more champagne.

Portland: Heart of Portland Sightseeing Cruise

4. Portland: Heart of Portland Sightseeing Cruise

Board the Portland Spirit and embark on a tour of Portland and the Willamette River from an entirely new perspective. Learn about the area, people and bridges from the historical narration, played on all three levels. You may sit indoors in the climate-controlled areas or outside in the open air. Take in the views of the Portland and Milwaukie waterfronts with a full-service bar and bistro menu available for purchase. The cruise will head south on the Willamette River to Milwaukie and then back to the dock.

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What people are saying about Oregon

What an incredible experience, to say the least. The customer service was lovely. The food was delicious. Beautiful live music. Beautiful views from your table and the opportunity to stand on the top deck to watch the sights. Neil was an amazing server as well, thanks so much

Trip was amazing! Pictures online seem unreal till you are actually sailing yourself and see the view for yourself amazing

Great customer service, good food, and nice boat ride to see Portland from a different view.

Very helpful crew: help my mom (on wheelchair) get on and off the ramp.

The tour was amazing and the crew members were nice