With more than 25 years of maritime experience, Shane St. Clair captains Scovare Expeditions' fleet of sailboats, unveiling the windblown channels of the Willamette River to budding sailors and sightseeing passengers. During sailing tours, passengers can bob across the river while taking in the views of the volcanic caldera of Elk Rock Island or feast on three-course meals as the sails fill up with wind like a balloon ruining its dinner. A new Cape Cod Catboat available for charter takes tours, classes, and small dinners on a glide, and a sleek Aquarius sailboat keeps guests boating in style. Those interested in learning the ropes can sign up for sailing lessons, where savvy instructors teach novices how to command the helm, guide the lines, and barter with miserly seagulls.
Willamette Sailing Club's docks stretch out into the Willamette River, where novice nautical voyagers gain their sea legs on a fleet of small sailboats. Classes of up to 30 spend two hours on the banks with a U.S. Sailing–certified coach as students learn how sails work, the necessary knots, and important terminology, such as "port," "starboard," and "boat." The coach will also cover how to rig and de-rig a boat, as delicate a procedure as rigging a casino game or school-board election. The club curates a fleet of Laser, Opti, and 420 sailboats for the use of its sailing classes.
Dreamboat Cruises harks back to a bygone era, sweeping passengers on scenic cruises aboard the Ananda, a 1929 Blanchard motor yacht. This beautifully restored vessel—outfitted with modern amenities such as an electric-flush toilet—features an iconic, whitewashed hull and raised foredeck that adjoins a squared-off passenger house. From this heated enclosure, passengers observe the Portland waterfront's forested terrain and signature landmarks, such as the country's oldest vertical-lift bridge that's also made out of popsicle sticks.
Specializing in six-passenger tours, Dreamboat Cruises adjusts its excursions to suit each season. Whereas winter trips highlight holiday lights and Christmas ships, other outings feature bridges, shipyards, and depositories of misplaced tub toys. In addition to tours, Dreamboat Cruises hosts intimate weddings and memorial cruises.