Winter tours

It’s winter! Shorter days and often-rainy weather mean we focus in on some of the tours that celebrate food, wine, and our favorite waterfalls (they’re so much bigger in the winter!).

We offer a full menu of bike tours and outdoor adventures. The below tours are our favorite in the winter. Our custom and private tour offerings are as endless as your imagination; email us or call 503 889-6410 to learn more about options and large group discounts.

Small Wineries of the Willamette Valley Tour — $125*
10 a.m. Daily

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Delve into the world-class Pinot Noir of the Willamette Valley and discover some of its lesser-known varieties as well in this tour meant to explore wineries whose names you may not have heard before — but you won’t forget. We’ll take you to four wineries with smaller case production but very big stories, views and flavors. Expect a deep and broad exploration of the terroir, history, and geology of the Willamette Valley and the surrounding regions that influence its wines. Tasting fees are not included; a nosh platter will be served.
Our tour will get you back to Portland in time for dinner. Pickup in or near downtown Portland included.

Columbia Gorge Day Hiking Tour — $125
9 a.m. Daily

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The 80 miles of the Columbia River Gorge’s steep rocky sides offer some of the most spectacular hiking in the world, complete with pounding waterfalls, eagles, century-old trees, ferns, flowers, and ancient rocks. Join us for a day of exploring with 2-4 hikes aimed at pushing you to new heights both physical and experiential. Based on your group’s fitness level and the season, hikes could include Hamilton Mountain, Rowena Crest, Beacon Rock, Dog Mountain, Falls Creek Falls, and many others. Coffee, vegetarian picnic lunch and snacks included; your naturalist guide will accompany you on most of the day’s hikes. Expect 4-12 miles of hiking; elevation gain dependent on group. Pickup and drop-off in or near downtown Portland.

Portland Meditative Garden Tour — $120
10 a.m. Daily

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Experience Portland’s gardens in a deeper way. Our vehicle tour will delve into garden design as it is meant to access your higher self and touch all your senses — including your sense of spiritual connectedness. Our about five-hour tour includes admission to the Lan Su Chinese Garden and the Japanese Garden, guided meditations, and visits our guide’s favorite downtown meditative gardens and places. The tour is meant as a philosophical and historical approach to the garden as it is used in urban spaces, but one with a significant sense of delight in the encounter.

Pickup at lodging in Central Portland. Garden admission and snacks provided.

Urban Winery and Farm-to-Table tour — $100*
2:00 p.m. Wednesdays, Thursdays and Saturdays; other days available (please call)

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The urban wineries of Portland are growing to stand among their world-class Willamette Valley siblings; not just beautifully-made wine from some of the region’s best vineyards, but also showcases for exquisite farm-to-table cuisine. Our Urban Winery and Farm to Table tour is an experience that finally recognizes that.

With both the Willamette Valley’s and the Columbia Valley’s American Viticulture Areas (AVAs) providing the grapes, Portland’s urban wineries represent a distillation of the region, nearly 2,000 vineyards and dozens of varieties. The city’s wineries are also a hotbed of innovation. The wild variety of growing regions and fruit is matched only by the creativity of the makers crushing, fermenting and blending their wine in the industrial and residential neighborhoods of the inner city.

And then there’s the food! We will visit three carefully hand-picked urban wineries, the last one which will include seasonal, vegetable-rich pairings of inventive local farm-to-table cuisine. Wineries are chosen the same way they are in the top sommelier-led tours: our expert guides taste through the flights regularly to select only our favorites.

Price includes farm-to-table small plates at the final stop and transportation in a Mercedes Sprinter or other comfortable vehicle; tasting fees are not included.

Hiking and Biking: Columbia Gorge Hidden Waterfalls — $90*
8:30 a.m. Weekdays; afternoon openings available (please call)

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Hike to waterfalls, bike the beautiful curves of the Historic Columbia River Highway, and see the Columbia Gorge beyond the experience of most tourists. The gorge is so rich, with waterfalls spouting off 800- to 1,000-foot-tall towering basalt walls in view of the freeway; but our tour is off the interstate. We start at our favorite viewpoint in the gorge, seeing the river and two states’ worth of beauty laid out before us; then we get on our bikes and ride down twisting, quiet historic highways to our favorite waterfall hikes. We’ll lock up our bikes and hike the 2.5-mile loop to a waterfall a gentle climb up the side of Larch Mountain. After the loop, a short bike ride takes us to two more tucked-away waterfalls, before we get back on the interstate to see still more. Tour includes vegetarian snacks, and coffee or tea, as well as fitted bike and helmet. One of our enthusiastic guides will ride and hike along with you; ours are the only fully-supported gorge bike tours available! (Please note most of our ride is on historic highways that do have moderate vehicle traffic in busy seasons; for traffic-free options, ask for a custom tour.)

Oregon Coast Encounter — $125*
8:30 a.m. daily


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The Oregon Coast is an experience like no other and our Oregon Coast Encounter is a tour you’ll only find with us. From Astoria to Oceanside, our tour guides pick the best of the coast: hikes to waterfalls hidden from everyday view; up-close encounters with the iconic monoliths that make the Oregon Coast so unusual; lunch stops in sweet beach towns; maritime and fishing museums; our favorite cinnamon rolls, pie or ice cream; sand (if you want it) between your toes. Exact tour itinerary varies with season and preferences (your group and the guide will set the plan at the beginning of the day); but all tours include comfortable transportation to and from the coast, at least one hike onto a gorgeous Oregon beach, plenty of stunning vistas, snacks and water, and an enthusiastic guide. Tour will run 8-10 hours from pickup to drop off.

Wish you were here! Columbia Gorge Waterfalls Tour — $60*
8:30 a.m. and 1:30 p.m. Daily

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We wish you were here! And everyone we know wishes they could spend more time in the 80 mile (130 km) long Columbia River Gorge. Its wonders include stunning views, moss-heavy temperate rainforests, and, in the winter, hundreds of waterfalls and the trails that lead to them — not least of which is the Pacific Crest Trail, where Cheryl Strayed finished her journey of her book and the movie, Wild. Through it all winds the Historic Columbia River Highway, skirting the steep basalt walls of the Oregon side of the gorge to lead to sweeping views for dozens of miles. We’ll drive in a comfortable Mercedes sprinter or other vehicle about 35 minutes from Portland to our favorite bit of the historic highway, visiting two amazing viewpoints (one featuring a castle-like rest stop) and several waterfalls, with very short hikes. Among our stops will be Multnomah Falls, famous for its scenic Benson Footbridge and its height (the falls is the tallest in Oregon and among the tallest permanent year-round waterfalls in the U.S.). Lest your friends forget you, we’ll send them home postcards (you pick from our signature custom-made cards!) from one of the nation’s smallest post offices, Bridal Veil, established 1886 and still hand-cancelling mail.

*These tours require an extra fee for bookings of one guest only. Please contact us at 503-889-6410 for single guest bookings.