Oregon Winter Multi-Sport 6-day / 5-night

Oregon Winter Multi-Sport 6-day / 5-night

Quick Summary

Itinerary Detail

Day 1: Arrive in Portland

Arrive in Portland
Daily Summary

Your private guide will meet you at Portland International Airport and transport you 1.5 hours west to Oregon's tallest peak, Mt. Hood, your homebase for winter activities for two nights.

Scenic Snowcat Ride

For the ultimate Mt Hood experience, take a snowcat ride up the flanks of Mt. Hood. Toast the exhilarating mountain air with a glass of Timberline wine and marvel at the unparalleled views of the Cascade Range. Weather permitting, we’ll take you to the top of the world-famous Palmer Snowfield, 8,500 foot elevation of Mt. Hood. This experience includes a one hour snowcat ride for up to 6 people (from a maximum of two households), a bottle of red or white wine, and a fruit and cheese platter that can be enjoyed at the top of your ride.

Day 2: Mt. Hood

Mt. Hood
Daily Summary

Your private guide will take you on a full day snowshoe excurstion to some of the region's most treasured snowshoeing trails to scenic mountian lakes and waterfalls. Fuel up inbetween hikes with a picnic lunch featuring local product and craft beer. Learn about the Cascade Mountain Range's unique geology and history while taking in the fresh mountain air.

Day 3: Mt. Hood / Bend

Mt. Hood / Bend

After check out you'll depart from Mt. Hood, heading 2.5 hours south to Central Oregon. Along the way you'll stop at Smith Rock State Park, one of the "Seven Wonders of Oregon" where you'll explore the 650 acre park with your naturalist guide.

From there you'll make your way the high desert mountain town of Bend, known to many as an outdoor recreationalist mecca. Flanked by the Cascade Range and high desert, the peaks, lakes, rivers and endless miles of trails are home to year-round outdoor activities. The town itself packs plenty of charm as a historic outpost for the lumber industry. And with one brewery for every 4,500 people Bend has the most breweries per capita in the state of Oregon. Your guide will take you on a craft beer tour where you'll sample a variety of local favorites and take in the ambiance with dinner at a brewery.

Day 4: Crater Lake / Bend

Crater Lake / Bend
Daily Summary

Today your group will take a day trip two hours south to Crater Lake National Park for a snowmobile excursion.

Crater Lake Snowmobile Tour

Visit Crater Lake National Park, North America's deepest lake, on a high-adrenaline adventure by snowmobile. Departing from nearby Diamond Lake you'll zip along a 9-mile route through a tree lined snowscape from the north entrance of the park all the way to the caldera’s rim. From there you'll be able to peer into the immense pure blue waters. The expereince is approximately 3 hours and includes lunch.

Day 5: Bend

Daily Summary

Enjoy a free morning in downtown Bend where you can explore the many local boutiques, shops, galleries and eateries. Your guide will pick you up after lunch for your afternoon and evening activities.

Prohibition Cave Tour

Scattered around the sage-covered High Desert sourrounding Bend lie ancient caves, buried by the volcanic upheavals in centuries known to past peoples. Join us on this epic subterranean tour on Bend’s ponderosa pine-studded high desert were you'll explore a cave with a professional naturalist guide in a system known to have been used to distill spirits during Prohibition. This incredible under ground experience is combined with a visit to a local distillery, where you'll tour the facility and learn both the history and process of distilling (legally). After caving, it’s on to tasting these Oregon produced spirits. We’ll enjoy local libations close to the cave tour location - outside in the fresh air. From your most favored spirit we’ve included a happy hour cocktail of your choosing.

Bonfire Snowshoe Tour

Cruising on snowshoes under the light of the solar system’s twinkling lights through the powdery snow-filled forest, your naturalist guide will take you into the Cascade Mountains to a hand-carved amphitheater in the snow where a crackling bonfire awaits. When the whiff of pine hits our nostrils anticipation will grow for a taste of delectable desserts and hazelnut espresso vodka-laced hot cocoa. Our naturalist guides will point out planets, stars and constellations as we relax in the glow of the fire. The hushed ambience of the forest will stir your soul. The magic of this wholly unique experience will remain instilled within you forever.

Day 6: Depart from Bend / Portland

Depart from Bend / Portland

As your Oregon Winter trip comes you a close you can depart from Bend via the Redmond Airport (20 minutes from downtown Bend) or Portland International Airport (3.5 hours). For departures out of Portland, we recommend a late afternoon/early evening flight to allow for a scenic drive through the Columbia River Gorge National Scenic Area and lunch stop in the pleasant town of Hood River.


Mt. Hood Oregon Resort

Mt. Hood Oregon Resort

Formally known as the Resort at the Mountain, this full-service resort has everything you could possibly need or want for a stay on Mt. Hood. Tucked between a barrage of trees you'd have no idea this sprawling resort was a minute off the highway. As they put it, "Wonderfully secluded yet easily reachable." It's the epitome of why people flock to visit the Pacific Northwest and Mt. Hood specifically. The property has its own hiking trails plus many more nearby, as well as mountain biking, fishing, kayaking, rafting and of course the mountain snow sports. Add in their own golf course, spa and restaurants, and it beckons you to come stay a while. Enjoy one of their 157 villas, suites and fireside guest rooms paired with patios, views and access to a year-round heated pool.

Timberline Lodge

Timberline Lodge

Timberline Lodge & Ski Area is a National Historic Landmark which was built during the 1930s as part of the Works Progress Administration (WPA) program. Located at 6,000 feet on Mt. Hood, Timberline offers skiing and boarding on 1,000+ acres, equipment rentals, ski and snowboard schools. Additionally, Timberline's Palmer Snowfield offers the longest ski season in North America with four-season skiing. Timberline Lodge is also the only ski in ski out lodge in Oregon and each room has a unique rustic elegance, yet a modern and comfortable feel. All rooms have period furnishings, artwork and décor. Guests enjoy the year-round heated pool, spa and sauna. Amazing views, beautiful surroundings, first class cuisine and a full menu of amenities attract visitors from all over the world. Lodging also includes some dog friendly rooms.

Brasada Ranch

Brasada Ranch

Brasada Ranch, a 1,800-acre resort community 20 miles northeast of Bend, was named Top Resort in the Pacific Northwest by the readers of Conde Nast Traveler multiple years in a row and a Top 10 Resort in the West by Travel and Leisure in 2017. The Ranch is situated on the scenic Powell Buttes and offers luxurious accommodations, championship golf, world-class dining and amenities, and endless recreation. In fact, with nearly 300 days of sunshine and year-round recreation to enjoy, many days you can ski in the morning, golf in the afternoon, and wet a line for an evening of world class fly fishing. All within reach from this luxurious, laid-back resort.


McMenamin's Old St. Francis School Hotel

The Old St. Francis School in downtown Bend was transformed from a Catholic school built in 1936 into a hotel complete with classrooms-turned-lodging rooms in 2004. In addition, the property, part of the McMenamins portfolio or interesting, historic Northwest places, features a pub serving breakfast, lunch and dinner, a brewery, a movie theater (with second run movies, couches, and beer and food service), private meeting/event spaces and live music bookings throughout the week. Their outdoor patio areas have large fire pits popular throughout the year and locals and visitors alike enjoy exploring the grounds to discover additional spaces. All these amenities barely touch the coolness of their fantastic open air soaking pool that beckons travelers, skiers and families. In 2016, they completed two additional buildings – the Art House and Ed House – which brings their total number of guestrooms to 60. Optional amenities in the new buildings include patios, suites and kitchenettes, but, unlike the originals, all rooms have their own bathrooms. Add to your fun and search for the hidden bar and hidden rooms on the property.

Oxford Hotel Bend

Oxford Hotel Bend

The Oxford Hotel in Bend is a boutique eco-chic option for visitors looking for both luxury and the convenience of staying in the heart of downtown. The hotel prides itself on providing high end accommodations and amenities with minimal environmental impact.

Sunriver Resort

Sunriver Resort

Set in the foothills of the Cascade Mountains and minutes from the bustling town of Bend, Oregon, Sunriver Resort is a prime Central Oregon destination for adventure filled vacations. With 300 days of sunshine every year, enthusiasts flock to Sunriver Resort for endless outdoor recreation year round. You’ll never run out of things to do at the resort with four championship golf courses, a world class spa, skiing at nearby Mt. Bachelor, horseback riding, paddle-boarding, canoeing, white water rafting, 40 miles of biking trails and the list just goes on. Sunriver Resort boasts over 300 vacation rentals from condos to luxury homes and a hotel with 245 guestrooms and suites that will accommodate every need. Pet friendly accommodations are available too, so bring your furry friends.

Why First Nature Tours?

Why First Nature Tours?


First Nature is an outfitter based in Portland, Oregon that provides professional guide services for private luxury tours of the Pacific Northwest as well as small group trips to several international destinations. We can be your personal concierge here in the Cascade region, helping you to create a custom adventure that combines beautiful destinations, exciting activities and unique local attractions to create an experience that is truly one of a kind and perfectly suited to your interests.


There are many facets to sustainability. At First Nature we strive to meet the highest standards of sustainability, whether social, ecological, economic, or cultural. We provide knowledgeable tour guides and luxury bio-fueled transportation to connect travelers to sustainable adventures like hiking, kayaking, cycling and rock climbing. It is part of our mission to educate each of our guests about the natural and cultural history of a place we visit together, while leaving no trace of our passage.


First Nature aims to enhance the communities we come in contact with by connecting travelers with unique destinations that are not overrun with tourists. Destinations that welcome the economic stimulation that tourism brings. First Nature is an equal opportunity employer that encourages workplace diversity and donates to organizations that promote social justice and education. First Nature uses products that are fair-trade, local and organic whenever possible. We eliminate excess waste by offering re-usable and recyclable products on our tours. First Nature partners with other businesses that share the same philosophy