Teton Mountain Bike Tours - Tour of the Tetons

Ride, Paddle, Roam: Multi-Day Jackson Hole Adventures That Go Beyond the Guidebook

Let’s be honest—there’s only so much you can feel from behind the windshield. You don’t come all the way to Jackson Hole to just look at the Tetons. You come to experience them. 

Multi-day adventure vacations are the way to do Jackson Hole right. They’re for the traveler who knows the difference between checking off a list and getting truly off-grid. And the best part? There are local guides who know every inch of this place—and they’ll take you into parts of Yellowstone and Grand Teton that most folks never lay eyes on.

Here are three unforgettable, multi-day trips that do more than scratch the surface.

Ride Through the Wild: 5-Day Tour of the Tetons with Teton Mountain Bike Tours

Teton Mountain Bike Tours - Tour of the Tetons

Let’s start with a classic: the five-day Tour of the Tetons by Teton Mountain Bike Tours. This is not your average saddle time. You’ll ride where the pavement ends—along dirt roads, across alpine meadows, through aspen groves, and under the jagged shadows of the Tetons.

• Day 1: Wide Open & Teton - The Teton View Ride takes cyclists across sagebrush flats where bison roam with ancient indifference. Panoramic views stretch to five mountain ranges, with pronghorn watching from the distance. Spend the night at Cowboy Village Resort—hot shower, cozy cabin, and that unmistakable Western welcome.
• Day 2: Pines, Peaks & Quiet Trails - Ride south into Bondurant, tracing Cliff Creek through aspen and pine forest. It’s quiet out here—just creeks, ridgelines, and the Gros Ventre and Wyoming Ranges rolling by. After the ride, it’s back to Cowboy Village to rest and recharge.
• Day 3: Whitewater Reset - Swap the saddle for a paddle and take on the Snake River—a mix of scenic float and splashy rapids through rugged canyon country. Wildlife sightings? Likely. Adrenaline? Guaranteed. Then back to town for a warm bed and deep sleep.
• Day 4: Geysers & Steam in Yellowstone - Pedal into Yellowstone along the Firehole River, stopping at Lone Star Geyser, Old Faithful, and secret geothermal spots the crowds don’t reach. End the day at Hatchet Lodge,tucked near the park’s wild edge.
• Day 5: Ride into the Wild - Roll down from Angle Mountain into the wildflower-strewn Buffalo River Valley. Wetlands, wildlife, and wide-open air close out the trip. Lunch, goodbyes, and one last look at the Tetons before heading home.

This trip blends pedal-powered discovery with creature comforts—lodges, hot meals, and guides who actually live here. It’s for folks who want to break a sweat and still sleep in a cozy cabin.

📞 Visit Teton Mountain Bike Tours to book or learn more.

Paddle Into the Unknown: Grand Teton National Park Kayak Adventures

Rendezvrous River Sports - Grand Teton Multi-Day Kayak Adventures

Now for the hidden gem. This 3-day kayak trip on Jackson Lake will take you places even many locals haven’t seen. Operated by Rendezvous River Sports, this is a fully guided, fully immersive wilderness trip into the heart of Grand Teton National Park.

• No Roads, No Crowds: Kayak to campsites you can’t hike to. Silence, space, and nothing but the sound of water hitting the shore.
• Moose, Otters, Eagles—Right There: Wildlife doesn’t pose. It just shows up. And on this trip, you’re in its living room.
• Sunrise on the Lake, Coffee in Hand: Lake like glass. Tetons glowing. No emails. Just sky.
• Boots Hit Trail, Not Pavement:Paddle to hidden trailheads. Hike to waterfalls and alpine lakes that don’t show up on your hotel map.
• Guided by Locals Who Live This Life: Your guides aren’t just certified—they’re Jackson Hole locals with deep roots and stories to tell. They know the terrain like the back of their paddle.
• Campfires, Real Meals, and the Kind of Tired You Earn: At night, you eat well, sleep deep, and tell stories under a sky full of stars.
• No Signal. All Connection: With no cell service and zero distractions, this trip pulls you into the present moment—where real memories are made.
• No Experience Needed—Just Hunger for Wild: Whether you’re a seasoned paddler or just starting out, the trip is designed for active travelers with a sense of curiosity, not just physical endurance.

Your guides cook hot meals, teach paddle technique, and keep you safe in the backcountry. And yeah—you’ll be camping. But trust us, when you unzip your tent to see the Tetons mirrored in still water, you'll forget all about the plumbing.

Book online or request more info at the Rendezvous Rivers Sports website for the Grand Teton Kayaking Adventure.

Customize the Wild: Tailored Multiday Tours with Great Western Expeditions

Great Western Expeditions - Custom Tours

Some travelers follow maps. Others rewrite them.

Great Western Expeditions is for the second kind. If your group’s got a mix of bucket lists—or you just want something that doesn't come pre-packaged—this crew builds fully customized multi-day adventures across Jackson Hole, Grand Teton, Yellowstone, and the wilds beyond.

No templates. No tourist traps. Just deep-dive travel with locals who know every bend in the road and every story behind it.

Build Your Own Adventure:

• Track wolves and grizzlies in Yellowstone, guided by people who know where they roam and why.
• Explore outlaw country in Dubois or soak in hot springs surrounded by history in Thermopolis.
• Wander dinosaur dig sites, walk through Native American heritage centers, or explore a world-class military vehicle museum hidden in the hills.
• Ride the Aerial Tram, float the Snake River, hike the Tetons, or dine like a local in Jackson—this is the best of Wyoming, your way.

What You Get:

• Custom itineraries built around your timeline, interests, and pace.
• Local guides who bring the land to life through story, science, and raw experience.
• Luxury or rustic lodging, from five-star resorts to backcountry glampsites.
• Seamless logistics—they handle it all: transport, gear, permits, meals, reservations, and access.

This isn’t just about seeing Grand Teton or Yellowstone. It’s about experiencing them on your terms, and then going beyond the parks—into the backroads, the small towns, the lesser-known legends of the West.

Want to mix cowboy culture with fossil hunting? Done. Want a kid-friendly trip with a splash of wilderness and a glass of wine at the end of the day? They’ve got that dialed too.

Whether it’s a 2-day sprint or a 7-day deep dive, Great Western Expeditions builds trips that feel like they were made for you—because they are.

Visit their site to start crafting a trip that tells your story, not someone else's itinerary.

Find Your Own Wild

Whether you’re chasing geysers, coasting through meadows, or paddling past the edge of the map, these Jackson Hole multi-day tours offer more than just scenery. They give you a story worth telling.

Explore each outfitter above to find the adventure vacation that fits your pace, your people, and your personal wild.