Luxury Under the Big Sky: Exploring Montana, Yellowstone & Jackson Hole

Your adventure begins in Montana’s stunning Paradise Valley, where wide-open landscapes and rugged beauty set the perfect tone for your trip. After arriving in Bozeman, you’ll pick up your rental car and take a scenic drive to the luxurious Sage Lodge — your home base for relaxation and adventure. This high-end Michelin-starred cozy retreat sits right along the Yellowstone River, offering stunning views, crackling outdoor fire pits and the perfect blend of comfort and wilderness.

Once you’ve checked in, take some time to unwind and explore the property — whether that means indulging in a spa treatment, grabbing a drink at the bar or just soaking in the views of Emigrant Peak while breathing the mountain air. If you’re up for a little activity, take a leisurely walk along the trails or dip into one of the lodge’s outdoor hot tubs for some serious relaxation.

Grab some southern BBQ — in Montana!

When hunger strikes, head to Follow Yer Nose BBQ, a local favorite serving up house-smoked meats and deep-south homegrown recipes. This outdoor BBQ shack is the real deal — authentic, smoky and packed with flavor. Open seasonally from April to mid-October, it’s the perfect spot to fuel up for your Montana adventure.

Catch a show at Pine Creek Lodge

If you're in the mood for live music and a laid-back Montana vibe, Pine Creek Lodge is the place to be. This cozy retreat in Paradise Valley is known for its great food, vibrant community and incredible live performances — making it the perfect way to wrap up your first day under the Big Sky. As the night winds down, return to Sage Lodge, grab a drink and sit by the fire pit under a star-studded sky.

Today is all about immersing yourself in Montana’s natural beauty, from casting a line in the legendary Yellowstone River to soaking in geothermal hot springs and wrapping up the night with live music at an iconic Western saloon.

Morning: Fly fishing on the Yellowstone

Kick off the day with a half-day, walk-and-wade or float fly fishing trip on the Yellowstone River. With expert guides leading the way, you’ll experience world-class trout fishing in the crystal-clear waters of Yellowstone National Park. Whether you're a seasoned angler or a total beginner, this is a chance to slow down, connect with nature and maybe even reel in a legendary catch.

Afternoon: Soak at Chico Hot Springs

After a morning on the river, it's time to relax and recharge at Chico Hot Springs, a beloved Montana retreat that has been welcoming travelers for over 100 years. Set against the stunning backdrop of Paradise Valley, the two steaming geothermal pools are the perfect place to soak tired muscles while taking in the crisp mountain air. Want to treat yourself? Book a spa treatment or enjoy a cocktail poolside before heading back to Sage Lodge.

Evening: Catch a show at The Old Saloon

End the night with a dose of true Montana culture at The Old Saloon, a legendary watering hole dating back to 1902. With its rustic charm, live music and strong whiskey pours, this historic spot is where locals, ranchers and travelers come together for good food, great stories and an authentic Western experience. Kick back with a drink, soak in the live tunes and enjoy a perfect Montana night under the stars.

If a lively saloon scene isn’t your vibe tonight, head back to Sage Lodge for a delicious farm-to-table dinner at The Grill. With a menu showcasing locally sourced meats, fresh seasonal ingredients and bold Montana flavors, you can indulge in elevated comfort food with stunning views of Paradise Valley. Whether you're savoring a perfectly cooked steak or a fresh-caught trout, it’s the perfect way to unwind and reflect on an amazing day in the wild.

Tomorrow, the adventure continues as you head into Yellowstone — so soak up every wild and wonderful moment of today!

Start your morning with a scenic drive as you check out from Sage Lodge and head toward Yellowstone National Park, an easy 30-minute journey to the North Entrance. Be sure to stop for a quick photo at the iconic Roosevelt Arch before heading to Mammoth Hot Springs, where you’ll walk the boardwalks and admire the breathtaking travertine terraces (about one hour).

Next, continue your journey through the park, stopping at the Norris Geyser Basin for a quick peek at Steamboat Geyser, one of the world’s most active geysers (30 minutes). Then, make your way to the Grand Canyon of Yellowstone, where you’ll marvel at the Lower Falls from Artist Point — a must-see spot for incredible views (1.5 hours). Keep an eye out for wildlife in Hayden Valley as you drive south through the park, before stopping at Yellowstone Lake for a picnic lunch or a bite at one of the general stores.

In the afternoon, head to Old Faithful and time your visit to witness the famous geyser eruption (30–60 minutes). Take a stroll around the nearby geyser basin if you have time, then exit Yellowstone via the South Entrance with a quick stop at Lewis Falls for a final photo op.

As you leave the park, you'll drive through Grand Teton National Park, stopping at Oxbow Bend or Snake River Overlook for more stunning photos of the jagged peaks and winding rivers. Continue your scenic drive into Jackson, WY, and check in to the historic Wort Hotel around 6 pm.

After a full day of exploring, enjoy a delicious dinner at Silver Dollar Bar at the Wort Hotel - live music will keep your toes tapping all night long.

Start your day bright and early with a 7 AM hike through Grand Teton National Park — with its towering peaks and breathtaking scenery, it’s a great opportunity to connect with nature. Choose from some of the top trails, like Jenny Lake Loop or Cascade Canyon, that offer stunning views and the chance to spot local wildlife. Whether you’re a seasoned hiker or just looking for a leisurely stroll, there’s a trail for everyone in this mountain paradise.

After your hike, head to Dornan's for a well-earned cold beer while soaking in the panoramic views of the Tetons. It’s the perfect place to unwind and chat about your adventure.

Next, it's time to get into the true spirit of the West — head over to Encounter Hat Company or Kemo Sabe to get a custom cowboy hat made! These iconic stores can craft a personalized hat that’s just right for you, and you’ll have it ready in time for the evening’s festivities at the Jackson Hole Rodeo.

At 8 PM, head to the Jackson Hole Rodeo for an unforgettable Western experience. Watch cowboys and cowgirls showcase their skills in events like bull riding, barrel racing and roping. It’s the perfect way to cap off your day in true Jackson fashion, surrounded by rodeo fans, great energy and a true taste of the Wild West! The perfect mix of adventure, culture and local charm — today’s one to remember!

Today’s all about combining river serenity, thrilling history and legendary nightlife to create a truly unforgettable day in Jackson Hole.

Start your morning with a peaceful 10-mile float trip down the Snake River — one of the most scenic adventures in Grand Teton National Park. Jackson Hole Float Trips, booked through Snake River Angler, will take you on a relaxing journey through the river, with the soft sounds of water and breathtaking views of the willows and towering cottonwoods. Keep your eyes peeled for wildlife — bald eagles, otters, elk and even the elusive moose are known to roam the area. It’s the perfect way to connect with the natural beauty of the region while enjoying a tranquil escape. Your float trip is confirmed with a minimum of four guests, so if you’re up for a peaceful paddle through paradise, get ready for a day of adventure!

After your float, dive into some Wild West history with the Town Square Shootout, a Jackson tradition that’s been thrilling visitors since 1950. Gather at the northeast corner of Town Square around 5:30 pm to watch the famous Shootout Gang reenact the Old West with gun-slinging action and plenty of drama. It’s a fun, free experience that’s perfect for families or anyone looking to enjoy a taste of Jackson’s rich frontier past.

As the evening sets in, it’s time to saddle up (literally!) for a night at the Million Dollar Cowboy Bar, one of Jackson Hole’s most famous landmarks. Whether you’re in the mood for dancing to live country tunes or simply enjoying the Western vibe in the historic venue, the Cowboy Bar is the place to be. With its iconic saddle seats, historic charm and stellar performances by both local and touring acts, you’ll be tapping your boots and enjoying the lively energy of this Jackson institution. So, grab your cowboy hat, hit the dance floor, and let loose under the neon lights of the Million Dollar Cowboy Bar!

Get ready for an unforgettable road trip through two iconic national parks, winding through the rugged beauty of Grand Teton and Yellowstone National Parks. Today, you’ll experience the ultimate scenic drive, filled with dramatic mountain views, crystal-clear lakes and a chance to spot some of the most remarkable wildlife in the West.

Start your day early in Jackson, WY, and set your sights on the Teton Range. Your journey kicks off with a short drive to Jenny Lake, where you can stretch your legs with a leisurely stroll along the shore — be sure to have your binoculars handy, as elk sightings are common in the area. Continue north along Teton Park Road, capturing views of Jackson Lake before making your way to Colter Bay Village for a relaxing stop by the lake or a treat at the general store.

After you leave Colter Bay, you’ll enter Yellowstone National Park through the South Entrance. Stop at Lewis Falls for a great photo op before heading to West Thumb Geyser Basin, where you can explore the geothermal wonders of Yellowstone Lake. Don’t forget to take a break here and enjoy a picnic lunch as you soak in the natural beauty.

If you missed it on your way into Jackson, then continue your journey up to Old Faithful, the iconic geyser that never disappoints. Time it just right, and you’ll witness its spectacular eruption, while soaking up the surrounding geothermal features. A quick detour to Grand Prismatic Spring will leave you in awe of its vibrant, colorful waters — perfect for a few photos.

After leaving the West Entrance, enjoy a peaceful drive to Big Sky, where you’ll follow the Gallatin River and might even spot moose, elk or deer along the way. The final stretch to Big Sky is nothing short of stunning, as the iconic Lone Peak looms ahead, signaling your arrival at this mountain paradise.

After an epic road trip, it’s time to check in to the Montage Big Sky, your luxurious mountain retreat for the next few nights. Nestled at the base of Lone Peak, this upscale resort offers the perfect blend of rustic elegance and world-class amenities. From the moment you arrive, you’ll be greeted by breathtaking views and exceptional service. Whether you’re unwinding in the spa, savoring gourmet dining or taking in the alpine scenery from your suite, the Montage Big Sky sets the stage for a memorable stay. Get ready to experience the magic of Big Sky in style!

Start your day with an unforgettable horseback riding experience through Montana’s stunning landscapes. Choose from one of three exciting options based on your time and comfort level:

1-Hour Ride: Ideal for those with limited time or new to horseback riding. In the early season (May and June), this ride takes you through flat fields, offering a taste of Montana’s beauty. Available in July through September, this ride crosses the river and skirts the hills, giving a hint of the rugged terrain. $85pp.

2-Hour Ride: For those looking for a bit more adventure, this ride takes you into the foothills of the Custer Gallatin National Forest. Explore the Gallatin Canyon as you cross rivers, climb hills and enjoy breathtaking views. Your guide will share fascinating insights about the area, with plenty of stops for photos. $105pp.

3-Hour Ride: For experienced riders ready to push their limits, this ride ventures even deeper into the hills. It’s an unforgettable journey for those who enjoy a challenge and want to immerse themselves in the wild beauty of the Montana wilderness. Get ready for a ride that’ll leave you feeling accomplished (and sore!).

After your ride, you’ll feel connected to the Montana wilderness in a whole new way — so get ready for an afternoon of relaxation and reflection at your luxurious Montage Big Sky retreat!

Start your day by checking out from Montage Big Sky, but not before soaking in your last few moments of breathtaking mountain views. Then, lace up your hiking boots for a scenic exploration of Big Sky's natural beauty. Whether you're looking to take a peaceful walk or challenge yourself on a more strenuous trail, the area has something for everyone. Popular hikes include the easy-going Ousel Falls Trail, which leads you to a stunning waterfall, or the Beehive Basin Trail, which offers a serene alpine lake surrounded by towering peaks. Keep your eyes peeled for wildlife and let the fresh mountain air fuel your adventure. For more trail options, check out AllTrails for the most up-to-date trail information and reviews.

After your hike, it’s time to head into Bozeman for some urban exploration. This vibrant town is the perfect blend of small-town charm and modern flair, with a historic Main Street filled with quirky shops, art galleries and local eateries. Spend the afternoon browsing unique boutiques, checking out local art. Don’t forget to visit some breweries, too. Mountains Walking Brewery or MAP for a refreshing local beer or pop into one of the many coffeehouses, like Tree Line Coffee (a local favorite) for a pick-me-up.

In the late afternoon, check in to the Kimpton Armory Hotel Bozeman for a relaxing end to your day. The hotel offers a cozy, chic ambiance with excellent amenities, perfect for unwinding after your day of adventure. Take time to rest before heading out to explore Bozeman’s downtown dining scene. Grab a nice dinner at standout spots like Blackbird or Little Star Diner before calling it a night.

As your unforgettable trip through Montana and Wyoming comes to a close, take the morning to reflect on all the incredible experiences you’ve had. After checking out from Kimpton Armory Hotel Bozeman, you’ll have some time for one last stroll around Bozeman or a leisurely breakfast at one of the local spots. For a delicious breakfast to fuel your travels, try the Western Cafe for a true cowboy breakfast. If mimosas are more your style, grab a bite at Revelry or Jam!

Depending on your flight time, you’ll head to the Bozeman Yellowstone International Airport, just a short drive away. As you board your flight, reflect on your incredible journey through two stunning national parks, charming towns and epic outdoor adventures. With memories of Grand Teton National Park, Yellowstone and Big Sky fresh in your mind, it’s time to head home.