we’ve all pinned that picture-perfect Aspen scene: the snowy peaks, the charming streets, the perfectly chic outfit in front of a roaring fire. But what’s it really like to plan a trip there? As someone who’s fallen head-over-heels for this place, let me tell you, it’s even better in person. The magic isn’t just in the scenery; it’s in the feeling you get when you’re there. So, grab your favorite cozy blanket and let’s daydream and plan your perfect Aspen holiday together.
Finding Your Happy Place: Where to Lay Your Head
Choosing where to stay in Aspen is like choosing the flavor of your holiday. Do you want to be right in the heart of the glittering social scene, or tucked away in your own quiet storybook cabin?
If your dream is to roll out of bed and onto the ski lift, you simply can’t beat The Little Nell. It’s the definition of slope-side elegance, with service that makes you feel like royalty. For a similar vibe with a legendary twist, The St. Regis feels like a grand mountain castle, complete with a daily champagne ritual that is absolutely worth experiencing.
Now, if you’re like me and you adore a place with a story, you have to step into Hotel Jerome. Walking through its doors feels like stepping into Aspen’s rich history, but with all the cozy comforts of today. It’s an institution for a reason.
And for those of us who crave a home-away-from-home feeling, renting a beautiful condo or a charming cabin is the way to go. Imagine having your own fireplace and kitchen for a lazy morning pancake breakfast before heading out. It’s pure magic.
A Culinary Adventure for Every Mood
Let’s talk about the food, because let’s be real, a huge part of the vacation joy is eating and drinking wonderfully.
For the most delightful, “I can’t believe we’re in the mountains” seafood experience, you must get a table at Clark’s Oyster Bar. It’s cozy, chic, and their lobster roll is a thing of beauty. For that once-in-a-trip, blow-out amazing dinner,Element 47 at The Little Nell is an unforgettable culinary journey.
But perhaps my favorite ritual is apres-ski at Ajax Tavern. There’s nothing quite like sitting on that sunny patio at the base of the mountain, sharing a plate of their legendary truffle fries with friends, and watching the world go by. It’s the heart of Aspen’s social scene.
When you need a break from the rich food, pop into Spring Cafe for a vibrant, healthy lunch that will make your body sing. And for your morning fuel, skip the big chains and join the locals at Harvest for a truly great cup of coffee.
And for cocktails? The historic J-Bar at Hotel Jerome is a must for a classic, sophisticated drink. But if you’re in the mood for a hidden gem, seek out Hooch Cocktail Bar for some of the most creative drinks you’ll ever taste.
Packing Your Winter Wonderland Wardrobe
Packing for Aspen is an art form I like to call “mountain chic.” It’s all about being warm and comfortable without sacrificing an ounce of style.
Start from the skin out with a good base layer. Trust me, a high-quality merino wool top and bottom will be your best friend on the mountain. Your ski jacket is your statement piece, so choose one you love in a color that makes you happy.
Once you’re off the slopes, the uniform is effortlessly cozy. Think the softest cashmere sweaters you own, perfect-fitting jeans, and comfortable yet stylish booties. I live in a big, chunky cardigan that I can throw over everything.
And for your feet, you need two heroes: a sturdy, waterproof boot for trekking through snow (I’m a Sorel girl myself), and a sleeker pair for dinners and shopping. Oh, and don’t you dare forget your swimsuit for that hot tub under the stars!
The Unwritten Rules of Aspen Bliss
A few little tips from a frequent visitor to make your trip seamless. First, book your dinners way in advance. We’re talking weeks, maybe even months for the hot spots. They fill up fast!
Second, water is your new best friend. The altitude is real, and staying hydrated is the secret to feeling great and enjoying that apres-ski champagne. And speaking of the elements, the sun is powerful up there. Slather on that sunscreen every single morning.
And finally, don’t be shy about exploring! The free bus can take you to the other amazing mountains like Snowmass or Highlands. Each one has its own personality and is worth a day of exploration.
Seeing Aspen Through a Local’s Eyes
To truly fall in love with Aspen, you have to wander beyond the main streets. While everyone is on Aspen Mountain, many locals are hiking the epic Highland Bowl at Aspen Highlands for views that will literally take your breath away.
For shopping, step into a local institution like Ute Mountaineer for your gear, or get lost in Gorsuch for the most beautiful Aspen-inspired clothing and home goods.
And for a moment of pure, quiet peace, try snowshoeing or cross-country skiing on the trails at the Aspen Snowmass Cross Country Center. It’s just you and the silent, snowy woods. It’s absolutely magical.
Your Story is Waiting in the Snow
An Aspen holiday is more than a trip; it’s a feeling you carry home with you. It’s the cold air on your face, the warmth of the fire, and the joy of a perfect winter day. I hope this guide helps you plan an adventure that’s every bit as wonderful as you’ve dreamed.
