This year Valentine’s Day is on Wednesday, February 14, the perfect time to visit Aspen mid-week whether or not you’re looking for romance. You’ll be glad you took advantage of the opportunity. Not only will ski traffic on I-70 be somewhat tame, but you’ll have better access to the slopes, dining, lodging, and entertainment in town, the perfect set up for finding love in Aspen.

Start with a beverage

A cocktail or glass of wine is perfect for settling in once you make it to Aspen. You might as well go iconic with a stop at The Little Nell Hotel’s famed Element 47. Once seated, you can peruse the pages of one of the world’s most famous wine lists. Many of Aspen’s dining options don’t open until 4:30 or 5:00 pm, so a beverage here at the mountain’s base is a beautiful way to spend aprés or unwind following the drive up from the city.

Once 5:00 pm finally does roll around, a stop at Hooch, one of Aspen’s delightful moody underground cocktail caves, is a must. The beverage menu changes constantly and features creative concoctions featuring an eclectic array of world spirits.

Dinner for Two

If you’re dining in Aspen with a large group, you’re braver than I am. I love the romance and intimacy of a visit for just two people. With so many outstanding dining options in town, choosing a place to make a reservation is nearly impossible, especially if you’re only visiting for a couple of nights. Although Aspen is known for its luxurious dining scene, a less frequently mentioned factor is the turnover rate in Aspen restaurants.

As you can imagine, lease rates are sky-high in this market. Not to mention, the competition is fierce, and the transience of the clientele means getting open, and staying open is a nearly impossible feat that only some concepts manage to overcome.

When searching for a dinner experience that consistently offers the level of quality plates and beverages you can be sure will satisfy, consider dining at one of these two local restaurants, both of which have been area staples for many years.

Since 1991, Kenichi has been delighting diners with fresh cuts of premium sashimi and an impressive selection of saké and Japanese spirits. The preparation of yellowtail and Otoro sashimi with serrano is incredible. For a cocktail, the Kenichi Saketini with ginger and fresh cucumber is the definition of a visit to Aspen.

Another exceptional sushi experience can be found at the legendary Matsuhisa. The menu and wine list are next-level, and the signature cocktail, The Gardener, is divine.

For a casual yet polished meal in Aspen, you can’t fail with a stop at The White House Tavern. The restaurant presents a condensed lineup of great plates, any one of which you’ll find yourself daydreaming about well into the future. They are open all day, every day. While they don’t accept reservations in the tiny space, you can frequently score a cozy booth or bar seat immediately if you show up at slightly off-peak hours.

The debate is hot on whether the French dip or the crispy chicken sandwich is the most delicious thing to happen between two pieces of bread. Whichever way you go, order a kale salad with peanut vinaigrette to share.

Best of all, wine prices are the most reasonable I’ve come across in Aspen. Following the model of their Hillstone parent company, White House offers killer glass pours. For example, the Schramsburg Blanc de Blancs at a perfectly painless $15 and Belle Gloss Pinot for $17, both wines that would easily go for around $20 – $22 a glass in Denver restaurants.

When looking for something more upscale, consider a reservation at Ellina for remarkable Italian fare or Catch Steak, where every dinner feels like a special occasion.

Where to Stay

Your selection of hotel accommodation in Aspen sets the tone for the visit and establishes a hub for the dining and entertainment experiences ahead. With many suites commanding several thousands of dollars per night, finding a hotel can seem like a barrier to entry. While it’s unlikely you’ll score any rate below $600 in town during the peak seasons of winter and summer, there are a few options that are accessible to visitors seeking (slightly) more modest rates.

The Limelight Hotel is a concept built on the idea of community and creating spaces to gather and enjoy the local surroundings. With a prime position downtown, the hotel is a short walking distance to everything on this list, as well as the Silver Queen Gondola at Aspen Mountain.

The hotel’s lounge is a hub for cocktails and chatter over a pizza and drinks and often presents live music during aprés ski. The pool, hot tubs, and rooftop deck offer additional spaces to relax, and the well-appointed guest rooms are available in flexible configurations. Guests can even test drive the impressive Audi e-tron as an amenity during their stay. Another perk, the property is pet-friendly too.

If you’re not skiing but want to get a little exercise while taking in panoramic views of town, then a hike on Smuggler Mountain Road is a great option. If the snow is reasonably packed, you can make the hour-long trek with moderate effort. The natural beauty of Aspen is well worth it from the overlook! If you’re a fan of live music, check the schedule for upcoming shows at Belly Up Aspen well in advance of your arrival. The tiny venue is one of the best places on earth to see an intimate concert.

Whether you make it to the mountains this Valentine’s Day or save these recommendations for a future visit, I sincerely hope you enjoy the magic of my hometown and fall in love with Aspen.

About The Author

Montana Rae

Montana Rae is a CMS Certified Sommelier and WSET Level III residing in Denver, Colorado. She offers private wine tastings, classes, and dinners at clients’ homes and businesses around Colorado, as well as product recommendations, tips, recipes, and more through her company, The Wine Ship.


Montana is also a commercial real estate broker specializing in sales and leasing of restaurant and retail spaces in Denver.


Contact Montana at montana@thewineship.com and follow her on Instagram @montana.rae.sommelier

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