Denver, CO & Aspen, CO

Day 1: Arrive!

Morning: To maximize your time, fly in early to Denver International Airport (DEN) and pick up your rental car from your preferred provider. We use Avis. First things first, if you haven’t flown into the Denver Airport before, you need to read this article regarding Denver Airport Conspiracy Theories (we are not endorsing these theories, just think it’s entertaining and interesting to know before you go!).

Afternoon: Your hotel, The Maven, is located in an area of Denver called Dairy Block. This is a revived area of downtown within walking distance of restaurants, bars, and attractions. When you’re ready to eat, choose from one of sixteen vendors at the Milk Market on the first floor of your hotel.

There’s plenty of museums around Denver, we recommend exploring the area around your hotel on foot, or renting a scooter.

NOTE: Similar price point and location, you can opt to stay at The Oxford, Denver’s oldest hotel. Either way, we have you scheduled to grab a drink at The Cruise Room in The Oxford tomorrow night.

Evening: For a pre-dinner drink or appetizer, check out Union Station. Most people aren’t aware of the second floor bar called Cooper Lounge, so ask the hostess when you arrive if they can provide you directions up to the mezzanine level.

Day 2: Explore Denver

Morning: Wake up and treat yourself to a biscuit at Denver Biscuit Company at one of two locations, depending on how you want to spend your day.

1. OPTION A: Breakfast at Denver Biscuit Company - Broadway before renting bikes or scooters (there’s tons of options around Denver) and riding along the Cherry Creek trail, this goes for MILES.

2. OPTION B: Breakfast at the Denver Biscuit Company - Colfax before walking the Denver City Park and visiting either the Zoo or Natural History Museum, or both!

The Denver Botanical Gardens is close to both locations and is one of Denver’s most prized attractions.

Afternoon: While you’re in the area either on foot or by bike, stop and try the Green Chile Relleno Burger at Cherry Cricket, you won’t regret it. Head back to the hotel for free happy hour.

Evening: We know you’ve been active today, but dinner isn’t far from the hotel. Opt to walk or you can always call a ride-sharing service to take you to dinner at El Five. Request a table with a view and book a reservation close to sunset. The views from this restaurant can’t be beat.

Close your time in Denver with a visit to the speakeasy at The Oxford, a red-lit bar called The Cruise Room.

Day 3: Head to Aspen, CO - Visit Independence Pass

Morning: Grab breakfast at a café or taco shop near the hotel, there’s many!, and begin the drive to Aspen by 9am. It’s about 3.5 hrs without stops, and the drive is gorgeous.

Afternoon: Make a pit stop in Vail, CO for pizza at Pazzo’s. The Figioli and Cabo Pazzo are unique flavors we recommend. Think about switching drivers so your travel companion has the chance to enjoy the scenery from the passenger seat. It’s remarkable! With this stop you will arrive in Aspen, CO by 3pm. Drop your bags at The Limelight Hotel and park your rental car in their garage.

• Note: Aspen has a reputation for being expensive, for a reason. The Limelight Hotel is ~$600/night. We found it was the best bang for your buck. If you’re looking for a more affordable option, look into staying in the close by town of Snowmass, or seeing available options on Airbnb.

Evening: After settling in, you have a quick window to visit the town shops before most close at 6pm. If you’re looking for a nice dinner without paying an arm and a leg, we recommend The White House Tavern. The Dip Duo is an absolutely must order. After dinner, enjoy a drink at the famous Jerome Hotel in either the J Bar, The Living Room, or Bad Harriet.

Day 4: Maroon Bells & Ashcroft Pine Creek Cookhouse

Morning: Wake up early, this will be a full day! Maroon Bells near Aspen is the inspiration for this trip. There’s a couple ways you can visit, but Maroon Bells is generally only open from Mid-May to Early-November, which is why we suggest taking this trip during the summer months.

1. Option A: Drive! Take your rental car to Aspen Highlands Plaza, where you can park in the garage and hop on the shuttle for Maroon Bells. Keep in mind the shuttle runs between 8am-5pm. Try to get on an early shuttle.

2. Option B: Bike! Our preferred option. Rent a bike from Four Mountain Sports, located at Aspen Highlands, and ride 8 miles to Maroon Bells. Depending on your fitness level, you can rent an e-bike or road bike.

Note: It’s important to know the Maroon Bells shuttle typically operates from June - October, check here before booking your trip.

Afternoon: Before leaving for your trip, make a reservation at Ashcroft Pine Creek Cookhouse for lunch. Times are limited to either 1:30pm or 3:30pm, so plan accordingly. If you opt for a later morning start to Maroon Bells, you should pack an afternoon snack and choose a 3:30pm lunch time. The Cookhouse is located about 30 min from Aspen (directions here), but worth the drive.

When you’re back from lunch, depending on timing, seal the deal by picking up a custom hat at Kemo Sabe. Often with a line outside, this Instagram worth shop has a hat for everyone. A souvenir you’ll wear for years to come.

Evening: If you had a late lunch, this is a great night to order in from Acquolina, a popular Italian restaurant in town. Pick up a bottle of wine from Of Grape & Grain, close to the hotel, before 9pm and enjoy your dinner before jumping in the hot tub.

Day 5: Travel day - head home!

Morning: If you’re travelling between June - September, take the Independence Pass Route back to Denver (south out of Aspen). There is a great lookout at the top, and could be a last opportunity to snag a frameable picture. Drop your rental car back off at the airport, and take the shuttle to your terminal. You’re probably already looking for a way to come back to Colorado. You’re in luck! One of our favorite destinations, we’re working on multiple itineraries to get you there. Check back soon.

Checklist Before You Go:

1. Book your roundtrip flight to arrive in Denver, CO (DEN) on Day 1 and depart Denver, CO (DEN) on Day 5.

2. Book your rental car to pick up and drop off at Denver International Airport (DEN).

   1. To save a little $$, you could book the rental car for to pick up the morning of Day 3. You would need to take the train from the airport to Denver, then Uber to the car rental location the morning you want to pick it up.

3. Book your rooms at The Maven in Denver for 2 nights (Day 1 - 2)

4. Book your room at The Limelight Hotel in Aspen for 2 nights (Day 3 - 4)

5. Make reservations at suggested restaurants in Denver and Aspen.

6. Check the schedule for Maroon Bells tour and book tickets.

7. Check the weather and pack accordingly!

Other Considerations:

POINTS, POINTS, POINTS!!!!! All of the hotel recommendations are available on Chase Travel using your Chase Credit Card points. We cannot stress enough how valuable a credit card with a good points system can be. In our experience, Chase Sapphire Reserve is the best credit card for points.

Cost: This itinerary focused on value for your money, without sacrificing quality. In order to cut the cost, consider staying in Snowmass. You can also view the alternatives below.

Flights: If you can fly Southwest into Denver, do it! Coming from Houston or other major hubs, you can often find flights to Denver for under $200. We recommend booking well in advance, though.