Help with May trip

Question

Hello!

I'm getting organized for our first CO trip from May 13 to 20. I've been doing lots of reading online and have a few questions. I'm specifically trying to figure out where to stay each night.

We are flying into DEN, arriving at noon and departing at 5 PM. At this point we intend on staying in CO the whole trip. It'll be two adults (one who has mild asthma so likely just some easy, short hikes).

At this point I have us staying in Denver for two nights, and Colorado Springs the last two nights. That leaves three nights on the road and that's where I'm looking for your expert opinions!

In terms of attractions/cities, here's a mini list of what we were hoping to do (in no particular order):

-Check out Denver/Boulder

-Rocky Mountain Natl Park

-Breckenridge/Aspen

-CO Nat'l Monument

-Maroon Bells

-Black Canyon Natl Park

-Telluride

-Royal Gorge Bridge

-Great Sand Dunes Natl Park

-Garden of the Gods

I try to stay entirely at Marriott properties because of my AMEX. Any help with the best way to do this itinerary would be great!

Answer

Planning a Colorado trip in May can be fantastic because the weather is starting to warm up, though higher elevation areas like Rocky Mountain National Park, Aspen, and Telluride may still have some lingering snow. Since you have one adult with mild asthma, sticking to shorter, lower-elevation hikes or scenic drives is a smart idea.

Given your preferences and the list of attractions, here’s a suggested itinerary for your 7-night trip:

Day 1–2: Denver

Arriving around noon on May 13, you can spend the first two nights in Denver. This gives you time to adjust to the altitude and explore the city without rushing.

Stay at a Marriott property in Denver: options include Denver Marriott City Center or JW Marriott Denver Cherry Creek.
Activities: Explore LoDo (Lower Downtown), Union Station, the Denver Art Museum, and take a short drive or stroll around Boulder for scenic views of the Flatirons.

Day 3: Rocky Mountain National Park

Drive from Denver to Estes Park (about 1.5–2 hours), the gateway to Rocky Mountain National Park. Since your companion prefers easy hikes, you can do short trails like Bear Lake, Sprague Lake, or Alberta Falls. Even just scenic drives along Trail Ridge Road (if open in May) are beautiful.

Stay in Estes Park Marriott or consider nearby towns with Marriott options like Longmont or Loveland if Estes Park availability is limited.

Day 4: Breckenridge/Aspen

From Estes Park, you can drive towards Breckenridge (roughly 2.5–3 hours). Breckenridge is charming and walkable, with plenty of shops, restaurants, and scenic viewpoints. If you prefer Aspen, it’s a longer drive (~4 hours), but the Maroon Bells area is breathtaking. For a first trip, focusing on Breckenridge may reduce driving stress.

Stay at Breckenridge Grand Vacations or other Marriott-affiliated property in Breckenridge.
Activities: Walk the historic town, easy nature strolls, and enjoy local dining.

Day 5: Black Canyon of the Gunnison / Telluride area

From Breckenridge, drive southwest towards Montrose (~5–6 hours), which positions you for exploring Black Canyon of the Gunnison. You can do short rim hikes or scenic viewpoints. If you want to include Telluride, it’s another ~2 hours from Montrose, but May can be tricky due to snow at higher elevations. Depending on your tolerance for driving, you might opt to skip Telluride this trip or just drive through for scenic views.

Stay in Montrose (Marriott options may be limited; you could consider nearby hotel alternatives if loyalty points are a priority).

Day 6: Colorado Springs

Drive east from Montrose to Colorado Springs (~5 hours). Check in to a Marriott property like The Broadmoor or Courtyard Colorado Springs. This sets you up to explore:

Garden of the Gods
Royal Gorge Bridge & Park (a ~1-hour drive from Colorado Springs, so can be a half-day trip)

Day 7: Great Sand Dunes National Park / Departure Prep

If you have time and energy, you could do a morning drive to Great Sand Dunes (~2.5–3 hours from Colorado Springs). May is a good time to enjoy the dunes before it gets too hot. Afterward, return to Colorado Springs for your last night.

Alternative: If driving to Great Sand Dunes is too ambitious, enjoy more time in Colorado Springs, easy walks, or visit nearby Pikes Peak via scenic drive.

Day 8: Departure from Denver

Drive back to Denver (~1.5 hours from Colorado Springs) for your 5 PM flight. Make sure to leave plenty of buffer time for traffic and car return.

Overall, your itinerary balances scenic drives, city exploration, and short, accessible hikes for a first-time Colorado visit. Some longer drives are unavoidable if you want to hit Maroon Bells, Black Canyon, and Telluride in one week, so you may need to prioritize which destinations matter most. Staying at Marriott properties is feasible in Denver, Breckenridge, and Colorado Springs, but some smaller mountain towns like Aspen, Montrose, or Estes Park may have limited Marriott options, so consider a mix of loyalty points stays and other highly-rated hotels.

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