Ultimate 21-Day Colorado Vacation Itinerary in May: Mountains, Cities & Adventure

Day 1: Denver City Exploration

Denver, Colorado

8:00AM

Breakfast at Snooze, an A.M. Eatery

Kick off your trip with creative breakfast dishes and excellent coffee at this popular Denver spot.
$15, 1 hour

9:30AM

Denver Art Museum

Explore notable Western American art and contemporary exhibits in this architecturally striking museum.
$13, 2 hours

12:00PM

Lunch at Union Station

Dine at one of the many restaurants inside this beautifully renovated train station offering diverse options.
$20, 1 hour

1:30PM

Visit Denver Botanic Gardens

Enjoy serene garden walks featuring native and exotic plants in a tranquil setting.
$15, 2 hours

4:00PM

Walk Larimer Square

Stroll through Denver's oldest and most historic block full of boutiques, galleries, and cafes.
Free, 1.5 hours

6:30PM

Dinner at Mercantile Dining & Provision

Savor farm-to-table cuisine at this renowned Denver eatery within Union Station.
$40, 1.5 hours
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Day 2: Denver Day Two - Culture & Views

Denver, Colorado

8:00AM

Breakfast at Watercourse Foods

Enjoy a delicious vegan breakfast in Denver’s Five Points neighborhood.
$12, 1 hour

9:30AM

Denver Museum of Nature & Science

Explore fascinating exhibits like dinosaur skeletons, space, and gems; ideal for all ages.
$19, 3 hours

12:30PM

Lunch at City O’ City

Taste innovative vegetarian dishes for an energizing midday meal.
$18, 1 hour

2:00PM

Hike at Red Rocks Park and Amphitheatre

Visit the iconic natural amphitheater and hike scenic trails with stunning red rock formations.
Free, 3 hours

6:00PM

Dinner at El Five

Dine on globally inspired small plates with panoramic views of the city skyline.
$45, 1.5 hours
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Day 3: Denver to Boulder

Denver to Boulder, Colorado

8:00AM

Breakfast and Drive to Boulder

Early breakfast in Denver then a 45-minute drive northwest to Boulder via US-36 W.
$15, 1.5 hours including drive

10:00AM

Walk Pearl Street Mall

Explore Boulder's vibrant pedestrian street filled with shops, street performers, and cafes.
Free, 2 hours

12:30PM

Lunch at The Kitchen

Enjoy locally sourced American cuisine at this elegant Boulder restaurant.
$25, 1 hour

2:00PM

Visit Boulder Farmers Market

Browse fresh local produce and artisan goods (open Saturdays during May).
Free entry, 1 hour

3:30PM

Afternoon at Chautauqua Park

Relax or hike at this historic park with breathtaking views of the Flatirons rock formations.
Free, 3 hours

7:00PM

Dinner at Frasca Food and Wine

Celebrate your first day in Boulder with an exquisite Italian-inspired dinner at this acclaimed restaurant.
$60, 2 hours
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Day 4: Rocky Mountain National Park

Boulder to Estes Park, Colorado

7:00AM

Drive to Rocky Mountain National Park

An early 1-hour drive from Boulder to Estes Park to beat the crowds and enjoy mountain fresh air.
Free; $30 for park entrance per vehicle, 1 hour

8:30AM

Breakfast in Estes Park at Notchtop Bakery & Cafe

Refuel with rustic pastries and coffee in downtown Estes Park.
$15, 1 hour

10:00AM

Hiking Bear Lake Trail

Gentle 0.6-mile loop hike to beautiful Bear Lake with views of Hallett Peak.
Included with park entrance, 1.5 hours

12:00PM

Lunch Picnic at Sprague Lake

Pack or pick up a picnic lunch to enjoy near this serene alpine lake known for spectacular scenery.
Picnic costs vary, 1 hour

2:00PM

Trail Ridge Road Scenic Drive

Take America’s highest continuous paved road for breathtaking views up to 12,000 feet.
Included with park entrance, 3 hours

6:30PM

Dinner at The Rock Inn Mountain Tavern

Winding down with hearty mountain fare and live music in Estes Park’s welcoming tavern.
$30, 1.5 hours
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Day 5: Exploring Rocky Mountain National Park

Estes Park, Colorado

8:00AM

Breakfast at Kind Coffee

Grab a fresh pastry and coffee at this cozy local café to start your day.
$10, 1 hour

9:30AM

Hike Emerald Lake Trail

A moderately challenging 3.5-mile round trip hike passing Nymph and Dream Lakes, ending at picturesque Emerald Lake.
Included with park entrance, 3 hours

1:00PM

Lunch in Estes Park at Bird & Jim

Contemporary American cuisine with a focus on regional ingredients.
$25, 1 hour

2:30PM

Visit Estes Park Memorial Observatory

Afternoon visit and possibly an early evening stargazing session (check schedule).
Free, 2 hours

6:30PM

Dinner at Smokin’ Dave’s BBQ & Taphouse

Savor authentic Southern barbecue in a casual atmosphere.
$25, 1.5 hours
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Day 6: Relaxation in Estes Park

Estes Park, Colorado

8:30AM

Breakfast at Notchtop Bakery & Cafe

Another round of fresh pastries and coffee to fuel a leisurely day.
$15, 1 hour

10:00AM

Spa day at The Estes Park Spa

Treat yourself to a relaxing massage and wellness treatments to rejuvenate after days of hiking.
$100+ per treatment, 3 hours

1:00PM

Lunch at Mountain Home Café & Tavern

Enjoy comfort food with a cozy mountain ambiance near downtown Estes Park.
$20, 1 hour

2:30PM

Visit local shops and art galleries

Explore Estes Park’s charming boutiques and galleries at your leisure.
Varies, 3 hours

6:30PM

Dinner at The Wild Rose Food & Spirit

Savor farm-to-table cuisine in a stylish setting to close your period in Estes Park.
$35, 1.5 hours
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Day 7: Estes Park to Colorado Springs

Start in Estes Park, Colorado to Colorado Springs, Colorado

7:30AM

Breakfast at your hotel or local café

Early bite and prepare for the scenic 2.5-hour drive south to Colorado Springs via US-34 E and I-25 S.
$15, 3.5 hours including drive

11:00AM

Garden of the Gods Visitor Center

Start exploring the awe-inspiring red rock formations with informative exhibits and a short nature walk.
Free, 2 hours

1:00PM

Lunch at The Rabbit Hole

Enjoy eclectic dishes in a whimsical, Alice in Wonderland-themed restaurant in downtown Colorado Springs.
$25, 1 hour

2:30PM

Climb or drive through Garden of the Gods Park

Take a scenic drive or hike to see famous rock formations like Balanced Rock and Kissing Camels.
Free, 3 hours

6:30PM

Dinner at Four by Brother Luck

Dine on innovative dishes from a James Beard semi-finalist blending global and local flavors.
$50, 1.5 hours
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Day 8: Pikes Peak Excursion

Colorado Springs, Colorado

7:00AM

Breakfast at Urban Steam

Start early with a hearty breakfast and coffee at this unique downtown café housed in an old steam plant.
$15, 1 hour

8:30AM

Drive or take Pikes Peak Cog Railway

Ascend the 14,115-foot summit via the scenic cog railway or car, weather permitting.
$38 for railway, Free for driving, 4 hours round trip

1:00PM

Lunch at The Famous Steak House

Relax with a classic American steak lunch back in Colorado Springs.
$30, 1 hour

3:00PM

Visit Cheyenne Mountain Zoo

Spend the afternoon exploring America’s highest zoo with mountain animals and beautiful views.
$25, 3 hours

7:00PM

Dinner at Shuga’s

Unwind with flavorful small plates and cocktails in an artsy, intimate space.
$35, 1.5 hours
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Day 9: Colorado Springs to Great Sand Dunes

Colorado Springs to Great Sand Dunes National Park, Colorado

7:30AM

Breakfast at Peak Place Café

Enjoy a wholesome breakfast in Colorado Springs before the road trip south.
$15, 1 hour

8:30AM

Drive to Great Sand Dunes National Park via Alamosa

Approximately 3.5 hours drive through scenic southern Colorado via US-285 S and US-160 W.
Park entrance fee $25 per vehicle, 3.5 hours

12:30PM

Lunch at San Luis Valley Brewing Company in Alamosa

Fuel up with local brews and hearty pub fare before exploring dunes.
$20, 1 hour

2:00PM

Explore Great Sand Dunes National Park

Hike the tallest sand dunes in North America and enjoy unique desert landscapes.
Included with park entrance, 3 hours

5:30PM

Set up camp or check into lodging nearby

Options include camping inside the park or staying in Alamosa nearby.
Varies, 1 hour

7:00PM

Dinner at Days Inn & Suites Restaurant or local Alamosa eatery

Simple relaxed dining to rest after your adventure day.
$20, 1 hour
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Day 10: Great Sand Dunes Adventure

Great Sand Dunes National Park, Colorado

8:00AM

Breakfast at your lodging or campground

Start early to enjoy cool morning air and minimal crowds at the dunes.
Varies, 1 hour

9:00AM

Sandboarding or sledding on dunes

Rent gear locally and experience the thrill of sliding down towering sand dunes.
$30 rental fee approx., 3 hours

12:00PM

Lunch picnic at the dunes

Bring a packed lunch or buy supplies in Alamosa and enjoy an outdoor meal surrounded by dunes.
Picnic cost varies, 1 hour

1:30PM

Visit Zapata Falls

Short 0.5-mile hike to a stunning waterfall tucked in a narrow canyon nearby.
Free, 2 hours

4:00PM

Relax at lodging or campsite

Rest and refresh after a full day of outdoor activities.
Varies, 2 hours

6:30PM

Dinner at Alamosa Brewery

Try local craft beers and delicious food in a lively atmosphere.
$25, 1.5 hours
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Day 11: Alamosa to Durango

Alamosa to Durango, Colorado

8:00AM

Breakfast at Main Street Bagels, Alamosa

Grab tasty bagels and coffee before your 2-hour drive to Durango.
$10, 1 hour

9:30AM

Drive to Durango

Scenic 2-hour drive southwest through San Juan Mountains to Durango via US-160 W and CO-172 W.
Free, 2 hours

11:30AM

Lunch at Steamworks Brewing Company

Enjoy craft brews and pub fare in the historic downtown area.
$20, 1 hour

1:00PM

Durango & Silverton Narrow Gauge Railroad Museum

Learn about the history of the iconic steam train and plan your next adventure ride.
$10, 1 hour

2:30PM

Stroll Historic Main Avenue

Explore shops, galleries, and cafes in Durango’s charming downtown.
Varies, 2 hours

5:00PM

Dinner at El Moro Spirits & Tavern

Enjoy New American cuisine with creative cocktails in a relaxed setting.
$35, 1.5 hours
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Day 12: Mesa Verde National Park

Durango to Mesa Verde National Park, Colorado

7:30AM

Breakfast at the hotel or local café

Early meal before a short 45-minute drive to Mesa Verde National Park.
$15, 1 hour

9:00AM

Explore Cliff Palace

Take a ranger-led tour of the largest cliff dwelling in North America (book in advance).
$10 plus park admission $15, 2 hours

11:30AM

Visit Spruce Tree House

Self-guided tour of this well-preserved cliff dwelling site with interpretive signage.
Included with park fee, 1 hour

1:00PM

Lunch at Far View Terrace Café

Dine inside the park with simple meals and stunning views of the canyon.
$18, 1 hour

2:30PM

Chapman Hill Trail Hike

1.5 miles hiking trail offering views of additional ruins and the natural environment.
Included with park admission, 2 hours

5:00PM

Return to Durango

Drive back to Durango for dinner and overnight stay.
Free, 45 minutes

6:00PM

Dinner at The Ore House

Steakhouse and seafood in an upscale rustic atmosphere, perfect for winding down.
$50, 1.5 hours
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Day 13: Durango to Aspen

Durango to Aspen, Colorado

7:00AM

Breakfast at Jean-Pierre Bakery & Café

Enjoy French-style pastries and strong coffee before a longer drive east.
$15, 1 hour

8:30AM

Drive to Aspen via CO-145 N and CO-82 E

A stunning 5-hour drive through the San Juan and Elk Mountains with opportunities to stop in small towns.
Free, 5 hours

1:30PM

Lunch at Paradise Bakery & Café, Aspen

Casual lunch with hearty sandwiches and salads perfect after the drive.
$15, 1 hour

3:00PM

Stroll Aspen’s downtown

Explore luxury shops, galleries, and cafes in this mountain town.
Varies, 2 hours

6:30PM

Dinner at Matsuhisa Aspen

Indulge in world-renowned Japanese fusion cuisine by Chef Nobu Matsuhisa.
$60, 1.5 hours
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Day 14: Maroon Bells Hike

Aspen, Colorado

7:00AM

Breakfast at Victoria’s Espresso and Wine Bar

Fuel up with coffee and light bites before your morning adventure.
$12, 1 hour

8:00AM

Bus to Maroon Bells Scenic Area

Take a shuttle from Aspen, required in May to preserve the environment (check schedules).
$10 round trip, 1 hour

9:00AM

Hike Maroon Lake Scenic Trail

Easy 1.5-mile loop trail offering exceptional views of iconic Maroon Bells peaks.
Included with shuttle, 1.5 hours

11:00AM

Longer hike option - Crater Lake Trail

For more experienced hikers, continue to this moderate 3.6-mile round-trip trail offering panoramic views.
Included with shuttle, 3 hours

2:30PM

Return shuttle to Aspen

Travel back for a late lunch and to rest.
Included with shuttle, 1 hour

4:00PM

Lunch at White House Tavern

Relax with casual American cuisine on Aspen’s main street.
$25, 1 hour

6:30PM

Dinner at Element 47

Fine dining featuring Colorado-sourced ingredients in the Little Nell Hotel.
$70, 1.5 hours
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Day 15: Relax and Explore Aspen

Aspen, Colorado

8:00AM

Breakfast at the hotel or local café

Leisurely start with coffee and bakery items.
$12, 1 hour

9:30AM

Visit Aspen Art Museum

Contemporary art exhibits in a striking modern building with free entry.
Free, 2 hours

12:00PM

Lunch at Victoria’s Espresso and Wine Bar

Light lunch with pastries and coffee or wine.
$15, 1 hour

1:30PM

Afternoon stroll along the Rio Grande Trail

Enjoy a scenic 5-mile multi-use trail following the river, perfect for walking or biking.
Free, 2 hours

4:00PM

Spa treatment at Remède Spa Aspen

Relax with luxurious treatments in a tranquil environment.
$100+, 2 hours

7:00PM

Dinner at Cache Cache

French-American bistro dining with regional ingredients and excellent wine list.
$50, 1.5 hours
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Day 16: Aspen to Denver

Aspen to Denver, Colorado

8:00AM

Breakfast at Paradise Bakery & Café

Last breakfast in Aspen with fresh baked goods and coffee.
$15, 1 hour

9:30AM

Drive to Denver

Take a scenic 3.5-hour drive on CO-82 E and I-70 E to Denver International Airport area for your departure or next plans.
Free, 3.5 hours

1:30PM

Lunch at Avanti Food & Beverage

Enjoy a casual food hall experience on Denver’s south side with views of downtown.
$20, 1 hour

3:00PM

Optional visit to Denver Botanic Gardens or relax at hotel

Depending on your flight schedule, explore another spot or relax before departure.
$15 or Free, 2 hours

6:00PM

Dinner at Guard and Grace

Enjoy a top-tier steakhouse meal in Denver for your final evening.
$50, 1.5 hours
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Day 17: Additional Exploration: Colorado National Monument

Grand Junction area, Colorado

7:00AM

Fly or drive early from Denver to Grand Junction (1-hour flight or 4-hour drive)

Travel west toward Colorado National Monument for dramatic desert canyons.
$50 flight or rental car cost, 4 hours driving or 1 hour flying

11:00AM

Lunch at 626 on Rood

Dine on modern American cuisine on Grand Junction’s main street.
$25, 1 hour

12:30PM

Drive Colorado National Monument Scenic Drive

Explore breathtaking overlooks and short hikes in this canyonland park.
$20 park entry, 4 hours

5:00PM

Check-in and Dinner at Bin 707 Foodbar

Enjoy farm-to-table dinner in Grand Junction’s vibrant dining scene.
$40, 1.5 hours
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Day 18: Grand Junction and Fruita Outdoor Fun

Grand Junction and Fruita, Colorado

8:00AM

Breakfast at Main Street Bagels Grand Junction

Hearty breakfast for the day’s adventures.
$10, 1 hour

9:30AM

Mountain biking in Fruita

Explore world-class mountain bike trails or hiking routes in nearby Fruita.
Free or rental fees ~$50, 4 hours

2:00PM

Lunch at The Moxie Bread Co.

Fresh sandwiches and baked goods in downtown Grand Junction.
$15, 1 hour

3:30PM

Visit Western Colorado Botanical Gardens

Relax amid desert-adapted plants and beautiful displays.
$7, 1.5 hours

6:00PM

Dinner at Juicy Lucy’s Steakhouse

End the day with classic steakhouse dinner.
$40, 1.5 hours
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Day 19: Return to Denver

Grand Junction to Denver, Colorado

8:00AM

Breakfast at hotel or café

Prepare for journey back to Denver.
$15, 1 hour

9:30AM

Drive or fly back to Denver

Option of 4-hour drive or 1-hour flight from Grand Junction.
$50 flight or rental car, 4 hours driving or 1 hour flying

2:00PM

Lunch at Avanti Food & Beverage (if returning by car)

Enjoy casual meal shortly upon arrival.
$20, 1 hour

3:30PM

Relax or visit Denver Museum of Nature & Science

Use your extra time in Denver for a museum visit or leisure time.
$19, 2 hours

6:30PM

Dinner at Root Down

Savor global fusion cuisine in a trendy setting.
$45, 1.5 hours
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Day 20: Day Trip to Boulder

Denver to Boulder, Colorado

8:00AM

Breakfast at Denver Biscuit Company

Enjoy hearty biscuit sandwiches and coffee before day trip to Boulder.
$15, 1 hour

9:30AM

Drive to Boulder

45-minute drive on US-36 W to Boulder.
Free, 45 minutes

10:30AM

Hike Mount Sanitas Trail

Popular moderate 3.3-mile hike with beautiful mountain views.
Free, 3 hours

2:00PM

Lunch at Mountain Sun Pub & Brewery

Casual pub food paired with local craft beers.
$20, 1 hour

3:30PM

Explore Pearl Street Mall

Shopping, street music, and cafes in Boulder’s famous pedestrian street.
Varies, 2 hours

6:00PM

Drive back to Denver

Return 45-minute drive to Denver for overnight stay.
Free, 45 minutes

7:00PM

Dinner at Rioja Restaurant

Upscale Mediterranean dining in Denver’s Larimer Square.
$50, 1.5 hours
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Day 21: Departure Day

Denver, Colorado

8:00AM

Breakfast at Jelly Café

Final hearty breakfast in Denver with creative breakfast plates.
$15, 1 hour

10:00AM

Pack and check out

Allow enough time to prepare for your flight home.
Free, 1.5 hours

12:00PM

Transfer to Denver International Airport

Drive or take shuttle to the airport (about 45 mins to 1 hour).
$50 approx for taxi or rideshare, 1 hour
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