27 days in United States Itinerary

27 days in United States Itinerary

Created using Inspirock United States itinerary planner

Plan created by another user.Make it yours

Route & dates

Start: Milwaukee
Fly:  4 h 30 min
1
Denver
— 3 nights
Drive:  45 min
2
Black Hawk
— 1 night
Drive:  3 h 15 min
3
Aspen
— 7 nights
Drive:  1 h
4
Glenwood Springs
— 1 day
Drive:  1 h 15 min
5
Vail
— 7 nights
Fly:  10 h 15 min
6
Honolulu
— 7 nights
Fly:  11 h 45 min
End: Milwaukee

3
nights
Denver

Denver ©
Aptly nicknamed the "Mile-High City," Denver sits at an altitude of 1,600 m (5,280 ft) above sea level, located right where the Great Plains give way to the Rocky Mountains.
Your day-by-day itinerary now includes The Denver Center for the Performing Arts, Pepsi Center and Red Rocks Park and Amphitheatre. There's much more to do: admire the masterpieces at Denver Art Museum, sample the tasty concoctions at Mockery Brewing, get a taste of the local shopping with 16th Street Mall, and steep yourself in history at Denver Union Station.

To see ratings, traveler tips, more things to do, and more tourist information, you can read our Denver trip planning app.

Milwaukee to Denver is an approximately 5-hour flight. You can also drive; or take a bus. Traveling from Milwaukee to Denver, you'll gain 1 hour due to the time zone difference. While traveling from Milwaukee, expect a bit warmer days and about the same nights in Denver, ranging from highs of 44°F to lows of 21°F. Finish your sightseeing early on the 16th (Sat) so you can drive to Black Hawk.

Things to do in Denver

Historic Sites Nightlife Museums

Side Trip

Red Rocks Park and Amphitheatre
Highlights from your plan
Denver Union Station ©
Denver Union Station
Denver Art Museum ©
Denver Art Museum
Denver Museum of Nature & Science ©
Denver Museum of Nature & Science

1
night
Black Hawk

Black Hawk ©
The City of Black Hawk is a Home Rule Municipality in Gilpin County, Colorado, United States. Kick off your visit on the 16th (Sat): try to win big at Monarch Casino Resort Spa, thentry your luck at Isle Casino, and then try your luck at Ameristar Casino Resort Spa.

To see where to stay, other places to visit, maps, and tourist information, refer to the Black Hawk trip itinerary builder app.

Getting from Denver to Black Hawk by car takes about an hour. Traveling from Denver in January, expect nights in Black Hawk to be slightly colder, around 7°F, while days are cooler, around 17°F. Wrap up your sightseeing on the 17th (Sun) early enough to travel to Aspen.

Things to do in Black Hawk

Casinos Fun & Games
Highlights from your plan
Ameristar Casino Resort Spa ©
Ameristar Casino Resort Spa
Monarch Casino Resort Spa ©
Monarch Casino Resort Spa

7
nights
Aspen

Aspen ©
Known as a ski resort town, Aspen's history goes back to its roots as a silver-mining village tucked away in an isolated valley of the Rocky Mountains.
Your day-by-day itinerary now includes Aspen Brewing Company as well as Belly Up. Take a break from the city and head to Aspen Highlands and Aspen Mountain / Ajax. There's more to do: fly down the slopes at Aspen Snowmass.

Planning Aspen trip won't be overwheling when you use's Insprock itinerary maker.

Traveling by car from Black Hawk to Aspen takes 3.5 hours. Expect a bit warmer weather when traveling from Black Hawk in January: highs in Aspen hover around 34°F, while lows dip to 8°F. You will leave for Glenwood Springs on the 24th (Sun).

Things to do in Aspen

Parks Outdoors Winter Sports

Side Trip

Aspen Snowmass
Highlights from your plan
Aspen Snowmass ©
Aspen Snowmass
Aspen Mountain / Ajax ©
Aspen Mountain / Ajax
Belly Up ©
Belly Up

1
day
Glenwood Springs

Glenwood Springs occupies a scenic location at the junction of the Colorado River and the Roaring Fork River, halfway between Vail and Aspen along the Front Range of the Rocky Mountains.
Your day-by-day itinerary now includes Thermal Spas. On the 24th (Sun), boost your wellbeing at a local thermal spa.

Quickly create a custom-made itinerary for Glenwood Springs using our trip planner.

Getting from Aspen to Glenwood Springs by car takes about an hour. Other options: take a shuttle; or take a bus. While traveling from Aspen, expect a bit cooler days and somewhat warmer nights in Glenwood Springs, ranging from highs of 27°F to lows of 17°F. Wrap up your sightseeing on the 24th (Sun) to allow time to drive to Vail.

Things to do in Glenwood Springs

Spas
Highlights from your plan
Thermal Spas

7
nights
Vail

Vail ©
Originally built as a base for Vail Ski Resort, the town of Vail has blossomed into its own destination, but still has less than 6,000 permanent residents.
Your list of things to see and do now includes Vail Backcountry Tours, 10th Mountain Whiskey & Spirit Company, Roger's Snowbike Rentals, and other attractions. Get outdoors at Vail Mountain Resort and Vail / Beaver Creek Resort. Explore Vail's surroundings by going to Keystone Ski Area (in Keystone) and Breckenridge (Main Street, Spas, &more). There's more to do: hit the slopes at Beaver Creek Ski Area.

Inspirock's itinerary builder makes planning a Vail trip simple and quick.

Traveling by car from Glenwood Springs to Vail takes 1.5 hours. Alternatively, you can take a bus. January in Vail sees daily highs of 25°F and lows of 14°F at night. Wrap up your sightseeing on the 31st (Sun) early enough to travel to Honolulu.

Things to do in Vail

Outdoors Parks Winter Sports

Side Trips

Breckenridge, Keystone, Beaver Creek
Highlights from your plan
Vail Mountain Resort ©
Vail Mountain Resort
Beaver Creek Ski Area ©
Beaver Creek Ski Area
Keystone Ski Area ©
Keystone Ski Area

7
nights
Honolulu

Honolulu ©
In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Take a break from the city and head to Diamond Head State Monument and Waikiki Beach. Change things up with these side-trips from Honolulu: Haleiwa (Waimea Bay, Sunset Beach Park, &more), Kailua (Kailua Beach Park & Lanikai Beach) and Pu’u O Mahuka Heiau State Monument (in Pupukea). The adventure continues: explore the activities along Hanauma Bay Nature Preserve, get to know the fascinating history of Makapuu Lighthouse Trail, stroll through Makiki Trail, and explore the different monuments and memorials at USS Arizona Memorial.

To see reviews, photos, where to stay, and more tourist information, refer to the Honolulu trip itinerary tool.

You can fly from Vail to Honolulu in 10.5 hours. Traveling from Vail to Honolulu, you'll gain 3 hours due to the time zone difference. Prepare for warmer weather when traveling from Vail in January: high temperatures in Honolulu hover around 81°F and lows are around 67°F. Finish your sightseeing early on the 7th (Sun) so you can travel back home.

Things to do in Honolulu

Parks Outdoors Beaches

Side Trips

Haleiwa, Oahu, Kailua, Turtle Bay Beach, Swim with Dolphins
Highlights from your plan
Diamond Head State Monument ©
Diamond Head State Monument
Waikiki Beach ©
Waikiki Beach
Swim with Dolphins

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