5 days in Missouri Itinerary

5 days in Missouri Itinerary

Created using Inspirock Missouri trip itinerary builder

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Route & dates

5 days in Missouri Itinerary

Start: Chicago
Fly + Drive:  3​h 45​min
1
Weston
— Few hours
Drive:  4​h 15​min
2
Branson
— 2 nights
Drive:  3​h 30​min
3
New Haven
— 1 night
Drive:  1​h 15​min
4
Saint Louis
— 1 night
Fly:  3​h 15​min
End: Chicago

few
hours
Weston

Weston ©
Weston is a city in Platte County, Missouri, United States. On the 5th (Fri), do a tasting at Pirtle Winery and then sample the fine beverages at Holladay Distillery.

To see ratings, where to stay, photos, and other tourist information, read Weston holiday planner .

Chicago to Weston is an approximately 4-hour flight. You can also drive. In July, daily temperatures in Weston can reach 87°F, while at night they dip to 68°F. Wrap up your sightseeing on the 5th (Fri) early enough to travel to Branson.

Things to do in Weston

Breweries & Distilleries Wineries
Highlights from your plan
Holladay Distillery ©
Holladay Distillery
Pirtle Winery ©
Pirtle Winery

2
nights
Branson

Branson ©
Nestled in Missouri's beautiful Ozark Mountains lies one of the country's most attractive vacation towns for year-round family entertainment.
Kick off your visit on the 6th (Sat): browse the different shops at Relics Antique Mall, then stop by Bass Pro Shops Outdoor World, then examine the collection at Titanic Museum, and finally buy something for everyone on your list at Branson Landing. Get ready for a full day of sightseeing on the 7th (Sun): cool off at Silver Dollar City.

For ratings, maps, other places to visit, and other tourist information, go to the Branson tour itinerary planning tool .

You can drive from Weston to Branson in 4 hours. Another option is to fly. Expect a daytime high around 87°F in July, and nighttime lows around 68°F. Wrap up your sightseeing on the 7th (Sun) early enough to travel to New Haven.

Things to do in Branson

Theme Parks Shopping Museums

Side Trip

Springfield
Highlights from your plan
Branson Landing ©
Branson Landing
Bass Pro Shops Outdoor World ©
Bass Pro Shops Outdoor World
Relics Antique Mall ©
Relics Antique Mall

1
night
New Haven

New Haven ©
New Haven is a city in Franklin County, Missouri, United States. On the 8th (Mon), do a tasting at Robller Vineyard, brush up on your knowledge of spirits at Pinckney Bend Distillery, and then take in the exciting artwork at Astral Glass Studio and Gallery.

To see more things to do, reviews, traveler tips, and tourist information, you can read our New Haven trip planner .

You can drive from Branson to New Haven in 4 hours. Expect a daytime high around 86°F in July, and nighttime lows around 67°F. Wrap up your sightseeing by early afternoon on the 8th (Mon) to allow time for the car ride to Saint Louis.

Things to do in New Haven

Wineries Shopping Museums
Highlights from your plan
Pinckney Bend Distillery ©
Pinckney Bend Distillery
Astral Glass Studio and Gallery ©
Astral Glass Studio and Gallery

1
night
Saint Louis

Saint Louis ©
Test the local claim that Saint Louis is second only to Washington, D.C.
Kick off your visit on the 9th (Tue): pause for some serene contemplation at Cathedral Basilica of Saint Louis, stop by Ted Drew's Frozen Custard, then examine the collection at Cardinals Hall of Fame and Museum, and finally take in panoramic vistas at The Gateway Arch.

For photos, reviews, more things to do, and other tourist information, use the Saint Louis day trip app .

You can drive from New Haven to Saint Louis in 1.5 hours. In July, daily temperatures in Saint Louis can reach 89°F, while at night they dip to 68°F. Wrap up your sightseeing on the 9th (Tue) to allow time to travel back home.

Things to do in Saint Louis

Shopping Historic Sites Museums
Highlights from your plan
The Gateway Arch ©
The Gateway Arch
Ted Drew's Frozen Custard ©
Ted Drew's Frozen Custard
Cathedral Basilica of Saint Louis ©
Cathedral Basilica of Saint Louis

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