9 days in Bloomington & Kissimmee Itinerary

Bloomington is a city in and the county seat of Monroe County in the southern region of the U.S. state of Indiana. Take a break from Bloomington with a short trip to Holiday World & Splashin' Safari in Santa Claus, about 1h 55 min away. Next up on the itinerary: engage your brain at WonderLab, explore the activities along Monroe Lake, hike along Pate Hollow Trail, and learn about winemaking at Oliver Winery.

For other places to visit, traveler tips, reviews, and other tourist information, go to the Bloomington trip planning tool.

Chicago to Bloomington is an approximately 3-hour flight. You can also drive; or take a bus. The time zone changes from Central Standard Time (CST) to Eastern Standard Time (EST), which is usually a 1 hour difference. In July in Bloomington, expect temperatures between 83°F during the day and 64°F at night. Wrap up your sightseeing on the 19th (Sun) to allow time to fly to Kissimmee.

A popular vacation destination in the central part of Florida, Kissimmee's major claim to fame remains its sunny weather and proximity to a large Disney entertainment complex.

Explore Kissimmee's surroundings by going to St. Pete Beach (in St. Pete Beach), Legoland Florida Resort (in Winter Haven) and St. Petersburg (Morean Art Center & Outerlife Studios - Escape Room St. Pete). There's still lots to do: take a tour by water with Boat Tours & Water Sports, get in on the family fun at Fun Spot America, enjoy some diversion at Machine Gun America, and try for a hole-in-one at Congo River Golf.

To see photos, maps, ratings, and more tourist information, go to the Kissimmee road trip planner.

You can fly from Bloomington to Kissimmee in 4 hours. Alternatively, you can drive; or take a bus. Traveling from Bloomington in July, things will get somewhat warmer in Kissimmee: highs are around 90°F and lows about 75°F. Cap off your sightseeing on the 24th (Fri) early enough to catch the flight back home.