16 days in West Bend & Kissimmee Itinerary

16 days in West Bend & Kissimmee Itinerary

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Route & dates

16 days in West Bend & Kissimmee Itinerary

Start: Milwaukee
Drive:  1​h
West Bend
— 6 nights
Fly:  8​h 30​min
— 8 nights
Fly:  5​h 15​min
End: Milwaukee

West Bend

West Bend ©
West Bend is the county seat of Washington County, Wisconsin, United States, in southeastern Wisconsin. Family-friendly places like Horicon Marsh and Lion's Den Gorge Nature Preserve will thrill your kids. Do your shopping at Capitol Civic Center and The Downtown West Bend Farmers' Market. Get out of town with these interesting West Bend side-trips: Bookworm Gardens (in Sheboygan), EAA Aviation Museum (in Oshkosh) and Devil's Lake State Park (in Baraboo). Next up on the itinerary: tour the pleasant surroundings at Gibraltar Rock State Natural Area, take in nature's colorful creations at Labyrinth Garden Earth Sculpture, look for all kinds of wild species at Woodland Dunes Nature Center, and take in the exciting artwork at Santa Fe Shop.

To find where to stay, other places to visit, more things to do, and more tourist information, read our West Bend travel itinerary planner .

Milwaukee to West Bend is an approximately 1-hour car ride. In May, daily temperatures in West Bend can reach 65°F, while at night they dip to 44°F. Finish up your sightseeing early on the 31st (Fri) so you can travel to Kissimmee.

Things to do in West Bend

Parks Wildlife Shopping

Side Trips

Bookworm Gardens, Santa Fe Shop, Horicon Marsh, Woodland Dunes Nature Center, Gibraltar Rock State Natural Area
Highlights from your plan
Bookworm Gardens ©
Bookworm Gardens
Horicon Marsh ©
Horicon Marsh
Lion's Den Gorge Nature Preserve ©
Lion's Den Gorge Nature Preserve


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.
Your day-by-day itinerary now includes Discovery Cove. Give yourself a bit of retail therapy at Ron Jon Surf Shop and Celebration Farmers Market. Take a break from the city and head to Ellie Schiller Homosassa Springs Wildlife State Park and Tampa Electric's Manatee Viewing Center. Get out of town with these interesting Kissimmee side-trips: Cocoa Beach (in Cocoa Beach), NASA Kennedy Space Center Visitor Complex (in Titusville) and Fishing Charters & Tours (in Port Canaveral). Plan for a day of cool, family-friendly fun on the 6th (Thu) at Legoland Florida Resort. There's lots more to do: enjoy the sand and surf at Beach at Daytona Beach, admire the natural beauty at Dunlawton Sugar Mill Gardens, take in the architecture and atmosphere at First United Methodist Church, and have fun at Congo River Golf.

For other places to visit, more things to do, maps, and more tourist information, you can read our Kissimmee online road trip planner .

The Route module can help you plan travel from West Bend to Kissimmee. Due to the time zone difference, you'll lose 1 hour traveling from West Bend to Kissimmee. Expect a bit warmer temperatures when traveling from West Bend in June; daily highs in Kissimmee reach 89°F and lows reach 74°F. Finish your sightseeing early on the 9th (Sun) to allow enough time to travel back home.

Things to do in Kissimmee

Parks Outdoors Beaches

Side Trips

Cocoa Beach, Discovery Cove, Celebration Farmers Market, Tampa Electric's Manatee Viewing Center, Legoland Florida Resort
Highlights from your plan
Discovery Cove ©
Discovery Cove
Fishing Charters & Tours

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