30 days in Overland Park, Orlando & Portland Itinerary

30 days in Overland Park, Orlando & Portland Itinerary

Created using Inspirock United States tour itinerary maker

Make it your trip
Drive
1
Overland Park
— 6 nights
Fly
2
Orlando
— 11 nights
Fly
3
Portland
— 12 nights
Bus to Logan International Airport, Fly to Kansas City

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Overland Park

— 6 nights
Overland Park is the second most populous city in the U.S. state of Kansas. Museum-lovers will appreciate Shawnee Indian Mission State Historic Site and Mahaffie Stagecoach Stop & Farm Historic Site. Deepen your sense of the past at sights like Fort Scott National Cemetery and Fort Scott National Historic Site. Change things up with these side-trips from Overland Park: Tonganoxie Community Historical Society and Museum (in Tonganoxie), Carroll Mansion (in Leavenworth) and Lawrence (Freedom's Frontier National Heritage Area, Watkins Museum of History, &more). There's lots more to do: get to know the resident critters at Deanna Rose Children's Farmstead, take an in-depth tour of Shawnee Town 1929, learn more about the world around you at Prairie Fire Museum, and make a trip to Museum at Prairiefire.

To find where to stay, ratings, reviews, and other tourist information, read our Overland Park trip maker website.

Kansas City to Overland Park is an approximately half hour car ride. You can also take a bus. Wrap up your sightseeing by early afternoon on the 9th (Fri) to allow time for travel to Orlando.

Things to do in Overland Park

Museums · Historic Sites · Childrens Museums · Theme Parks

Side Trips

Orlando

— 11 nights

Theme Park Capital of the World

For most people, any mention of Orlando immediately conjures up images of sprawling theme parks filled with characters plucked right out of popular animated movies.
Get a sense of the local culture at Madame Tussauds Orlando and Basilica of the National Shrine of Mary, Queen of the Universe. Take a break from the city and head to Pirate's Cove Adventure Golf and Dunlawton Sugar Mill Gardens. Explore Orlando's surroundings by going to Ponce Inlet (Lighthouse Point Park & Marine Science Center) and Boat Tours & Water Sports (in Kissimmee). Next up on the itinerary: get in on the family fun at SeaWorld, make an unforgettable trip to Avatar Flight of Passage, cool off at Disney’s Blizzard Beach Water Park, and try out the rides at World of Disney.

To find where to stay, reviews, more things to do, and more tourist information, go to the Orlando online journey planner.

Traveling by flight from Overland Park to Orlando takes 8 hours. Alternatively, you can drive; or take a bus. Traveling from Overland Park to Orlando, you'll lose 1 hour due to the time zone difference. In July, daytime highs in Orlando are 91°F, while nighttime lows are 75°F. Wrap up your sightseeing on the 20th (Tue) to allow time to travel to Portland.

Things to do in Orlando

Theme Parks · Museums · Parks · Outdoors

Side Trips

Portland

— 12 nights

The Forest City

Maine's biggest and perhaps most vibrant city, Portland was established as a fishing village in 1633 and grew to become New England's largest port.
You'll explore the less-touristy side of things at Marginal Way Walkway and Portland Museum of Art. Attractions like Portland Head Light and Old Port make great kid-friendly stops. Explore the numerous day-trip ideas around Portland: Wells (Wells Auto Museum, Rachel Carson National Wildlife Refuge, &more), Nubble Lighthouse (in York) and Perkins Cove (in Ogunquit). There's lots more to do: take in the architecture and atmosphere at St. Ann's Episcopal Church, enjoy the sand and surf at Jenness State Beach, explore the landscape on two wheels at Eastern Promenade Trail, and examine the collection at Maine Maritime Museum.

For other places to visit, reviews, more things to do, and other tourist information, you can read our Portland day trip planning site.

Fly from Orlando to Portland in 6.5 hours. Alternatively, you can drive; or do a combination of train and bus. Traveling from Orlando in July, things will get a bit cooler in Portland: highs are around 79°F and lows about 61°F. Finish up your sightseeing early on the 1st (Sun) so you can travel back home.

Things to do in Portland

Parks · Outdoors · Museums · Beaches

Side Trips