60 days in Central Florida Itinerary

60 days in Central Florida Itinerary

Created using Inspirock Central Florida trip planner

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Route & dates

60 days in Central Florida Itinerary

Start: Chicago
Fly:  5​h
— 16 nights
Drive:  1​h 30​min
— 15 nights
Drive:  2​h 45​min
— 14 nights
Drive:  1​h 15​min
— 14 nights
bus + foot + Fly:  6​h 30​min
End: Chicago


Orlando ©
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.
Explore the numerous day-trip ideas around Orlando: Spas (in Mount Dora), Kissimmee (Osceola County Welcome Center and History Museum, Fishing Charters & Tours, & more) and Clermont (Showcase of Citrus & Joseph Steed's Archery). There's still lots to do: get in on the family fun at Walt Disney World Resort, discover the magic at Magic Kingdom Park, take in a show at Happily Ever After Fireworks, and try out the rides at Discovery Cove.

For other places to visit, maps, and other tourist information, you can read our Orlando trip itinerary tool .

Chicago to Orlando is an approximately 5-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. Plan for somewhat warmer temperatures traveling from Chicago in May, with highs in Orlando at 88°F and lows at 69°F. Cap off your sightseeing on the 17th (Sun) early enough to go by car to Ocala.

Things to do in Orlando

Theme Parks Fun & Games Parks

Side Trips

Kissimmee, Winter Park, Winter Garden, Clermont, Annunciation Catholic Church
Find places to stay May 1 — 17:
Highlights from your plan
Walt Disney World Resort ©
Walt Disney World Resort
Universal Orlando Resort ©
Universal Orlando Resort
Universal's Islands of Adventure ©
Universal's Islands of Adventure


Ocala ©
Ocala is a city located in Northern Florida. Explore Ocala's surroundings by going to Dunnellon (Ross Prairie Trailhead, Blue Run of Dunnellon Park, & more), Lady Lake (Uncle Donald's Farm, Orange Blossom Hills Golf & Country Club, & more) and Bushnell (Dade Battlefield Historic State Park & Florida National Cemetery). Next up on the itinerary: get a taste of life in the country at Gypsy Gold Horse Farm, examine the collection at Don Garlits Museum of Drag Racing, have some family-friendly fun at Monkey Junction Inc, and admire the majestic nature at Rainbow Springs State Park.

To plan Ocala vacation without wasting time, ask Inspirock to design an itinerary.

Getting from Orlando to Ocala by car takes about 1.5 hours. Other options: take a bus; or do a combination of bus and taxi. Plan for slightly colder nights when traveling from Orlando in May since evenings lows in Ocala dip to 63°F. Wrap up your sightseeing on the 1st (Mon) to allow time to travel to Sebring.

Things to do in Ocala

Parks Outdoors Nature

Side Trips

Dunnellon, Leesburg, Lady Lake, Bushnell, Umatilla
Find places to stay May 17 — Jun 1:
Highlights from your plan
Gypsy Gold Horse Farm ©
Gypsy Gold Horse Farm
Farm Tours of Ocala ©
Farm Tours of Ocala
Sholom Park ©
Sholom Park


Sebring ©
Sebring is a city in Highlands County, Florida, United States, nicknamed "The City on the Circle", in reference to Circle Drive, the center of the Sebring Downtown Historic District. You'll find plenty of places to visit near Sebring: Lake Wales (Westgate River Ranch Resort, St. Anne Shrine, & more) and Arcadia (The Arcadia Opera House, Morgan Park, & more). There's still lots to do: immerse yourself in nature at Highlands Hammock State Park, have fun and explore at Childrens Museum of The Highlands, brush up on your military savvy at Military Sea Services Museum, and kick back and relax at City Pier Beach.

For photos, ratings, maps, and other tourist information, read Sebring road trip planning tool .

Getting from Ocala to Sebring by car takes about 3 hours. In June, daytime highs in Sebring are 88°F, while nighttime lows are 70°F. On the 15th (Mon), you're off toLakeland.

Things to do in Sebring

Parks Nature Wildlife

Side Trips

Lake Wales, Arcadia
Find places to stay Jun 1 — 15:
Highlights from your plan
Highlands Hammock State Park ©
Highlands Hammock State Park
Sebring International Raceway ©
Sebring International Raceway
Military Sea Services Museum ©
Military Sea Services Museum


Lakeland ©
Lakeland is a city in Polk County, Florida, located along Interstate 4 east of Tampa. Explore Lakeland's surroundings by going to Lake Wales (Spook Hill, Bok Tower Gardens, & more), Davenport (Posner Park Shopping Mall - Posner Commons Stores, ChampionsGate Golf Resort, & more) and Winter Haven (Legoland Florida Resort, Willowbrook Golf Course, & more). There's lots more to do: look for all kinds of wild species at Circle B Bar Reserve, take in nature's colorful creations at Hollis Garden, explore the activities along Lake Morton, and explore the landscape on two wheels at University Boulevard/Research Way Trails.

To see where to stay, maps, reviews, and other tourist information, go to the Lakeland trip itinerary site .

Drive from Sebring to Lakeland in 1.5 hours. In June, daily temperatures in Lakeland can reach 89°F, while at night they dip to 71°F. Wrap up your sightseeing on the 29th (Mon) early enough to travel back home.

Things to do in Lakeland

Outdoors Parks Golf

Side Trips

Winter Haven, Haines City, Lake Wales, Davenport, Bartow
Find places to stay Jun 15 — 29:
Highlights from your plan
Holloway Park ©
Holloway Park
Circle B Bar Reserve ©
Circle B Bar Reserve
Legoland Florida Resort ©
Legoland Florida Resort