60 days in Central Florida Itinerary

60 days in Central Florida Itinerary

Created using Inspirock Central Florida trip planner

Plan created by another user.Make it yours

Route & dates

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
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.
Get out of town with these interesting Orlando side-trips: Kissimmee (Osceola County Welcome Center and History Museum, Fishing Charters & Tours, &more), The Artistic Hand Gallery & Studio (in Oviedo) and Clermont (Showcase of Citrus & Joseph Steed's Archery). The adventure continues: find something for the whole family at Walt Disney World Resort, discover the magic at Magic Kingdom Park, try out the rides at Happily Ever After Fireworks, and kick back and relax at Discovery Cove.

For where to stay, reviews, more things to do, and tourist information, use the Orlando trip planning website.

Chicago to Orlando is an approximately 5.5-hour flight. You can also drive; or take a train. The time zone difference when traveling from Chicago to Orlando is 1 hour. Prepare for a bit warmer weather when traveling from Chicago in May: high temperatures in Orlando hover around 88°F and lows are around 69°F. Wrap up your sightseeing on the 17th (Sun) to allow time to drive to Ocala.

Things to do in Orlando

Theme Parks Fun & Games Outdoors

Side Trips

Kissimmee, Winter Park, Winter Garden, Clermont, The Artistic Hand Gallery & Studio
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. Change things up with these side-trips from Ocala: Bushnell (Dade Battlefield Historic State Park & Florida National Cemetery), Dunnellon (Ross Prairie Trailhead, Blue Run of Dunnellon Park, &more) and Lady Lake (Uncle Donald's Farm, Orange Blossom Hills Golf & Country Club, &more). Next up on the itinerary: get a taste of life in the country at Gypsy Gold Horse Farm, have some family-friendly fun at Monkey Junction Inc, take in the views from Landbridge Trailhead, and learn about winemaking at Katya Vineyards.

For more things to do, photos, where to stay, and tourist information, refer to the Ocala trip planner.

Traveling by car from Orlando to Ocala takes 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and taxi. Plan for a bit cooler nights when traveling from Orlando in May since evenings lows in Ocala dip to 63°F. Wrap up your sightseeing on the 1st (Mon) early enough 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
Sholom Park ©
Sholom Park
Farm Tours of Ocala ©
Farm Tours of Ocala


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. Explore Sebring's surroundings by going to Arcadia (The Arcadia Opera House, Morgan Park, &more) and Lake Wales (Westgate River Ranch Resort, St. Anne Shrine, &more). And it doesn't end there: admire the majestic nature at Highlands Hammock State Park, enjoy some friendly competition at Heartland Bowl, browse the different shops at Lakeshore Mall, and bet on your favorite at Sebring International Raceway.

To find reviews, other places to visit, traveler tips, and tourist information, use the Sebring online route planner.

Traveling by car from Ocala to Sebring takes 3 hours. Expect a daytime high around 88°F in June, and nighttime lows around 70°F. On the 15th (Mon), you'll travel to Lakeland.

Things to do in Sebring

Parks Nature Shopping

Side Trips

Lake Wales, Arcadia
Find places to stay Jun 1 — 15:
Highlights from your plan
Highlands Hammock State Park ©
Highlands Hammock State Park
Lake Istokpoga ©
Lake Istokpoga
Struthers' Honey ©
Struthers' Honey


Lakeland ©
You'll find plenty of places to visit near Lakeland: Winter Haven (Legoland Florida Resort, Willowbrook Golf Course, &more), Davenport (Posner Park Shopping Mall - Posner Commons Stores, ChampionsGate Golf Resort, &more) and Lake Wales (Spook Hill, Bok Tower Gardens, &more).

To see ratings, traveler tips, where to stay, and other tourist information, refer to the Lakeland trip itinerary tool.

Traveling by car from Sebring to Lakeland takes 1.5 hours. In June in Lakeland, expect temperatures between 89°F during the day and 71°F at night. Finish up your sightseeing early on the 29th (Mon) so you can travel back home.

Things to do in Lakeland

Parks Outdoors Golf

Side Trips

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