60 days in Florida & Chicago Itinerary

60 days in Florida & Chicago Itinerary

Created using Inspirock United States trip builder

Make it your trip
Fly
1
Miami
— 5 nights
Drive
2
Everglades National Park
— 5 nights
Fly
3
Key West
— 7 nights
Drive
4
Marathon
— 6 nights
Drive
5
Islamorada
— 5 nights
Drive
6
Key Largo
— 6 nights
Fly
7
Orlando
— 7 nights
Fly
8
Fort Walton Beach
— 6 nights
Fly
9
Chicago
— 12 nights
Fly

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Miami

— 5 nights

Magic City

Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
Change things up with these side-trips from Miami: JP Outfitters Inc. (in Hollywood), Panther Ridge Conservation Center (in Wellington) and Fort Lauderdale (Stranahan House & Fort Lauderdale Beach). And it doesn't end there: kick back and relax at South Beach, get to know the fascinating history of Art Deco Historic District, browse the different shops at Bayside Marketplace, and take a stroll through Lincoln Road.

You can plan Miami trip in no time by asking Inspirock to help create your itinerary.

Kyiv (Kiev), Ukraine to Miami is an approximately 16.5-hour flight. You'll gain 7 hours traveling from Kyiv (Kiev) to Miami due to the time zone difference. Traveling from Kyiv (Kiev) in June, things will get a bit warmer in Miami: highs are around 37°C and lows about 29°C. Wrap up your sightseeing on the 6th (Mon) early enough to travel to Everglades National Park.

Things to do in Miami

Parks · Outdoors · Museums · Shopping

Side Trips

Everglades National Park

— 5 nights

Largest Subtropical Wilderness in the United States

A vast expanse of pristine wetlands, Everglades National Park holds the distinction of being the largest tropical wilderness in the U.S. Overflow from Lake Okeechobee into the Florida Bay formed these wetlands, which are home to manatees, American crocodiles, Florida panthers, and an array of wading birds, land birds, and birds of prey.
Everglades National Park is known for wildlife, trails, and parks. Your trip includes some of its best attractions: stroll through Shark Valley Visitor Center, head off the coast to Long Pine Key, hike along Old Ingraham Highway, and contemplate the waterfront views at Slough Slog.

To find maps, photos, ratings, and tourist information, refer to the Everglades National Park travel website.

Use the Route module to find suitable travel options from Miami to Everglades National Park. In June, plan for daily highs up to 38°C, and evening lows to 30°C. Wrap up your sightseeing on the 11th (Sat) to allow time to fly to Key West.

Things to do in Everglades National Park

Parks · Outdoors · Trails · Nature

Key West

— 7 nights

Conch Republic

Located just 140 km (90 mi) from Cuba, Key West is an island only about 6.4 km (4 mi) long and 1.6 km (1 mi) wide.
Key West is known for museums, adventure, and wildlife. Your trip includes some of its best attractions: examine the collection at The Ernest Hemingway Home and Museum, enjoy the sand and surf at Fort Zachary Taylor, see the vivid underwater world at Vandenberg Wreck, and take a tour by water with Boat Tours & Water Sports.

To find photos, traveler tips, more things to do, and tourist information, go to the Key West sightseeing planning app.

Traveling by flight from Everglades National Park to Key West takes 2.5 hours. Alternatively, you can take a bus; or take a bus. In June in Key West, expect temperatures between 36°C during the day and 30°C at night. Cap off your sightseeing on the 18th (Sat) early enough to go by car to Marathon.

Things to do in Key West

Museums · Parks · Outdoors · Historic Sites

Marathon

— 6 nights

Heart of the Florida Keys

A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
You'll find plenty of places to visit near Marathon: SpaTerre at Little Palm Island Resort (in Little Torch Key), Fishing Charters & Tours (in Big Pine Key) and Everglades National Park (in Florida City). Next up on the itinerary: stroll through Bahia Honda State Park, snap pictures at Seven Mile Bridge, see the vivid underwater world at Coffins Patch, and head outdoors with Gemini Dream Charters.

To see maps, ratings, traveler tips, and tourist information, use the Marathon online day trip planner.

Getting from Key West to Marathon by car takes about 1.5 hours. Other options: take a bus. In June, plan for daily highs up to 38°C, and evening lows to 30°C. Finish your sightseeing early on the 24th (Fri) to allow enough time to drive to Islamorada.

Things to do in Marathon

Parks · Wildlife · Outdoors · Nature

Side Trips

Islamorada

— 5 nights

The Village of Islands

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Islamorada is known for wildlife, adventure, and museums. Your trip includes some of its best attractions: see what you can catch with a fishing tour, admire the majestic nature at Lignumvitae Key Botanical State Park, get outside with Satisfaction Charters Inc., and get engrossed in the history at History of Diving Museum.

Start your trip to Islamorada by creating a personalized itinerary on Inspirock.

Traveling by car from Marathon to Islamorada takes an hour. Alternatively, you can take a bus. June in Islamorada sees daily highs of 38°C and lows of 30°C at night. Finish up your sightseeing early on the 29th (Wed) so you can go by car to Key Largo.

Things to do in Islamorada

Outdoors · Parks · Nature · Museums

Key Largo

— 6 nights

Diving Capital of the World

The northernmost island of the Florida Keys, Key Largo provides stunning scenery, a number of watersports opportunities, and plenty of areas to relax on vacation.
Key Largo is known for wildlife, nature, and adventure. Your trip includes some of its best attractions: discover the deep blue sea with a scuba or snorkeling tour, immerse yourself in nature at John Pennekamp Coral Reef State Park, get a dose of the wild on Capt. Sterling's Everglades Eco-Tours, and take a tour of African Queen Canal Cruise.

To see more things to do, other places to visit, maps, and more tourist information, use the Key Largo road trip planning app.

Key Largo is just a stone's throw from Islamorada. In June in Key Largo, expect temperatures between 36°C during the day and 28°C at night. Cap off your sightseeing on the 5th (Tue) early enough to catch the flight to Orlando.

Things to do in Key Largo

Wildlife · Parks · Outdoors · Tours

Orlando

— 7 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.
Take a break from Orlando with a short trip to Osceola County Welcome Center and History Museum in Kissimmee, about 34 minutes away. Have a day of magic on the 7th (Thu) at Walt Disney World Resort. Pack the 8th (Fri) with family-friendly diversions at Universal's Islands of Adventure. There's lots more to do: find something for the whole family at Universal Orlando Resort, make an unforgettable trip to Disney's Animal Kingdom Theme Park, make a splash at Discovery Cove, and head outdoors with Outdoor Activities.

To see other places to visit, photos, traveler tips, and tourist information, read Orlando online travel planner.

Getting from Key Largo to Orlando by flight takes about 3 hours. Other options: drive; or take a bus. In July in Orlando, expect temperatures between 38°C during the day and 28°C at night. Finish your sightseeing early on the 12th (Tue) so you can fly to Fort Walton Beach.

Things to do in Orlando

Theme Parks · Museums · Tours · Outdoors

Side Trip

Fort Walton Beach

— 6 nights
Fort Walton Beach is a city in southern Okaloosa County, Florida, United States. You'll find plenty of places to visit near Fort Walton Beach: Santa Rosa Beach (Blue Mountain Beach & Santa Rosa Beach), Pensacola Beach (Jolly Sailing and Dolphin Cruises & Gulf Islands National Seashore) and Pensacola (Gulf Islands & National Naval Aviation Museum). The adventure continues: stroll through Navarre Beach, kick back and relax at Panama City Beach, contemplate the waterfront views at Destin Harbor, and step off the mainland to explore Santa Rosa Island.

To find maps, other places to visit, and more tourist information, refer to the Fort Walton Beach road trip planner.

Getting from Orlando to Fort Walton Beach by flight takes about 3.5 hours. Other options: drive; or take a bus. Traveling from Orlando to Fort Walton Beach, you'll gain 1 hour due to the time zone difference. Expect a daytime high around 37°C in July, and nighttime lows around 27°C. Cap off your sightseeing on the 18th (Mon) early enough to catch the flight to Chicago.

Things to do in Fort Walton Beach

Parks · Outdoors · Beaches · Nature

Side Trips

Chicago

— 12 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
When in Chicago, make a side trip to see First Division Museum at Cantigny in Wheaton, approximately Wheaton away. There's much more to do: explore the world behind art at The Art Institute of Chicago, get to know the resident critters at Lincoln Park Zoo, take a stroll through The Magnificent Mile, and observe the fascinating underwater world at Shedd Aquarium.

To find more things to do, ratings, maps, and more tourist information, go to the Chicago planning tool.

Fly from Fort Walton Beach to Chicago in 4 hours. Alternatively, you can drive; or take a bus. Expect a bit cooler temperatures when traveling from Fort Walton Beach in July; daily highs in Chicago reach 33°C and lows reach 22°C. Finish your sightseeing early on the 30th (Sat) so you can fly back home.

Things to do in Chicago

Museums · Parks · Childrens Museums · Outdoors

Side Trips

Florida travel guide

4.4
Disney Parks & Activities · Beaches · Theme Parks
The Sunshine State
The “Sunshine State,” Florida became a favorite winter destination for the affluent crowd over a century ago. Today, the state attracts visitors from around the world with its golden beaches and modern theme parks. You can spend your entire vacation enjoying the state's highly developed seaside areas, but remember that some of Florida's best-kept secrets are in secluded locations. Visit the big cities and their comfortable resorts offering top-notch dining and nightlife, but leave some time to see the peninsula's swampy landscape, filled with wild creatures and native plants. Farther away from the tourist-packed urban areas, the untamed wetlands of Florida offer a selection of things to do, such as kayaking, boat rides, and numerous other outdoor activities.