15 days in Florida Itinerary

15 days in Florida Itinerary

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Route & dates

15 days in Florida Itinerary

Start: Chicago
Fly:  5​h 15​min
1
Miami
— 2 nights
Drive:  1​h 15​min
2
Key Largo
— 2 nights
Drive:  1​h 15​min
3
Marathon
— 1 night
Drive:  30​min
4
Big Pine Key
— 1 night
bus:  45​min
5
Key West
— 2 nights
ferry:  2​h 30​min
6
Marco Island
— 1 night
Drive:  4​h 15​min
7
Orlando
— 5 nights
Fly:  5​h
End: Chicago

2
nights
Miami

Miami ©
Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
Kick off your visit on the 5th (Wed): shop like a local with Lincoln Road. Get ready for a full day of sightseeing on the next day: enjoy the sand and surf at South Beach and then appreciate the views at Shark Valley.

For traveler tips, maps, other places to visit, and other tourist information, use the Miami day trip tool .

Chicago to Miami is an approximately 5.5-hour flight. You can also do a combination of flight and bus; or drive. The time zone difference moving from Central Standard Time (CST) to Eastern Standard Time (EST) is 1 hour. Traveling from Chicago in June, things will get a bit warmer in Miami: highs are around 89°F and lows about 77°F. Wrap up your sightseeing on the 7th (Fri) early enough to drive to Key Largo.

Things to do in Miami

Parks Outdoors Trails

Side Trips

Everglades National Park, Miami Beach, Venetian Pool
Highlights from your plan
Shark Valley Visitor Center ©
Shark Valley Visitor Center
Gumbo Limbo Trail ©
Gumbo Limbo Trail
South Beach ©
South Beach

2
nights
Key Largo

Key Largo ©
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.
You've now added Key Largo Parasail to your itinerary. Kick off your visit on the 8th (Sat): stop by Robert Is Here, then glide through the air with Key Largo Parasail, then get up close and personal with brilliant marine life at Dolphins Plus Marine Mammal Responder, and finally identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center. Keep things going the next day: get your bearings at Key Largo Chamber of Commerce and Florida Keys Visitor Center and then hike along Anhinga Trail.

To see ratings, traveler tips, and more tourist information, go to the Key Largo holiday planner .

Traveling by car from Miami to Key Largo takes 1.5 hours. Alternatively, you can take a bus. In June, plan for daily highs up to 88°F, and evening lows to 75°F. Wrap up your sightseeing on the 9th (Sun) early enough to drive to Marathon.

Things to do in Key Largo

Parks Wildlife Outdoors

Side Trips

Robert Is Here, Anhinga Trail
Highlights from your plan
Anhinga Trail ©
Anhinga Trail

1
night
Marathon

Marathon ©
A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Your day-by-day itinerary now includes Spirit Snorkeling as well as Catch 'Em All. Start off your visit on the 10th (Mon): see what you can catch with Catch 'Em All, then enjoy the sand and surf at Sombrero Beach, and then discover the deep blue sea with Spirit Snorkeling.

To find ratings, traveler tips, more things to do, and more tourist information, use the Marathon trip planner .

You can drive from Key Largo to Marathon in 1.5 hours. Another option is to take a bus. In June, daily temperatures in Marathon can reach 90°F, while at night they dip to 79°F. Finish your sightseeing early on the 10th (Mon) to allow enough time to take a bus to Big Pine Key.

Things to do in Marathon

Outdoors Wildlife Tours
Highlights from your plan
Sombrero Beach ©
Sombrero Beach
Catch 'Em All ©
Catch 'Em All
Spirit Snorkeling ©
Spirit Snorkeling

1
night
Big Pine Key

Big Pine Key ©
Big Pine Key is a census-designated place and unincorporated community in Monroe County, Florida, United States, on an island of the same name in the Florida Keys. Start off your visit on the 11th (Tue): look for all kinds of wild species at National Key Deer Refuge, then stop by Out of the Blue Gallery, and then stroll through Bahia Honda State Park.

To find ratings, other places to visit, reviews, and other tourist information, go to the Big Pine Key online attractions planner .

Big Pine Key is very close to Marathon. June in Big Pine Key sees daily highs of 90°F and lows of 79°F at night. Finish your sightseeing early on the 11th (Tue) so you can take a bus to Key West.

Things to do in Big Pine Key

Parks Outdoors Beaches
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
National Key Deer Refuge ©
National Key Deer Refuge
Out of the Blue Gallery ©
Out of the Blue Gallery

2
nights
Key West

Key West ©
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.
On the 12th (Wed), take a leisurely stroll along Mallory Square and then look for all kinds of wild species at Key West Butterfly & Nature Conservatory. Get ready for a full day of sightseeing on the next day: examine the collection at The Ernest Hemingway Home and Museum and then make a trip to Duval Street.

To see reviews, photos, other places to visit, and other tourist information, read Key West trip itinerary builder app .

Take a bus from Big Pine Key to Key West in an hour. Alternatively, you can drive. In June, daily temperatures in Key West can reach 88°F, while at night they dip to 79°F. Finish your sightseeing early on the 13th (Thu) so you can ride a ferry to Marco Island.

Things to do in Key West

Museums Parks Wildlife
Highlights from your plan
The Ernest Hemingway Home and Museum ©
Mallory Square ©
Mallory Square

1
night
Marco Island

Marco Island ©
Marco Island is a city in Collier County, Florida, United States, located on an island by the same name in the Gulf of Mexico off the coast of Southwest Florida. Your day-by-day itinerary now includes The Dolphin Explorer as well as Capt. Ron's Awesome Everglades Adventures. Start off your visit on the 14th (Fri): see majestic marine mammals with The Dolphin Explorer, then get some thrills out on the water with Capt. Ron's Awesome Everglades Adventures, and then look for gifts at Keep In Touch.

For other places to visit, where to stay, traveler tips, and other tourist information, read Marco Island trip planner .

Ride a ferry from Key West to Marco Island in 2.5 hours. Alternatively, you can drive. Expect little chillier evenings in Marco Island when traveling from Key West in June, with lows around 74°F. Finish your sightseeing early on the 14th (Fri) to allow enough time to drive to Orlando.

Things to do in Marco Island

Outdoors Wildlife Tours
Highlights from your plan

5
nights
Orlando

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.
Your day-by-day itinerary now includes Aquatica. Attractions like Universal Orlando Resort and Discovery Cove make great kid-friendly stops. Pack the 18th (Tue) with family-friendly diversions at Universal's Islands of Adventure. And it doesn't end there: make an unforgettable trip to Epcot, have some family-friendly fun at Nomadic, and test your problem-solving skills at The Escape Game Orlando.

Plan trip to Orlando with our itinerary maker to find out where to go and what to do.

You can drive from Marco Island to Orlando in 4.5 hours. Alternatively, you can do a combination of bus and flight; or take a bus. In June in Orlando, expect temperatures between 91°F during the day and 73°F at night. Finish up your sightseeing early on the 19th (Wed) so you can travel back home.

Things to do in Orlando

Theme Parks Outdoors Beaches
Highlights from your plan
Universal Orlando Resort ©
Universal Orlando Resort
Universal's Islands of Adventure ©
Universal's Islands of Adventure
Discovery Cove ©
Discovery Cove

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