8 days in Florida Itinerary

8 days in Florida Itinerary

Created using Inspirock Florida trip maker

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Route & dates

8 days in Florida Itinerary

Start: Chicago
Fly:  5​h 45​min
1
Miami Beach
— 2 nights
Fly:  4​h
2
Orlando
— 1 night
Fly + shuttle:  5​h 30​min
3
Islamorada
— 1 day
Drive:  45​min
4
Marathon
— 1 night
bus:  1​h 15​min
5
Key West
— 2 nights
Fly:  5​h 45​min
End: Chicago

2
nights
Miami Beach

Miami Beach ©
Separated by water from the neighboring city of Miami, Miami Beach sits on a barrier island between Biscayne Bay and the Atlantic Ocean.
Kick off your visit on the 22nd (Fri): take a stroll through Collins Avenue. On your second day here, take a stroll through Lincoln Road, then grab your bike and head to Shark Valley, and then browse the different shops at Bayside Marketplace.

Planning Miami Beach trip won't be overwheling when you use's Insprock itinerary maker.

Chicago to Miami Beach is an approximately 6-hour flight. You can also drive; or take a bus. The time zone changes from Central Standard Time to Eastern Standard Time, which is usually a 1 hour difference. Traveling from Chicago in March, expect Miami Beach to be warmer, temps between 81°F and 65°F. Wrap up your sightseeing on the 24th (Sun) to allow time to drive to Orlando.

Things to do in Miami Beach

Shopping Outdoors Parks

Side Trips

Aventura Mall, Bayside Marketplace, Shark Valley
Highlights from your plan
Lincoln Road ©
Lincoln Road
Shark Valley ©
Shark Valley
South Beach ©
South Beach

1
night
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.
Start off your visit on the 25th (Mon): get in on the family fun at Discovery Cove.

To find traveler tips, other places to visit, where to stay, and other tourist information, read our Orlando day trip planning tool .

Drive from Miami Beach to Orlando in 4 hours. Alternatively, you can take a bus; or take a train. Traveling from Miami Beach in March, plan for slightly colder nights in Orlando, with lows around 58°F. Cap off your sightseeing on the 25th (Mon) early enough to go by car to Islamorada.

Things to do in Orlando

Beaches Parks Outdoors
Highlights from your plan
Discovery Cove ©
Discovery Cove

1
day
Islamorada

Islamorada ©
Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
On the 26th (Tue), take a tour by water with Boat Tours & Water Sports, take in the exciting artwork at Michelle Nicole Lowe Art Gallery, identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center, then take in the exciting artwork at Old Road Gallery, and finally stop by Bella Sol Fragrance Bar and Gifts.

For other places to visit, ratings, maps, and more tourist information, read our Islamorada online trip builder .

Traveling by car from Orlando to Islamorada takes 5.5 hours. Alternatively, you can take a bus; or do a combination of train and bus. Traveling from Orlando in March, expect somewhat warmer with lows of 69°F in Islamorada. Wrap up your sightseeing on the 26th (Tue) early enough to drive to Marathon.

Things to do in Islamorada

Wildlife Outdoors Tours

Side Trip

Florida Keys Wild Bird Rehabilitation Center
Highlights from your plan
Fishing Charters & Tours
Bella Sol Fragrance Bar and Gifts ©
Bella Sol Fragrance Bar and Gifts

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.
Start off your visit on the 27th (Wed): identify plant and animal life at Crane Point Museum & Nature Center, tour the pleasant surroundings at Sombrero Beach, and then kick back and relax at Bahia Honda State Park.

For other places to visit, ratings, maps, and other tourist information, read our Marathon vacation planner.

Getting from Islamorada to Marathon by car takes about an hour. Other options: take a bus. Expect a daytime high around 81°F in March, and nighttime lows around 69°F. Cap off your sightseeing on the 27th (Wed) early enough to catcht the bus to Key West.

Things to do in Marathon

Parks Beaches Outdoors

Side Trip

Bahia Honda State Park
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
Crane Point Museum & Nature Center ©
Crane Point Museum & Nature Center
Sombrero Beach ©
Sombrero Beach

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.
Kick off your visit on the 28th (Thu): see what you can catch with a fishing tour, view the masterpieces at Alan S. Maltz Gallery, and then look for all kinds of wild species at Key West Butterfly & Nature Conservatory. On the next day, look for all kinds of wild species at Wildlife Areas, then take in the exciting artwork at 7 Artists & Friends, and then admire the majestic nature at Fort Zachary Taylor.

To find more things to do, other places to visit, traveler tips, and tourist information, read Key West trip planner .

Traveling by bus from Marathon to Key West takes 1.5 hours. Alternatively, you can drive. In March, daytime highs in Key West are 79°F, while nighttime lows are 69°F. Finish your sightseeing early on the 29th (Fri) so you can travel back home.

Things to do in Key West

Outdoors Wildlife Tours
Highlights from your plan
Alan S. Maltz Gallery ©
Alan S. Maltz Gallery
Fishing Charters & Tours

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