8 days in Florida Keys Itinerary

8 days in Florida Keys Itinerary

Created using Inspirock Florida Keys travel planner

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Route & dates

8 days in Florida Keys Itinerary

Start: Chicago
Fly + shuttle:  7​h 15​min
1
Key Largo
— 2 nights
Drive:  45​min
2
Islamorada
— 2 nights
bus:  2​h
3
Key West
— 3 nights
Fly:  5​h 45​min
End: Chicago

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 Dolphins Plus Marine Mammal Responder to your itinerary. Kick off your visit on the 9th (Tue): fulfill a lifelong dream with Dolphins Plus Marine Mammal Responder, identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center, then identify plant and animal life at Molasses Reef, and finally grab your bike and head to Florida Keys Visitor Center. On the next day, see the vivid underwater world at Spiegel Grove, take a memorable tour with Tours, and then get a new perspective on things with Boat Tours & Water Sports.

Take the guesswork out of planning a Key Largo vacation by using our trip itinerary maker.

Chicago to Key Largo is an approximately 7.5-hour combination of flight and shuttle. You can also drive; or do a combination of bus and shuttle. You'll lose 1 hour traveling from Chicago to Key Largo due to the time zone difference. Traveling from Chicago in June, expect Key Largo to be somewhat warmer, temps between 88°F and 75°F. Wrap up your sightseeing on the 10th (Wed) early enough to drive to Islamorada.

Things to do in Key Largo

Wildlife Parks Tours
Find places to stay Jun 8 — 10:
Highlights from your plan
Spiegel Grove ©
Spiegel Grove
Dolphins Plus Marine Mammal Responder ©

2
nights
Islamorada

Islamorada ©
Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Kick off your visit on the 11th (Thu): look for all kinds of wild species at Dolphin Research Center, then sample the tasty concoctions at Islamorada Brewery & Distillery, and then look for all kinds of wild species at Wildlife Areas. On the next day, glide through the air with a parasailing or paragliding tour, then identify plant and animal life at Crane Point Museum & Nature Center, and then look for all kinds of wild species at Sombrero Reef.

For maps, photos, traveler tips, and other tourist information, go to the Islamorada trip itinerary app .

Traveling by car from Key Largo to Islamorada takes an hour. Alternatively, you can do a combination of taxi and bus. Expect a daytime high around 90°F in June, and nighttime lows around 79°F. Wrap up your sightseeing on the 12th (Fri) to allow time to take a bus to Key West.

Things to do in Islamorada

Wildlife Parks Outdoors

Side Trip

Marathon
Find places to stay Jun 10 — 12:
Highlights from your plan
Dolphin Research Center ©
Dolphin Research Center
Crane Point Museum & Nature Center ©
Parasailing & Paragliding

3
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.
You'll get in some beach time at Bahia Honda State Park and Fort Zachary Taylor. Take a break from the city and head to Kayaking & Canoeing and Stand-Up Paddleboarding. And it doesn't end there: look for all kinds of wild species at Key West Butterfly & Nature Conservatory, glide through the air with a parasailing or paragliding tour, zoom along the surf with a waterskiing or jet-skiing adventure, and visit a coastal fixture at Key West Lighthouse and Keeper's Quarters Museum.

To see where to stay, maps, and tourist information, go to the Key West itinerary website .

Take a bus from Islamorada to Key West in 2 hours. Alternatively, you can drive. Expect a daytime high around 88°F in June, and nighttime lows around 79°F. Finish your sightseeing early on the 15th (Mon) so you can travel back home.

Things to do in Key West

Outdoors Adventure Tours

Side Trip

Bahia Honda State Park
Find places to stay Jun 12 — 15:
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
Kayaking & Canoeing

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