5 days in Florida Itinerary

5 days in Florida Itinerary

Created using Inspirock Florida trip builder

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Route & dates

5 days in Florida Itinerary

Start: Chicago
Fly:  5​h
1
Sanibel Island
— Few hours
Fly + bus:  4​h
2
Marathon
— 2 nights
+2
shuttle + Fly + Drive:  6​h 15​min
3
St. Augustine
— 1 day
bus:  1​h
4
Daytona Beach
— 1 night
shuttle + Fly:  6​h
End: Chicago

few
hours
Sanibel Island

Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
For where to stay, photos, ratings, and more tourist information, refer to the Sanibel Island online tour itinerary planner .

Chicago to Sanibel Island is an approximately 5-hour flight. You can also do a combination of subway, bus, and flight; or drive. Due to the time zone difference, you'll lose 1 hour traveling from Chicago to Sanibel Island. In May, Sanibel Island is a bit warmer than Chicago - with highs of 90°F and lows of 69°F. Cap off your sightseeing on the 19th (Sun) early enough to travel to Marathon.

Things to do in Sanibel Island

Spas
Highlights from your plan
Spas & Wellness

2
nights
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 20th (Mon): take in the views from Old Seven Mile Bridge, take an in-depth tour of History of Diving Museum, and then indulge your thirst for a good beer at Florida Keys Brewing Company. On your second day here, paddle through the water with a kayaking and canoeing tour and then enjoy the sand and surf at Sunset Park Beach.

To see maps, ratings, reviews, and other tourist information, you can read our Marathon day trip planning tool .

Do a combination of flight and bus from Sanibel Island to Marathon in 4 hours. Alternatively, you can drive; or do a combination of ferry and bus. Expect somewhat warmer evenings in Marathon when traveling from Sanibel Island in May, with lows around 77°F. Wrap up your sightseeing on the 21st (Tue) to allow time to travel to St. Augustine.

Things to do in Marathon

Outdoors Tours Adventure

Side Trips

Islamorada, Sunset Park Beach
Highlights from your plan
Kayaking & Canoeing
Florida Keys Brewing Company ©
Florida Keys Brewing Company
History of Diving Museum ©
History of Diving Museum

1
day
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Start off your visit on the 22nd (Wed): take in the history at Mission of Nombre de Dios, stroll through Vilano Beach, and then get up close to creatures of the deep with a dolphin and whale watching tour.

To find ratings, maps, other places to visit, and tourist information, refer to the St. Augustine day trip planning site .

Getting from Marathon to St. Augustine by combination of shuttle, flight, and car takes about 6.5 hours. Other options: drive; or do a combination of shuttle, flight, and bus. Prepare for little chillier weather when traveling from Marathon in May: high temperatures in St. Augustine hover around 83°F and lows are around 67°F. Finish your sightseeing early on the 22nd (Wed) so you can take a bus to Daytona Beach.

Things to do in St. Augustine

Outdoors Parks Beaches
Highlights from your plan
Vilano Beach ©
Vilano Beach
Dolphin & Whale Watching

1
night
Daytona Beach

Daytona Beach ©
The iconic seaside destination of Daytona Beach once supported sugar mill plantations, but now entertains up to 8 million visitors a year.
Kick off your visit on the 23rd (Thu): admire the natural beauty at Dunlawton Sugar Mill Gardens, then appreciate the history behind Jackie Robinson Ballpark and Statue, and then kick back and relax at Andy Romano Beachfront Park.

For maps, traveler tips, ratings, and other tourist information, refer to the Daytona Beach day trip site .

You can take a bus from St. Augustine to Daytona Beach in an hour. Another option is to drive. In May, daily temperatures in Daytona Beach can reach 85°F, while at night they dip to 66°F. Finish your sightseeing early on the 23rd (Thu) to allow enough time to travel back home.

Things to do in Daytona Beach

Parks Outdoors Beaches

Side Trips

Andy Romano Beachfront Park, Dunlawton Sugar Mill Gardens
Highlights from your plan
Dunlawton Sugar Mill Gardens ©
Dunlawton Sugar Mill Gardens
Jackie Robinson Ballpark and Statue ©

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