14 days in Florida Itinerary

14 days in Florida Itinerary

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Route & dates

14 days in Florida Itinerary

Start: Chicago
Fly:  4​h 15​min
1
Tampa
— Few hours
Drive:  1​h 15​min
2
Sarasota
— 2 nights
Drive:  4​h 15​min
3
St. Augustine
— 2 nights
Drive + Fly:  5​h 15​min
4
Miami Beach
— 1 night
Drive:  2​h 30​min
5
Marco Island
— 2 nights
Drive:  5​h 15​min
6
Daytona Beach
— 2 nights
Drive:  3​h 15​min
7
West Palm Beach
— 3 nights
Fly:  5​h
End: Chicago

few
hours
Tampa

Tampa ranks among the country's most livable cities, attracting newcomers with its growing economy and status as a major port on the Gulf of Mexico.
To find reviews, traveler tips, maps, and tourist information, you can read our Tampa trip itinerary planner.

Chicago to Tampa is an approximately 4.5-hour flight. You can also drive; or take a bus. The time zone changes from Central Standard Time (CST) to Eastern Standard Time (EST), which is usually a 1 hour difference. Expect somewhat warmer temperatures when traveling from Chicago in September; daily highs in Tampa reach 90°F and lows reach 76°F. Cap off your sightseeing on the 29th (Sat) early enough to go by car to Orlando.

Things to do in Tampa

Fun & Games Historic Sites
Highlights from your plan
Room Escape Games
Sacred Heart Catholic Church ©
Sacred Heart Catholic Church

2
nights
Sarasota

Sarasota ©
Sarasota is a city in Sarasota County on the southwestern coast of the U.S. Start off your visit on the 30th (Sun): meet the residents at Mote Marine Laboratory and Aquarium and then tour the pleasant surroundings at Siesta Beach. Get ready for a full day of sightseeing on the 1st (Mon): admire the masterpieces at The Ringling and then make a trip to St. Armands Circle.

To find photos, reviews, maps, and more tourist information, use the Sarasota trip planning tool .

Drive from Tampa to Sarasota in 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 89°F in September, and nighttime lows around 74°F. Wrap up your sightseeing on the 1st (Mon) early enough to drive to St. Augustine.

Things to do in Sarasota

Parks Shopping Beaches

Side Trip

Siesta Beach
Highlights from your plan
Siesta Beach ©
Siesta Beach
The Ringling ©
The Ringling
Mote Marine Laboratory and Aquarium ©

2
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Kick off your visit on the 2nd (Tue): brush up on your knowledge of spirits at St. Augustine Distillery, enjoy the sea views from St. Augustine Lighthouse & Maritime Museum, and then contemplate the long history of Castillo de San Marcos. Get ready for a full day of sightseeing on the next day: explore and take pictures at Flagler College, examine the collection at The Ximenez-Fatio House, and then stroll through St. Augustine Beach.

For ratings, photos, maps, and more tourist information, go to the St. Augustine holiday builder tool .

Drive from Sarasota to St. Augustine in 4.5 hours. Alternatively, you can take a bus; or do a combination of bus and flight. Traveling from Sarasota in October, you will find days in St. Augustine are slightly colder (80°F), and nights are about the same (67°F). Cap off your sightseeing on the 3rd (Wed) early enough to go by car to Miami Beach.

Things to do in St. Augustine

Beaches Parks Outdoors
Highlights from your plan
St. Augustine Beach ©
St. Augustine Beach
Flagler College ©
Flagler College

1
night
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.
On the 4th (Thu), enjoy the sand and surf at South Beach, appreciate the extensive heritage of Art Deco Historic District, and then take a stroll through Lincoln Road.

To see other places to visit, more things to do, traveler tips, and other tourist information, use the Miami Beach trip planner .

You can drive from St. Augustine to Miami Beach in 5.5 hours. Alternatively, you can do a combination of bus, flight, and tram; or do a combination of bus, flight, and train. In October, Miami Beach is a bit warmer than St. Augustine - with highs of 87°F and lows of 74°F. Wrap up your sightseeing on the 4th (Thu) to allow time to drive to Marco Island.

Things to do in Miami Beach

Neighborhoods Historic Sites Parks
Highlights from your plan
Lincoln Road ©
Lincoln Road
South Beach ©
South Beach
Art Deco Historic District ©
Art Deco Historic District

2
nights
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. Kick off your visit on the 5th (Fri): get interesting insight from Tours and then take a memorable tour with Tours. Here are some ideas for day two: take a memorable tour with Tours and then take a memorable tour with Tours.

For traveler tips, ratings, reviews, and more tourist information, go to the Marco Island trip builder .

You can drive from Miami Beach to Marco Island in 2.5 hours. Other options are to do a combination of bus and taxi; or do a combination of bus and taxi. Traveling from Miami Beach in October, you can expect nighttime temperatures to be a bit cooler in Marco Island, with lows of 68°F. Cap off your sightseeing on the 6th (Sat) early enough to travel back home.

Things to do in Marco Island

Tours Outdoors Adventure

Side Trip

Everglades City
Highlights from your plan
Parasailing & Paragliding
Waterskiing & Jetskiing
Speed Boats Tours

2
nights
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 7th (Sun): enjoy breathtaking views from Ponce de Leon Inlet Lighthouse & Museum, then explore and take pictures at Dunlawton Sugar Mill Gardens, and then kick back and relax at Beach at Daytona Beach. On the 8th (Mon), you'll have a packed day of sightseeing: steep yourself in history at Stetson Mansion and then explore and take pictures at Daytona International Speedway.

To find photos, reviews, more things to do, and tourist information, use the Daytona Beach day trip planning tool .

You can drive from Marco Island to Daytona Beach in 5.5 hours. Other options are to do a combination of taxi, bus, flight, and shuttle; or do a combination of taxi and bus. In October, daytime highs in Daytona Beach are 83°F, while nighttime lows are 67°F. Wrap up your sightseeing by early afternoon on the 9th (Tue) to allow time for travel back home.

Things to do in Daytona Beach

Historic Sites Parks Beaches

Side Trips

Ponce de Leon Inlet Lighthouse & Museum, Dunlawton Sugar Mill Gardens, Stetson Mansion
Highlights from your plan
Stetson Mansion ©
Stetson Mansion
Beach at Daytona Beach ©
Beach at Daytona Beach
Daytona International Speedway ©
Daytona International Speedway

3
nights
West Palm Beach

West Palm Beach ©
With a warm climate and sandy stretches, it's no surprise that West Palm Beach is a popular vacation spot.
On the next day, identify plant and animal life at Lion Country Safari and then buy something for everyone on your list at CityPlace.

To see other places to visit, reviews, ratings, and other tourist information, read West Palm Beach trip maker tool .

You can drive from Daytona Beach to West Palm Beach in 3.5 hours. Other options are to do a combination of shuttle, flight, and bus; or take a bus. Traveling from Daytona Beach in October, expect a bit warmer with lows of 73°F in West Palm Beach. Wrap up your sightseeing by early afternoon on the 12th (Fri) to allow enough time to travel back home.

Things to do in West Palm Beach

Wildlife Parks Shopping

Side Trips

Lion Country Safari, Henry Morrison Flagler Museum, Loggerhead Marinelife Center
Highlights from your plan
Lion Country Safari ©
Lion Country Safari
Loggerhead Marinelife Center ©
Loggerhead Marinelife Center
Henry Morrison Flagler Museum ©
Henry Morrison Flagler Museum

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