8 days in Florida Itinerary

8 days in Florida Itinerary

Created using Inspirock Florida vacation planner

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Route & dates

8 days in Florida Itinerary

Start: Chicago
Fly + taxi:  6​h
1
Destin
— 1 night
Drive:  6​h 15​min
2
St. Augustine
— 1 night
+2
Drive + Fly + shuttle:  7​h 30​min
3
Marathon
— 1 day
Drive:  4​h
4
Marco Island
— 1 night
Drive:  1​h 30​min
5
Sanibel Island
— 2 nights
Fly:  5​h
End: Chicago

1
night
Destin

Destin ©
With emerald water and white beaches, Destin is one of America's favorite vacation destinations.
On the 15th (Wed), get some thrills on the water with a speed boat tour.

To see photos, maps, more things to do, and tourist information, refer to the Destin trip planning site .

Chicago to Destin is an approximately 6-hour combination of flight and taxi. You can also do a combination of flight and bus; or drive. Plan for a bit warmer temperatures traveling from Chicago in August, with highs in Destin at 91°F and lows at 78°F. Wrap up your sightseeing on the 16th (Thu) early enough to drive to St. Augustine.

Things to do in Destin

Beaches Parks Nature

Side Trip

Air Force Armament Museum
Highlights from your plan
Henderson Beach State Park ©
Henderson Beach State Park
Air Force Armament Museum ©
Air Force Armament Museum

1
night
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 17th (Fri): examine the collection at St. Augustine Pirate & Treasure Museum, then tour the pleasant surroundings at St. Augustine Beach, then examine the collection at The Lightner Museum, and finally take an in-depth tour of Medieval Torture Collection. On your second day here, admire all the interesting features of Fort Matanzas National Monument.

To see where to stay, reviews, photos, and tourist information, read our St. Augustine online vacation maker .

Traveling by car from Destin to St. Augustine takes 6.5 hours. Alternatively, you can do a combination of taxi, flight, and bus; or do a combination of bus and flight. Traveling from Destin to St. Augustine, you'll lose 1 hour due to the time zone difference. August in St. Augustine sees daily highs of 89°F and lows of 75°F at night. Finish up your sightseeing early on the 18th (Sat) so you can go by car to Marathon.

Things to do in St. Augustine

Parks Nature Historic Sites
Highlights from your plan
St. Augustine Beach ©
St. Augustine Beach
Medieval Torture Collection ©
Medieval Torture Collection
St. Augustine Pirate & Treasure Museum ©

1
day
Marathon

Marathon ©
A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
On the 19th (Sun), enjoy the sand and surf at Sombrero Beach, then look for all kinds of wild species at The Turtle Hospital, and then immerse yourself in nature at Bahia Honda State Park.

For ratings, traveler tips, more things to do, and other tourist information, go to the Marathon online route planner .

You can drive from St. Augustine to Marathon in 7.5 hours. Other options are to do a combination of bus, flight, and shuttle; or do a combination of bus and flight. In August, daytime highs in Marathon are 92°F, while nighttime lows are 80°F. Cap off your sightseeing on the 19th (Sun) early enough to go by car to Marco Island.

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
Sombrero Beach ©
Sombrero Beach
The Turtle Hospital ©
The Turtle Hospital

1
night
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 20th (Mon): view the masterpieces at Malenda Trick Art Gallery, then glide through the air with a parasailing or paragliding tour, and then get some thrills out on the water with a waterskiing or jet-skiing adventure.

To see other places to visit, traveler tips, where to stay, and more tourist information, use the Marco Island driving holiday planner .

Getting from Marathon to Marco Island by car takes about 4 hours. Other options: do a combination of bus and ferry. In August, daytime highs in Marco Island are 92°F, while nighttime lows are 76°F. Wrap up your sightseeing on the 20th (Mon) to allow time to drive to Sanibel Island.

Things to do in Marco Island

Adventure Tours Outdoors
Highlights from your plan
Waterskiing & Jetskiing
Parasailing & Paragliding

2
nights
Sanibel Island

Sanibel Island ©
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
Kick off your visit on the 21st (Tue): take in nature's colorful creations at In The Garden, then stroll through Bowman's Beach, and then tour the pleasant surroundings at Captiva Beach. Here are some ideas for day two: enjoy the sea views from Sanibel Island Lighthouse, enjoy the sand and surf at Fort Myers Beach, and then see the interesting displays at The Bailey-Matthews National Shell Museum.

For traveler tips, ratings, photos, and tourist information, you can read our Sanibel Island trip itinerary planning website .

You can drive from Marco Island to Sanibel Island in 1.5 hours. Another option is to do a combination of bus and taxi. In August in Sanibel Island, expect temperatures between 92°F during the day and 75°F at night. Finish up your sightseeing early on the 22nd (Wed) so you can travel back home.

Things to do in Sanibel Island

Parks Beaches Outdoors

Side Trips

Fort Myers Beach, Captiva Beach
Highlights from your plan
Bowman's Beach ©
Bowman's Beach
Fort Myers Beach ©
Fort Myers Beach
Captiva Beach ©
Captiva Beach

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