5 days in Florida Itinerary

5 days in Florida Itinerary

Created using Inspirock Florida trip builder

©
This plan was created by another user. Make it your plan

Route & dates

Start: Chicago
Fly:  5 h
1
Sanibel Island
— Few hours
Fly + Bus:  4 h
2
Marathon, Florida Keys
— 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

Sanibel Island
Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
On the 19th (Sun), relax and rejuvenate at some of the top local wellness centers.

For where to stay, more things to do, reviews, and more tourist information, go to the Sanibel Island trip 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. Traveling from Chicago in May, things will get a bit warmer in Sanibel Island: highs are around 90°F and lows about 69°F. Finish up your sightseeing early on the 19th (Sun) so you can travel to Marathon.

Things to do in Sanibel Island

Spas
Find places to stay May 19 — 20:

2
nights
Marathon, Florida Keys

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 20th (Mon), snap pictures at Old Seven Mile Bridge, take an in-depth tour of History of Diving Museum, and then sample the tasty concoctions at Florida Keys Brewing Company. Here are some ideas for day two: add some adventure to your tour with a kayaking and canoeing tour and then kick back and relax at Sunset Park Beach.

For where to stay, more things to do, traveler tips, and more tourist information, use the Marathon planning app.

Getting from Sanibel Island to Marathon by combination of flight and bus takes about 4 hours. Other options: drive; or do a combination of ferry and bus. Traveling from Sanibel Island in May, Marathon is a bit warmer at night with lows of 77°F. Cap off your sightseeing on the 21st (Tue) early enough to travel to St. Augustine.

Things to do in Marathon

Outdoors Tours Adventure

Side Trips

Islamorada, Sunset Park Beach
Find places to stay May 19 — 21:
Highlights from your plan
Sunset Park Beach ©
Sunset Park Beach
Florida Keys Brewing Company ©
Florida Keys Brewing Company
History of Diving Museum ©
History of Diving Museum

1
day
St. Augustine

St. Augustine ©
St. Start off your visit on the 22nd (Wed): take in the history at Mission of Nombre de Dios, kick back and relax at Vilano Beach, and then get a new perspective on things with Boat Tours & Water Sports.

To find more things to do, other places to visit, ratings, and tourist information, read our St. Augustine trip itinerary website.

Traveling by combination of shuttle, flight, and car from Marathon to St. Augustine takes 6.5 hours. Alternatively, you can drive; or do a combination of shuttle, flight, and bus. Plan for slightly colder temperatures traveling from Marathon in May, with highs in St. Augustine at 83°F and lows at 67°F. Wrap up your sightseeing on the 22nd (Wed) early enough to take a bus to Daytona Beach.

Things to do in St. Augustine

Outdoors Beaches Parks
Find places to stay May 21 — 22:
Highlights from your plan
Vilano Beach ©
Vilano Beach
Mission of Nombre de Dios ©
Mission of Nombre de Dios
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.
On the 23rd (Thu), identify plant and animal life 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 other places to visit, maps, more things to do, and more tourist information, go to the Daytona Beach day trip planning app.

You can take a bus from St. Augustine to Daytona Beach in an hour. Alternatively, you can drive. May in Daytona Beach sees daily highs of 85°F and lows of 66°F at night. Wrap up your sightseeing on the 23rd (Thu) to allow time to travel back home.

Things to do in Daytona Beach

Parks Beaches Outdoors

Side Trips

Dunlawton Sugar Mill Gardens, Andy Romano Beachfront Park
Find places to stay May 22 — 23:
Highlights from your plan
Dunlawton Sugar Mill Gardens ©
Dunlawton Sugar Mill Gardens
Jackie Robinson Ballpark and Statue ©
Jackie Robinson Ballpark and Statue

Similar Plans

9 days in Florida & Grand Bahama Island BY A USER FROM CANADA April, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems Preferences: April, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium 6 days in Florida BY A USER FROM UNITED STATES October, culture, outdoors, relaxing, romantic, beaches, historic sites, shopping, popular sights Preferences: October, culture, outdoors, relaxing, romantic, beaches, historic sites, shopping Attraction style: Popular sights Pace: Medium 8 days in Florida BY A USER FROM SWEDEN July, outdoors, beaches, historic sites, shopping, wildlife, popular sights Preferences: July, outdoors, beaches, historic sites, shopping, wildlife Attraction style: Popular sights Pace: Medium 7 days in Florida BY A USER FROM UNITED ARAB EMIRATES July, culture, outdoors, relaxing, romantic, beaches, historic sites, shopping, wildlife, slow & easy, popular sights Preferences: July, culture, outdoors, relaxing, romantic, beaches, historic sites, shopping, wildlife Attraction style: Popular sights Pace: Slow & easy 7 days in Florida BY A USER FROM UNITED STATES April, teens, outdoors, beaches, shopping, popular & hidden gems Preferences: April, teens, outdoors, beaches, shopping Attraction style: Popular & hidden gems Pace: Medium 7 days in Texas & Florida BY A USER FROM TURKEY June, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular sights Preferences: June, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular sights Pace: Medium 6 days in Florida BY A USER FROM UNITED STATES July, outdoors, relaxing, romantic, beaches, museums, shopping, wildlife, popular & hidden gems Preferences: July, outdoors, relaxing, romantic, beaches, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium 4 days in Florida BY A USER FROM PUERTO RICO July, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, fast-paced, popular & hidden gems Preferences: July, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Fast-paced 15 days in Florida BY A USER FROM DENMARK August, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems Preferences: August, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium 22 days in Florida BY A USER FROM SWITZERLAND December, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights Preferences: December, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular sights Pace: Medium 15 days in Florida BY A USER FROM FRENCH GUIANA May, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems Preferences: May, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife Attraction style: Popular & hidden gems Pace: Medium 15 days in Florida BY A USER FROM UNITED STATES July, teens, kids, culture, outdoors, beaches, historic sites, museums, popular sights Preferences: July, teens, kids, culture, outdoors, beaches, historic sites, museums Attraction style: Popular sights Pace: Medium
See more plans