28 days in Florida Itinerary
Created using Klarna Trips Florida holiday planner
Start: Chicago
Fly
1
Orlando
— 4 nights
Drive
2
St. Augustine
— 2 nights
Fly
3
Key Largo
— 3 nights
Drive
4
Islamorada
— 3 nights
Drive
5
Marathon
— 4 nights
Drive
6
Key West
— 5 nights
Fly
7
Everglades National Park
— 3 nights
Bus
8
Miami
— 3 nights
Fly
End: Chicago
Mon, Apr 3 - Sun, Apr 30
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Orlando — 4 nights

Theme Park Capital of the World
Have a day of magic on the 4th (Tue) at Walt Disney World Resort. Pack the 6th (Thu) with family-friendly diversions at Universal's Islands of Adventure. There's lots more to do: get in on the family fun at Universal Orlando Resort, test your problem-solving skills at popular escape rooms, discover the magic at Epcot, and explore the world behind art at Museum Of Illusions Orlando.
For traveler tips, reviews, photos, and more tourist information, read Orlando trip planner.
Chicago to Orlando is an approximately 4.5-hour flight. You can also drive; or take a bus. Due to the time zone difference, you'll lose 1 hour traveling from Chicago to Orlando. Prepare for much hotter weather when traveling from Chicago in April: high temperatures in Orlando hover around 84°F and lows are around 65°F. Wrap up your sightseeing on the 7th (Fri) early enough to drive to St. Augustine.
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For traveler tips, reviews, photos, and more tourist information, read Orlando trip planner.
Chicago to Orlando is an approximately 4.5-hour flight. You can also drive; or take a bus. Due to the time zone difference, you'll lose 1 hour traveling from Chicago to Orlando. Prepare for much hotter weather when traveling from Chicago in April: high temperatures in Orlando hover around 84°F and lows are around 65°F. Wrap up your sightseeing on the 7th (Fri) early enough to drive to St. Augustine.
Find places to stay Apr 3 — 7:
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St. Augustine — 2 nights

On the 8th (Sat), gain insight at Flagler College, then test your team's savvy at popular escape rooms, then learn about wildlife with up-close encounters at St. Augustine Wild Reserve, and finally look for all kinds of wild species at Wildlife Areas. On the 9th (Sun), you'll have a packed day of sightseeing: step into the grandiose world of Castillo de San Marcos National Monument, then take a tour by water with Boat Tours & Water Sports, and then brush up on your knowledge of spirits at St. Augustine Distillery.
To find where to stay, more things to do, photos, and tourist information, read our St. Augustine road trip planner.
You can drive from Orlando to St. Augustine in 2 hours. Another option is to take a bus. Traveling from Orlando in April, expect nights in St. Augustine to be about the same, around 62°F, while days are slightly colder, around 78°F. Finish up your sightseeing early on the 9th (Sun) so you can catch the flight to Key Largo.
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To find where to stay, more things to do, photos, and tourist information, read our St. Augustine road trip planner.
You can drive from Orlando to St. Augustine in 2 hours. Another option is to take a bus. Traveling from Orlando in April, expect nights in St. Augustine to be about the same, around 62°F, while days are slightly colder, around 78°F. Finish up your sightseeing early on the 9th (Sun) so you can catch the flight to Key Largo.
Side Trip
Find places to stay Apr 7 — 9:
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Key Largo — 3 nights
©
Diving Capital of the World
Key Largo is known for wildlife, nature, and adventure. Your trip includes some of its best attractions: take a tour by water with Boat Tours & Water Sports, relax and rejuvenate at some of the best spas, look for all kinds of wild species at Florida Keys Wild Bird Rehabilitation Center, and admire the majestic nature at John Pennekamp Coral Reef State Park.
To see where to stay, other places to visit, reviews, and more tourist information, go to the Key Largo trip maker site.
You can fly from St. Augustine to Key Largo in 3 hours. Alternatively, you can drive; or take a bus. Expect somewhat warmer evenings in Key Largo when traveling from St. Augustine in April, with lows around 69°F. Wrap up your sightseeing on the 12th (Wed) early enough to drive to Islamorada.
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To see where to stay, other places to visit, reviews, and more tourist information, go to the Key Largo trip maker site.
You can fly from St. Augustine to Key Largo in 3 hours. Alternatively, you can drive; or take a bus. Expect somewhat warmer evenings in Key Largo when traveling from St. Augustine in April, with lows around 69°F. Wrap up your sightseeing on the 12th (Wed) early enough to drive to Islamorada.
Find places to stay Apr 9 — 12:
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Islamorada — 3 nights

The Village of Islands
Islamorada is known for wildlife, adventure, and museums. Your trip includes some of its best attractions: fulfill a lifelong dream with Theater of the Sea, view the masterpieces at Lobster Trap Art Gift Shop and Gallery, sample the tasty concoctions at Islamorada Brewery & Distillery - MM82, and step off the mainland to explore Windley Key.
To find ratings, reviews, and other tourist information, use the Islamorada trip planning website.
Islamorada is just a stone's throw from Key Largo. Expect a bit warmer evenings in Islamorada when traveling from Key Largo in April, with lows around 75°F. Wrap up your sightseeing on the 15th (Sat) to allow time to drive to Marathon.
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To find ratings, reviews, and other tourist information, use the Islamorada trip planning website.
Islamorada is just a stone's throw from Key Largo. Expect a bit warmer evenings in Islamorada when traveling from Key Largo in April, with lows around 75°F. Wrap up your sightseeing on the 15th (Sat) to allow time to drive to Marathon.
Find places to stay Apr 12 — 15:
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Marathon — 4 nights

Heart of the Florida Keys
Venture out of the city with trips to Fishing Charters & Tours (in Big Pine Key), SpaTerre at Little Palm Island Resort (in Little Torch Key) and Everglades National Park (in Florida City). There's lots more to do: kick back and relax at Bahia Honda State Park, pause for some serene contemplation at San Pablo Catholic Church, shop like a local with Paradise Produce, and tour the pleasant surroundings at Sombrero Beach.
To find other places to visit, more things to do, maps, and tourist information, read our Marathon itinerary website.
Traveling by car from Islamorada to Marathon takes an hour. Alternatively, you can take a bus. In April, daily temperatures in Marathon can reach 86°F, while at night they dip to 75°F. Finish your sightseeing early on the 19th (Wed) so you can drive to Key West.
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To find other places to visit, more things to do, maps, and tourist information, read our Marathon itinerary website.
Traveling by car from Islamorada to Marathon takes an hour. Alternatively, you can take a bus. In April, daily temperatures in Marathon can reach 86°F, while at night they dip to 75°F. Finish your sightseeing early on the 19th (Wed) so you can drive to Key West.
Side Trips
Find places to stay Apr 15 — 19:
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Key West — 5 nights

Conch Republic
Spend the 21st (Fri) exploring nature at Dry Tortugas National Park. There's lots more to do: see the interesting displays at The Ernest Hemingway Home and Museum, steep yourself in history at Truman Little White House, see some colorful creatures with a scuba or snorkeling tour, and get a taste of the local shopping with Alan S. Maltz Gallery.
To see maps, ratings, and tourist information, refer to the Key West holiday planner.
Getting from Marathon to Key West by car takes about 1.5 hours. Other options: take a bus. In April, plan for daily highs up to 83°F, and evening lows to 74°F. Wrap up your sightseeing on the 24th (Mon) early enough to fly to Everglades National Park.
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To see maps, ratings, and tourist information, refer to the Key West holiday planner.
Getting from Marathon to Key West by car takes about 1.5 hours. Other options: take a bus. In April, plan for daily highs up to 83°F, and evening lows to 74°F. Wrap up your sightseeing on the 24th (Mon) early enough to fly to Everglades National Park.
Find places to stay Apr 19 — 24:
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Everglades National Park — 3 nights

Largest Subtropical Wilderness in the United States
Everglades National Park is known for wildlife, trails, and nature. Your trip includes some of its best attractions: identify plant and animal life at Shark Valley Visitor Center, contemplate the waterfront views at Mrazek Pond, trek along Pa-hay-okee Trail, and stroll through Gumbo Limbo Trail.
Quickly create a custom-made itinerary for Everglades National Park using our trip planner.
Traveling by flight from Key West to Everglades National Park takes 2.5 hours. Alternatively, you can take a bus; or take a bus. April in Everglades National Park sees daily highs of 86°F and lows of 75°F at night. Finish up your sightseeing early on the 27th (Thu) so you can catch the bus to Miami.
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Quickly create a custom-made itinerary for Everglades National Park using our trip planner.
Traveling by flight from Key West to Everglades National Park takes 2.5 hours. Alternatively, you can take a bus; or take a bus. April in Everglades National Park sees daily highs of 86°F and lows of 75°F at night. Finish up your sightseeing early on the 27th (Thu) so you can catch the bus to Miami.
Find places to stay Apr 24 — 27:
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Miami — 3 nights

Magic City
Explore Miami's surroundings by going to Florida Airboat Rides (in Boca Raton), Panther Ridge Conservation Center (in Wellington) and Aventura Mall (in Aventura). And it doesn't end there: stroll around Lincoln Road, take an in-depth tour of Black Police Precinct and Courthouse Museum, get the lay of the land with Walking tours, and take in nature's colorful creations at Fairchild Tropical Botanic Garden.
To see other places to visit, maps, where to stay, and more tourist information, use the Miami trip itinerary planner.
Traveling by bus from Everglades National Park to Miami takes 1.5 hours. Alternatively, you can take a train. Expect a daytime high around 85°F in April, and nighttime lows around 71°F. Cap off your sightseeing on the 30th (Sun) early enough to catch the flight back home.
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To see other places to visit, maps, where to stay, and more tourist information, use the Miami trip itinerary planner.
Traveling by bus from Everglades National Park to Miami takes 1.5 hours. Alternatively, you can take a train. Expect a daytime high around 85°F in April, and nighttime lows around 71°F. Cap off your sightseeing on the 30th (Sun) early enough to catch the flight back home.
Side Trips
Miami Beach, Fairchild Tropical Botanic Garden, Florida Airboat Rides, Panther Ridge Conservation Center, Aventura Mall
Find places to stay Apr 27 — 30:
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Florida travel guide
The Sunshine State
The “Sunshine State,” Florida became a favorite winter destination for the affluent crowd over a century ago. Today, the state attracts visitors from around the world with its golden beaches and modern theme parks. You can spend your entire vacation enjoying the state's highly developed seaside areas, but remember that some of Florida's best-kept secrets are in secluded locations. Visit the big cities and their comfortable resorts offering top-notch dining and nightlife, but leave some time to see the peninsula's swampy landscape, filled with wild creatures and native plants. Farther away from the tourist-packed urban areas, the untamed wetlands of Florida offer a selection of things to do, such as kayaking, boat rides, and numerous other outdoor activities.