28 days in Florida Itinerary

28 days in Florida Itinerary

Created using Inspirock Florida trip itinerary planner
Make it your trip
Fly
1
Orlando
— 1 night
Drive
2
Tampa
— 3 nights
Drive
3
Orlando
— 6 nights
Drive
4
Clearwater
— 2 nights
Drive
5
Sanibel Island
— 2 nights
Drive
6
Miami
— 3 nights
Drive
7
Key Largo
— 2 nights
Drive
8
Islamorada
— 2 nights
Drive
9
Marathon
— 3 nights
Drive
10
Key West
— 3 nights
Fly

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Orlando — 1 night

For most people, any mention of Orlando immediately conjures up images of sprawling theme parks filled with characters plucked right out of popular animated movies.
Kick off your visit on the 12th (Sun): buy something for everyone on your list at Disney Springs, discover the magic at Disney's Typhoon Lagoon Water Park, and then stop by M&M's Disney Springs. On the next day, examine the collection at Madame Tussauds Orlando, then discover the magic at Disney’s Blizzard Beach Water Park, and then get outside with Outdoor Activities.

To see photos, other places to visit, where to stay, and tourist information, go to the Orlando trip maker tool.

Milwaukee to Orlando is an approximately 4.5-hour flight. You can also drive; or take a bus. The time zone difference moving from Central Standard Time (CST) to Eastern Standard Time (EST) is 1 hour. Prepare for somewhat warmer weather when traveling from Milwaukee in June: high temperatures in Orlando hover around 91°F and lows are around 73°F. Finish your sightseeing early on the 13th (Mon) so you can drive to Tampa.
Theme Parks · Shopping · Museums · Tours
Side Trip

Tampa — 3 nights

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.
Start off your visit on the 14th (Tue): learn about wildlife with up-close encounters at ZooTampa at Lowry Park and then get a new perspective on things with Boat Tours & Water Sports. Keep things going the next day: find something for the whole family at Busch Gardens Tampa Bay.

To see reviews, more things to do, traveler tips, and other tourist information, read our Tampa trip planning site.

You can drive from Orlando to Tampa in 1.5 hours. Other options are to take a bus; or take a train. In June, daytime highs in Tampa are 91°F, while nighttime lows are 76°F. Finish your sightseeing early on the 16th (Thu) so you can drive to Orlando.
Theme Parks · Parks · Wildlife · Tours
Side Trip

Orlando — 6 nights

Attractions like Universal Orlando Resort and Discovery Cove make great kid-friendly stops. Have a day of magic on the 16th (Thu) at Walt Disney World Resort. Pack the 17th (Fri) with family-friendly diversions at Universal's Islands of Adventure. Enjoy Orlando some more: get in on the family fun at SeaWorld, discover the magic at Epcot, take an unforgettable tour with a helicopter tour, and tee off at Pirate's Cove Adventure Golf.

For where to stay, more things to do, other places to visit, and more tourist information, use the Orlando trip planner.

Getting from Tampa to Orlando by car takes about 1.5 hours. Other options: take a bus; or take a train. Finish your sightseeing early on the 22nd (Wed) so you can drive to Clearwater.
Theme Parks · Outdoors · Golf · Tours

Clearwater — 2 nights

Holding the record for most consecutive days of sunshine in a single year, Clearwater offers long sandy beaches and proximity to other major cities in the Tampa Bay area.
Start off your visit on the 23rd (Thu): get up close and personal with brilliant marine life at Clearwater Marine Aquarium, then get some thrills out on the water with a waterskiing or jet-skiing adventure, then take a leisurely stroll along Pier 60, and finally contemplate in the serene atmosphere at Church of Scientology Information Center. Get ready for a full day of sightseeing on the next day: take a leisurely stroll along John's Pass Village & Boardwalk and then kick back and relax at Clearwater Beach.

Before you visit Clearwater, use our trip planner to discover what you can do and see there.

You can drive from Orlando to Clearwater in 2 hours. Alternatively, you can do a combination of train and taxi; or take a bus. Expect a daytime high around 90°F in June, and nighttime lows around 75°F. Finish your sightseeing early on the 24th (Fri) to allow enough time to drive to Sanibel Island.
Parks · Outdoors · Beaches · Zoos & Aquariums
Side Trip

Sanibel Island — 2 nights

Take a trip to Sanibel Island if you like pretty sunsets and luxurious resorts.
Start off your visit on the 25th (Sat): explore and take pictures at Sanibel Causeway, then stop by Three Crafty Ladies, and then kick back and relax at Bowman's Beach. Get ready for a full day of sightseeing on the 26th (Sun): head outdoors with Outdoor Activities and then stroll through Captiva Beach.

To find more things to do, photos, traveler tips, and tourist information, read our Sanibel Island holiday builder.

Traveling by car from Clearwater to Sanibel Island takes 3 hours. Alternatively, you can do a combination of taxi and bus; or do a combination of flight, bus, and taxi. In June in Sanibel Island, expect temperatures between 91°F during the day and 74°F at night. Cap off your sightseeing on the 26th (Sun) early enough to go by car to Miami.
Outdoors · Parks · Beaches · Tours
Side Trip

Miami — 3 nights

Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
Attractions like Florida Airboat Rides and Lincoln Road make great kid-friendly stops. Get out of town with these interesting Miami side-trips: Wiener Museum of Decorative Arts (WMODA) (in Dania Beach) and Fort Lauderdale Beach (in Fort Lauderdale). Next up on the itinerary: stroll through South Beach, wander the streets of Espanola Way, appreciate the extensive heritage of Art Deco Historic District, and see the interesting displays at Vizcaya Museum and Gardens.

For traveler tips, where to stay, and more tourist information, use the Miami trip maker website.

Drive from Sanibel Island to Miami in 3.5 hours. Alternatively, you can do a combination of taxi and bus. In June, daily temperatures in Miami can reach 89°F, while at night they dip to 77°F. Wrap up your sightseeing on the 29th (Wed) to allow time to drive to Key Largo.
Outdoors · Parks · Beaches · Shopping
Side Trips

Key Largo — 2 nights

The northernmost island of the Florida Keys, Key Largo provides stunning scenery, a number of watersports opportunities, and plenty of areas to relax on vacation.
Here are some ideas for day two: admire the majestic nature at John Pennekamp Coral Reef State Park and then get outside with Outdoor Activities.

To see ratings, where to stay, more things to do, and more tourist information, you can read our Key Largo online tour planner.

Drive from Miami to Key Largo in 1.5 hours. Alternatively, you can take a bus. In June, daily temperatures in Key Largo can reach 88°F, while at night they dip to 75°F. Finish your sightseeing early on the 1st (Fri) so you can drive to Islamorada.
Wildlife · Parks · Tours · Outdoors

Islamorada — 2 nights

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Start off your visit on the 2nd (Sat): take an in-depth tour of History of Diving Museum, then sample the tasty concoctions at Islamorada Brewery & Distillery - MM82, and then fulfill a lifelong dream with Theater of the Sea. Get ready for a full day of sightseeing on the 3rd (Sun): enjoy the sand and surf at Anne's Beach and then tour the pleasant surroundings at Alligator Reef Light House.

For photos, traveler tips, ratings, and more tourist information, use the Islamorada trip itinerary builder tool.

Islamorada is very close to Key Largo. In July, daily temperatures in Islamorada can reach 92°F, while at night they dip to 81°F. Finish your sightseeing early on the 3rd (Sun) to allow enough time to drive to Marathon.
Wildlife · Parks · Outdoors · Tours

Marathon — 3 nights

A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Kids will enjoy Bahia Honda State Park and Scuba & Snorkeling. And it doesn't end there: kick back and relax at Sombrero Beach, snap pictures at Seven Mile Bridge, and stroll through Crane Point Museum & Nature Center.

To see traveler tips, reviews, and other tourist information, use the Marathon trip planner.

You can drive from Islamorada to Marathon in an hour. Another option is to take a bus. July in Marathon sees daily highs of 92°F and lows of 81°F at night. On the 6th (Wed), wrap the sightseeing up by early afternoon so you can drive to Key West.
Parks · Wildlife · Outdoors · Beaches
Side Trip

Key West — 3 nights

Located just 140 km (90 mi) from Cuba, Key West is an island only about 6.4 km (4 mi) long and 1.6 km (1 mi) wide.
On the 6th (Wed), shop like a local with Key West Local Luxe -Jewelry Store. On the 7th (Thu), you'll have a packed day of sightseeing: examine the collection at Mel Fisher Maritime Heritage Museum, see the interesting displays at The Ernest Hemingway Home and Museum, then stroll through Key West Butterfly & Nature Conservatory, and finally discover the deep blue sea with a scuba or snorkeling tour.

To see more things to do, photos, traveler tips, and tourist information, you can read our Key West trip itinerary site.

You can drive from Marathon to Key West in 1.5 hours. Another option is to take a bus. In July in Key West, expect temperatures between 89°F during the day and 81°F at night. On the 9th (Sat), you'll have the morning to explore before heading back home.
Parks · Wildlife · Museums · Tours

Florida travel guide

4.3
Disney Parks & Activities · Beaches · Theme Parks
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.

Florida Keys travel guide

4.3
Scuba & Snorkeling · Landmarks · Parasailing & Paragliding
An archipelago of about 1,700 islands extending in a gentle arc south and southwest of Florida's mainland, the Florida Keys divide the Atlantic from the Gulf of Mexico. Many visitors on vacation come to scuba dive in the coral reefs, fossilized and exposed as sea levels declined over thousands of years. In addition to being one of the world's top diving and fishing spots, the Keys feature hundreds of shops, restaurants, bars, and various tourist attractions, most of them crowded all year long with visitors on vacation. To soak up the Keys' atmosphere and discover writer Ernest Hemingway's former haunts, drive from one island to the other all the way to Key West, located just 140 km (90 mi) from Cuba.