28 days in Florida Itinerary

28 days in Florida Itinerary

Created using Inspirock United States travel planner

Make it your trip
Fly
1
Orlando
— 5 nights
Drive
2
St. Pete Beach
— 5 nights
Drive
3
Clearwater
— 1 day
Drive
4
Tampa
— 4 nights
Drive
5
Anna Maria
— 1 day
Drive
6
Siesta Key
— 6 nights
Unknown
7
Key West
— 7 nights
Fly

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Orlando

— 5 nights

Theme Park Capital of the World

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.
Your day by day itinerary now includes SeaWorld, The Wheel at ICON Park, Orlando International Premium Outlets, and other attractions you added.

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

Milwaukee to Orlando is an approximately 5.5-hour flight. You can also fly; or drive; or do a combination of bus and subway. The time zone difference when traveling from Milwaukee to Orlando is 1 hour. In April, Orlando is warmer than Milwaukee - with highs of 84°F and lows of 65°F. You will leave for St. Pete Beach on the 26th (Sun).

Things to do in Orlando

Theme Parks · Outdoors · Beaches · Parks

Side Trips

St. Pete Beach

— 5 nights
St. St. Pete Beach is known for beaches, wildlife, and adventure. Your plan includes some of its best attractions: explore the world behind art at The Dali Museum, kick back and relax at Upham Beach, take a leisurely stroll along John's Pass Village & Boardwalk, and tour the pleasant surroundings at Saint Pete Beach.

To find reviews, photos, and more tourist information, you can read our St. Pete Beach online trip planner.

You can drive from Orlando to St. Pete Beach in 2.5 hours. Another option is to do a combination of train and taxi. In April, plan for daily highs up to 82°F, and evening lows to 69°F. You'll have a few hours on the 1st (Fri) to wrap things up before traveling to Clearwater.

Things to do in St. Pete Beach

Beaches · Parks · Outdoors · Museums

Side Trips

Clearwater

— 1 day

Fun and Sun for All

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.
You've now added Clearwater Beach to your itinerary. On the 1st (Fri), kick back and relax at Clearwater Beach.

To see photos, ratings, reviews, and tourist information, you can read our Clearwater trip itinerary maker tool.

Traveling by car from St. Pete Beach to Clearwater takes an hour. Alternatively, you can take a bus. In May in Clearwater, expect temperatures between 87°F during the day and 70°F at night. Finish your sightseeing early on the 1st (Fri) to allow enough time to drive to Tampa.

Things to do in Clearwater

Beaches · Parks · Outdoors
Highlights from your trip

Tampa

— 4 nights

Big Guava

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.
Your day by day itinerary now includes Seminole Hard Rock Casino Tampa, Busch Gardens Tampa Bay and Channelside Bay Plaza.

To find maps, reviews, where to stay, and tourist information, use the Tampa vacation planner.

Drive from Clearwater to Tampa in an hour. Alternatively, you can take a bus. In May, daytime highs in Tampa are 89°F, while nighttime lows are 71°F. You will have some time to spend on the 5th (Tue) before leaving for Anna Maria.

Things to do in Tampa

Theme Parks · Fun & Games · Casinos · Shopping

Anna Maria

— 1 day
Anna Maria, is a city in Manatee County, Florida, United States. Your day by day itinerary now includes Bridge Street Pier as well as Beach Bums Island Attitude. Start off your visit on the 5th (Tue): head outdoors with Beach Bums Island Attitude, kick back and relax at Bean Point, and then take in the waterfront at Bridge Street Pier.

For other places to visit, ratings, maps, and tourist information, refer to the Anna Maria visit planner.

Traveling by car from Tampa to Anna Maria takes 1.5 hours. In May, plan for daily highs up to 87°F, and evening lows to 68°F. Cap off your sightseeing on the 5th (Tue) early enough to go by car to Siesta Key.

Things to do in Anna Maria

Outdoors · Beaches · Parks

Side Trips

Siesta Key

— 6 nights
Siesta Key draws most of its visitors with soft, white-quartz sand beaches and translucent ocean water.
You've added Crescent Beach, Legacy Trail, Siesta Key Village, and other attractions to your itinerary. There's more to do: browse the different shops at St. Armands Circle.

To find other places to visit, maps, and more tourist information, go to the Siesta Key trip tool.

Traveling by car from Anna Maria to Siesta Key takes 1.5 hours. Alternatively, you can drive. In May, daytime highs in Siesta Key are 87°F, while nighttime lows are 68°F. You will have some time to spend on the 11th (Mon) before leaving for Key West.

Things to do in Siesta Key

Outdoors · Parks · Beaches · Nightlife

Side Trip

Key West

— 7 nights

Conch Republic

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.
You've added Aqua Nightclub, Bourbon Street Pub, Hard Rock Cafe, and other attractions to your itinerary. There's still lots to do: take in the waterfront at Mallory Square, explore the wealth of natural beauty at Dry Tortugas National Park, and don't miss a visit to Duval Street.

For more things to do, photos, and tourist information, go to the Key West online trip itinerary maker.

You can ride a ferry from Siesta Key to Key West in 4 hours. Alternatively, you can fly; or drive; or do a combination of bus, taxi, and ferry. Traveling from Siesta Key in May, plan for a bit warmer nights in Key West, with lows around 77°F. Wrap up your sightseeing on the 18th (Mon) to allow time to travel back home.

Things to do in Key West

Nightlife · Parks · Beaches · Outdoors

Florida travel guide

4.4
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.

Anna Maria Island travel guide

4.8
Beaches · Fishing Charters & Tours · Piers & Boardwalks