28 days in Florida Itinerary

28 days in Florida Itinerary

Created using Inspirock United States travel planner

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

Route & dates

Start: Milwaukee
Fly:  3 h
1
Orlando
— 5 nights
Drive:  30 min
2
St. Pete Beach
— 5 nights
Drive:  1 h
3
Clearwater
— 1 day
Drive:  1 h
4
Tampa
— 4 nights
Drive:  1 h 30 min
5
Anna Maria
— 1 day
Drive:  30 min
6
Siesta Key
— 6 nights
ferry:  4 h
7
Key West
— 7 nights
Fly + Bus:  7 h
End: Milwaukee

5
nights
Orlando

Orlando ©
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.

To see ratings, photos, where to stay, and more tourist information, use the Orlando travel site.

Milwaukee to Orlando is an approximately 5.5- hour flight. You can also do a combination of bus and flight; or drive. 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

Side Trips

Cocoa Beach, NASA Kennedy Space Center Visitor Complex
Highlights from your plan
Universal Orlando Resort ©
Universal Orlando Resort
Universal's Islands of Adventure ©
Universal's Islands of Adventure
SeaWorld ©
SeaWorld

5
nights
St. Pete Beach

St. Pete Beach ©
St. St. Pete Beach is known for beaches, wildlife, and adventure. Your plan includes some of its best attractions: admire the masterpieces at The Dali Museum, take a leisurely stroll along John's Pass Village & Boardwalk, tour the pleasant surroundings at Saint Pete Beach, and enjoy the sand and surf at Upham Beach.

To find where to stay, traveler tips, and tourist information, read our St. Pete Beach driving holiday planner.

You can drive from Orlando to St. Pete Beach in 2.5 hours. Alternatively, you can do a combination of train and taxi. In April, plan for daily highs up to 82°F, and evening lows to 69°F. On the 1st (Fri), you'll have the morning to explore before heading off to Clearwater.

Things to do in St. Pete Beach

Beaches Outdoors Parks

Side Trips

St. Petersburg, John's Pass Village & Boardwalk
Highlights from your plan
Saint Pete Beach ©
Saint Pete Beach
The Dali Museum ©
The Dali Museum
John's Pass Village & Boardwalk ©
John's Pass Village & Boardwalk

1
day
Clearwater

Clearwater ©
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.

For other places to visit, more things to do, photos, 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 Outdoors Parks
Highlights from your plan
Clearwater Beach ©
Clearwater Beach

4
nights
Tampa

Tampa ©
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 ratings, traveler tips, 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 Casinos Fun & Games
Highlights from your plan
Busch Gardens Tampa Bay ©
Busch Gardens Tampa Bay
Seminole Hard Rock Casino Tampa ©
Seminole Hard Rock Casino Tampa
Channelside Bay Plaza ©
Channelside Bay Plaza

1
day
Anna Maria

Anna Maria ©
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 traveler tips, other places to visit, maps, and tourist information, refer to the Anna Maria visit planner.

Traveling by car from Tampa to Anna Maria takes 1.5 hours. Alternatively, you can take a bus. 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

Bridge Street Pier, Beach Bums Island Attitude
Highlights from your plan
Bean Point ©
Bean Point
Bridge Street Pier ©
Bridge Street Pier

6
nights
Siesta Key

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

To see other places to visit, traveler tips, where to stay, 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 take a bus. 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

Side Trip

Sarasota
Highlights from your plan
Lido Beach ©
Lido Beach
Crescent Beach ©
Crescent Beach
Legacy Trail ©
Legacy Trail

7
nights
Key West

Key West ©
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.

To see maps, other places to visit, ratings, and tourist information, go to the Key West online trip itinerary maker.

You can do a combination of bus and flight from Siesta Key to Key West in 7 hours. Alternatively, you can drive; or do a combination of bus 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
Highlights from your plan
Green Parrot Bar ©
Green Parrot Bar
Mallory Square ©
Mallory Square
Duval Street ©
Duval Street

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