26 days in Florida Itinerary

26 days in Florida Itinerary

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Route & dates

26 days in Florida Itinerary

Start: Milwaukee
Fly:  3 h
1
Orlando
— 3 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

3
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 list of things to see and do now includes The Wheel at ICON Park, Cocoa Beach, NASA Kennedy Space Center Visitor Complex, and other attractions.

To find ratings, other places to visit, more things to do, and other tourist information, use the Orlando trip itinerary maker.

Milwaukee to Orlando is an approximately 5.5- hour flight. You can also do a combination of bus and flight; or drive. Traveling from Milwaukee to Orlando, you'll lose 1 hour due to the time zone difference. Traveling from Milwaukee in April, things will get much hotter in Orlando: highs are around 84°F and lows about 65°F. You'll have a few hours on the 26th (Sun) to wrap things up before traveling to St. Pete Beach.

Things to do in Orlando

Theme Parks Outdoors Parks

Side Trips

NASA Kennedy Space Center Visitor Complex, Cocoa Beach
Find places to stay Apr 23 — 26:
Highlights from your plan
Universal Orlando Resort ©
Universal Orlando Resort
Universal's Islands of Adventure ©
Universal's Islands of Adventure

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: explore the world behind art at The Dali Museum, don't miss a visit to John's Pass Village & Boardwalk, enjoy the sand and surf at Saint Pete Beach, and tour the pleasant surroundings at Upham Beach.

To see more things to do, photos, where to stay, and more tourist information, use the St. Pete Beach online journey planner.

Traveling by car from Weeki Wachee to St. Pete Beach takes 1.5 hours. Alternatively, you can take a bus. Plan for a bit warmer nights when traveling from Weeki Wachee in May since evenings lows in St. Pete Beach dip to 73°F. Finish your sightseeing early on the 8th (Fri) to allow enough time to drive to Clearwater.

Things to do in St. Pete Beach

Parks Beaches Outdoors

Side Trips

St. Petersburg, John's Pass Village & Boardwalk
Find places to stay Apr 26 — May 1:
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.
Clearwater Beach has been added to your itinerary. Start off your visit on the 8th (Fri): kick back and relax at Clearwater Beach.

To see reviews, where to stay, more things to do, and more tourist information, read Clearwater online travel planner.

Traveling by car from St. Pete Beach to Clearwater takes an hour. Alternatively, you can take a bus. In May, daytime highs in Clearwater are 87°F, while nighttime lows are 70°F. Wrap up your sightseeing on the 8th (Fri) early enough to drive to Tampa.

Things to do in Clearwater

Parks Beaches Outdoors
Find places to stay May 1 — 2:
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 see traveler tips, where to stay, ratings, and other tourist information, read our Tampa tour itinerary builder.

Getting from Clearwater to Tampa by car takes about an hour. Other options: 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
Find places to stay May 1 — 5:
Highlights from your plan
Busch Gardens Tampa Bay ©
Busch Gardens Tampa Bay
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. Kick off your visit on the 5th (Tue): get outside with Beach Bums Island Attitude, then enjoy the sand and surf at Bean Point, and then take a leisurely stroll along Bridge Street Pier.

For photos, maps, other places to visit, and tourist information, refer to the Anna Maria route tool.

You can drive from Tampa to Anna Maria in 1.5 hours. Another option is to take a bus. In May, daily temperatures in Anna Maria can reach 87°F, while at night they dip to 68°F. Wrap up your sightseeing on the 5th (Tue) to allow time to drive to Siesta Key.

Things to do in Anna Maria

Outdoors Parks Beaches

Side Trips

Bridge Street Pier, Beach Bums Island Attitude
Find places to stay May 5 — 6:
Highlights from your plan
Bean Point ©
Bean Point

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: buy something for everyone on your list at St. Armands Circle.

To find maps, other places to visit, ratings, and more tourist information, refer to the Siesta Key trip itinerary builder.

You can drive from Anna Maria to Siesta Key in 1.5 hours. Another option is to take a bus. In May in Siesta Key, expect temperatures between 87°F during the day and 68°F at night. You'll have a few hours on the 11th (Mon) to wrap things up before traveling to Key West.

Things to do in Siesta Key

Outdoors Parks Beaches

Side Trip

Sarasota
Find places to stay May 5 — 11:
Highlights from your plan
Lido Beach ©
Lido Beach
St. Armands Circle ©
St. Armands Circle
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 lots more to do: take in the waterfront at Mallory Square, explore the striking landscape of Dry Tortugas National Park, and make a trip to Duval Street.

To see maps, ratings, where to stay, and more tourist information, refer to the Key West trip planning site.

You can do a combination of bus and flight from Siesta Key to Key West in 7 hours. Other options are to drive; or do a combination of bus and ferry. Traveling from Siesta Key in May, you can expect nighttime temperatures to be somewhat warmer in Key West, with lows of 77°F. Wrap up your sightseeing on the 18th (Mon) early enough to travel back home.

Things to do in Key West

Nightlife Parks Beaches
Find places to stay May 11 — 18:
Highlights from your plan
Green Parrot Bar ©
Green Parrot Bar
Mallory Square ©
Mallory Square
Dry Tortugas National Park ©
Dry Tortugas National Park

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