34 days in Florida Itinerary

34 days in Florida Itinerary

Created using Inspirock Florida itinerary planner

Make it your trip
Fly
1
Orlando
— 5 nights
Drive
2
Weeki Wachee
— 1 day
Drive
3
Clearwater
— 5 nights
Drive
4
St. Pete Beach
— 5 nights
Drive
5
Tampa
— 5 nights
Drive
6
Anna Maria
— 1 day
Drive
7
Siesta Key
— 6 nights
+2
Bus to Fort Myers, FL - McDonalds, Taxi to Fort Myers Beach, FL, Ferry to Key West
8
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 Orlando International Premium Outlets, Celebration Bike Rental and Bicycle Tours, La Nouba - Cirque du Soleil, and other attractions you added. Pack the 23rd (Sat) with family-friendly diversions at Universal's Islands of Adventure.

For photos, reviews, and tourist information, read our Orlando trip itinerary maker app.

Milwaukee to Orlando is an approximately 4.5-hour flight. You can also drive; or do a combination of bus and subway. Due to the time zone difference, you'll lose 1 hour traveling from Milwaukee to Orlando. In April, Orlando is warmer than Milwaukee - with highs of 84°F and lows of 65°F. You'll have a few hours on the 25th (Mon) to wrap things up before traveling to Weeki Wachee.

Things to do in Orlando

Theme Parks · Outdoors · Parks · Beaches

Side Trips

Weeki Wachee

— 1 day
Weeki Wachee is a city located in Hernando County, Florida, United States. Your day by day itinerary now includes Weeki Wachee Springs State Park as well as Weeki Wachee Kayaking. On the 25th (Mon), cool off at Weeki Wachee Springs State Park and then add some adventure to your tour with Weeki Wachee Kayaking.

For ratings, reviews, photos, and tourist information, go to the Weeki Wachee trip planner.

Drive from Orlando to Weeki Wachee in 2 hours. Alternatively, you can drive; or do a combination of bus and taxi; or do a combination of train and taxi. Traveling from Orlando in April, Weeki Wachee is little chillier at night with lows of 60°F. Finish up your sightseeing early on the 25th (Mon) so you can go by car to Clearwater.

Things to do in Weeki Wachee

Outdoors · Adventure · Tours · Theme Parks

Side Trip

Highlights from your trip

Clearwater

— 5 nights

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 added Clearwater Beach, Clearwater Marine Aquarium, StarLite Majesty Dining Cruises, and other attractions to your itinerary. It doesn't end there: take a leisurely stroll along Pier 60 and try your luck at Tampa Bay Downs.

To find reviews, maps, ratings, and tourist information, use the Clearwater road trip planning tool.

Getting from Weeki Wachee to Clearwater by car takes about 1.5 hours. Other options: take a bus. Traveling from Weeki Wachee in April, you can expect nighttime temperatures to be a bit warmer in Clearwater, with lows of 67°F. On the 30th (Sat), you'll have the morning to explore before heading off to St. Pete Beach.

Things to do in Clearwater

Parks · Outdoors · Beaches · Fun & Games

Side Trip

St. Pete Beach

— 5 nights
St. You've added The Dali Museum, John's Pass Village & Boardwalk, Treasure Island Beach, and other attractions to your itinerary.

To find maps, ratings, reviews, and more tourist information, you can read our St. Pete Beach trip itinerary builder app.

You can drive from Clearwater to St. Pete Beach in an hour. Another option is to take a bus. In April in St. Pete Beach, expect temperatures between 82°F during the day and 69°F at night. Finish your sightseeing early on the 5th (Thu) to allow enough time to drive to Tampa.

Things to do in St. Pete Beach

Outdoors · Parks · Beaches · Museums

Side Trips

Tampa

— 5 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 list of things to see and do now includes Seminole Hard Rock Casino Tampa, Busch Gardens Tampa Bay, Ybor City Saturday Market, and other attractions.

To see traveler tips, reviews, photos, and more tourist information, go to the Tampa trip itinerary planning app.

Drive from St. Pete Beach to Tampa in an hour. Alternatively, you can take a bus. In May in Tampa, expect temperatures between 89°F during the day and 71°F at night. On the 10th (Tue), you'll have the morning to explore before heading off to Anna Maria.

Things to do in Tampa

Theme Parks · Fun & Games · Casinos · Parks

Anna Maria

— 1 day
Anna Maria, is a city in Manatee County, Florida, United States. Your day by day itinerary now includes Manatee Public Beach as well as Bean Point. Start off your visit on the 10th (Tue): enjoy the sand and surf at Bean Point and then enjoy the sand and surf at Manatee Public Beach.

To find traveler tips, ratings, where to stay, and tourist information, refer to the Anna Maria online journey planner.

Traveling by car from Tampa to Anna Maria takes 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 87°F in May, and nighttime lows around 68°F. Finish up your sightseeing early on the 10th (Tue) so you can go by car to Siesta Key.

Things to do in Anna Maria

Parks · Outdoors · Beaches

Side Trip

Siesta Key

— 6 nights
Siesta Key draws most of its visitors with soft, white-quartz sand beaches and translucent ocean water.
You've added Gilligan's Island Bar & Grill, St. Armands Circle, Lido Beach, and other attractions to your itinerary. There's still lots to do: look for gifts at Silver City Sarasota and get a taste of the local shopping with AlexArt International Art Gallery.

For photos, where to stay, traveler tips, and more tourist information, use the Siesta Key sightseeing planning site.

You can drive from Anna Maria to Siesta Key in an hour. Alternatively, you can take a bus. Expect a daytime high around 87°F in May, and nighttime lows around 68°F. You will have some time to spend on the 16th (Mon) before leaving for Key West.

Things to do in Siesta Key

Outdoors · Parks · Beaches · Shopping

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.
Your list of things to see and do now includes Green Parrot Bar, Bobby's Monkey Bar, Virgilio's, and other attractions. The adventure continues: take a leisurely stroll along Mallory Square.

To see maps, more things to do, where to stay, and other tourist information, read our Key West travel route planner.

You can fly from Siesta Key to Key West in 3 hours. Alternatively, you can drive; or do a combination of bus, taxi, and ferry. Traveling from Siesta Key in May, Key West is somewhat warmer at night with lows of 77°F. You will have some time to spend on the 23rd (Mon) before leaving for home.

Things to do in Key West

Nightlife · Parks · Outdoors · Adventure

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.