34 days in Florida Itinerary

34 days in Florida Itinerary

Created using Inspirock Florida tour 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

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.
Take a break from the city and head to Cocoa Beach and Celebration Bike Rental and Bicycle Tours. Take a break from Orlando with a short trip to NASA Kennedy Space Center Visitor Complex in Merritt Island, about 1h 10 min away. Pack the 18th (Fri) with family-friendly diversions at Universal's Islands of Adventure. There's still lots to do: see a one-of-a-kind show at La Nouba - Cirque du Soleil and revel in the low prices at Orlando International Premium Outlets.

To see ratings, other places to visit, more things to do, and tourist information, you can read our Orlando online trip planner.

Milwaukee to Orlando is an approximately 4.5-hour flight. You can also drive; or take a bus. Traveling from Milwaukee to Orlando, you'll lose 1 hour due to the time zone difference. Expect a bit warmer temperatures when traveling from Milwaukee in June; daily highs in Orlando reach 91°F and lows reach 73°F. You will have some time to spend on the 20th (Sun) before leaving for Weeki Wachee.
Theme Parks · Outdoors · Beaches · Parks
Side Trips

Weeki Wachee — 1 day

Weeki Wachee is a city located in Hernando County, Florida, United States. Start off your visit on the 20th (Sun): make a splash at Weeki Wachee Springs State Park and then paddle through the water with Weeki Wachee Kayaking.

For where to stay, ratings, more things to do, and tourist information, use the Weeki Wachee online journey planner.

Traveling by car from Orlando to Weeki Wachee takes 2 hours. Alternatively, you can drive; or do a combination of train and car; or do a combination of bus and taxi. In June, daytime highs in Weeki Wachee are 90°F, while nighttime lows are 72°F. Finish your sightseeing early on the 20th (Sun) to allow enough time to drive to Clearwater.
Outdoors · Adventure · Tours · Theme Parks
Side Trip

Clearwater — 5 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.
Step out of the city life by going to Clearwater Beach and StarLite Majesty Dining Cruises. There's lots more to do: meet the residents at Clearwater Marine Aquarium, stroll around Sand Key Park, try to win big at Tampa Bay Downs, and take a leisurely stroll along Pier 60.

To see photos, more things to do, other places to visit, and more tourist information, read Clearwater trip planner.

You can drive from Weeki Wachee to Clearwater in 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 90°F in June, and nighttime lows around 75°F. On the 25th (Fri), you'll have the morning to explore before heading off to St. Pete Beach.
Parks · Outdoors · Beaches · Fun & Games
Side Trip

St. Pete Beach — 5 nights

St. Visit St. Pete Beach and Treasure Island Beach for some beach relaxation. The adventure continues: see majestic marine mammals with Dolphin Landings Charter Boat Center, explore the world behind art at Chihuly Collection, see the interesting displays at The Dali Museum, and take a leisurely stroll along John's Pass Village & Boardwalk.

For photos, more things to do, maps, and tourist information, read our St. Pete Beach trip itinerary maker app.

Getting from Clearwater to St. Pete Beach by car takes about an hour. Other options: take a bus. In June, daily temperatures in St. Pete Beach can reach 88°F, while at night they dip to 77°F. Wrap up your sightseeing on the 30th (Wed) early enough to drive to Tampa.
Outdoors · Beaches · Parks · Museums
Side Trips

Tampa — 5 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.
Tampa is known for theme parks, zoos & aquariums, and sightseeing. Your trip includes some of its best attractions: find something for the whole family at Busch Gardens Tampa Bay, walk around Sparkman Wharf, go for a walk through Tampa Riverwalk, and try your luck at Seminole Hard Rock Casino Tampa.

For traveler tips, maps, other places to visit, and other tourist information, go to the Tampa online trip itinerary builder.

Drive from St. Pete Beach to Tampa in an hour. Alternatively, you can take a bus. In June, plan for daily highs up to 91°F, and evening lows to 76°F. You will have some time to spend on the 5th (Mon) before leaving for Anna Maria.
Theme Parks · Fun & Games · Casinos · Historic Sites

Anna Maria — 1 day

Anna Maria, is a city in Manatee County, Florida, United States. Kick off your visit on the 5th (Mon): stroll through Bean Point and then kick back and relax at Manatee Public Beach.

For where to stay, more things to do, maps, and tourist information, use the Anna Maria trip itinerary maker app.

Getting from Tampa to Anna Maria by car takes about 1.5 hours. Other options: take a bus. July in Anna Maria sees daily highs of 91°F and lows of 76°F at night. Wrap up your sightseeing on the 5th (Mon) early enough to drive to Siesta Key.
Outdoors · Beaches · Parks
Side Trip

Siesta Key — 6 nights

Siesta Key draws most of its visitors with soft, white-quartz sand beaches and translucent ocean water.
Step out of the city life by going to Parasail Siesta and Siesta Beach. And it doesn't end there: enjoy the sand and surf at Crescent Beach, stop by Silver City Sarasota, join in the after-dark buzz at Gilligan's Island Bar & Grill, and buy something for everyone on your list at St. Armands Circle.

To find photos, maps, reviews, and other tourist information, use the Siesta Key trip planner.

Traveling by car from Anna Maria to Siesta Key takes an hour. Alternatively, you can take a bus. July in Siesta Key sees daily highs of 91°F and lows of 76°F at night. You'll have a few hours on the 11th (Sun) to wrap things up before traveling to Key West.
Outdoors · Beaches · Parks · Shopping
Side Trip

Key West — 7 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.
Key West is known for sightseeing, museums, and adventure. Your trip includes some of its best attractions: glide through the air with a parasailing or paragliding tour, join in the after-dark buzz at Bourbon Street Pub, don't miss a visit to Duval Street, and take in the waterfront at Mallory Square.

To see reviews, maps, more things to do, and more tourist information, you can read our Key West driving holiday planner.

Getting from Siesta Key to Key West by flight takes about 3 hours. Other options: drive; or do a combination of bus, taxi, and ferry. In July in Key West, expect temperatures between 89°F during the day and 81°F at night. You'll have a few hours on the 18th (Sun) to wrap things up before traveling home.
Nightlife · Adventure · Tours · Outdoors

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.