57 days in Wisconsin & Florida Itinerary

57 days in Wisconsin & Florida Itinerary

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Route & dates

57 days in Wisconsin & Florida Itinerary

Start: Perth
Fly:  31​h
1
Madison
— 4 nights
Drive:  4​h 15​min
2
Fish Creek
— 4 nights
+3
Drive + bus + taxi + Fly:  11​h
3
Key West
— 5 nights
bus:  1​h 15​min
4
Marathon
— 4 nights
Drive:  1​h 15​min
5
Key Largo
— 4 nights
Drive:  1​h 15​min
6
Miami
— 4 nights
Drive:  2​h 15​min
7
Naples
— 4 nights
Drive:  2​h
8
Sarasota
— 3 nights
Drive:  2​h 15​min
9
Orlando
— 4 nights
Drive:  2​h
10
St. Augustine
— 5 nights
Drive:  5​h 30​min
11
Panama City Beach
— 4 nights
Drive:  2​h 15​min
12
Pensacola
— 7 nights
Fly:  29​h
End: Perth


Learn more about your trip

4
nights
Madison

Madison ©
Madison might be the capital of Wisconsin, but students rather than politicians give the city its identity.
Get outdoors at Zipline and Devil's Lake State Park. Let the collections at Harley-Davidson Museum and National Mississippi River Museum & Aquarium capture your imagination. Venture out of the city with trips to Ulysses S. Grant Home (in Galena), Taliesin Preservation: Frank Lloyd Wright Visitor Center (in Spring Green) and Milwaukee (Milwaukee Art Museum & Pabst Mansion). There's still lots to do: look for all kinds of wild species at Horicon Marsh, stop by Baraboo Candy Company, examine the collection at Mr Marvel's Wondertorium, and get a sense of history and politics at Wisconsin State Capitol.

For other places to visit, reviews, photos, and tourist information, read our Madison road trip planning website .

Perth, Australia to Madison is an approximately 31-hour flight. The time zone difference when traveling from Perth to Madison is minus 14 hours. Plan for a bit warmer temperatures traveling from Perth in September, with highs in Madison at 28°C and lows at 13°C. Finish your sightseeing early on the 11th (Sat) to allow enough time to drive to Fish Creek.

Things to do in Madison

Parks Museums Historic Sites

Side Trips

Milwaukee, Baraboo, Wisconsin Dells, Horicon Marsh, Taliesin Preservation: Frank Lloyd Wright Visitor Center
Highlights from your plan
Harley-Davidson Museum ©
Harley-Davidson Museum
Milwaukee Art Museum ©
Milwaukee Art Museum
Ulysses S. Grant Home ©
Ulysses S. Grant Home

4
nights
Fish Creek

Fish Creek ©
Fish Creek is an unincorporated community located in Door County, Wisconsin, United States, within the town of Gibraltar and is located on Highway 42 along Green Bay.HistoryThe first settler of Fish Creek was Increase Claflin and his family circa 1844, but the village founder is considered to be entrepreneur Asa Thorp. Satisfy your inner culture vulture at Green Bay Packer Hall of Fame and J. Jeffrey Taylor. Step out of the city life by going to Peninsula State Park and The Manistique Boardwalk and River Walk. Explore the numerous day-trip ideas around Fish Creek: Palms Book State Park (in Manistique), Iron Mountain (Menominee Range Historical Museum & Fumee Lake Natural Area) and Garden (Fayette Historic State Park & Historical Village Fayette Park). Next up on the itinerary: walk around Cave Point County Park and take in the exciting artwork at Water Street Gallery.

To find photos, other places to visit, ratings, and other tourist information, go to the Fish Creek online trip itinerary planner .

You can drive from Madison to Fish Creek in 4.5 hours. Alternatively, you can do a combination of bus and taxi; or do a combination of bus and car. While traveling from Madison, expect a bit cooler days and about the same nights in Fish Creek, ranging from highs of 24°C to lows of 12°C. Wrap up your sightseeing on the 15th (Wed) early enough to travel to Key West.

Things to do in Fish Creek

Parks Nature Wildlife

Side Trips

Iron Mountain, Garden, Manistique, Water Street Gallery, Cave Point County Park
Highlights from your plan
Green Bay Packer Hall of Fame ©
Green Bay Packer Hall of Fame
Peninsula State Park ©
Peninsula State Park
Fayette Historic State Park ©
Fayette Historic State Park

5
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.
Explore hidden gems such as Scuba & Snorkeling and Dolphin & Whale Watching. Get outdoors at Waterskiing & Jetskiing and Fort Zachary Taylor. Spend the 17th (Fri) exploring nature at Dry Tortugas National Park. And it doesn't end there: examine the collection at The Ernest Hemingway Home and Museum, identify plant and animal life at Key West Butterfly & Nature Conservatory, shop like a local with 7 Artists & Friends, and learn about all things military at U.S. Coast Guard Cutter Ingham Maritime Museum.

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

You can do a combination of car, bus, and flight from Fish Creek to Key West in 11 hours. Other options are to do a combination of car and flight; or drive. The time zone difference when traveling from Fish Creek to Key West is 1 hour. Traveling from Fish Creek in September, expect nights in Key West to be warmer, around 31°C, while days are somewhat warmer, around 36°C. Finish up your sightseeing early on the 21st (Tue) so you can catcht the bus to Marathon.

Things to do in Key West

Outdoors Tours Wildlife
Highlights from your plan
Dry Tortugas National Park ©
Dry Tortugas National Park
Dolphin & Whale Watching
Scuba & Snorkeling

4
nights
Marathon

Marathon ©
A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Eschew the tourist crowds and head to Fishing Charters & Tours and Dolphin Research Center. Get a sense of the local culture at Shady Palm Art Gallery & Photography and San Pablo Catholic Church. Take a break from Marathon with a short trip to National Key Deer Refuge in Big Pine Key, about 34 minutes away. And it doesn't end there: identify plant and animal life at The Turtle Hospital, see some colorful creatures with a scuba or snorkeling tour, take in the views from Seven Mile Bridge, and tour the pleasant surroundings at Sombrero Beach.

To see where to stay and other tourist information, use the Marathon online vacation planner .

You can take a bus from Key West to Marathon in 1.5 hours. Another option is to drive. Expect a daytime high around 38°C in September, and nighttime lows around 30°C. Finish your sightseeing early on the 25th (Sat) so you can drive to Key Largo.

Things to do in Marathon

Wildlife Parks Outdoors

Side Trip

Big Pine Key
Highlights from your plan
The Turtle Hospital ©
The Turtle Hospital
Dolphin Research Center ©
Dolphin Research Center
Fishing Charters & Tours

4
nights
Key Largo

The northernmost island of the Florida Keys, Key Largo provides stunning scenery, a number of watersports opportunities, and plenty of areas to relax on vacation.
Explore hidden gems such as Molasses Reef and Anhinga Trail. Visiting Scuba & Snorkeling and Fishing Charters & Tours will get you outdoors. Step out of Key Largo with an excursion to Everglades Alligator Farm in Homestead--about 36 minutes away. There's lots more to do: identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center, explore the landscape on two wheels at Key Largo Chamber of Commerce and Florida Keys Visitor Center, admire nature's wide array of creatures at Dolphins Plus Marine Mammal Responder, and explore the gorgeous colors at Spiegel Grove.

For maps, other places to visit, more things to do, and tourist information, read our Key Largo trip itinerary maker website .

Traveling by car from Marathon to Key Largo takes 1.5 hours. Alternatively, you can take a bus. In September, daytime highs in Key Largo are 36°C, while nighttime lows are 28°C. Wrap up your sightseeing on the 29th (Wed) to allow time to drive to Miami.

Things to do in Key Largo

Wildlife Parks Outdoors

Side Trips

Islamorada, Everglades Alligator Farm, Anhinga Trail
Highlights from your plan
Scuba & Snorkeling
Fishing Charters & Tours
Anhinga Trail ©
Anhinga Trail

4
nights
Miami

Miami ©
Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
Get some cultural insight at Vizcaya Museum and Gardens and Lock & Load Museum. Explore hidden gems such as Everglades National Park and Shark Valley. You'll find plenty of places to visit near Miami: Sawgrass Mills (in Sunrise) and Fort Lauderdale Beach (in Fort Lauderdale). There's much more to do: get a new perspective on things with Boat Tours & Water Sports, explore the world behind art at Wynwood Walls, and get to know the fascinating history of Art Deco Historic District.

For more things to do, photos, reviews, and other tourist information, use the Miami online driving holiday planner .

You can drive from Key Largo to Miami in 1.5 hours. Alternatively, you can take a bus. In September, daily temperatures in Miami can reach 38°C, while at night they dip to 29°C. Cap off your sightseeing on the 3rd (Sun) early enough to go by car to Naples.

Things to do in Miami

Parks Nature Outdoors

Side Trips

Fort Lauderdale Beach, Art Deco Historic District, Everglades National Park, Sawgrass Mills, Shark Valley Visitor Center
Highlights from your plan
Lock & Load Museum ©
Lock & Load Museum
Shark Valley Visitor Center ©
Shark Valley Visitor Center
Vizcaya Museum and Gardens ©
Vizcaya Museum and Gardens

4
nights
Naples

Naples is a city in Collier County, Florida, United States. Escape the urban bustle at Fishing Charters & Tours and Lovers Key State Park. Museum-lovers will get to explore Edison & Ford Winter Estates and The Bailey-Matthews National Shell Museum. Venture out of the city with trips to Marco Island (Waterskiing & Jetskiing & Parasailing & Paragliding), Lorne's Art Gallery (in Cape Coral) and J.N. "Ding" Darling National Wildlife Refuge (in Sanibel Island). Next up on the itinerary: get up close to creatures of the deep with a dolphin and whale watching tour and take in the waterfront at Naples Pier.

To see traveler tips, reviews, more things to do, and other tourist information, read Naples day trip planning app .

Drive from Miami to Naples in 2.5 hours. Alternatively, you can take a bus. In October, plan for daily highs up to 36°C, and evening lows to 25°C. Finish your sightseeing early on the 7th (Thu) to allow enough time to drive to Sarasota.

Things to do in Naples

Wildlife Tours Outdoors

Side Trips

Marco Island, Sanibel Island, Lorne's Art Gallery, Edison and Ford Winter Estates, Lovers Key State Park
Highlights from your plan
Fishing Charters & Tours
Dolphin & Whale Watching
Waterskiing & Jetskiing

3
nights
Sarasota

Sarasota ©
Sarasota is a city in Sarasota County on the southwestern coast of the U.S. You'll explore the less-touristy side of things at Bean Point and Marie Selby Botanical Gardens. Your cultural itinerary includes sights like Sarasota National Cemetery and The Ringling. Explore Sarasota's surroundings by going to Saint Pete Beach (in St. Pete Beach) and The Dali Museum (in St. Petersburg). There's still lots to do: cruise along Myakka River State Park, brush up on your knowledge of spirits at Siesta Key Rum, and enjoy the sand and surf at Siesta Beach.

To find more things to do, other places to visit, where to stay, and tourist information, use the Sarasota visit planner.

Traveling by car from Naples to Sarasota takes 2 hours. Alternatively, you can take a bus. In October, daytime highs in Sarasota are 35°C, while nighttime lows are 23°C. Wrap up your sightseeing on the 10th (Sun) early enough to drive to Orlando.

Things to do in Sarasota

Parks Outdoors Beaches

Side Trips

The Dali Museum, Saint Pete Beach, Siesta Beach, Bean Point
Highlights from your plan
Saint Pete Beach ©
Saint Pete Beach
Bean Point ©
Bean Point
Marie Selby Botanical Gardens ©
Marie Selby Botanical Gardens

4
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.
Get some cultural insight at Stetson Mansion and Charles Hosmer Morse Museum of American Art. You'll explore the less-touristy side of things at Fishing Charters & Tours and Ponce de Leon Inlet Lighthouse & Museum. You'll find plenty of places to visit near Orlando: American Space Museum & Space Walk of Fame (in Titusville), Ellie Schiller Homosassa Springs Wildlife State Park (in Homosassa Springs) and Stand-Up Paddleboarding (in Crystal River). Next up on the itinerary: make an unforgettable trip to Happily Ever After Fireworks, take in panoramic vistas at The Wheel at ICON Park, and test your team's savvy at popular escape rooms.

To find where to stay, reviews, maps, and other tourist information, go to the Orlando trip itinerary planning site .

Traveling by car from Sarasota to Orlando takes 2.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. October in Orlando sees daily highs of 34°C and lows of 24°C at night. Wrap up your sightseeing on the 14th (Thu) to allow time to drive to St. Augustine.

Things to do in Orlando

Tours Outdoors Wildlife

Side Trips

Stetson Mansion, American Space Museum & Space Walk of Fame, Ponce de Leon Inlet Lighthouse & Museum, Fishing Charters & Tours, Ellie Schiller Homosassa Springs Wildlife State Park
Highlights from your plan
Stetson Mansion ©
Stetson Mansion
Fishing Charters & Tours

5
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. Step off the beaten path and head to Fort Matanzas National Monument and St. Augustine Alligator Farm Zoological Park. Deepen your sense of the past at sights like Cathedral Basilica of St. Augustine and St. Augustine Lighthouse & Maritime Museum, Inc.. Explore St. Augustine's surroundings by going to Ormond Beach (in Ormond Beach) and Beach at Daytona Beach (in Daytona Beach). The adventure continues: enjoy the sand and surf at St. Augustine Beach, admire the landmark architecture of Old Jail, shop like a local with High Tide Gallery Art & Gifts, and deepen your understanding at Flagler College.

To see reviews, photos, ratings, and other tourist information, use the St. Augustine trip itinerary builder site .

Traveling by car from Orlando to St. Augustine takes 2 hours. Alternatively, you can take a bus. Traveling from Orlando in October, expect nights in St. Augustine to be about the same, around 22°C, while days are a bit cooler, around 31°C. Finish your sightseeing early on the 19th (Tue) so you can drive to Panama City Beach.

Things to do in St. Augustine

Parks Historic Sites Outdoors

Side Trips

Beach at Daytona Beach, Ormond Beach
Highlights from your plan
St. Augustine Beach ©
St. Augustine Beach
Ormond Beach ©
Ormond Beach

4
nights
Panama City Beach

Boasting 43 km (27 mi) of white sandy beaches and plenty of sunshine, Panama City Beach is an ideal choice for a relaxing holiday.
Visiting Swim with Dolphins and St. Andrews State Park will get you outdoors. Your itinerary includes some good beach time at Henderson Beach State Park and Panama City Beach. Explore the numerous day-trip ideas around Panama City Beach: Florida Caverns State Park (in Marianna) and Bear Creek Feline Center (in Panama City). And it doesn't end there: see majestic marine mammals with a dolphin and whale watching tour, take a leisurely stroll along Village of Baytowne Wharf, browse the different shops at Pier Park, and learn about winemaking at Panama City Beach Winery.

To see other places to visit, reviews, more things to do, and other tourist information, read our Panama City Beach trip app .

Drive from St. Augustine to Panama City Beach in 5.5 hours. Alternatively, you can do a combination of bus and flight; or do a combination of bus, flight, and taxi. Traveling from St. Augustine in October, Panama City Beach is a bit cooler at night with lows of 17°C. Cap off your sightseeing on the 23rd (Sat) early enough to go by car to Pensacola.

Things to do in Panama City Beach

Outdoors Parks Wildlife

Side Trips

Destin, Florida Caverns State Park, Bear Creek Feline Center
Highlights from your plan
Dolphin & Whale Watching
Swim with Dolphins
Henderson Beach State Park ©
Henderson Beach State Park

7
nights
Pensacola

Pensacola ©
Surrounded on three sides by water, Pensacola offers access to white-sand beaches and emerald-green ocean unspoiled by large resorts.
Step out of the city life by going to Fishing Charters & Tours and Gulf Islands National Seashore. Relax by the water at Navarre Beach and Gulf State Park Fishing Pier. Venture out of the city with trips to Malbis Memorial Church (in Malbis), Orange Beach (Dolphin & Whale Watching, Orange Beach Waterfront Park, & more) and Air Force Armament Museum (in Fort Walton Beach). There's still lots to do: take in the history at Fort Morgan State Historic Site, admire the majestic nature at Gulf State Park, deepen your knowledge of military history at Pensacola Naval Air Station, and steep yourself in history at Fort Pickens Area.

To see reviews, photos, more things to do, and other tourist information, read our Pensacola day trip planning site .

Traveling by car from Panama City Beach to Pensacola takes 2.5 hours. You'll gain 1 hour traveling from Panama City Beach to Pensacola due to the time zone difference. In October, daily temperatures in Pensacola can reach 32°C, while at night they dip to 20°C. Finish up your sightseeing early on the 30th (Sat) so you can travel back home.

Things to do in Pensacola

Outdoors Parks Beaches

Side Trips

Orange Beach, Pensacola Beach, Gulf Shores, Fort Morgan State Historic Site, Navarre Beach
Highlights from your plan
Pensacola Lighthouse and Museum ©
Pensacola Lighthouse and Museum
Dolphin & Whale Watching
Navarre Beach ©
Navarre Beach

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