57 days in Wisconsin & Florida Itinerary

57 days in Wisconsin & Florida Itinerary

Created using Inspirock United States itinerary builder

Plan created by another user. Make it yours
1
Madison
— 4 nights
2
Fish Creek
— 4 nights
3
Key West
— 5 nights
4
Marathon
— 4 nights
5
Key Largo
— 4 nights
6
Miami
— 4 nights
7
Naples
— 4 nights
8
Sarasota
— 3 nights
9
Orlando
— 4 nights
10
St. Augustine
— 5 nights
11
Panama City Beach
— 4 nights
12
Pensacola
— 7 nights

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4
nights
Madison

Madison ©
Madison might be the capital of Wisconsin, but students rather than politicians give the city its identity.
Deepen your sense of the past at sights like Ulysses S. Grant Home and Pabst Mansion. Appreciate the collections at Harley-Davidson Museum and Milwaukee Art Museum. Explore Madison's surroundings by going to Baraboo (Devil's Lake State Park & Baraboo Candy Company), National Mississippi River Museum & Aquarium (in Dubuque) and Taliesin Preservation: Frank Lloyd Wright Visitor Center (in Spring Green). The adventure continues: look for all kinds of wild species at Horicon Marsh, kick your exploration up a notch at some of the top local zipline courses and adventure parks, and ponder the world of politics at Wisconsin State Capitol.

To find other places to visit, photos, reviews, and more tourist information, you can read our Madison route planner.

Perth, Australia to Madison is an approximately 32-hour flight. The time zone difference moving from Australian Western Standard Time to Central Standard Time is minus 14 hours. Plan for somewhat warmer temperatures traveling from Perth in September, with highs in Madison at 28°C and lows at 13°C. Wrap up your sightseeing on the 11th (Sat) early enough to drive to Fish Creek.

Things to do in Madison

Parks · Museums · Historic Sites

Side Trips

Milwaukee, Baraboo, Horicon Marsh, National Mississippi River Museum & Aquarium, Ulysses S. Grant Home
Highlights from your plan
Ulysses S. Grant Home ©
Ulysses S. Grant Home
Harley-Davidson Museum ©
Harley-Davidson Museum
Milwaukee Art Museum ©
Milwaukee Art Museum

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. Eschew the tourist crowds and head to Peninsula State Park and Fayette Historic State Park. Escape the urban bustle at Palms Book State Park and Fumee Lake Natural Area. Change things up with these side-trips from Fish Creek: Menominee Range Historical Museum (in Iron Mountain), The Manistique Boardwalk and River Walk (in Manistique) and Green Bay Packer Hall of Fame (in Green Bay). The adventure continues: take in the exciting artwork at J. Jeffrey Taylor, shop like a local with Water Street Gallery, contemplate the long history of Historical Village Fayette Park, and walk around Cave Point County Park.

To see other places to visit, reviews, more things to do, and more tourist information, read Fish Creek travel 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 little chillier days and about the same nights in Fish Creek, ranging from highs of 24°C to lows of 12°C. Finish your sightseeing early on the 15th (Wed) so you can travel to Key West.

Things to do in Fish Creek

Parks · Nature · Wildlife

Side Trips

Garden, Iron Mountain, Manistique, Water Street Gallery, Green Bay Packer Hall of Fame
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.
Do some cultural sightseeing at 7 Artists & Friends Gallery and The Ernest Hemingway Home and Museum. Fort Zachary Taylor and Key West Cemetery will appeal to history buffs. Spend the 17th (Fri) exploring nature at Dry Tortugas National Park. There's much more to do: get up close to creatures of the deep with a dolphin and whale watching tour, enjoy the sea views from Key West Lighthouse and Keeper's Quarters Museum, make a trip to Truman Little White House, and stop by Isle Cook Key West.

To see photos, where to stay, traveler tips, and other tourist information, refer to the Key West road trip planner.

You can do a combination of car and flight from Fish Creek to Key West in 11.5 hours. Other options are to drive; or do a combination of car, bus, and shuttle. You'll lose 1 hour traveling from Fish Creek to Key West due to the time zone difference. Traveling from Fish Creek in September, you will find days in Key West are somewhat warmer (36°C), and nights are warmer (31°C). Finish your sightseeing early on the 21st (Tue) to allow enough time to drive 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

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 The Turtle Hospital and Bahia Honda State Park. Let the collections at Shady Palm Art Gallery & Photography and Crane Point Museum & Nature Center capture your imagination. There's lots more to do: look for all kinds of wild species at Dolphin Research Center, take a tour by water with Boat Tours & Water Sports, kick back and relax at Sombrero Beach, and take in the architecture and atmosphere at San Pablo Catholic Church.

To find other places to visit, traveler tips, maps, and more tourist information, read our Marathon trip itinerary builder.

Drive from Key West to Marathon in 1.5 hours. Alternatively, you can take a bus. In September, daytime highs in Marathon are 38°C, while nighttime lows are 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
Scuba & Snorkeling

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.
Escape the urban bustle at Fishing Charters & Tours and Spiegel Grove. You'll explore the less-touristy side of things at Molasses Reef and Dolphins Plus Marine Mammal Responder. Explore the numerous day-trip ideas around Key Largo: Anhinga Trail (in Everglades National Park), Scuba & Snorkeling (in Islamorada) and Everglades Alligator Farm (in Homestead). The adventure continues: take a tour by water with Boat Tours & Water Sports, grab your bike and head to Florida Keys Visitor Center, admire the majestic nature at John Pennekamp Coral Reef State Park, and identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center.

To see other places to visit, reviews, photos, and other tourist information, refer to the Key Largo trip builder site.

Getting from Marathon to Key Largo by car takes about 1.5 hours. Other options: take a bus. In September, daily temperatures in Key Largo can reach 36°C, while at night they dip to 28°C. Finish your sightseeing early on the 29th (Wed) to allow enough time to drive to Miami.

Things to do in Key Largo

Wildlife · Parks · Outdoors

Side Trips

Islamorada, Anhinga Trail, Everglades Alligator Farm
Highlights from your plan
Fishing Charters & Tours
Anhinga Trail ©
Anhinga Trail
Dolphins Plus Marine Mammal Responder ©
Dolphins Plus Marine Mammal Responder

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.
Eschew the tourist crowds and head to Waterskiing & Jetskiing and Art Deco Historic District. Get some cultural insight at Vizcaya Museum and Gardens and Wynwood Walls. Venture out of the city with trips to Fort Lauderdale Beach (in Fort Lauderdale), Shark Valley Visitor Center (in Everglades National Park) and Sawgrass Mills (in Sunrise). Spend the 3rd (Sun) exploring nature at Everglades National Park. Next up on the itinerary: see the interesting displays at Lock & Load Museum.

To find traveler tips, more things to do, other places to visit, and more tourist information, read our Miami holiday planner.

Traveling by car from Key Largo to Miami takes 1.5 hours. Alternatively, you can take a bus. In September, plan for daily highs up to 38°C, and evening lows to 29°C. Finish your sightseeing early on the 3rd (Sun) to allow enough time to drive to Naples.

Things to do in Miami

Parks · Nature · Outdoors

Side Trips

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

4
nights
Naples

Satisfy your inner culture vulture at Edison and Ford Winter Estates and The Bailey-Matthews National Shell Museum. Get outdoors at Dolphin & Whale Watching and Lovers Key State Park. Venture out of the city with trips to Lorne's Art Gallery (in Cape Coral), Marco Island (Waterskiing & Jetskiing & Parasailing & Paragliding) and J.N. "Ding" Darling National Wildlife Refuge (in Sanibel Island).

To find other places to visit, reviews, ratings, and more tourist information, refer to the Naples road trip planning site.

Drive from Miami to Naples in 2.5 hours. Alternatively, you can take a bus. In October, daytime highs in Naples are 36°C, while nighttime lows are 25°C. Finish up your sightseeing early on the 7th (Thu) so you can go by car to Sarasota.

Things to do in Naples

Wildlife · Tours · Outdoors

Side Trips

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

3
nights
Sarasota

Sarasota ©
Sarasota is a city in Sarasota County on the southwestern coast of the U.S. Your inner history buff will appreciate Marie Selby Botanical Gardens and Sarasota National Cemetery. Escape the urban bustle at Saint Pete Beach and Myakka River State Park. Venture out of the city with trips to Bean Point (in Anna Maria) and The Dali Museum (in St. Petersburg). There's lots more to do: admire the masterpieces at The Ringling, stroll around Siesta Beach, and brush up on your knowledge of spirits at Siesta Key Rum.

Use Inspirock's suggestions to plan your Sarasota trip and find the best activities and attractions for your vacation.

You can drive from Naples to Sarasota in 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 · Beaches · Outdoors

Side Trips

Saint Pete Beach, Bean Point, Siesta Beach, The Dali Museum
Highlights from your plan
Sarasota National Cemetery ©
Sarasota National Cemetery
Saint Pete Beach ©
Saint Pete Beach
Bean Point ©
Bean Point

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.
Step off the beaten path and head to Ponce de Leon Inlet Lighthouse & Museum and Stetson Mansion. Your cultural itinerary includes sights like Charles Hosmer Morse Museum of American Art and American Space Museum & Space Walk of Fame. Change things up with these side-trips from Orlando: Fishing Charters & Tours (in Port Canaveral), Stand-Up Paddleboarding (in Crystal River) and Ellie Schiller Homosassa Springs Wildlife State Park (in Homosassa Springs). The adventure continues: discover the magic at Happily Ever After Fireworks and test your problem-solving skills at popular escape rooms.

For traveler tips, where to stay, and tourist information, read our Orlando online journey planner.

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) early enough to drive to St. Augustine.

Things to do in Orlando

Tours · Outdoors · Wildlife

Side Trips

Charles Hosmer Morse Museum of American Art, Fishing Charters & Tours, American Space Museum & Space Walk of Fame, Ponce de Leon Inlet Lighthouse & Museum, Stand-Up Paddleboarding
Highlights from your plan
Charles Hosmer Morse Museum of American Art ©
Stetson Mansion ©
Stetson Mansion
Fishing Charters & Tours

5
nights
St. Augustine

St. Augustine ©
St. Step out of the city life by going to St. Augustine Beach and Beach at Daytona Beach. Get a sense of the local culture at Fort Matanzas National Monument and Lightner Museum. Change things up with a short trip to Ormond Beach in Ormond Beach (about 56 minutes away). There's lots more to do: take in the spiritual surroundings of Cathedral Basilica of St. Augustine, sample the fine beverages at St. Augustine Distillery, deepen your understanding at Flagler College, and identify plant and animal life at St. Augustine Alligator Farm Zoological Park.

To see reviews, other places to visit, and other tourist information, read St. Augustine itinerary planning 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 slightly colder, around 31°C. Finish up your sightseeing early on the 19th (Tue) so you can go by car to Panama City Beach.

Things to do in St. Augustine

Parks · Historic Sites · Outdoors

Side Trips

Ormond Beach, Beach at Daytona Beach
Highlights from your plan
St. Augustine Beach ©
St. Augustine Beach
Fort Matanzas National Monument ©
Fort Matanzas National Monument
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.
Relax by the water at St. Andrews State Park and Henderson Beach State Park. Get in touch with nature at Swim with Dolphins and Bear Creek Feline Center. When in Panama City Beach, make a side trip to see Florida Caverns State Park in Marianna, approximately Marianna away. There's still lots to do: buy something for everyone on your list at Pier Park, get up close to creatures of the deep with a dolphin and whale watching tour, take a leisurely stroll along The Village of Baytowne Wharf, and enjoy the sand and surf at Panama City Beach.

To see other places to visit, photos, and other tourist information, use the Panama City Beach trip itinerary planning tool.

Traveling by car from St. Augustine to Panama City Beach takes 5.5 hours. Alternatively, you can fly. Plan for a bit cooler nights when traveling from St. Augustine in October since evenings lows in Panama City Beach dip to 17°C. Finish up your sightseeing early on the 23rd (Sat) so you can go by car to Pensacola.

Things to do in Panama City Beach

Outdoors · Parks · Wildlife

Side Trips

Destin, Bear Creek Feline Center, Florida Caverns State Park
Highlights from your plan
Swim with Dolphins
St. Andrews State Park ©
St. Andrews State Park
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.
You'll explore the less-touristy side of things at Pensacola Beach and Dolphin & Whale Watching. We've included these beaches for you: Navarre Beach and Gulf Islands National Seashore. You'll find plenty of places to visit near Pensacola: Malbis Memorial Church (in Malbis), Orange Beach (Orange Beach Waterfront Park, Fishing Charters & Tours, &more) and Air Force Armament Museum (in Fort Walton Beach). Next up on the itinerary: witness the site of a historic battle at Fort Morgan State Historic Site, visit a coastal fixture at Pensacola Lighthouse & Maritime Museum, take in the waterfront at Gulf State Park Fishing Pier, and view the masterpieces at Blue Morning Gallery.

To see where to stay, more things to do, ratings, and other tourist information, refer to the Pensacola trip planner.

You can drive from Panama City Beach to Pensacola in 2.5 hours. The time zone difference moving from Eastern Standard Time (EST) to Central Standard Time (CST) is minus 1 hour. October in Pensacola sees daily highs of 32°C and lows of 20°C at night. 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, Malbis Memorial Church, Air Force Armament Museum
Highlights from your plan
Pensacola Lighthouse & Maritime Museum ©
Pensacola Lighthouse & Maritime Museum
Dolphin & Whale Watching
Navarre Beach ©
Navarre Beach

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