11 days in Wisconsin & Florida Itinerary

11 days in Wisconsin & Florida Itinerary

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Route & dates

11 days in Wisconsin & Florida Itinerary

Start: Milwaukee
Train:  2​h
1
Wisconsin Dells
— 1 night
+2
Train + Bus + Fly:  8​h
2
Orlando
— 3 nights
Drive:  4​h 15​min
3
Marco Island
— 1 night
Ferry:  2​h 30​min
4
Key West
— 2 nights
Bus:  2​h
5
Islamorada
— 1 night
Drive:  45​min
6
Key Largo
— 1 night
Shuttle + Fly:  7​h
End: Milwaukee

1
night
Wisconsin Dells

Wisconsin Dells ©
Named after a nearby scenic gorge famous for its steep sandstone formations, Wisconsin Dells features more than 20 water parks, making it one of the most popular vacation areas in this region.
On the 12th (Tue), kick your exploration up a notch at some of the top local zipline courses and adventure parks, then test your problem-solving skills at Elusive Escape Rooms, then have some family-friendly fun at Laser Warfare, and finally see the interesting displays at Mr Marvel's Wondertorium. On the 13th (Wed), you'll have a packed day of sightseeing: make a splash at Noah's Ark Water Park and then admire the landmark architecture of Taliesin Preservation: Frank Lloyd Wright Visitor Center .

To see reviews, ratings, more things to do, and tourist information, read our Wisconsin Dells online route maker .

Milwaukee to Wisconsin Dells is an approximately 2-hour train ride. You can also drive; or take a bus. In May, daytime highs in Wisconsin Dells are 68°F, while nighttime lows are 46°F. Finish up your sightseeing early on the 13th (Wed) so you can travel to Orlando.

Things to do in Wisconsin Dells

Theme Parks Outdoors Fun & Games

Side Trip

Taliesin Preservation: Frank Lloyd Wright Visitor Center
Highlights from your plan
Elusive Escape Rooms ©
Elusive Escape Rooms
Zipline
Noah's Ark Water Park ©
Noah's Ark Water Park

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.
Orlando is known for theme parks, nightlife, fun & games, shopping, and museums. Your plan includes some of its best attractions: make an unforgettable trip to Walt Disney World Resort, add some entertainment to your itinerary with Happily Ever After Fireworks, try out the rides at Disney’s Hollywood Studios, and find something for the whole family at Universal Orlando Resort.

To see where to stay, more things to do, ratings, and other tourist information, use the Orlando attractions app .

You can do a combination of train and flight from Wisconsin Dells to Orlando in 8 hours. Alternatively, you can do a combination of bus and flight; or drive. Due to the time zone difference, you'll lose 1 hour traveling from Wisconsin Dells to Orlando. Traveling from Wisconsin Dells in May, expect nights in Orlando to be much warmer, around 69°F, while days are somewhat warmer, around 88°F. Wrap up your sightseeing on the 17th (Sun) to allow time to drive to Marco Island.

Things to do in Orlando

Theme Parks Fun & Games Nightlife
Highlights from your plan
Universal's Islands of Adventure ©
Universal's Islands of Adventure
Walt Disney World Resort ©
Walt Disney World Resort
Universal Orlando Resort ©
Universal Orlando Resort

1
night
Marco Island

Marco Island is a city in Collier County, Florida, United States, located on an island by the same name in the Gulf of Mexico off the coast of Southwest Florida. Start off your visit on the 18th (Mon): see majestic marine mammals with a dolphin and whale watching tour, get interesting insight from Tours, and then zoom along the surf with a waterskiing or jet-skiing adventure.

To see where to stay, reviews, more things to do, and tourist information, read our Marco Island online vacation planner .

You can drive from Orlando to Marco Island in 4.5 hours. Alternatively, you can do a combination of flight and bus; or take a bus. In May, plan for daily highs up to 88°F, and evening lows to 69°F. Finish your sightseeing early on the 18th (Mon) to allow enough time to ride a ferry to Key West.

Things to do in Marco Island

Outdoors Tours Adventure
Highlights from your plan
Dolphin & Whale Watching
Waterskiing & Jetskiing
Parasailing & Paragliding

2
nights
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.
Start off your visit on the 19th (Tue): see some colorful creatures with a scuba or snorkeling tour, look for all kinds of wild species at Key West Butterfly & Nature Conservatory, then take a tour by water with Boat Tours & Water Sports, and finally explore the different monuments and memorials at Key West Cemetery. Get ready for a full day of sightseeing on the next day: examine the collection at The Ernest Hemingway Home and Museum and then kick back and relax at Bahia Honda State Park.

To see traveler tips, reviews, and tourist information, go to the Key West trip maker app .

Traveling by ferry from Marco Island to Key West takes 2.5 hours. Alternatively, you can drive. Traveling from Marco Island in May, you can expect nighttime temperatures to be a bit warmer in Key West, with lows of 77°F. Wrap up your sightseeing on the 20th (Wed) early enough to take a bus to Islamorada.

Things to do in Key West

Outdoors Tours Wildlife

Side Trip

Bahia Honda State Park
Highlights from your plan
Scuba & Snorkeling
Bahia Honda State Park ©
Bahia Honda State Park

1
night
Islamorada

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Start off your visit on the 21st (Thu): look for all kinds of wild species at Dolphin Research Center and then see what you can catch with a fishing tour.

To find ratings, traveler tips, more things to do, and other tourist information, refer to the Islamorada day trip planning tool .

Take a bus from Key West to Islamorada in 2 hours. Alternatively, you can drive. Expect a daytime high around 88°F in May, and nighttime lows around 77°F. Finish your sightseeing early on the 21st (Thu) to allow enough time to drive to Key Largo.

Things to do in Islamorada

Wildlife Outdoors Tours

Side Trip

Dolphin Research Center
Highlights from your plan
Fishing Charters & Tours
Dolphin Research Center ©
Dolphin Research Center

1
night
Key Largo

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.
Kick off your visit on the 22nd (Fri): take a memorable tour with Tours, then meet the residents at Island Dolphin Care, and then look for all kinds of wild species at Florida Keys Wild Bird Rehabilitation Center.

Before you visit Key Largo, use our trip planner to discover what you can do and see there.

You can drive from Islamorada to Key Largo in an hour. Another option is to do a combination of bus and taxi. Plan for a bit cooler nights when traveling from Islamorada in May since evenings lows in Key Largo dip to 72°F. Wrap up your sightseeing on the 22nd (Fri) early enough to travel back home.

Things to do in Key Largo

Wildlife Outdoors Tours
Highlights from your plan
Island Dolphin Care ©
Island Dolphin Care
Scuba & Snorkeling

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