44 days in Florida Itinerary

44 days in Florida Itinerary

Created using Inspirock Florida route planner

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Route & dates

44 days in Florida Itinerary

Start: Springfield
+2
bus + taxi + Fly:  8​h 45​min
1
Key West
— 6 nights
bus:  1​h 15​min
2
Marathon
— 5 nights
Drive:  45​min
3
Islamorada
— 5 nights
Drive:  45​min
4
Key Largo
— 5 nights
Drive:  1​h 15​min
5
Miami
— 5 nights
Drive:  2​h 15​min
6
Naples
— 5 nights
Drive:  2​h 45​min
7
Tampa
— 5 nights
Drive:  1​h 30​min
8
Orlando
— 6 nights
Fly:  7​h
End: Springfield

6
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.
Spend the 28th (Sat) exploring nature at Dry Tortugas National Park. There's lots more to do: examine the collection at The Ernest Hemingway Home and Museum, take a leisurely stroll along Mallory Square, make a trip to Southernmost Point, and discover the deep blue sea with a scuba or snorkeling tour.

To find traveler tips, ratings, photos, and other tourist information, you can read our Key West day trip planner.

Springfield to Key West is an approximately 9-hour combination of bus and flight. You can also fly; or drive. Traveling from Springfield to Key West, you'll lose 1 hour due to the time zone difference. Traveling from Springfield in December, expect Key West to be much warmer, temps between 79°F and 71°F. Cap off your sightseeing on the 30th (Mon) early enough to catcht the bus to Marathon.

Things to do in Key West

Outdoors Wildlife Tours
Highlights from your plan
Alan S. Maltz Gallery ©
Alan S. Maltz Gallery
The Ernest Hemingway Home and Museum ©

5
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.
Change things up with these side-trips from Marathon: Big Pine Key (National Key Deer Refuge & Grimal Grove) and Sugarloaf Key Bat Tower (in Sugarloaf). There's still lots to do: enjoy the sand and surf at Bahia Honda State Park, tour the pleasant surroundings at Sombrero Beach, snap pictures at Seven Mile Bridge, and identify plant and animal life at Crane Point Museum & Nature Center.

For more things to do, other places to visit, maps, and other tourist information, read our Marathon route website .

Getting from Key West to Marathon by bus takes about 1.5 hours. Other options: drive. In December, plan for daily highs up to 80°F, and evening lows to 71°F. Wrap up your sightseeing on the 4th (Sat) to allow time to drive to Islamorada.

Things to do in Marathon

Parks Wildlife Outdoors

Side Trips

Big Pine Key, Sugarloaf Key Bat Tower
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
National Key Deer Refuge ©
National Key Deer Refuge
Gemini Dream Charters ©
Gemini Dream Charters

5
nights
Islamorada

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Step out of Islamorada with an excursion to 99 Mile Wilderness Waterway in Everglades National Park--about 1h 15 min away. There's lots more to do: see what you can catch with a fishing tour, enjoy the sand and surf at Anne's Beach, immerse yourself in nature at Lignumvitae Key Botanical State Park, and sample the tasty concoctions at Islamorada Brewery & Distillery.

You can plan Islamorada trip in no time by asking Inspirock to help create your itinerary.

You can drive from Marathon to Islamorada in an hour. Another option is to take a bus. In January, daytime highs in Islamorada are 77°F, while nighttime lows are 66°F. Finish your sightseeing early on the 9th (Thu) so you can drive to Key Largo.

Things to do in Islamorada

Outdoors Tours Wildlife

Side Trip

99 Mile Wilderness Waterway
Highlights from your plan
Fishing Charters & Tours
99 Mile Wilderness Waterway ©
99 Mile Wilderness Waterway
Lignumvitae Key Botanical State Park ©

5
nights
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.
You'll find plenty of places to visit near Key Largo: Anhinga Trail (in Everglades National Park) and Homestead (Everglades Alligator Farm, Coral Castle, & more). The adventure continues: identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center, take a tour of USCG Duane, take a tour by water with Boat Tours & Water Sports, and have fun at Kiffney's Firearms and Indoor Range.

To see traveler tips and other tourist information, read our Key Largo visit planning site .

You can drive from Islamorada to Key Largo in an hour. Alternatively, you can do a combination of bus and taxi. Traveling from Islamorada in January, you can expect nighttime temperatures to be little chillier in Key Largo, with lows of 61°F. Finish your sightseeing early on the 14th (Tue) to allow enough time to drive to Miami.

Things to do in Key Largo

Parks Wildlife Outdoors

Side Trips

Homestead, Anhinga Trail
Highlights from your plan
Island Dolphin Care ©
Island Dolphin Care
Anhinga Trail ©
Anhinga Trail

5
nights
Miami

Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
Explore Miami's surroundings by going to Shark Valley Visitor Center (in Everglades National Park) and Thalatta Estate Park (in Palmetto Bay). There's lots more to do: take in nature's colorful creations at Fairchild Tropical Botanic Garden, get to know the fascinating history of Art Deco Historic District, admire the masterpieces at The Wolfsonian - Florida International University, and see the interesting displays at Lock & Load Museum.

Plan a Miami trip in moments using our itinerary builder.

Traveling by car from Key Largo to Miami takes 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 77°F in January, and nighttime lows around 63°F. Cap off your sightseeing on the 19th (Sun) early enough to go by car to Naples.

Things to do in Miami

Parks Museums Shopping

Side Trips

Miami Beach, Coral Gables, Shark Valley Visitor Center, Thalatta Estate Park
Highlights from your plan
Walking tours
Shark Valley Visitor Center ©
Shark Valley Visitor Center
Fairchild Tropical Botanic Garden ©
Fairchild Tropical Botanic Garden

5
nights
Naples

Naples is a city in Collier County, Florida, United States. Explore Naples' surroundings by going to Edison and Ford Winter Estates (in Fort Myers), Waterskiing & Jetskiing (in Marco Island) and Sanibel Island (J.N. "Ding" Darling National Wildlife Refuge & Sanibel Public Library). There's lots more to do: cast your line with a fishing tour, get to know the resident critters at Naples Zoo at Caribbean Gardens, look for all kinds of wild species at Wildlife Areas, and take a leisurely stroll along Naples Pier.

For maps, ratings, more things to do, and other tourist information, read Naples tour itinerary planner.

Traveling by car from Miami to Naples takes 2.5 hours. Alternatively, you can take a bus. Traveling from Miami in January, you can expect nighttime temperatures to be little chillier in Naples, with lows of 58°F. Cap off your sightseeing on the 24th (Fri) early enough to go by car to Tampa.

Things to do in Naples

Wildlife Parks Outdoors

Side Trips

Sanibel Island, Marco Island, Ten Thousand Islands National Wildlife Refuge, Ave Maria Oratory, Edison and Ford Winter Estates
Highlights from your plan
Fishing Charters & Tours
Dolphin & Whale Watching
Waterskiing & Jetskiing

5
nights
Tampa

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.
Change things up with these side-trips from Tampa: Sarasota (Siesta Key Rum, Sarasota National Cemetery, & more), Florida Exotic Bird Sanctuary (in Hudson) and Scuba & Snorkeling (in Crystal River). There's much more to do: cast your line with a fishing tour, do a tasting at Murielle Winery, find something for the whole family at Busch Gardens, and appreciate the history behind 9/11 Fallen Heroes Memorial.

To see maps, reviews, where to stay, and other tourist information, read our Tampa road trip tool .

Traveling by car from Naples to Tampa takes 3 hours. Alternatively, you can take a bus. Plan for slightly colder nights when traveling from Naples in January since evenings lows in Tampa dip to 53°F. Wrap up your sightseeing on the 29th (Wed) early enough to drive to Orlando.

Things to do in Tampa

Outdoors Tours Wildlife

Side Trips

Sarasota, Clearwater, Florida Exotic Bird Sanctuary, Scuba & Snorkeling, Imagine Museum
Highlights from your plan
Fishing Charters & Tours
Scuba & Snorkeling
Busch Gardens Tampa Bay ©
Busch Gardens Tampa Bay

6
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: find something for the whole family at Walt Disney World Resort, make an unforgettable trip to Happily Ever After Fireworks, test your team's savvy at The Escape Game Orlando, and explore the world behind art at Charles Hosmer Morse Museum of American Art.

For traveler tips, other places to visit, photos, and tourist information, you can read our Orlando trip builder app .

Traveling by car from Tampa to Orlando takes 1.5 hours. Alternatively, you can take a bus; or take a train. In January in Orlando, expect temperatures between 71°F during the day and 52°F at night. Finish your sightseeing early on the 4th (Tue) to allow enough time to travel back home.

Things to do in Orlando

Theme Parks Parks Wildlife

Side Trip

Charles Hosmer Morse Museum of American Art
Highlights from your plan
Walt Disney World Resort ©
Walt Disney World Resort
Universal Orlando Resort ©
Universal Orlando Resort
Universal's Islands of Adventure ©
Universal's Islands of Adventure

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