22 days in Florida Itinerary

22 days in Florida Itinerary

Created using Inspirock Florida route planner

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Route & dates

22 days in Florida Itinerary

Start: Norfolk
Fly:  3​h 45​min
1
Orlando
— 4 nights
train:  30​min
2
Kissimmee
— 1 night
Fly:  4​h 30​min
3
Key West
— 5 nights
bus:  45​min
4
Big Pine Key
— 2 nights
Drive:  30​min
5
Marathon
— 3 nights
Drive:  1​h 15​min
6
Key Largo
— 3 nights
Drive:  1​h 15​min
7
Miami
— 3 nights
Fly:  4​h 15​min
End: Norfolk

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.
Stetson Mansion and St James Roman Catholic Cathedral will appeal to history buffs. Shop till you drop at Franklin Anderson Gallery and Plant Street Market. Change things up with a short trip to Scuba & Snorkeling in Crystal River (about 1h 45 min away). The adventure continues: get in on the family fun at Discovery Cove, make an unforgettable trip to Disney's Animal Kingdom, try out the rides at Disney's Hollywood Studios, and take in a show at Happily Ever After Fireworks.

To see more things to do, maps, other places to visit, and more tourist information, read Orlando holiday planner.

Norfolk to Orlando is an approximately 4-hour flight. You can also drive; or take a train. While traveling from Norfolk, expect much warmer days and a bit warmer nights in Orlando, ranging from highs of 77°F to lows of 59°F. Finish your sightseeing early on the 31st (Tue) so you can take a train to Kissimmee.

Things to do in Orlando

Theme Parks Parks Outdoors

Side Trips

Crystal River, Plant Street Market, Charles Hosmer Morse Museum of American Art, Stetson Mansion
Highlights from your plan
Stetson Mansion ©
Stetson Mansion
Scuba & Snorkeling

1
night
Kissimmee

Kissimmee ©
A popular vacation destination in the central part of Florida, Kissimmee's major claim to fame remains its sunny weather and proximity to a large Disney entertainment complex.
Kick off your visit on the 1st (Wed): stop by Black Market Minerals, then wander the streets of Old Town, and then learn about winemaking at Island Grove Wine Company at Formosa Gardens.

For reviews, other places to visit, ratings, and tourist information, use the Kissimmee tour itinerary builder site .

Kissimmee is just a short distance from Orlando. In December in Kissimmee, expect temperatures between 76°F during the day and 59°F at night. Finish your sightseeing early on the 1st (Wed) so you can travel to Key West.

Things to do in Kissimmee

Neighborhoods Wineries Shopping
Highlights from your plan
Old Town ©
Old Town
Black Market Minerals ©
Black Market Minerals

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.
The Ernest Hemingway Home and Museum and 7 Artists & Friends will appeal to museum buffs. Deepen your sense of the past at sights like Truman Little White House and Fort Zachary Taylor. Next up on the itinerary: identify plant and animal life at Key West Butterfly & Nature Conservatory, cast your line with a fishing tour, take in the exciting artwork at Collections Key West, and take in the architecture and atmosphere at Saint Mary Star of the Sea.

To find traveler tips, photos, other places to visit, and tourist information, refer to the Key West trip itinerary planner .

Getting from Kissimmee to Key West by flight takes about 4.5 hours. Other options: drive; or do a combination of bus and train. Traveling from Kissimmee in January, expect somewhat warmer with lows of 66°F in Key West. Wrap up your sightseeing on the 6th (Mon) early enough to take a bus to Big Pine Key.

Things to do in Key West

Wildlife Outdoors Tours
Highlights from your plan
The Ernest Hemingway Home and Museum ©
Truman Little White House ©
Truman Little White House

2
nights
Big Pine Key

Big Pine Key ©
Big Pine Key is a census-designated place and unincorporated community in Monroe County, Florida, United States, on an island of the same name in the Florida Keys. Start off your visit on the 7th (Tue): kick back and relax at Calusa Beach, then enjoy the sand and surf at Bahia Honda State Park, and then make a trip to Adolphus Busch. Here are some ideas for day two: look for gifts at Out of the Blue Gallery, then look for all kinds of wild species at National Key Deer Refuge, and then view the masterpieces at Artists in Paradise Gallery.

For more things to do, maps, reviews, and more tourist information, you can read our Big Pine Key day trip planning app .

Getting from Key West to Big Pine Key by bus takes about an hour. Other options: drive. In January in Big Pine Key, expect temperatures between 77°F during the day and 66°F at night. Cap off your sightseeing on the 8th (Wed) early enough to go by car to Marathon.

Things to do in Big Pine Key

Parks Outdoors Beaches
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
National Key Deer Refuge ©
National Key Deer Refuge
Artists in Paradise Gallery ©
Artists in Paradise Gallery

3
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.
You'll enjoy a bit of beach vacationing at Sombrero Beach and Sunset Park Beach. Satisfy your inner culture vulture at Indian Key State Historic Site and Shady Palm Art Gallery & Photography. Take a break from Marathon with a short trip to Florida Keys Brewing Company in Islamorada, about 38 minutes away. There's more to do: look for all kinds of wild species at Crane Point Museum & Nature Center and see what you can catch with a fishing tour.

To find traveler tips, ratings, and other tourist information, refer to the Marathon tour itinerary builder tool .

Marathon is just a stone's throw from Big Pine Key. In January, daytime highs in Marathon are 77°F, while nighttime lows are 66°F. Cap off your sightseeing on the 11th (Sat) early enough to go by car to Key Largo.

Things to do in Marathon

Parks Wildlife Outdoors

Side Trips

Islamorada, Sunset Park Beach
Highlights from your plan
Crane Point Museum & Nature Center ©
The Turtle Hospital ©
The Turtle Hospital
Dolphin Research Center ©
Dolphin Research Center

3
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.
Museum-lovers will appreciate Pasta Pantaleo Signature Gallery and Old Road Gallery. Do some cultural sightseeing at Michelle Nicole Lowe Art Gallery and Homestead Historic Town Hall Museum. Get out of town with these interesting Key Largo side-trips: Fishing Charters & Tours (in Islamorada) and Anhinga Trail (in Everglades National Park). There's much more to do: look for all kinds of wild species at Florida Keys Wild Bird Rehabilitation Center, get a new perspective on things with Boat Tours & Water Sports, fulfill a lifelong dream with a swim-with-the-dolphins experience, and stop by Petals With Pizzazz.

For photos, where to stay, traveler tips, and tourist information, use the Key Largo trip planner .

Traveling by car from Marathon to Key Largo takes 1.5 hours. Alternatively, you can take a bus. Traveling from Marathon in January, expect a bit cooler with lows of 61°F in Key Largo. Finish your sightseeing early on the 14th (Tue) so you can drive to Miami.

Things to do in Key Largo

Wildlife Outdoors Tours

Side Trips

Islamorada, Anhinga Trail, Homestead Historic Town Hall Museum
Highlights from your plan
Fishing Charters & Tours
Scuba & Snorkeling

3
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.
Satisfy your inner culture vulture at Lincoln Road and Lock & Load Museum. Head to Aventura Mall and Collins Avenuefor plenty of shopping. You'll find plenty of places to visit near Miami: Panther Ridge Conservation Center (in Wellington) and Shark Valley Visitor Center (in Everglades National Park). Next up on the itinerary: kick back and relax at South Beach, admire the masterpieces at The Wolfsonian - Florida International University, and get to know the fascinating history of Art Deco Historic District.

To find ratings and more tourist information, read Miami trip itinerary maker site .

Drive from Key Largo to Miami in 1.5 hours. Alternatively, you can take a bus. In January, daily temperatures in Miami can reach 77°F, while at night they dip to 63°F. Finish your sightseeing early on the 17th (Fri) so you can travel back home.

Things to do in Miami

Parks Shopping Neighborhoods

Side Trips

Miami Beach, Panther Ridge Conservation Center, Shark Valley Visitor Center, Aventura Mall
Highlights from your plan
Shark Valley Visitor Center ©
Shark Valley Visitor Center
Lincoln Road ©
Lincoln Road
Art Deco Historic District ©
Art Deco Historic District

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