14 days in Miami, Key West & Orlando Itinerary

14 days in Miami, Key West & Orlando Itinerary

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Route & dates

14 days in Miami, Key West & Orlando Itinerary

Start: Winston Salem
Drive:  13​h 30​min
1
Miami
— 1 night
Drive:  4​h 30​min
2
Key West
— 3 nights
Drive:  8​h 30​min
3
Orlando
— 9 nights
Drive:  10​h 30​min
End: Winston Salem

1
night
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.
To see other places to visit, photos, ratings, and other tourist information, go to the Miami trip itinerary planning website .

Winston Salem to Miami is an approximately 7-hour combination of bus and flight. You can also do a combination of bus, flight, and train; or drive. Traveling from Winston Salem in May, things will get a bit warmer in Miami: highs are around 87°F and lows about 74°F. Finish up your sightseeing early on the 2nd (Sun) so you can travel to Key West.

Things to do in Miami

Outdoors Tours Parks

3
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.
Kick off your visit on the 3rd (Mon): don't miss a visit to Southernmost Point, then don't miss a visit to Duval Street, then steep yourself in history at Truman Little White House, and finally take in the waterfront at Mallory Square. Here are some ideas for day two: look for all kinds of wild species at Wildlife Areas and then take a tour by water with Boat Tours & Water Sports.

To find maps, reviews, where to stay, and other tourist information, use the Key West online tour itinerary planner .

Traveling by flight from Miami to Key West takes 2.5 hours. Alternatively, you can do a combination of bus and flight; or drive. In May, daily temperatures in Key West can reach 85°F, while at night they dip to 77°F. Wrap up your sightseeing on the 5th (Wed) early enough to travel to Orlando.

Things to do in Key West

Wildlife Tours Outdoors
Highlights from your plan
Fishing Charters & Tours
Mallory Square ©
Mallory Square
Duval Street ©
Duval Street

9
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.
Your list of things to see and do now includes Spas, Downtown Orlando, Gods & Monsters, and other attractions. Have a day of magic on the 7th (Fri) at Magic Kingdom Park. Have a day of magic on the 11th (Tue) at Disney's Animal Kingdom. The adventure continues: make an unforgettable trip to Disney's Hollywood Studios.

For photos, more things to do, other places to visit, and other tourist information, use the Orlando itinerary maker app .

Getting from Key West to Orlando by flight takes about 4.5 hours. Other options: drive; or take a bus. Traveling from Key West in May, you can expect nighttime temperatures to be slightly colder in Orlando, with lows of 69°F. On the 14th (Fri), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Orlando

Theme Parks Shopping Wildlife
Highlights from your plan
Magic Kingdom Park ©
Magic Kingdom Park
Disney's Animal Kingdom ©
Disney's Animal Kingdom
Epcot ©
Epcot

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