7 days in Kissimmee, Key West & Miami Beach Itinerary

7 days in Kissimmee, Key West & Miami Beach Itinerary

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Route & dates

7 days in Kissimmee, Key West & Miami Beach Itinerary

Start: Orlando
train:  30​min
1
Kissimmee
— 1 night
Fly:  4​h 30​min
2
Key West
— 2 nights
Fly:  3​h
3
Miami Beach
— 3 nights
Fly:  3​h 30​min
End: Orlando

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.
On the 24th (Tue), wander the streets of Old Town, experience the excitement of The Twilight Zone Tower of Terror, and then stop by Black Market Minerals. Here are some ideas for day two: enjoy some diversion at Machine Gun America, identify plant and animal life at Circle B Bar Reserve, and then test your problem-solving skills at popular escape rooms.

To find maps, photos, where to stay, and other tourist information, read our Kissimmee online trip builder .

Orlando to Kissimmee is an approximately half hour train ride. You can also take a bus; or drive. In September, daytime highs in Kissimmee are 89°F, while nighttime lows are 74°F. Finish your sightseeing early on the 25th (Wed) to allow enough time to travel to Key West.

Things to do in Kissimmee

Neighborhoods Fun & Games Parks

Side Trip

Lakeland
Highlights from your plan
Old Town ©
Old Town
Circle B Bar Reserve ©
Circle B Bar Reserve
Machine Gun America ©
Machine Gun America

2
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.
Kick off your visit on the 26th (Thu): see the interesting displays at The Ernest Hemingway Home and Museum, identify plant and animal life at Key West Butterfly & Nature Conservatory, get a new perspective on things with Boat Tours & Water Sports, then take a leisurely stroll along Mallory Square, and finally appreciate the history behind Florida Keys Historical Military Memorial. On the next day, get up close to creatures of the deep with a dolphin and whale watching tour, don't miss a visit to Southernmost Point, then make a trip to Duval Street, and finally stroll the grounds of Key West Cemetery.

To see other places to visit, ratings, maps, and other tourist information, refer to the Key West travel planning app .

Traveling by flight from Kissimmee to Key West takes 4.5 hours. Alternatively, you can drive; or do a combination of bus and train. Traveling from Kissimmee in September, you can expect nighttime temperatures to be somewhat warmer in Key West, with lows of 80°F. Wrap up your sightseeing on the 27th (Fri) early enough to travel to Miami Beach.

Things to do in Key West

Tours Wildlife Outdoors
Highlights from your plan
The Ernest Hemingway Home and Museum ©
Parasailing & Paragliding

3
nights
Miami Beach

Miami Beach ©
Separated by water from the neighboring city of Miami, Miami Beach sits on a barrier island between Biscayne Bay and the Atlantic Ocean.
You've now added Bayside Marketplace to your itinerary. When in Miami Beach, make a side trip to see Scuba & Snorkeling in Key Largo, approximately 1h 20 min away. There's still lots to do: kick back and relax at South Beach, examine the collection at Lock & Load Museum, look for gifts at The Official Art Deco Gift Shop, and enjoy some diversion at Lock & Load Miami.

To see reviews, photos, maps, and tourist information, read our Miami Beach visit planning app .

Traveling by flight from Key West to Miami Beach takes 3 hours. Alternatively, you can drive; or take a bus. In September, daily temperatures in Miami Beach can reach 90°F, while at night they dip to 77°F. Finish your sightseeing early on the 30th (Mon) to allow enough time to travel back home.

Things to do in Miami Beach

Shopping Neighborhoods Outdoors

Side Trips

Miami, Scuba & Snorkeling
Highlights from your plan
Bayside Marketplace ©
Bayside Marketplace
South Beach ©
South Beach
Scuba & Snorkeling

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