7 days in Kissimmee, Charleston & Williamsburg Itinerary

7 days in Kissimmee, Charleston & Williamsburg Itinerary

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Route & dates

7 days in Kissimmee, Charleston & Williamsburg Itinerary

Start: Orlando
train:  30​min
1
Kissimmee
— 1 day
Drive:  7​h
2
Charleston
— 2 nights
Drive:  7​h 45​min
3
Williamsburg
— 1 night
Drive:  12​h 45​min
End: Orlando

1
day
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.
Start off your visit on the 20th (Sun): pause for some serene contemplation at Corpus Christi Catholic Church, then try for a hole-in-one at Disney's Winter Summerland Miniature Golf Course, and then wander the streets of Old Town.

To find traveler tips, other places to visit, ratings, and more tourist information, you can read our Kissimmee trip itinerary maker tool .

Orlando to Kissimmee is an approximately half hour train ride. You can also drive; or take a bus. In October, plan for daily highs up to 84°F, and evening lows to 68°F. Finish your sightseeing early on the 20th (Sun) so you can drive to Charleston.

Things to do in Kissimmee

Neighborhoods Fun & Games Historic Sites

Side Trip

Corpus Christi Catholic Church
Highlights from your plan
Old Town ©
Old Town
Corpus Christi Catholic Church ©
Corpus Christi Catholic Church

2
nights
Charleston

Many visitors describe their Charleston holiday as a warm embrace by an old, dear friend--who lived about 200 years ago.
You'll explore the less-touristy side of things at Fort Moultrie and St. Michael's Church. Your cultural itinerary includes sights like Hopsewee Plantation and Magnolia Plantation & Gardens. Next up on the itinerary: see majestic marine mammals with a dolphin and whale watching tour, admire the striking features of Cathedral of Saint John the Baptist, take a tour by water with Boat Tours & Water Sports, and don't miss a visit to Charleston Fire Department, Station 2/3.

To see more things to do, where to stay, other places to visit, and other tourist information, read Charleston holiday planning website .

Traveling by car from Kissimmee to Charleston takes 7 hours. Alternatively, you can fly; or do a combination of train and flight. Traveling from Kissimmee in October, expect Charleston to be little chillier, temps between 78°F and 60°F. Cap off your sightseeing on the 23rd (Wed) early enough to travel to Williamsburg.

Things to do in Charleston

Historic Sites Tours Outdoors

Side Trips

Hopsewee Plantation, Dolphin & Whale Watching, Fort Moultrie
Highlights from your plan
Dolphin & Whale Watching
Fort Moultrie ©
Fort Moultrie
St. Michael's Church ©
St. Michael's Church

1
night
Williamsburg

Williamsburg ©
Founded in 1632 as a fortified settlement on the high ground between two rivers, Williamsburg served as a colonial capital of Virginia for over 80 years.
On the 24th (Thu), steep yourself in history at Bassett Hall, contemplate the long history of Historic Jamestowne, and then steep yourself in history at Jamestown Settlement. Keep things going the next day: steep yourself in history at Colonial Williamsburg, contemplate in the serene atmosphere at St. Luke's Historic Church & Museum, and then stop by Quirks of Art.

To see maps, more things to do, where to stay, and tourist information, refer to the Williamsburg trip planner.

Getting from Charleston to Williamsburg by flight takes about 6.5 hours. Other options: do a combination of flight and bus; or drive. Traveling from Charleston in October, plan for slightly colder nights in Williamsburg, with lows around 55°F. Finish your sightseeing early on the 25th (Fri) so you can travel back home.

Things to do in Williamsburg

Historic Sites Museums Shopping

Side Trip

St. Luke's Historic Church & Museum
Highlights from your plan
Bassett Hall ©
Bassett Hall
St. Luke's Historic Church & Museum ©
Colonial Williamsburg ©
Colonial Williamsburg

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