12 days in Orlando, Hilton Head & Tennessee Itinerary

12 days in Orlando, Hilton Head & Tennessee Itinerary

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Route & dates

12 days in Orlando, Hilton Head & Tennessee Itinerary

Start: Milwaukee
Fly:  5​h 15​min
1
Orlando
— 3 nights
Drive:  5​h 30​min
2
Hilton Head
— 1 day
Fly:  6​h
3
Pigeon Forge
— 1 night
Drive:  2​h 45​min
4
Ducktown
— 1 night
Drive:  1​h 30​min
5
Chattanooga
— 2 nights
Drive:  2​h 15​min
6
Nashville
— 1 night
Drive:  3​h 30​min
7
Memphis
— 1 night
Fly + bus:  5​h 45​min
End: Milwaukee

3
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.
Have a day of magic on the 23rd (Tue) at Walt Disney World Resort. Pack the 22nd (Mon) with family-friendly diversions at Universal Orlando Resort. There's lots more to do: get in on the family fun at SeaWorld Orlando, have some family-friendly fun at 7D Dark Ride Adventure, test your team's savvy at The Escape Game Orlando, and discover the magic at Happily Ever After Fireworks.

Planning Orlando trip won't be overwheling when you use's Insprock itinerary maker.

Milwaukee to Orlando is an approximately 5.5-hour flight. You can also do a combination of bus and flight; or drive. You'll lose 1 hour traveling from Milwaukee to Orlando due to the time zone difference. Traveling from Milwaukee in July, things will get a bit warmer in Orlando: highs are around 91°F and lows about 75°F. Finish your sightseeing early on the 23rd (Tue) so you can drive to Hilton Head.

Things to do in Orlando

Theme Parks Fun & Games Nightlife
Highlights from your plan
Universal Orlando Resort ©
Universal Orlando Resort
Walt Disney World Resort ©
Walt Disney World Resort
SeaWorld ©
SeaWorld

1
day
Hilton Head

A Hilton Head vacation may be heaven for a golfer, but the area also offers all kinds of other options for sports fans.
On the 24th (Wed), test your problem-solving skills at popular escape rooms, then race across the water with a speed boat tour, and then get interesting insight from Tours.

To find ratings, maps, photos, and tourist information, use the Hilton Head trip itinerary planning tool .

Getting from Orlando to Hilton Head by car takes about 5.5 hours. Other options: do a combination of train and taxi; or fly. In July in Hilton Head, expect temperatures between 89°F during the day and 75°F at night. Finish your sightseeing early on the 24th (Wed) to allow enough time to travel to Pigeon Forge.

Things to do in Hilton Head

Tours Outdoors Adventure
Highlights from your plan
Waterskiing & Jetskiing
Speed Boats Tours
Room Escape Games

1
night
Pigeon Forge

A tiny town with big tourist appeal, Pigeon Forge bills itself as the "Center of Fun in the Smokies." Just a short drive from the national park protecting the diverse plant and animal life of the Great Smoky Mountains, the town features numerous places to visit, such as bars, restaurants, cafes, theaters, and shops.
Start off your visit on the 25th (Thu): contemplate the waterfront views at 5 Rivers Adventures, relax and float downstream with a rafting and tubing tour, and then brush up on your knowledge of spirits at Sugarlands Distilling Company. On the 26th (Fri), you'll have a packed day of sightseeing: have some family-friendly fun at The Escape Game Pigeon Forge, then identify plant and animal life at Roaring Fork, and then take in the awesome beauty at Mount LeConte.

To see photos, more things to do, other places to visit, and tourist information, use the Pigeon Forge day trip tool .

Traveling by flight from Hilton Head to Pigeon Forge takes 6 hours. Alternatively, you can drive; or do a combination of bus and flight. Traveling from Hilton Head in July, expect little chillier with lows of 69°F in Pigeon Forge. Wrap up your sightseeing on the 26th (Fri) to allow time to drive to Ducktown.

Things to do in Pigeon Forge

Adventure Tours Outdoors

Side Trips

Hartford, Great Smoky Mountains National Park, Sugarlands Distilling Company
Highlights from your plan
River Rafting & Tubing
Mount LeConte ©
Mount LeConte
The Escape Game Pigeon Forge ©
The Escape Game Pigeon Forge

1
night
Ducktown

Ducktown is a city in Polk County, Tennessee, United States. On the 27th (Sat), contemplate the waterfront views at Ocoee Outdoors, Inc., then take a memorable tour with Tours, and then explore and take pictures at Mercier Orchards.

To find ratings, maps, other places to visit, and other tourist information, you can read our Ducktown driving holiday planner .

Traveling by car from Pigeon Forge to Ducktown takes 3 hours. July in Ducktown sees daily highs of 84°F and lows of 66°F at night. Wrap up your sightseeing on the 27th (Sat) early enough to drive to Chattanooga.

Things to do in Ducktown

Adventure Tours Outdoors

Side Trips

Ocoee Outdoors, Inc., Mercier Orchards
Highlights from your plan
River Rafting & Tubing
Mercier Orchards ©
Mercier Orchards

2
nights
Chattanooga

Once saddled with the reputation of being one of the country's dirtiest cities, Chattanooga now boasts a pedestrian-friendly downtown with a network of leafy waterfront trails and free electric shuttles.
On the 28th (Sun), test your problem-solving skills at Escape Experience - Chattanooga, see what you can catch with a fishing tour, and then let the river carry you with a rafting and tubing tour. Get ready for a full day of sightseeing on the next day: observe the fascinating underwater world at Tennessee Aquarium and then explore the activities along Adventures Unlimited.

For traveler tips, other places to visit, reviews, and more tourist information, use the Chattanooga trip planner .

You can drive from Ducktown to Chattanooga in 1.5 hours. Another option is to do a combination of taxi and bus. When traveling from Ducktown in July, plan for somewhat warmer days in Chattanooga, with highs around 90°F, while nights are about the same with lows around 71°F. Wrap up your sightseeing on the 29th (Mon) to allow time to drive to Nashville.

Things to do in Chattanooga

Parks Tours Outdoors

Side Trip

Ocoee
Highlights from your plan
River Rafting & Tubing
Adventures Unlimited ©
Adventures Unlimited

1
night
Nashville

Nashville ©
Known as the capital of country music, the thriving city of Nashville combines old-world southern charm with a progressive urban flair.
Start off your visit on the 30th (Tue): contemplate the long history of Lotz House Museum, then get your game on at The Escape Game Nashville (Berry Hill), and then sample some tasty brews at a beer tour and tasting.

To see traveler tips, photos, maps, and other tourist information, you can read our Nashville planning site .

Getting from Chattanooga to Nashville by car takes about 2.5 hours. Other options: take a bus. Traveling from Chattanooga to Nashville, you'll gain 1 hour due to the time zone difference. In July, daily temperatures in Nashville can reach 90°F, while at night they dip to 70°F. Finish your sightseeing early on the 30th (Tue) to allow enough time to drive to Memphis.

Things to do in Nashville

Tours Fun & Games Museums

Side Trip

Lotz House Museum
Highlights from your plan
The Escape Game Nashville (Berry Hill) ©
Lotz House Museum ©
Lotz House Museum
Beer Tastings & Tours

1
night
Memphis

Memphis ©
The largest city on the Mississippi River, Memphis bills itself as both the "Birthplace of Rock" and "Home of the Blues." With such a rich musical heritage, it shouldn't come as a surprise that Elvis Presley chose to live in Memphis during his later years.
Start off your visit on the 31st (Wed): make a trip to Graceland and then pause for some photo ops at National Civil Rights Museum - Lorraine Motel.

For ratings, more things to do, reviews, and tourist information, refer to the Memphis trip itinerary planner.

Traveling by car from Nashville to Memphis takes 3.5 hours. Alternatively, you can take a bus; or fly. In July, daytime highs in Memphis are 91°F, while nighttime lows are 74°F. Wrap up your sightseeing on the 31st (Wed) early enough to travel back home.

Things to do in Memphis

Museums Historic Sites
Highlights from your plan
Graceland ©
Graceland

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