There are lots of places to visit on that route. Some of my recommendations would include DC. Outer Banks of NC, Wilmington, NC, Charleston , Savannah and St. Augustine FL.

There are some great trip reports written by lots of people who have done it. Recommendations will vary depending on the time of year you plan to travel. Will the entire 2 weeks be devoted to the drive?

suewoo has a nice list and I would add Williamsburgh/Jamestown VA

Get a copy of Jane and Michael Stern's book(s) about road food. Or Guy Fieri's Diners Driveins and Dives for really good local food.
In NC you must have at least one memorable BBQ meal.
Just a little inland in NC you could hit Winston Salem for its Old Salem historical town.

I would visit the Outer Banks for a night or two and head S to Pawley's Island. Spend a couple of nights in historic Charleston, SC. Stay in the HD and head S to Savannah, GA. Stop at St. Simons Island for a night or two and head S to Amelia Island, FL. Enjoy your trip.

Here's a few places to stop and rest on your way to FL. When you reach VA on I 95 at Exit 31 try Stony Creek Tastee Hut for good fried chicken or BBQ.
Take Exit 138 off I 95 at Rocky Mt., NC and go E on I 64 for 1 1/2 miles to Exit 466 and go S on N Winstead Ave. to Sunset Ave. Take a right and go to Gardner's BBQ. Gardner's has 3 locations in Rocky Mt., NC but this one on Sunset is the most convenient to I 95. You will pass a Hampton Inn on your right when you exit I 64 if you are planning to spend the night in Rocky Mt., NC.
Hampton Inn @ 530 North Winstead Avenue, Rocky Mount, NC 252 - 937 - 6333.
http://www.hamptoninn.com/en/hp/hotels/index.jhtml?ctyhocn=RWINCHX
Gardner's Barbecue @ 3651 Sunset Avenue, Rocky Mount, NC 252 - 443 - 3996.
http://www.gardnerfoods.com/Home.html
Get off I 95 at Exit 90 just S of Smithfield, NC to your right and turn back N on Highway 301 and go to White Swan BBQ just up the road for good BBQ.
White Swan BBQ @ 3198 South Brightleaf Blvd., Smithfield, NC 919 - 934 - 8913.
http://www.whiteswanbarbeque.com/
Take Exit # 138 going S on I 95 at Nashville, NC and go W on # 64 about 6 miles to Exit # 458. Turn back E on Western Ave. less than a mile for some outstanding BBQ at Doug Saul's.
Doug Saul's BBQ @ 813 Western Ave., Nashville, NC 252 - 459 - 4247.
For outstanding BBQ and country fried chicken get off I 95 at Exit 79 at Benson, NC and go W on E Main Street to N Fayetteville Street which is the first street to your right. Take a right and go N to E Church Street. Take a right and go to N Honeycutt Street. White Swan will be on your left.
White Swan BBQ and Fried Chicken @ 105 N Honeycutt St, Benson, NC 919 - 894 - 4446.
http://www.whiteswanbarbeque.com/
At Exit 73 in Dunn, NC get off I 95 going W on Cumberland go about a mile take a right on General Lee and next left on Broad for some fine fried chicken at Kim's. Don't let the name bother you. They sell a BBQ sandwich but 99% country food.
Kim's BBQ House @ 900 W. Broad St., Dunn, NC. 910 - 892 - 7750.
Heading N on I 95 at Exit 56 try Fuller's Old Fashioned BBQ at Fayetteville, NC. They sell a good burger and also a buffet lunch with fried chicken.
Fuller's Old Fashioned BBQ @ 113 N. Eastern Blvd., Fayetteville, NC. 910 - 484 - 5109.
http://www.fullersbbq.com/index.html
Get off I 95 at Exit 181A and go one mile to Highway 917. Take a left and go about 3 miles to Abingdon Manor Inn and Restaurant at Latta, SC. Spend the night in a soft bed in a grand old inn and have a fantastic dinner.
Abingdon Manor Inn and Restaurant @ 307 Church Street, Latta, SC 843 - 752 - 5090.
http://www.abingdonmanor.com/
Get off I 95 at Exit 160 A going S at Florence, SC and go E on # 20 less than a mile to Red Bone Alley in Florence Mall Shopping Center on Palmetto St. for a RBA Black and Bleu Burger or a Bubba Burger. Or go to Apple Annie's for good road food.
Redbone Alley @ 1903 West Palmetto St., Florence, SC 843 - 673 - 0035.
http://www.redbonealley.com/
Apple Annie's Deli and Pub @ 1720 W Palmetto Street, Florence, SC 843 - 669 - 6247.

Get off I 95 in Summerton, SC at Exit # 108 and go N less than a mile to Church St. and good country cooking at Summerton Diner.
Summerton Diner @ 32 Church St., Summerton, SC 803 - 485 - 6835.
Get off I 95 at Exit 119 at Manning, SC and go E on Highway 261 to N Brooks Street. Take a left and go to McCabe's for good BBQ.
McCabe's Bar B Que @ 480 N. Brooks St., Manning, SC. 803 - 435 - 2833.
Get off I 95 at Exit 119 at Manning, SC and go E to Scott's for outstanding BBQ.
Scott's Variety Store and BBQ @ SC Hwy. 261, Hemingway, SC. 843 - 558 - 3629.
http://www.thescottsbbq.com/
Get off I 95 at Exit 98 at Santee, SC and go W on Highway 6 to the 1st street on your left which is Britain. Turn left and go to Maurice's for good BBQ. Get off I 95 at Exit 98 and go W on Highway 6. Take a right on State Park Road and go to Lonestar BBQ for good southern food. Clark's Inn and Restaurant is a very fine place to spend the night and have breakfast, lunch or dinner.
Maurice's Gourmet BBQ @ 263 Britain St, Santee, SC 803 - 854 - 3889.
http://www.mauricesbbq.com/
Lonestar BBQ @ 2212 State Park Rd., Santee, SC. 803 - 854 - 2000
http://www.lonestarbbq.net/
Clark's Inn and Restaurant @ 114 Bradford Boulevard, Santee, SC 803 - 854 - 2101.
http://www.clarksinnandrestaurant.com/
Get off I 95 at Exit 38 at Yemassee, SC and go SE on Highway 68 to Castle Hall Road to Ray's Rib King for good BBQ.
Ray's Rib King @ 4 Castle Hall Road, Yemassee, SC 843 - 589 - 2919.
Get off I 95 at Exit 57 at Walterboro, SC for good BBQ @ Duke's. Low Country is good but Duke's is best.
Duke's BBQ @ 949 Robertson Blvd., Walterboro, SC 843 - 549 - 1446.
Low Country BBQ @ 635 South Jefferies Blvd., Walterboro, SC 843 - 549 - 8355.
Get off I95 at Exit 21 at Ridgeland, SC and go E on Grahamville Road to State Road S/27/13 and take a right. Take your next left and go to The Old House Smokehouse on Highway 336 or Old House Road for good steaks and seafood. Get off I 95 at Exit 21 at Ridgeland, SC and have great pulled or chopped port at BBQ Grill. They also have BBQ ribs and chicken. I think it's better than Dukes.
Old House Smokehouse @ Hwy. 462 @ hwy.336, Ridgeland, SC 843 - 258 - 4444.
BBQ Grill @ 8084 East Main St., Ridgeland, SC 843 - 645 - 4414.
Duke's BBQ @ 690 South Jacob Smart Blvd., Ridgeland, SC 843 - 726 - 6244.
Get off I 95 at Exit 102 at Pooler. GA and go W on Highway 80 4/5 blocks to Don's Famous BBQ.
Don's Famous BBQ @ 217 US Highway 80 E., Pooler, GA 912 - 748 - 8400.
Get off I 95 at Exit 5 at Hardeville, SC and go S on Highway 17 which is Speedway Boulevard. Go 5.5 miles and take a left on Highway 170A which is S 27 34 and go 3.5 miles to Oakatie Highway. Take a right and go to The Pink Pig.
The Pink Pig @ 3508 South Okatie Highway, Hardeeville, SC 843 - 784 - 3635.
http://www.the-pink-pig.com/
Get off I 95 at Exit 87 at Richmond Hill, GA and go W on Highway 17 half a mile to Smoking Pig BBQ next to the BP Station on N side of Highway 17. The ribs and chicken are excellent. This is probably your best stop for BBQ in GA.
Smokin Pig BBQ @ 3986 U.S. 17, Richmond Hill, GA. 912 - 756 - 7850.
Get off I 95 at Exit 76 at Midway, GA and go E on Highway 38 to Sunbury Rd. Take a left and go to Brigantine Dunmore Rd. Take a left and go to Sunbury Crab Co. which is open for dinner serving outstanding fresh seafood. This might be the best place you stop for the seafood is outstanding.
Sunbury Crab Co. @ 539 Brigantine Dunmore Road Midway, GA 912 - 884 - 8640.
http://sunburycrabco.wp.net/
Get off I 95 at Exit 67 at Townsend, GA to the right and go S on Highway 17 for 1.2 miles then take a left going E onto Harris Neck Road just past a small church. Go 5.7 miles E to the Jessie Grant Road and look for the purple OSD sign on your left. Turn to the right at the sign for about 100 feet to Old School Diner for the best fresh seafood around. OSD is open for dinner Wednesday/Saturday and Noon to 10 PM on Sunday. They are closed on Monday and Tuesday. This might be the best road food you will have on your trip.
Old School Diner @ 1080 Jesse Grant Road, Townsend, GA 912 - 832 - 2136.
http://oldschooldiner.com/
Get off I 95 at Exit 58 at Townsend, GA to the right on Highway 99 and go less than a mile to Highway 17. Turn left and go N about 2 miles to Pine Harbor Rd. Take a right and go E about 2 miles to Sepelo Station Crossing and fantastic fresh local seafood and hand cut steaks.
Sapelo Station Crossing @ 1172 Pine Harbor Marina Road, Townsend, GA 912 - 832 - 3555.
Get off I 95 at Exit 49 to the right at Darien, GA and go NW on Highway 251 less than a mile to Smokey Joe's BBQ. It is between two hotels on the left and has excellent pulled pork.
If you want the best fresh seafood on your trip get off I 95 at Exit 49 in Darien, GA to the right and go E on Highway 251 to Highway 17. Take a right on Highway 17 and go S for 1.2 miles. Turn right on Broad St. just before crossing the bridge. Go one block and take your first left on Screven St. and have some outstanding fresh seafood at Skipper's Fish Camp. [size=3 font="times new roman"].
Smokey Joe's BBQ @ State Hwy. 251, Darien, GA. 912 - 437 - 2555.
Skipper's Fish Camp @ 85 Screven St., Darien, GA 912 - 437 - 3474.
http://www.skippersfishcamp.com/
Get off I 95 at Exit 1 and go W on St. Mary's which turns into Scrubby Bluff Rd. and go to Jack's BBQ. Or you can get off I 95 at Exit 3 at Kingsland, GA and cross E King Ave. to Boone Ave. which is the next street then take a left to Blue's BBQ at the Chevron Market for good BBQ.
Jack's BBQ @ 1359 Scrubby Bluff Rd., Kingsland, GA 912 - 729 - 1500.
Blue's BBQ @ 1330 Boone Ave. Extension E, Kingsland, GA 912 - 576 - 8682.
Get off I 95 at Exit 29 and go W on Highway 82 about a mile to Gary Lee's Market for good road food.
Gary Lee's Market @ 3636 U. S. Hwy. 82, Brunswick, GA. 912 - 265 - 1925.
When you get to Jacksonville, FL on I 95 get off at Exit 353 C on W Union St. and go about 8 blocks to Pearl and take a left to Jenkin's Quality BBQ which is home owned by the Jenkins' Family for over 50 years. Get off I 95 at Exit 373 and go W to Callahan's BBQ.
Jenkin's Quality BBQ @ 830 North Pearl Street, Jacksonville, FL 904 - 353 - 6388.
http://www.jenkinsqualitybarbecue.com/
Callahan's BBQ @ 45007 State Rd 200, Callahan, FL 904 - 879 - 4675.

Littleman: You are amazing!

We are contemplating something similar for our spring break this year (but starting in Brooklyn and stopping in Georgia), so I'm interested to see the responses to this post too! Charleston and Savannah are on our list (plus a stop in the Shenandoah Valley). LIttleman, your food intel is amazing!

I currently live in NC and have lived in DC and Baltimore. Having said that, I would "second" the recommendations for the Shenandoah Mountains, (camping/cabins there are wonderful); the Outer Banks of NC; Charleston; and Savannah. IMHO, I wouldn't bother with Winston-Salem but, if you want to venture inland, Asheville and the Biltmore are terrific...

With only 2 weeks, you might first decide if you want the eastern route or the western one which would include Asheville, and the Shenandoahs. But again, we can help you decide if you tell us what time of year you plan to travel.

In spring you may want to look at the Azalea Festival in Wilmington, NC and the Festival of Flowers at Biltmore.

Strongly seconding US 17. Except around Myrtle Beach it pretty well takes you to places full of real people: New Bern and Wilmington, NC; Georgetown, Pawley's Island, Charleston, and Beaufort, SC; Savannah and St Simons Island, GA; and Fernandina Beach and Amelia Island, FL, after you leave 17. There is a great little ferry from Amelia Island to the mainland that will thrill the kids and bypass Jacksonville. St Augustine is on your route, then you can get back to the horror of I-95 and blast your way south to Miami.

Thank you for the question.
Of those we plan on 8 days (max 10) of road time in the first part of August.

Suewoo, what is the difference in the western and eastern route?
Aknards, any recommendations on cabins to stay at? And any more specifics on your ideas?

many thanks to each of you for these great suggestions

Eastern: coastal, Western: mountains.

You might want to add Cape Canaveral/Kennedy Space Center to your Florida list.

I'm ready to hit the road and it has been a daunting prep.

a big thanks to Littleman for the recommendations!

I'll post my experience here for those interested in our trip results. Thanks