Published: March, 2022
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College Tour: Charleston to Orlando

Plan, plan and plan, and then plan some more.
— Cynthia Pillsbury
  • More about your Oliver Guide:
  • Trip type: Adult, Family, Beach, City
  • Activity level: moderate
  • Ideal length of trip: One day per city/college.

to & from

I love a road trip… really I do and this trip is quite a (charming) doozy. Fly into Charlotte (CLT) or Greensboro (GSO), tour Wake Forest and Elon, (only 45 minutes apart) then drive (about 4.5 hours) to Charleston, SC, spend a night or two, tour College of Charleston… then either fly or drive (9 hours) to Winter Park, FL and tour Rollins College… if you are not a road trippin’-type … fly to Orlando!

Where to Stay

Based on a close friend’s recommendation who toured Wake Forest we opted to stay at Graylyn Estate in the charming shopping center of Reynolda, NC. The area has a few shops, (Monkee’s is a local favorite) cafe, restaurants and a museum, I wish we had time to explore. Winston-Salem is the closet (10 minutes) town and we did a drive through and noticed a very cool hotel, The Katharine. I would consider staying there!

Thanks to our Charleston Oliver Guide and our friend and travel agent, Polly Bade, we checked into the Planters Inn and went directly to dinner at their restaurant, Peninsula Grill. The scene is charming + sophisticated and food, delicious! There are so many options in Charleston, it’s all about the location and vibe you are after…

In Rollins we were in and out, but if we had stayed (which I wish we had… ) we would opt for The Alfond Inn, it comes highly recommended.

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