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.

Where to Eat and Drink

In Winston-Salem, we arrived late to the hotel and ate dinner there. It was sub-par (being generous). I wish we had arrived an hour earlier to have dinner at one of the few restaurants in Reynold Village.

We built in an extra day to shop, eat, tour College of Charleston (tour at 12:15) and even made it out to Sullivan’s Island for a dose of beach. We were blown away by the caliber of food and shopping in this little strip of a beach town. It felt like a bit like Stinson Beach, but better shopping! Check out our Charleston Guide for more information- but DO NOT MISS The Obstinate Daughter… the food is as good as the name.

We also had the good fortune to happen upon the bar at FIG in Charleston and enjoyed a delicious dinner. A local friend says this is her favorite restaurant in Charleston, which is saying a lot.

What to Do

Wake-Forest was not offering tours when we visited so were lucky to have a tour by a friend. Then we drove to Elon (only 45 minutes) and made the 2pm tour. Elon is impressive, highly organized and the info session and tour is very thorough (and long).

After the tour at Elon we were Charleston bound. The drive is easy, but long (5 hours).

We got up early had breakfast at Caviar & Bananas  (on College of Charleston Campus) and met our tour at 12:15.

For those road warriors among us, we got up EARLY the next am and drove 9 hours (yes, 9 hours) to Winter Park, FL, home to Rollins College. Our tour was at 1:30pm. If you have more time, Winter Park is an adorable town, shopping, eating galore!

inside scoop

We drove a lot, so comfortable clothes. College tours are often miles in length, so comfortable shoes is a must. Don’t be late for tours, they start on time and it’s very worthwhile. And don’t overpack, because you will very likely end up shopping, especially if you go to Charleston!

College Tour: Charleston to Orlando - Suggestions from the Oliver Community


    So glad you are back! The Jevne’s stayed at the Alfond Inn, we loved it. Such cool art, and there was a wedding going on, which is always a bonus for people watching!

  • Courtney Leary Says

    Wake Forest- arrived into town for the 2pm tour and had 10 minutes to eat before so we grabbed crepes at Penny Path Cafe and Crepe shop in Reynolda Village (darling!) that were great. For dinner we ate at Mozelle’s a couple of miles from campus which was super- wonderful fresh food, wines, and fun atmosphere. We hit up Bobby Boy Bakeshop on our way out of town in the morning for great pastries and delicious coffee– the line was out the door!
    We stayed at the Graylynn which was very convenient to campus and had really gorgeous grounds. Our room was in the Mews building which I would NOT recommend — the room itself was tired, dark and without expected amenities like a mini-fridge or coffee maker. We were able to get coffee at 7am in the keepers room close by but I am guessing the rooms and experience in the main building are better as this is definitely one of THE places to stay in the area. Next time we would try the Kimpton however.

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