The Preppy Towns You Should Follow on Instagram

Winter Park, Florida

It should come as no surprise that we love all things preppy here at Sloane Ranger. We love a good tartan plaid, our Hunter wellies, a good blazer, hair bows and all the preppy things that go with it. We’re always on the hunt for preppy places to travel to and are constantly adding places to our travel bucket list. Some preppy towns make it so easy to want to make a visit through their gorgeous instagram accounts and we’re sharing them with you today! You may want to hold off making travel plans until you see these preppy places.

Charleston, SC

preppy towns to visit

It seems we’ve never come across a bad photo of this charming southern town. The architecture, the food, the palm trees all make us giddy with excitement. We’re big fans of the @ExploreCharleston account, but we also love the imagery from @holycitychic because #wehavethisthingswithdoors.

Alexandria, VA

Visit Alexandria Virginia

Nestled just outside of our nation’s capital, Alexandria, Virginia lacks nothing in charm. This quaint town is a must-see for many who make the trek to Washington, DC. It’s a nice respite from the hustle and bustle of DC. It boasts riverfront dining and shopping, art museums and activities for the whole family. Take a look @visitalexva for more reasons to visit.

Boston, MA

Why you should visit Boston

What prepster does not want to visit Boston? It’s one of our oldest and most history-rich cities and has quite the food and dining scene. Plan a trip in the spring or summer and catch a game at Fenway. Then hop on the famous Duck Tours that give you a comprehensive history of Boston by land and sea. Make sure to follow @igboston to keep up with this fast-paced city.

Winter Park, FL

Winter Park, Florida

This preppy gem may not have been on your radar, but it’s surely on ours! Located just outside of Orlando, it’s home to Rollins College – one of the best liberal arts colleges in the country. There’s no shortage of polo shirts, cable knits, and aviators in this place making any Sloanie feel right at home. Make sure you stop into Briarpatch for weekday lunch or weekend brunch. There’s also a slew of other great restaurants off the main drag – our favorite being Cask & Larder. They have a really good happy hour too! To keep up with all that happens in Winter Park give @aroundwinterpark a follow. One more tidbit – Rifle Paper Co. calls Winter Park home so @annariflebond shares snaps of this preppy place too!

What preppy places and instagrams make you swoon? Leave us a note here or tag us @sloaneranger on instagram. Did we inspire you to book a trip? Make sure you check out our packing guide posts here and here!