My Favorite Cities For A Road Trip

It’s summer and one thing I love to do in the summer is take road trips. I thought I’d tell you about my favorites, in case you want to do your own last minute road trip! Now I was an East Coast girl my whole life so most of these cities are on the east coast, but I have a couple farther west that I flew to, but particularly enjoyed.

Savannah, GA

Savannah is such an amazing city. I love history (that plays into a number of my favorite cities) and Savannah is certainly full of history! The best part is if you’re close by, it’s a good city to do a short weekend at a time – it doesn’t change much, so you don’t have to worry about missing something.

Must-Do List

  • Make sure you walk along the riverfront – first thing in the morning or around sunset is best, that’s when it’s prettiest.
  • Take a ghost tour. In fact, take a different one every time you visit. It’s worth it!
  • Shop in City Market. Block off the whole afternoon for this, because there are so many adorable and unique shops, you’ll want lots of time.
  • Visit Historic Savannah Theatre. You can see a show, but the real draw for me…outside is Chippewa Square, where Forrest Gump was shot. Also, drop by Savannah History Museum, where the bench actually is. I know, I’m a philistine sometimes.
  • Dine at Mrs. Wilkes Dining Room. It’s a landmark, for one, and also has some AMAZING food.
  • Visit the First African Baptist Church. Not only is it likely the oldest African-American church in America, it was a stop on the Underground Railroad.
  • Skip the hotel – book a house with a veranda. There’s nothing more classically southern than sipping sweet iced tea (or something stronger – it’s Georgia, so try an Arnold Palmer) on the veranda.

Boston, MA

Ok, for me, this wasn’t a road trip – I lived just outside Boston for a year. It is, to this day, one of my favorite cities! The history, the food, that big-city feeling. I just adore it. There’s no way to do everything in a few days – I was there for a year and missed stuff! But there’s some must-see stuff.

Must-Do List

  • Dine at Dick’s Last Resort. This is only for people with a wicked sense of humor. I know the restaurant is in other cities, but the Boston location will always be my favorite. We took my uncle there and got to throw whipped cream at him!
  • Visit the New England Aquarium. It’s the largest aquarium in New England, is absolutely beautiful, and has so many animals. It’s basically my happy place.
  • In the summer, go to Boston Common and watch the Shakespeare performances. They’re free, and it’s a relaxing evening in a beautiful setting. Boston is actually where I was living when I read my first Shakespeare play and discovered my love for the Bard.
  • Take a tour. I always liked the Freedom Trail, which is self-guided and takes you through the important spots from the American Revolution, but you may prefer the Movie Tour. And definitely take a ghost tour – I can’t remember which one I did, but you want a walking tour – they’re spookier.
  • Visit Faneuil Hall. This market is ridiculous – you can find everything and anything. Go hungry – there’s a bunch of food stalls, and you can eat your way through.
  • Dine at Legal Seafood. They have the best seafood in the country. Yeah, I’m sticking with that statement. Get the lobster roll or clam chowder for a true Bostonian experience. Afterwards, head over to Cheers for a drink!

Salem, MA

I love love love Salem. This place was…spiritual to me. Like, as soon as we set foot in the town, I could feel the history – good and bad – and the pagan impact. It was intense, and literally changed my life. That first visit to Salem is what I credit with my affinity to Paganism and Wicca. Regardless of your religion or spiritual beliefs, I strongly recommend making the trip – I think everyone walks away from here with an altered perspective and a kinder heart.

Must-Do List

Charleston, SC

I used to spend a few weeks every summer in Charleston, and loved it. It’s a beautiful town – despite the humidity. While I have no interest in living there, visiting is super fun, and it’s great for a road trip.

Must-Do List

  • Check out the houses on Rainbow Row. The Victorian townhouses are painted a rainbow of pastels, creating a stunning visual!
  • Hit Time Traveler Escape Rooms, which has some really cool twists on the classic escape room themes. From the first female serial killer to a speakeasy, you’ll have a lot of fun and learn a bit of history.
  • Go kayaking! I went years ago and it was so amazing – we had wild dolphins swimming right near the kayak! I may have gotten a bit stuck in the marsh, but it was totally worth it.
  • Dine at Bubba Gump’s and order some shrimp. It doesn’t matter what form, it’s all good (I don’t actually know, because I was already vegetarian the first time I visited Charleston, but I’ve heard it’s all good). And yes, this stop connects back to my love of Forrest Gump – it’s a great movie!
  • Take a cocktail cruise one evening. You get to relax on a cruise ship with fancy drinks and enjoy the view of the city as the sun sets! You may also see dolphins and sea turtles as you sail around the Harbor.

Helen, GA

I first visited Helen with a group of friends when I lived in Atlanta and it is an adorable little town. All of the buildings are Bavarian-style, which adds to the atmosphere, and it’s small, which means it’s perfect for a quick weekend trip. I strongly recommend you do this with a significant other – I don’t know why, but it’s romantic in a quaint way.

Must-Do List

  • Stay at the Heidi Motel in a windmill suite. The windmill actually works, and really where else can you do that in America?
  • Wander around the main shops. There’s basically one big stretch (big being a relative term) where everything is – candle makers, glass blowers, candy makers. Spend a few hours wandering and watching, and maybe even buying some souvenirs.
  • Go tubing down the Chattahoochee. If you visit the Helen Water Park and Tubing, you can go on some great slides, but the best part for me was the tubing. All day, just chilling in the water. It was awesome!
  • Take a horseback ride along the river. I don’t know about you, but if I can be on a horse, I want to be on a horse. It’s a pretty ride, and easiest enough for inexperienced riders.

Boone, NC

I adore Boone. This is another spiritual town for me – I feel very connected to nature here, which is weird because I’m not really an outdoors person. It’s a little college town in the North Carolina mountains with small shops, and I really think I could live there and be happy. However, a weekend is long enough to visit – at least the first time.

Must-Do List

  • Hike Grandfather Mountain. It’s a great opportunity to see some wildlife, check out some amazing views, and commune with nature.
  • Go shopping on King Street. There’s some amazing spiritual shops there, along with unique artisan shops where you can pick up some beautiful pieces.
  • Dine at Proper. The restaurant is located in the town’s old jail, which is pretty cool, plus they have some amazing food.

Las Vegas, NV

Who doesn’t love Vegas? I certainly did. Now sure, I spent some time in the casino, but mostly playing penny slots so I could drink free (love that part!). The rest of the time, we wandered the Strip, explored the different casinos/hotels, and engaged in whatever activities were going on.

Must-Do List

  • Visit Coyote Ugly in the New York, New York. We had a blast at this bar. There’s not really much more to say about it, but it was great.
  • Tour the casinos. If you ask them for a tour, you might get to see some really cool stuff (we get to watch a chef at the MGM make a wedding cake). Plus, they’re so happy you’re interested, the manager might give you free stuff (we got vouchers for Coyote Ugly, vouchers for restaurants, and so forth).
  • Eat the fanciest dinner you can find. Vegas is all about over-the-top luxury, and it’s home to some of the best restaurants, so take advantage and find some lavish menu that sounds interesting. If nothing else, it will be a great memory.
  • Get the yard-long margarita at Margaritaville. I literally drank one of these walking down the strip. Fortunately, tequila is my drink of choice, so I had enough tolerance to not pass out in an alley.

Philadelphia, PA

Another city that has a lot of history! So there are a lot of things to love about Philly, but the thing I was most impressed by was the food. I had some of the best things I’ve ever tasted there. However, you can’t fill a weekend with just food (or can you?) so I’ll suggest other things I enjoyed.

Must-Do List

  • Hit the Philadelphia Museum of Art. Let’s be real – we both know you’re dying to run the steps like Rocky. Everyone does it. I get it.
  • Eat a cheesesteak. You can’t go to Philly and not eat a cheesesteak – and this goes for vegetarians too. There are plenty of veggie options. I ate one at about five different restaurants.
  • Eat an apple and brie grilled cheese at Fergie’s Pub. I stumbled across this place by accident but it was the best thing I’ve ever had. I’ve tried to replicate it at home, and it’s just not the same. I ended up eating one (ok, more than one, sometimes) every day I was in Philly. I even got one to take to the airport with me. I’m not even sorry.
  • Visit the Franklin Institute. I went with my cousin, but if you don’t have kids with you, try to hit one of their adult nights. The exhibits are really interesting, no matter your age.
  • Visit the home of Edgar Allen Poe. It’s pretty creepy, but also very interesting, especially if you enjoy his work as much as I do. You’ll learn about his life and his inspirations. Afterwards, hit the Raven Lounge, a Poe-inspired bar.

So there you have it – my suggestions for some fun road trip cities. Do you have any you would add?

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