5 Insider Tips for Planning Your Ideal Trip to Charleston

5 Insider Tips for Planning Your Ideal Trip to Charleston

charleston attractions

Charleston is, by far, one of the best places in the world to take a vacation! Here are some of our little insider secrets on how to plan your perfect Charleston vacation: 

1. Best time of year to visit: Charleston can be enjoyed year-round but there are pros and cons to different times of the year. For example, the summer months (May – September) are perfect for lying out on the beach, partaking in watersports, and enjoying Charleston’s history-steeped waterways.

The downside to the summer months, however, is that restaurants, streets, and attractions can become extremely crowded, as this is the main tourist season. Also, temperatures can reach in the 90s, so for some people, this can be too hot to enjoy outdoor activities. May and September are a bit cooler, though (usually in the 70s / low 80s).

The cooler months (October – April) are extremely enjoyable, as well. Temperatures rarely go below the 50s during the day and outdoor activities can still be enjoyed without having to bundle up too much! In fact, there are some days in October and April when you can actually wear shorts. Also, in general, Charleston is not as crowded during the cooler months.

The downside to the cooler months is that you can’t really layout on the beach, go swimming, or enjoy any watersports. Sure, you can walk on the beach, but sitting out in your bathing suite would get really chilly.

Charleston beaches

2. Plan around popular Charleston events: Charleston has several annual events that bring in people from around the world. This can cause inflation in airline ticket prices, and it can also mean booked up hotels and restaurants. But, then again, you might want to visit Charleston around these popular times to attend the actual events and festivals!

Some of the most popular annual events and festivals in Charleston include:

  • The Cooper River Bridge Run (happening April 6, 2013)
  • Charleston Food & Wine Festival (happening February 28 – March 3, 2013)
  • Charleston Fashion Week (happening March 19 – 23, 2013)
  • Family Circle Cup (happening March 3 – April 7, 2013)

For a full list of annual Charleston events, click here.

3. Where to stay: If you have a large group of individuals in your party (between 8 and 20), you may want to consider renting a house on Isle of Palms or Sullivan’s Island. This way you can have your own private dwelling and enjoy dinners, cookouts, and drinks from the comfort of your own place. Also, many of the properties on Isle of Palms and Sullivan’s Island have their own, private pool or dock, or have direct access to the beach. Isle of Palms and Sullivan’s Island are a 20- to 25-minute drive from downtown Charleston. There are a handful of cab companies within Charleston, so getting downtown is not difficult.

For smaller parties—or if you would rather be immersed in the hustle and bustle of the downtown Charleston scene—booking with one of the downtown area’s hotels is a great way to explore Charleston culture and history, as well as its famous cuisine. There are a variety of hotels to choose from, so finding one within your price range won’t be difficult.

Some of our favorite properties in downtown Charleston include:

  • 2 Meeting Street Inn
  • Charleston Place
  • Market Pavilion
  • Marriot Courtyard (this property is not in the heart of downtown Charleston, but is located on Charleston harbor)
  • Francis Marion Hotel
  • Charleston Place Hotel
  • Market Pavilion

4. What to do: Whether you love history & culture, the beach, food & wine (or beer), live music, sports, or art, you will find dozens of things to do in Charleston that relate to your particular interests. Because we couldn’t possibly list all of the fantastic things to do in the area, we’ve created a list of categories and spotlighted a few activities to enjoy within those categories:

Food & Beverage

  • Visit Charleston during the annual Food & Wine Festival (happening February 28 – March 3, 2013)
  • Embark on a culinary tour through downtown Charleston with Charleston Culinary Tours or Culinary Tours of Charleston
  • Visit one of the areas local craft breweries (check out the list here)
  • Explore the best restaurants in Charleston on King St. and East Bay Street

History & Culture

charleston city market

The Charleston City Market


  • Sullivan’s Island Beaches
  • Isle of Palms Beaches
  • Folly Beach


  • Broad Street art galleries
  • Gibbes Museum of Art
  • Theatre 99
  • Black Fedora Mystery Theatre
  • PURE Theatre
  • North Charleston Coliseum

Live Music

  • The Pour House
  • Charleston Harbor Tours’ Blues & BBQ Cruise (these weekly cruises happen during the spring and summer months)
  • The Music Farm
  • Southern Ground Music Festival (an annual event)
  • North Charleston Coliseum

For a list of weekly live music events in Charleston, visit The Charleston City Paper’s online music section.

Blues & BBQ

The Charleston Harbor Tours' Blues & BBQ Cruise


  • River Dogs Baseball Games at Joe Riley Stadium
  • Stingray Hockey Games at the North Charleston Coliseum
  • If you are more interested in partaking in sports, some of the best in the area include paddle boarding, kayaking, ice skating, fishing, and bicycling

5. Where to eat: You will never be at a loss for amazing places to eat when you’re in Charleston. There are literally hundreds of fantastic restaurants located within downtown Charleston and on its outskirts that range in prices, cuisine offered, and ambiance. We’ve written a few blog posts in the past for best Lowcountry cuisine restaurants, best Italian restaurants, and the Charleston Harbor Tours’ staff picks for best Charleston restaurants, so please feel free to check some of those posts out to learn more about some of the best restaurants in Charleston.

Click the links below to view each post:

Delizioso! The Charleston Area’s Best Authentic Italian Restaurants

Charleston’s Best Wine & Cheese Shops & Bars

Eating Like the Locals: 5 Staple Ingredients in Every Charlestonian’s Kitchen

Top Lowcountry Cuisine Restaurants of Charleston

The Local Edge: Charleston Harbor Tours’ Staff Picks for Favorite Restaurants


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