Here Is the Ultimate Itinerary for 5 Days in Charleston

One week is hardly enough time to explore all that The Holy City has to offer. To make the most out of your trip, however, it helps to know where to start! Around every corner is something new to be discovered, which means that it could take hours to plan just one day’s worth of activities. Don’t sweat over trying to cram everything into your schedule. Leave the planning to us, and follow our perfectly crafted itinerary for five days in Charleston. If you want to ensure that you don’t leave any of the city’s top attractions, restaurants, or events out of your getaway, don’t forget to download our complimentary Destination Guide. Our guide is your key to the vacation of a lifetime!

Unlock the Guide

A Perfect Itinerary for 5 Days in Charleston

Whether you’re planning your fairytale honeymoon or just looking for a place to escape to for a few days, Charleston is the ideal destination. Delicious restaurants, exciting nightlife, and gorgeous weather are just a few of the things that you’ll uncover while you’re here. Get your vacation started today with our expertly crafted five-day itinerary.

Day 1: Welcome to Charleston

The Delaney House is just one of many history places in downtown Charleston.

Crossing the Cooper River bridge into Charleston is an iconic moment and a great way to start your trip. Enjoy the views of the sprawling marshland scenery as you make your way into downtown Charleston.

Depending on what time you make it into town, the first day is a great time to explore the city by foot. Whether you simply peruse the shops on king street or take a guided tour of the city, there are plenty of ways to embrace The Holy City’s unique charm!  

Complete your arrival with a taste of some of Charleston’s classic Lowcountry cuisine. Husk, Slightly North of Broad, and FIG are all fantastic choices. Take the rest of the night to settle in and recharge for an eventful week!

Day 2: The Beach

The fishing pier at sunrise, in Folly Beach, South Carolina.

When most people think of Charleston, they think of gorgeous beaches and stunning views of the Ocean. Is your favorite part of any vacation is sprawling out in the sand and enjoying the sun? Then you’ve come to the right spot.

If you’re looking for a beach that has a lot going on, Folly is probably your best option. Just be prepared to deal with larger crowds and fewer parking spaces within a few yards of the beach. For something a bit quieter, Sullivan’s Island is another great option. This beach offers a more secluded stretch of beach but still the same great views!

Day 3: The Water

view of shem creek waterway and restaurants

One of the best ways to see Charleston is from the water. Luckily, there are plenty of ways to get out on Charleston harbor. Between the private charters and group cruises, the perfect adventure is always waiting! For example, Schooner Pride offers romantic sunset cruises, private events, and daily sails!

End your day with fresh seafood at Charleston’s Oyster House or Hank’s Seafood Restaurant. If you’re looking for a night out on the town, The Watch’s rooftop bar is an excellent place for a sophisticated cocktail with a view. Alternatively, Uptown Social, Prohibition, or Cocktail Club are great options that put you right in the middle of the excitement on King Street.

Day 4: The History

view of fort sumter national monument from charleston harbor

You can’t visit Charleston without taking some time to appreciate the town’s layered history. Charleston Harbor was one of the key sites of the American Civil War, and there are plenty of national monuments and historic sites that commemorate the battle. Pay a visit to Fort Sumter or The Battery while you are here!

Additionally, the architecture and historic neighborhoods of Charleston are always exciting to explore! Have a great time and learn something new while you’re at it!

Day 5: Dealer’s Choice

flock of birds flying in the swamp at sunset

What is your favorite part about Charleston? If you’re a beach bum at heart, maybe your last day in The Holy City will best be spent with a return trip to the closest beach! If you’re in search of the town’s best cuisine, take a look at our Charleston Foodie’s Guide for some incredible dining options or irresistible brunch spots.

If you have time, a trip to one of Charleston’s best day spas is a great way to completely relax before you head back to the real world. No matter how you spend your last day, we can guarantee you’ll be counting down the days until you can return.

Here’s Why You Should Stay at Hotel Bella Grace

interior view of hotel bella grace's kingroomHotel Bella Grace is the perfect home base for your next Charleston getaway. Our boutique inn is located in the heart of downtown Charleston, seconds away from all of the city’s best things to do. Our complimentary breakfast, convenient location, and luxurious guest rooms are exactly what you need to sculpt the getaway that you’ve been dreaming about.

For example, our King Room is artfully designed to offer you the perfect blend of traditional luxury and modern sophistication. Enjoy a comfortable king-size bed, plush bathrobes and linens, and extraordinary customer service on your next stay. There isn’t a better way to complete your next visit to Charleston.

Book Now