Day One

  • South of Broad & the French Quarter

Spend a couple of hours meandering around Charleston's awe-inspiring Historic District, following our self-guided South of Broad walking tour or jumping on one with Charleston Footprints.

For a difficult but crucial history lesson on antebellum Charleston, visit the Old Slave Mart Museum, set in the same building where African Americans were once auctioned to the highest bidder. Continue on for a tour of the Nathaniel Russell House (for a heightened appreciation of the slave labor on which it was built), or time-travel to the 1700s with a tour of the Heyward-Washington House.

  • Dinner Make a reservation well in advance to feast at FIG or drop into 167 Raw (no reservations).
  • South of Broad & the French Quarter

After dinner, stroll the city a bit more, popping in and out of any cocktail bar that catches your eye. And for a great view of the city at night, be sure you make a stop at a rooftop place like Pavilion Bar or Rooftop at the Vendue.

Day Two

  • East Side, NoMo & Hampton Park

Have a wander through history in the Charleston Museum (founded in 1773, it's America's oldest), and if you're still keen on touring 19th-century homes, spring for the combo ticket that includes the Joseph Manigault House.

  • Lunch Stroll along King St browsing menus, and choose your spot. For Nashville-style hot quail legs, head straight for Virginia's on King.
  • East Side, NoMo & Hampton Park

Visit with some otters, rehabbing sea turtles and an albino alligator in the South Carolina Aquarium then jump on the afternoon Fort Sumter Boat Tour to see for yourself where the Civil War began.

  • Dinner Reserve a table at Zero Café + Bar well in advance, and splurge on the tasting menu (with wine pairings).
  • Harleston Village, Upper King & Cannonborough Elliottborough

Hit up a craft cocktail bar or two (Proof is great, and at Prohibition you can also swing dance) before settling in at Theatre 99 for some sidesplitting improv.

Day Three

  • Charleston County Sea Islands

Grab your sippin' lips and head for the Charleston Tea Plantation (America's only large-scale operation of the sort). Then sample the more intoxicating sweet tea vodka over at Firefly Distillery, and why not try the muscadine wine next door at Deep Water Vineyard while you're at it? Stay sober enough to drive yourself to the Angel Oak Tree, or plan on doing all of this as part of a Sea Island Tours 'Sip 'n' See' experience.

  • Lunch Unwind over an exotic sandwich at the Tattooed Moose on John's Island.
  • Charleston County Sea Islands

Spend a couple of hours at McLeod Plantation, the region's most important sight for understanding slavery in the South. Or if that feels too heavy after a day of boozing, set off on one of the Adventure Harbor Tours instead.

  • Dinner It's Italian night. Head to Wild Olive on Johns Island or return to the city to try Le Farfalle.
  • Charleston County Sea Islands

If you're still feeling young and feisty, check out a local band at the Pour House. If not so much, return downtown and see what's what at the Charleston Music Hall.

Day Four

  • Charleston

Visit the Ashley River plantations. Drayton Hall features the oldest plantation house in America. Magnolia Plantation offers wild gardens and a magnificent swamp tour. Middleton Place has the oldest gardens in the US, and they are exquisite. You'll only have the stamina for two of these. Go with your gut.

No trip to Charleston is complete without kicking back and trying some beer on a lazy afternoon. Staple stops include Holy City Brewing, Revelry Brewery and Edmund's Oast.

  • Dinner Stick around Edmund's Oast for fine gastropub fare, or venture into Workshop for experimental dishes from top chefs.
  • East Side, NoMo & Hampton Park

Attend a minor league ball game at Joseph P Riley Jr Park (The Joe) and root for the home team RiverDogs. If it's the off-season or you're not a sports fan, head back down south for one of Bulldog Tours' spooky but informative ghost walks.