Charleston Smart Splurges

Most of the original features of Francis Silas Rogers’ opulent French Empire estate were preserved when it was converted into Wentworth Mansion, and it’s easy to see why: Light streams in through original Tiffany stained-glass panels, crystal chandeliers hang from high ceilings, and ornate marble mantles frame fireplaces. Rooms are large and well-appointed; most have working fireplaces. Staff members are warm and welcoming, there’s a wine tasting each evening and a delightful breakfast served on the sun porch. Take time to explore the grounds which include a horse stable that’s been transformed into a luxury spa and a carriage house that’s now home to Circa 1886, the inn’s gourmet restaurant.

This downtown charmer, built in 1853, has a gracious interior courtyard with a fountain, an old-fashioned bar and lounge straight out of Gone with the Wind, and 214 rooms individually decorated with period furniture and canopied beds.

The grandest of the Ashley River Road plantations, this 18th-century estate features a large collection of antique furniture and art, massive, landscaped gardens, and an equestrian center with riding trails.

This modern, warmly lit bistro focuses on local, seasonal food that is casually, yet elegantly,...more

Beautiful people sip bellinis late into the night at the marble bar of this swank Italian restaurant, one of the best places to see and be seen. With occasional live jazz and DJs, you’ll feel just like you’re in Milano.

This genteel boutique sells jewelry and home and garden accessories inspired by Charleston architecture or modeled after items from historic plantations, as well gift items like soaps and dishes.

Home to innumerable golf courses and gated communities, this immaculately groomed sea island is a favorite second home spot for well-heeled Southerners who appreciate its peacefulness and exclusivity. It is, however, quite possible to rent a condo.