Number Rooms: 155

Location: Downtown Charleston, overlooking Merrion Square and easily walkable to the restaurants, shops, and bars of King Street.

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Located in the heart of downtown Charleston and featuring one of the city’s hottest bars on its roof, the Dewberry is the perfect home base from which to explore Chucktown in style. Honoring the history of the landmark L. Mendel Rivers Federal Building (circa 1964), The Dewberry captures the luxury and quiet restraint that are hallmarks of historic Charleston, with chic retro touches and cool vintage details. The hotel was brought to life over eight years by a team of architects and designers who shared Dewberry’s mission to present Charleston from a uniquely personal perspective. The result is a thoughtfully imagined juxtaposition of past and present that redefines what is possible when historic preservation is paramount.

What We Loved: If Don and Betty Draper were visiting Charleston, they would stay at the Dewberry. The meticulous mid-century details in the rooms are crowned by a stylish playful roof-top cocktail bar called the Citrus Club, the whipped cream atop the hot buttered rye of the hotel below. Plus, there’s service, and then there’s southern hospitality – the Dewberry’s staff could teach a master class in the latter.

What We Didn’t Love: 1960s office buildings aren’t usually known for their curb appeal, and in a city as architecturally distinguished as Charleston, the exterior of the hotel stands out as a bit of an eye sore.

Right For: Families, couples on a foodie foray, sophisticated bachelor parties – the Dewberry (and Charleston in general) fits the bill for many types of travelers.

Wrong For: If you prefer your southern vibes to skew more genteel country house than dapper city center, head a few blocks over to Zero George.

Best Time to Visit: Mid March-Mid May; September-Early November

TLF Tip: On Friday and Saturday evenings, catch Live Jazz & Libations in the Living Room bar, with the Joe Clark Trio playing from 7-10 pm. (Do as Mr. Draper would and order the signature Old Fashioned.)