Winter Escapes: Now Departing For...

Louisville
Delta 5446 // Three hours

Named for Louis XVI, this Kentucky city brings a note of regality to a state best known for folksy charm. The spires of Churchill Downs mark the high court of horse racing, while area distilleries craft bourbons fit for crystal snifters. Some $800 million in new downtown construction offsets Louisville's Victorian manses and seven big museums (one of which commemorates another king, native son Muhammad Ali).

Take off
Delta flies daily to Louisville, departing Logan at 1:50 p.m. Leave Friday and come back on Sunday's Flight 5445 at 5:10 p.m. 800-354-9822, delta.com.
Stay The year-old 21c Museum Hotel is filled with vibrant contemporary artwork and plush amenities—think Mass MoCA meets Nine Zero. Doubles from $159; 502-217-6300, 21cmuseumhotel.com.

Eat
Though Louisville has barbecue and home cookin' aplenty, for a change of pace check out the stiff cocktails and festive vibe at Mojito, a new Spanish tapas boîte. 502-425-0949.

Watch
The Humana Festival of New American Plays is the hottest ticket in town (2/24–3/30). The annual showcase draws international actors, critics, and audiences for debuts by the likes of Pulitzer darlings Beth Henley and Donald Margulies. 502-584-1205, actorstheatre.org/humana .htm.

Pack
Your Kovels. The shopping strip on Bardstown Road is a bargain-antiques paradise.

Montego Bay
US Airways 831 // Three hours, 15 minutes

Known to locals as Mo' Bay, Jamaica's resort capital offers more than the feverishly rowdy Margaritaville, the main street's most popular bar for giddy college kids. More-refined visitors migrate a few miles inland to sip spiced rum on the verandas of restored plantations, or go birding in the densely forested mountains.

Take off
Leave Logan on Saturday at 11 a.m. Return Flight 832 departs Montego Bay at 4:15 p.m. on the same day. 800-622-1015, usairways.com.

Stay
Clark Gable loved vacationing at Round Hill. And that was well before the resort's $6 million Ralph Lauren–designed renovation and double-vanishing-edge pool. Doubles from $590; 800-972-2159, round hilljamaica.com.

Eat
Jasmine at the Ritz-Carlton fuses Jamaican ingredients with Asian techniques to yield dishes like blue crab with spiced papaya and chili-infused lobster. 876-953-2800, ritzcarlton.com.

Heal
The hot springs in Doctor's Cave are rumored to have serious therapeutic powers. Even nonbelievers love soaking in the remarkably clear, calm water. 876-952-2566, doctorscavebathingclub.com.

Pack
Small bills. Service staffers here have been known to get ornery if stiffed on their tips.

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