SUNSET KEY ISLAND
Kick back on serene white sands, then head to Key West—10 minutes away by boat—for shopping and dinner.
When to go December through April, to avoid the rainy season.
Where to stay Westin Sunset Key Guest Cottages (westinsunsetkeycottages.com), which features bungalows, each with wrapround porch.
What to do Soak up the sun, take a dip in the pool or snorkel in temperate Gulf waters.
Where to eat The resort’s beachfront Latitude café for lunch; dinner at former Key West bordello Blue Heaven (blueheavenkw.com), where vegetarian gumbo, Jamaican jerk chicken and key lime pie are specialties.
Hop a flight to this thriving Caribbean isle and enjoy San Juan’s beautiful beaches and booming nightlife.
When to go December through April, when there’s no risk of hurricanes.
Where to stay Da’ House (dahousehotelpr.com), an art-filled hotel and former Spanish convent in the heart of Old San Juan.
What to do Work on your tan at Isla Verde, where you’ll find miles of popular beaches, or shop along the cobblestone streets of Calle San Francisco and Calle del Cristo. Later, enjoy the many city’s hot spots until 4 a.m.
Where to eat Sample oysters and ceviche at Aquaviva (oofrestaurants.com) then head to Pikayo (pikayo) for Chef Wilo Benet’s defining Puerto Rican cuisine.
Gossip among the grapevines as you sample fine wines in this more relaxed, less commercial version of Napa.
When to go September and October, during the harvest, for tons of fun events, from local fairs to grape stomps.
Where to stay The modern, 27-room El Dorado Hotel (eldoradosonoma.com) in downtown Sonoma.
What to do Visit wineries by limo, beginning with a private tasting at Sebastian Vineyards & Winery. Feeling adventurous? Take a horseback ride with the girls.
Where to eat The hotel’s El Dorado Kitchen good times and the curried fito misto and osso buco.
Soak up this treasured American city, where a great time is always guaranteed, even when it’s not Mardi Gras.
When to go Less humid spring or fall, when the mercury stays near 80 degrees.
Where to stay The House on Bayou Road (houseonbayouroad.com), an eight-room inn (remember to book early!).
What do do By day, stroll the French Quarter, browse the six miles of clothing and antiques shops on Magazine Street, and have your tarot cards read at Erzulie’s (erzulies.com) or the Bottom of the Cup Tea Room (bottomofthecup.com). By night, catch live music at Tipitina’s (tipitinas.com) or drop by the world-famous Pat O’Brien’s (patobriens.com) for a pint or two.
What to eat Café Du Monde (cafédumonde.com) for beignets and café au lait; Ralph’s on the Park (ralphsonthepark.com) for turtle soup, a local specialty.