1. Conch Republic Independence Celebration, Key West

• Best For: Those with an irreverent sense of humor. Think a passport should be required for Key West? There is one. In 1982, Key West declared a tongue-in-cheek secession from the United States, and the Conch Republic was born. Each year, locals celebrate their "independence" with free events like the Pirate Ball and Wrecker's Race during the Independence Celebration.
• Don't Miss: The kickoff weekend features the Drag Race (stilettos, not wheels). The last weekend offers the Great Battle for the Conch Republic, a shootout (with cannons) that culminates with the actual U.S. Coast Guard surrendering to the Conch Republic Navy. Sovereign State of Mind, April 16-25.
• Sleep: The soundtrack of fountains and even Jimmy Buffett while sipping the signature Southernmost Slammer is why we love Southernmost on the Beach. conchrepublic.com, southernmostresorts.com

2. Little Palm Island, Florida Keys

• Best For: Falling off the grid. Accessible only by boat, the Little Palm Island Resort & Spa is home to the Dining Room and the Keys' most romantic chef's table on what feels like your own private island.
• Best Eats: Chef Louis Pous starts his five- (or seven-) course meal with a tuna and foie-gras ceviche. Then go for his filet mignon with roasted corn, black beans, sweet plantains, cilantro hash and truffle chimichurri.
• Sleep: Rather than sail back to Little Torch, book a bungalow with an outdoor shower and four-poster bed, and order the chocolate-and-champagne turndown service.
• Morning Indulgence: The 80-minute Madrugada (Portuguese for dawn) Water Massage takes place on a table planted in the ocean in a screened-off private area.
• Price Tag: Don't ask, but it's totally worth the splurge. littlepalmisland.com

3. Hawks Cay, Duck Key

• Best For: Family reunions. Large groups will love this mega-resort on Duck Key, halfway between Miami and Key West, where adventurists can swim with dolphins.
• Offshore: Charter a fishing boat for the day, and resort chefs will prepare your fresh catch for dinner. Hop on a personal watercraft, and check out a sunken sailboat and car buried near the resort; then make your way to the Keys' flats, where the clear water is so shallow, you'll want to jump off for a quick dip.
• Kid Corner: Little ones love the Pirate Ship pool, while tweens and teens flock to the Cove, home to basketball courts and Xbox games.
• Two-Wheeling: Rent a bike for the crew to explore Duck Key's arched Venetian bridges. Pineapple ornamentation on columned balustrades reminds you that this archipelago is definitely in the tropics.
• Dining After Dark: Don your best resort wear for an exquisite night at Alma, where Latin influences like island spices grace the Keys' fresh catch. Sit on the terrace near a crackling fire pit as a local croons Van Morrison tunes. hawkscay.com

4. Full Moon Party, Islamorada

• Best For: Those who like to howl at the moon. Each month, Morada Bay and Pierre's restaurants transform the beach they share into the magical Full Moon Party. Family-friendly crowds gather around bonfires, mellowing to reggae bands as stilt walkers and fire jugglers roam. When the full moon zeniths, a conga line forms behind the Bahamian Junkanoo band and snakes along the water, followed by fireworks.
• Best Eats: Score a seat on Pierre's upstairs veranda and sample the Florida Keys hogfish meuniere while watching one of the most photographed sunsets in the Keys. Bonus: Free all-access to the party.
• Sleep: After a 2008 fire the "new" Cheeca Lodge & Spa returns with an elevated pool and floor-to-ceiling glass walls in 62 new rooms. Book a suite with an open-air, rain-shower tub for two.
• Insider Tip: The hotel's complimentary shuttle whisks you to the party. cheeca.com, pierres-restaurant.com

5. South Beach Wine & Food Festival

• Best For: Partygoers. If you like South Beach's festive atmosphere seasoned with food, drink and a dash of celebrity hype, this event (Feb. 25-28) has it all.
• Book Now: Tequila flows at Thursday's Patron's Late Night After Party. Friday evening, drink champagne beachside at Perrier-Jouet Bubble Q at the Delano. Saturday's Barilla Interactive Dinner, sponsored by FT+L, let's you go one on one with the first lady of Italian cooking, Lidia Bastianich. And for a Florida-centric crustacean high, there's Joe's Big Chill, the Sunday brunch at Joe's Stone Crab.
• Sleep: Z Ocean Hotel on the north end of Ocean Drive delivers on hipness. Splurge on an oversize roofop suite with city or beach views. And you'll be glad you did if only for the terrace's private hot tub. sobefest.com

6. Palms Hotel & Spa, Miami Beach

• Best For: Romantics. If Hemingway were alive today, he and his lady would check into this newly refurbished hotel, where terra-cotta tile floors, white columns and swirling paddle fans give the place a nostalgic and tropical vibe. Outside, ocean breezes snake across 50-plus palms surrounding the pool. Sip a Frozen Kiss on the Lips and lounge in a hammock.
• Relax: The small spa tucked away on the ground floor is home to the HydroCapsule, a warm, pod-like bed that's way more comfy than being wrapped in cellophane during body treatments.
• Good Taste: Lush, island-style landscaping surrounds the property, and the restaurant Essensia is no exception. Order the salmon with a spinach-gorgonzola crust, and dine under the stars.
• Insider Tip: The rooms here are small but comfy. Book one in the center of the building, where the view of the pool, boardwalk and beach beyond is nothing short of spectacular. thepalmshotel.com

7. Betsy Hotel, South Beach

• Best For: Beautiful people watching. Ocean Drive's historic British-colonial boutique property emerged from a long renovation with rooms that are the envy of interior designers. Relax in poster beds dressed with Frette linens in hues reminiscent of orchids; in fact, orchids themselves highlight every room. Settle into bathrooms designed with Thassos marble, where flat-panel television screens are tucked into mirrors.
• Eat: Chef-owner Laurent Tourondel's BLT steak restaurant is the focal point of the breezy lobby. A big blackboard lists offerings from certified Black Angus to Japanese Kobe beef.
• After Dark: Step outside into the South Beach scene where the people are the show; then stroll to La Marea at the Tides, a few blocks south, for dessert: Buñuelos (Spanish fritters) with caramelized mango, tamarind coulis and flan ice cream. thebetsyhotel.com

8. Art Basel Miami Beach

• Best For: Design (and party) aficionados. The Super Bowl of contemporary art returns to Miami for its 9th edition Dec. 1-4. While the show at the Miami Beach Convention Center serves as the main event, the city itself becomes a giant gallery space where virtually every hotel lobby, restaurant, lounge and warehouse earns an artistic touch.
• Best Eats: A short walk from the satellite art fairs in Midtown is the new Cheese Course. This little slice of France serves up baguettes and cheese trays that are best enjoyed on the landscaped patio while sipping espresso.
• Happy Hour: Pop into the sexy Bardot Lounge for wine, tapas and an informal fashion show featuring the city's most beautiful people.
• Sleep: Within walking distance of the convention center, Marrakesh and Miami intersect at Shore Club, an upscale outpost strewn with tribal rugs and tufted floor cushions. artbaselmiamibeach.com

9. Miami International Boat Show

• Best For: Sailors seeking the latest in watercraft—and art. If your idea of fun involves megayachts and sport-fishers, you need tickets to the Miami International Boat Show & Strictly Sail (Feb. 11-15). Throw back a cold one at the Marlin Bar; check out the latest boats; attend seminars from fishing experts; try the mechanical bull of the fishing world; or take free half-hour sail rides with a Discover Sailing skipper.
• Sleep: The boutique-like Ritz-Carlton, Coconut Grove is just close enough to the action of the show's two hot spots: Miami Beach Convention Center and Sea Isle Marina's in-water display on Biscayne Bay (and the spot for the annual Latitudes & Attitudes Miami Cruiser's Bash).
• Insider Tip: The Ritz is also close to the Coconut Grove Arts Festival, Feb. 13-15, and the Boat Show sells a double trunk ticket.
• Dine: The groovy Grove 'tude at the revamped Taurus on Main Highway means that the "Taurus" burger is back. miamiboatshow.com

10. The Blue, Miami

• Best For: Golfers with a gold card. It overlooks a sea of green, not blue, and that's exactly the view that links lovers want. The Blue is the new boutique hotel overlooking the Blue Monster, the infamously tough golf course in Doral. While golfers can spend their vacation battling the 7,215-yard Bermuda-grass behemoth, there's plenty under roof too. Suites are a generous 704 square feet, complete with balconies, fully equipped kitchens, and bathrooms with jetted tubs and rain showers.
• Best Eats: Look no farther than 5300 Chop House, only a pitching wedge away from the golf villas. Hand cut, farm-raised beef, organic veggies and the stellar Peruvian ceviche are tops.
• Insider Tip: If playing the Blue Monster is a must during your stay, avoid making the trek in early March. The CA Championship takes over the resort March 12-15. theblue.com

11. Hollywood

• Best For: Discovering a born-again beach town. The city of Hollywood is a sleepy spot just south of Fort Lauderdale whose retro cachet we love. Bandshell concerts pull in the crowds with a Dance Under the Moonlight Concert Series. The revamped Broadwalk is a major fave since the pedestrian-only strip is perfect for strolling day or night (when multi- hued LED lights keep the path aglow).
• Insider Tip: Wi-Fi on the beach is a plus, as are the great cabanas that anyone can rent for $20 a day just across from the Hollywood Beach Marriott.
• Eat: Giorgio's Bakery Market on the Intracoastal has casual Greek fare worth checking out, but don't miss Lola's on Harrison for inventive American cuisine.
• Just For Fun: Rent a bike at the Bike Shack (954.925.2453). It's the perfect people-watching mode of transport (and good exercise too).
• Sleep: This town's a haven for boutique-style hideaways. Check into Atlantic Sands, a cheery, tropical, family-run abode. visithollywoodfl.org

12. Fort Lauderdale

• Best For: Art lovers. The Fort Lauderdale Museum of Art in the city's Las Olas dining and shopping district has a reputation for bringing works of legendary artists to the forefront.
• Reason to Go: Norman Rockwell's set of 323 archival Saturday Evening Post covers spanning 47 years is on display through Feb. 7, followed by Edward Steichen's exhibition of photos taken while he was chief photographer for Vogue and Vanity Fair in the 1920s and '30s.
• Don't Miss: Sip a glass of champagne in the Museum Bookshop/Café and peruse tomes on topics from Cuban art to the Florida Highwaymen.
• Sleep: The boutique-like Lago Mar Resort and Club, with its guests-only 600-foot-long beach, balances the weekend.
• Eat: Enjoy Bimini Boatyard Bar & Grill's shrimp, poached in Jamaican beer, on the water- front patio bar. moaflnsu.org, lagomar.com

13. Delray Beach

• Best For: A tasty beach weekend. Never too crowded, Delray Beach always has space for another beach blanket. Dining is tops here from slices at Sazio's to 32 East's urbane fare, and shopping on Atlantic Avenue from A1A to Swinton Avenue is a close second.
• Ocean Fun: Rent kiteboarding and windsurfing gear, or sign up for lessons from a pro using a land simulator.
• Stay: The new Seagate Hotel & Spa exudes Bahamian inTuences. Fish tanks, seashell motifs and limestone fill its interior. The hotel's Atlantic Grille incorporates a tank full of jellyfish in a bar called Jellies. Dine on crispy fried oysters and center-cut filets; finish with Key-lime-mousse coconut pie.
• Insider Tip: The Delray Beach Garlic Festival (Feb. 12-14) brings chefs together for cook- ing demos & competitions. Sample dishes and groove to live music. theseagatehotel.com

14. PGA National Resort & Spa, Palm Beach Gardens

• Best For: A PGA 101 class. Not unlike hearing that Steve Jobs and Bill Gates are working on a new laptop together, David Leadbetter, father of the modern golf swing, and Dave Pelz, author of the best-selling Short Game Bible, have teamed up to create the Dave Pelz Scoring Game School and David Leadbetter Golf Academy. Now you can take lessons from the pros all day long.
• Insider Tip: Soak up Pelz and Leadbetter's know-how before facing down the 15th, 16th and 17th holes on the Champion Course. It's considered the toughest three-hole stretch on the PGA Tour.
• Sleep: The PGA National Resort and Spa features 339 freshly renovated guest rooms and 40 two-bedroom club cottages.
• For Overachievers: Soak in the spa's Waters of the World bath; minerals from the Dead Sea work wonders on those golf muscles you haven't used for a while. pgaresort.com

15. Palm Beach

• Best For: Shoppers with deep pockets Diamonds from Tiffany & Co. or Van Cleef & Arpels? The latest fashion statement from Italy's Valentino or America's Michael Kors? Tucked into bougainvillea-draped vias (tiny plazas with fountains and sculptures), Palm Beach's elite stores on Worth Avenue are where you'll find some of the world's finest merchandise. Window-shopping allowed.
• Eat: Ta-boó is as much Worth Avenue's see-and-be-seen lunch spot during season (ask your hotel's concierge to make your reservation) as it was when it opened in 1941. Do like the island's svelte ladies who lunch do and order a tuna carpaccio salad.
• Sleep: A new hotel hasn't opened in Palm Beach for quite a while, so be among the first to check into the Asian-inspired rooms at the Omphoy Ocean Resort.
• Pamper: The fusion massage (choose from uplifting, detoxifying or even relaxing) at the on-site Exhale Spa may be just what you need after a day of balancing shopping bags. worth-avenue.com, omphoy.com

16. Jupiter Beach

• Best For: Peace and quiet. The outdoor lifestyle reigns supreme in lush, laid-back Jupiter Beach, where boating and offshore fishing on the Atlantic Ocean thrive. Notably, Jupiter Inlet is home to a 17th-century shipwreck still being recovered (think silver ingots).
• Sleep: The Jupiter Beach Resort & Spa is a hidden coastline gem. The traditional British-Colonial design permeates with rich woods and palm-tree motifs. Nine floors up, pent- house bedding is ultra-luxe, as are the double balconies.
• Pamper: Sip luscious hot chocolate in the spa's quiet room, followed by a facial that uses a sugar concoction for your skin.
• Dine: Poolside at the Sandbar calls for crispy lobster and crab cakes, while the resort's premier venue for gourmet surf and turf is Sinclairs.
• Don't Miss: The Jupiter Inlet Lighthouse & Museum is celebrating its 150th anniversary. Be sure to climb the landmark's 100-plus steps. jupiterbeachresort.com, lrhs.org

17. Caribbean Court, Vero Beach

• Best For: Celebrating an anniversary. Nibble on croissants and sip cappuccino on the pool- side terrace of this chic oceanfront inn that looks like it truly belongs in Spain's Costa del Sol. Spanish tile and arched walkways lead to rooms with antique collectibles and balconies covered in bougainvillea.
• Eat In: No need to leave the premises to dine. Maison Martinique is by far the very best restaurant in town. Menu highlights include beluga caviar and sautéed snapper in a beurre blanc sauce.
• Light Up: Upstairs, Havana Nights is the perfect piano bar for after-dinner drinks. Choose a stogie from the cigar menu to enjoy on the rooftop terrace.
• Don't Miss: Just a five-minute drive into town on Saturday morning for the local farmers market is a must. thecaribbeancourt.com