Get Away & Stay Close to Home

Cheeca Lodge pier at dusk

We live in vacationland all year long—here are six ideas for a dazzling holiday break

Written by James Biagiotti, Marie Speed, and John Thomason

With overseas travel still a wish-list item and most cruises anchored in port, those of us seeking a winter getaway can find brilliant options in our own backyard. Here are a few of our picks for South Florida vacations just a short drive away.

Start packing.

Jupiter Beach Resort

DESTINATION: Jupiter Beach Resort, 5 N. A1A, Jupiter; 561/746-2511;


THE LOWDOWN: This four-diamond resort in the northern Palm Beaches is part of the posh Opal Collections brand, and is smack-dab on the Jupiter beachfront, at the intersection of Federal Highway and Indiantown Road. The West Indies meets Key West interior design, heavy on carved wood chandeliers and maritime art, evokes Florida at its most mythic and picturesque. While some resorts favor sprawl, amenities at this compact getaway are clustered together, from the spa and fitness center to the pool and Jacuzzi to the two restaurants and lounge. As Regional Sales Director Steve Crist says, “you’re never more than two minutes from anywhere.”

WHY YOU SHOULD GO: Location, location … you know the rest. Jupiter Beach Resort is steps away from the Atlantic Ocean coastline and the myriad water activities it entails. (Room bookings include rentals of beach chairs and umbrellas at no extra charge.) Not all of its guestrooms are oceanfront, but it’s worth splurging on one of the direct ocean-view suites, which offer endless aquamarine vistas best enjoyed from small, two-chair balconies. During turtle season (roughly March to October), you might spot the beach’s resident loggerheads lay their eggs; and because of the softer, turtle-friendly lighting all around the resort, there’s less light pollution—and more unobstructed views of starry skies. Sporty visitors can enjoy a lighted tennis court, billiards table and bicycle rentals, while foodies may appreciate the fin-to-fork cuisine at Sinclairs, the onsite restaurant, which produces smooth and serenely indulgent cocktails—the coconut mojito alone is worth this drive—as well as clever deconstructions of staples like Caesar and Caprese salads.

NEARBY ATTRACTIONS: The famed Jupiter Inlet Lighthouse, with its museum and nature trail, is just a few minutes’ drive, along with other eco-tourist favorites like the Blowing Rocks Nature Conservancy (closed from COVID at the time of this writing), Jupiter Ridge Natural Area and Carlin Park, which offers covered picnic pavilions and public beach access. The park, walking distance from the Resort, is also home to a favorite breakfast spot, the Lazy Loggerhead. Little Moir’s Food Shack, a hidden gem in a nondescript strip mall, is an essential stop, with its rich seafood menu and so-called “grown-up,” haute cuisine spins on comfort apps like nachos, mac & cheese and Brussels sprouts.

Cheeca Lodge & Spa

DESTINATION: Cheeca Lodge & Spa, 81801 Overseas Highway, Islamorada; 305/664-4651;

DRIVE TIME FROM BOCA: 2 hours, 30 minutes

THE LOWDOWN: The iconic Cheeca Lodge & Spa has been a staple of luxury in the Florida Keys for more than 70 years, and remains one of the country’s premier tropical vacation destinations. The Cheeca has hosted movie stars, world-famous athletes and a U.S. president in George H.W. Bush., with the latter even hosting his own fishing tournament at the resort for a decade. Not content to rest on its laurels, the Cheeca Lodge has undergone tens of millions of dollars worth of renovations over the last few years, and just this summer added 10 private villas—the Casitas—to offer an even more upscale experience. In addition to enjoying the full amenities of the resort, guests who reserve one of the Casitas have access to private beachfront and personal butler service.

WHY YOU SHOULD GO: Islamorada is a more manageable destination than the southern Keys, and once guests arrive at the Cheeca Lodge they can waste no time getting right into vacation mode. Tucked away among waterfalls and alluring vegetation, the Spa at Cheeca Lodge is an adults-only oasis of relaxation that offers a diverse menu of revitalizing treatments. When guests aren’t looking to unwind at the spa or on the resort’s pristine beaches, they can enjoy activities from paddleboarding to beach volleyball, or hit the links on a nine-hole golf course designed by Jack Nicklaus. The resort’s dining options include four unique restaurants, from a brand-new addition in the Nikai Sushi Bar to the resort’s storied flagship restaurant, Atlantic’s Edge, all of which include selections of fresh-caught local seafood. And with the resort’s Camp Cheeca available to entertain the resort’s young guests, parents can bring their kids along on vacation and not worry about losing out on a moment of leisure.

NEARBY ATTRACTIONS: The Cheeca Lodge is in the heart of Islamorada, often touted as the sportfishing capital of the world. A multitude of charters is available through the resort for fishing, snorkeling and parasailing. Nearby, the Theatre by the Sea and the History of Diving Museum are a short drive from the resort, but from the Cheeca Lodge all that the Florida Keys have to offer is accessible within just a few hours’ drive. As with any stay in the Keys, when visitors take to the Overseas Highway, the drive itself becomes part of the vacation.

Naples Grande

DESTINATION: Naples Grande, 475 Seagate Drive, Naples; 239/227-2182;


THE LOWDOWN: There’s nothing like history and an ironclad reputation, and the Naples Grande has both in spades. This four-diamond beach resort on the white sands of Naples is known for its verdant natural splendor and commitment to environmental sustainability, and offers a host of activities for both adult guests and family vacationers to enjoy an Old Florida sensibility in a welcoming and relaxed atmosphere.

WHY YOU SHOULD GO: Sometimes there’s just nothing like enjoying the warm waters of the Gulf of Mexico and watching the sun set from the beach rather than rise. The Naples Grande’s three miles of private beachfront offer paramount comfort and privacy while lounging on the shore. For guests looking to relax in style, the Naples Grande Spa hosts dozens of innovative therapies, and even offers an exclusive Spa Villa with a sun deck, whirlpool, sauna, steam room and meditation room. The Grande’s decadent dining options include seven different restaurants and bars, a Bloody Mary bar with 48,000 different combinations—yes, you did read that number correctly—and even a dedicated coffee and gelato restaurant. Outdoor activities surround the resort’s 23 waterfront acres, including 15 tennis courts, a world-class golf course, and excursions within the 200 acres of protected mangrove estuary surrounding the resort. Eco-tours through the mangroves are available by canoe or kayak, and guests can enjoy strolls along bridges and walking paths throughout the estuary. In lockstep with the eco-activities that the resort offers its guests, the Naples Grande is also an award-winning eco-resort, with practices that focus on and promote sustainability, so guests can rest assured that their stay will be free of any environmental guilt.

NEARBY ATTRACTIONS: The Naples Grande Golf Club is a short drive from the resort, and its Rees Jones-designed golf course has been named one of the top 100 resort courses in North America. Opportunities to revel in the resort’s natural surroundings are boundless, with local attractions such as The Conservancy of Southwest Florida, Manatee Park, and various Everglades explorations, from wildlife tours to a swamp walk, just a stone’s throw from the Grande.

Hyatt Centric Las Olas

DESTINATION: Hyatt Centric Las Olas, 100 E. Las Olas Blvd., Fort Lauderdale; 954/353-1234;


THE LOWDOWN: For staycationers seeking a getaway in the heart of a major Florida city, Hyatt’s new “Centric” property is easy to spot: Becoming the tallest building in downtown Fort Lauderdale when it opened April 2, it juts up like a beacon for weary travelers. The Centric occupies the first 14 floors of this sleek and impressive skyscraper, sharing the rest of it with residences. Amenities include an eighth-floor pool and adjacent bar offering craft cocktails and light bites, and the ground-floor Harborwood Urban Kitchen and Bar.

WHY YOU SHOULD GO: All Hyatt Centrics are so named because they’re in the center of the action—the Las Olas version being steps from downtown Fort Lauderdale attractions, three miles from the airport and four miles from the beach. Abutting the New River, and fashioned with the character of Fort Lauderdale in mind, the hotel is designed in a coastal palette of blues, whites and browns. The walls are studded with nautical details, and the seafaring theme is perhaps most noticeable in the array of unusually shaped light fixtures meant to evoke marine life. The spacious lobby—always a plus in these distanced times—feels like an inviting lounge, with eye-candy coffee table books and fun gewgaws to pass the time. Harborwood is its own delicious hangout, a chef-driven restaurant with an international menu and locally sourced ingredients. And we’d be remiss if we didn’t mention the champagne vending machine, which is totally Boca.

NEARBY ATTRACTIONS: The surrounding area is culture central, with the NSU Art Museum, Museum of Discovery and Science, Riverwalk and the Broward Center all within walking distance. Balcony rooms overlook Huizenga Park, which hosts concerts and events in normal times, and a ride on an upscale “gondola” is the most stylish way to experience the Venice of America, aka the New River.

Largo Mar Beach Resort

DESTINATION: Lago Mar Beach Resort, & Club, 1700 S. Ocean Lane, Fort Lauderdale, 855/209-5677;


THE LOWDOWN: This family-owned resort has been a Fort Lauderdale Beach mainstay for more than 60 years in the tradition of a classic and gracious family-friendly hotel. This is not a glitzy boutique trendsetter; it’s a time-honored and updated 204-room resort (with private spa) on 10 acres with one of the largest stretches of private beach in Broward County.

WHY YOU SHOULD GO: Lago Mar is a tried-and-true resort in the finest tradition of family beach vacations—comfortable yet elegant, with easy access to all its amenities, from its private beach and cabanas and lagoon-style pool to tennis, pickleball and a putting course. It is reminiscent of a more-old-school kind of vacation—the kind that families used to take year in and year out when they visited Florida back in the day—a vestige of old-fashioned upscale hospitality (and a prestigious private club as well) with all the bells and whistles of 2020 luxury. Plus you‘ve got great dining, particularly through its signature Acquario restaurant featuring mainstream modern American favorites.

NEARBY ATTRACTIONS: Lago Mar offers everything you’d want in a beach vacation, including water sports, but top Fort Lauderdale attractions are nearby, including the shops of Las Olas Boulevard, the water taxi, Bonnet House, The Museum of Discovery and Science and farther afield, Butterfly World and Flamingo Gardens. Families have been coming to Lago Mar for generations; it’s still the iconic destination for Fort Lauderdale vacations, with a charm that continues to prevail in the ever-changing South Florida hospitality industry.

Driftwood Resort


DESTINATION: Driftwood Resort, 3150 Ocean Drive, Vero Beach; 772/231-0550;

DRIVE TIME FROM BOCA: 1 hour, 40 minutes

THE LOWDOWN: Florida writer Theodore Pratt once called the Driftwood “the most unusual hotel in the country.” This historic beachfront landmark is the brainchild of Waldo Sexton, an eccentric citrus magnate, who gobbled up acres of mosquito-riddled land in 1920s Vero Beach for a song. Sexton built the Driftwood as an expansive seasonal home for his family, naming it after the material of its construction, repurposed from shipping containers hauled in from neighboring regions. Sexton opened Driftwood as a resort in the ‘30s, and the original structure—built without blueprints—is still intact, complete with a restaurant bearing Sexton’s name. The property has been extended with a time-share wing, two swimming pools and a shuffleboard court.

WHY YOU SHOULD GO: Waldo Sexton was what you might call a Vulcan Mind Meld between Addison Mizner and Miguel de Cervantes, and his resort is a veritable museum of his motley collection of stuff—bas reliefs of invading conquistadors greeting visitors near the front desk, a pair of cannons he found on a beach in Sebastian flanking the breezeway toward the beach. There are sculptures of gargoyles and mermaids and pelicans, Dutch tiles embedded haphazardly into walls and floors, ships’ wheels nailed wherever they fit, and iron bells aplenty—ancient, rusty, hulking ringers straight out of Victor Hugo. You’ll probably need a few tours of the property to notice all of it—the Murano sculptures, the mastodon teeth, the giant anchors—making every stroll a delight of discovery. The staff even offers a property-wide “scavenger hunt” for eagle-eyed guests.

NEARBY ATTRACTIONS: McKee Botanical Garden, another Waldo Sexton venture that opened in the 1920s as the massive McKee Jungle Garden, once housed exotic monkeys and elephants on its 80 acres of tropical hammock. Now, the species are more common, and the property spans 18 acres, but its rainforest ambience still soothes mind, body and soul, with 100,000 species of native and tropical plants and plenty of avian visitors; it’s just a few minutes’ drive from the Driftwood. Round Island Beach Park, 10 minutes away, features a 400-foot boardwalk overlooking manatees as they frolic in a lagoon. Kayaking is welcome (though you have to bring your own boat), and the gentle sea cows love to rub up against the vessels! If you’re lucky, you’ll spot dolphins, too.

This story is from the November/December 2020 issue of Boca magazine. For more content like this, subscribe to the magazine.