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Set at the end of Duval Street, near Sunset Pier and Mallory Square, Pier House takes advantage of its waterfront address with three tiers of balconies and a pocket-sized stretch of private beach. Its location means guests are within walking distance of all of Old Town’s highlights, from the Clinton Square Market to the Harry S. Truman Little White House. Many come to follow in the footsteps of the mayor of Margaritaville himself, Jimmy Buffet, who played his first gig in town in the hotel’s now infamous Chart Room Bar. Order a rum runner, then head to the heated outdoor pool; though it’s on the small side, it has sweet views to Key West Bight. After an adventure-packed day, the rooms and suites offer low-key comfort, decorated with traditional furniture and local art and overlooking the ocean or tropical gardens and koi ponds. Equally serene is the full-service spa, one of the few on Key West.

Wong Kei is a place all Londoners know. It’s the go-to restaurant in Chinatown when you want a big plate of noodles or sweet-and-sour pork, and you don’t want to pay a lot for it. The service was legendarily rude. In the old days you would arrive at the door and be barked at: “Upstairs!” The multi-level restaurant is always busy, so you’re sent to whichever level currently has space. Then you sit at a table with others, and you order your food, which will be brought to you when the waiters can be bothered. Disappointingly, the service is now thoroughly civil; I can only hope it’s a temporary blip. Either way, this is a must-have London experience, and you’ll easily come away with leftovers.

History is alive at this downtown property, housed in the iconic Temple Court building designed by architect James M. Farnsworth in 1881. At check-in, pause to appreciate the nine-story atrium and skylight, then head to one of the 287 fully appointed rooms, which include 35 suites and two penthouses with private rooftop terraces. Each space comes with luxurious amenities like Carrara marble-tiled bathrooms with oversized rain showers, exclusive D.S & Durga toiletries, and around-the-clock room service courtesy of chef Tom Colicchio’s Crafted Hospitality.

Should guests want to eat outside of their room, the hotel is also home to Daniel Boulud’s Le Gratin, a bistro inspired by the French chef’s hometown of Lyon, and Colicchio’s Temple Court, where classic dishes like Maine lobster and Berkshire pork chop fill the menu. Cocktail lounge Laissez Faire recently debuted with martini service and a DJ booth. Those requiring reservations beyond hotel doors should call upon the Les Clefs d’Or-recognized concierge team.

The Southernmost Point buoy, at the corner of Whitehead Street and South Street, marks not only the spot for the southernmost point of the continental United States but also the distance (90 miles) to the next country, Cuba. The buoy, installed by the city in 1983, is visited by thousands of people each day. (Before the buoy, a small sign stood at the spot alongside a line of seashells for purchase.) Taking a photo in front of the buoy is imperative for a first visit to Key West, so bring a tripod, or ask a stranger to snap a few shots. Buskers play music, and street vendors sell food and goofy souvenirs and slash open coconuts to drink.

Located a quick drive north from the Dallas-Fort Worth area, the WinStar offers a world-class casino practically at our doorstep. Among the largest casinos in the world (yes!), the theme at this Oklahoma complex is, well ... the world. Different nations are represented through festive decor in various corners of the facility, giving the place a welcoming global feel. Dining options abound from pizza to steaks, as well as the requisite casino buffet. One super-big draw to this place -- besides the bingo, poker room and slot machines -- is the world-class entertainers who perform here. From Bob Dylan and Toni Braxton to Keith Urban, a concert in the on-site music venue adds an extra level of pizzazz to any visit. Don’t forget to make time to visit the Spa Habitat for treatments or a massage. Pro tip: You should definitely shell out for the $30 Friday night seafood buffet, and fill your belly with mounds of King crab, fried shrimp, fried catfish and so much more.

September 2,1935, Labor Day - a hurricane hit the Florida Keys and was the first Category 5 Hurricane to make landfall in the United States. It was devastating! It struck at night and was terrifying as was recorded by any survivors.185 mile sustained winds fed the storm.The storm surge was 18 -20'. It destroyed everything in its way. Most buildings in Islamorada were leveled. The ramshackle camps of the railway workers in Windley Key and Lower Matecumbe Key were swept away. About 200 WW I Vets at the camps were killed. Henry Flagler’s dream of a railway that would connect the Keys to the mainland died that night. The railroad was torn up and was never rebuilt. A roadway -The Overseas Highway, US 1- was constructed in its place. The Keys were accessible by the road and its bridges. Only Gilbert (1988), and Wilma (2005) have surpassed the strength of the 1935 storm. The monument at MM 82 in Islamorada was unveiled in 1937 and about 4000 persons attended the dedication. The stone crypt in front of the marker holds the victims’ ashes from the makeshift pyres after the storm. In 1995, the memorial was added to the United States National Register of Historic Places. Locals, hurricane survivors, and descendants of the victims care for the monument. I stopped to visit the site. I stood there picturing the howling winds, the wall of water and recalled the stories and photos from that September, 1935. So many lost their lives and so many survivors’ lives changed overnight.

Crandon Park’s beautiful two-mile beach on Key Biscayne is known for its pristine sand and calm waters, as well as its mangroves, coastal dunes, and sea grass beds. There’s also an amusement center as well as a nature center where you can see exotic plants and rare fish and animals, and best of all for families, Crandon’s famous offshore sandbar protects swimmers from crashing surf. Sunseekers can rent cabanas at the south end of the beach.

You don’t have to go far to find fun at Hawks Cay, nor do you have to go far to relax by the water there. The resort, which takes up much of tiny Duck Key, is known for its lagoon, five pools (including one reserved for adults and another featuring a pirate ship slide), and a Dolphin Connection program that offers complimentary viewings and hands-on experiences. Water sports are plentiful as well, with kayaks, paddleboards, and boats to rent, and guests can book fishing trips, scuba and SNUBA diving, and kiteboarding instruction. There’s also a Cliff Drysdale tennis program, a spa and fitness center, and a kids club. The resort closed for one year after Hurricane Irma, reopening in September 2018 after a $50 million renovation to the main hotel, a project that included the redesign of all 177 rooms and suites, as well as the creation of a new upscale steakhouse, a seafood-focused café, and a marketplace with to-go options—these supplement the three poolside grills and cocktail bars. Privately owned two-and three-bedroom homes are also available to rent through the resort.

Chances are that when you return home after your trip to Key West, someone will ask you if you went to the Green Parrot. It’s that kind of iconic bar, the kind your parents’ friends ended up at over spring break in college long ago. The bar started as a local grocery store about a hundred years ago; the building became the Brown Derby, a bar that was popular first with the submarine sailors from the naval base down the street.


When the naval base closed in the ‘70s, the bar transitioned into a hangout for fishermen and local sailors and the hippies that began to drift into town. The Green Parrot still has the air of a honky-tonk, lit exclusively by spotlight and neon, with a roster of almost-nightly live music, mostly of the bluesy, rollicking sort.

Located on Fleming Street in the heart of Old Town Key West, the Marquesa has everything you might expect from a romantic coastal-Florida retreat. Wide porches overlook lush gardens and a bijou pool at the center of the complex, and brick paths shaded by large palms and tropical foliage give the 1884 Greek Revival–style property a secret hideaway feel. It’s understandable if you want to hole up in the guest rooms, which reside in traditional clapboard conch houses and are furnished with an eclectic collection of wood pieces sourced from around the world. In 2018, Marquesa 4-1-4 opened across the street, featuring a new compound of three buildings around a central swimming pool and courtyard. After a day spent exploring nearby Duval Street, make your way back to Café Marquesa, which is perennially packed with locals and visitors enjoying fresh seafood and an inventive menu.

When it opened in 2016, Playa Largo, part of Marriott’s Autograph Collection, was Key Largo’s first new luxury hotel in 21 years, and its casual, sun-drenched luxury was a welcome addition to the mellow Upper Keys. The resort’s 177 rooms and suites offer a range of accommodations—most with great bay views. Upgrade to one of the ten bungalows for a private back porch surrounded by lush gardens and a second-level balcony. For ultimate privacy—and luxury—book the Beach House with three master bedrooms, wrap-around balconies, a private pool, event lawn, and private beach. The property’s four restaurants (the toes-in-the-sand Sand Bar is ideal for watching sunset), spa, fitness center, pool, and beach offer plenty of ways to relax, or partake in activities like snorkeling, diving, kayaking, paddleboarding, parasailing, fishing, sailing, or a glass-bottomed boat ride. Pro tip: Hobnob with the school of more than 100 tarpon that linger near the resort by hand-feeding them from the resort dock.

Why we love it: A city slicker–approved beach retreat with a vibrant art collection

The Highlights:
- The secret indoor pool up a staircase from the main pool area
- Fresh-baked breads by pastry chef Simone Colla served daily in the Filosofía restaurant
- An entryway featuring a rare sculpture by KAWS and vintage armchairs hung like swings from the ceiling

The Review:
The people watching is just as entertaining as the artwork at Casa Malca, a mansion once maintained by Colombian drug lord Pablo Escobar but now owned by New York gallerist and art collector Leo Malca. Set on a Caribbean-facing swath of sand next to the Sian Ka’an Biosphere Reserve—and just a short bike ride from Tulum’s beachfront boutiques and restaurants—the hotel features 71 rooms, complete with polished concrete floors, floor-to-ceiling windows overlooking the ocean, and bold artwork from Malca’s personal collection. A black-and-white print inspired by Keith Haring covers the lobby bar, while antique baby dolls adorn the walls in one of the hotel’s three restaurants. The pool and beach areas are more sedate, with cerulean daybeds and colorful hammocks studded like jewels among the leafy palms.

Casa Morada’s dressed-down modern coastal style reflects a love of the ocean, island plant life, and luxurious comforts. The 16-suite boutique hotel—once a 1950s roadside motel—underwent an extensive renovation in the early 2000s that transformed it into one of the Key’s sexiest spots. The Raymond Jungles–designed gardens are lush, the outdoors showers and jacuzzis are impossibly romantic, and the resort’s private island features a freshwater pool. If you can rouse yourself for anything other than relaxing by the water, try your hand at a game of bocce, snorkle around the only living coral reef in North America, go on a sunset sail, or charter a boat tour with local resident Captain Bill to visit the Mangrove Islands or Three Sisters Bird Rookery. Pro Tip: Morning yoga classes are offered every Wednesday, Saturday, and Sunday at 9, but guests can book a private session anytime.

The Morada Bay Beach Cafe on the bay side of Islamorada is the perfect spot for a Keys lunch. Colorful chairs and tables dot the beach; the food is excellent and the restaurant regularly receives fantastic reviews. Try the Wagyu beef burger. It is delicious. Fresh fish and seafood are popular choices. The conch fritters and conch chowder hit the spot. The staff is very friendly, professional, and helpful. Island music or Jimmy Buffet songs waft across the beach.

Third-generation artisan Giorgio Santamaria oversees a team of eight craftspeople who meticulously produce for his shop accessories from alligator, ostrich, and crocodile leather in a workshop tucked away down a narrow lane in the city center. The ready-made selection includes belts, wallets, key chains, bags, and luggage in a wide range of colors, and practically anything can be made to order.