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  • 600 Fleming St, Key West, FL 33040, USA
    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.
  • No matter your passion, Portland has you covered. The tax-free shopping wonderland is loaded with stores to tickle the fancy of shoppers both casual and obsessed. From Powell’s City of Books—easily one of the best bookstores in the United States—to Wildfang, where the coolest patriarchy smashers hang, and, yes, all the chain stores, Portland’s got the goods. Some of the city’s shopping hubs include downtown Portland, Pioneer Place, 23rd Avenue, and the Pearl District. Fuel up with some java at the coffee shop of your choice because there is serious shopping to be done.
  • 30205 SW 217th Ave, Homestead, FL 33030, USA
    The craft beer scene is here in South Florida with the opening of the Miami Brewing Company—the region’s first craft brewery—at Schnebly Redland’s Winery in Homestead. The family-owned operation uses the tropical fruits and flavors of South Florida to make flavorful flagship and seasonal beers, including Big Rod Coconut Blonde Ale, Miami Vice IPA, and Little Havana Cafe con Leche Milk Stout. Stop in at the brewery for a craft beer tasting or pick up a to-go growler.
  • Far above the plains where lions roam, there’s another Kenya, where life moves slowly and the people run fast. Writer Matt Gross tries to keep up.
  • 729 Thomas St, Key West, FL 33040, USA
    Blue Heaven is a favorite in Key West—Jimmy Buffett even mentioned it in one of his famous beach tunes. The whimsical courtyard is filled with brightly colored tables and chairs, twinkly lights, foliage, and stray animals. The bar and restaurant is owned and operated by a husband and wife whose creative backgrounds in art and literature inspired the space. There’s a mini art gallery, a sandwich shop, and roaming roosters on the grounds. Once a boxing ring (with Ernest Hemingway as referee), the spot now pays tribute to the Caribbean, with bright accents and Cajun seasonings on the menu. Menu highlights include the scallops, which are locally celebrated, served with white wine and lemon butter with tomatoes, onions, mushrooms, and lots of garlic. Locals say the Key lime pie is one of the best in town.
  • If eating huge plates of pork, deciphering local slang, and snowshoeing through the woods of Québec can’t bring two siblings together, what can?
  • 14790 Captiva Dr, Captiva, FL 33924, USA
    Sugar sands, shallow waters, and consistently smooth seas are just a few factors that make Captiva Beach a Southwest Florida favorite. The shelling is great here, especially after storms, but it’s the sunsets that make it famous—and why Captiva is considered one of the most romantic beaches in the state. For a swim, stroll, or sunset viewing party, it can’t be beat. Be sure to keep your eyes peeled for the dolphins that are regularly spotted offshore.
  • N Ocean Dr
    Here’s your chance to ride on a hands-free Segway, where you can tour the boardwalk on a 30-ft promenade over three miles long. The Hollywood Beach Boardwalk is one of the best beachfront paths. You’ll see all kinds of restaurants, the gorgeous emerald waters of the Atlantic, and plenty of locals. You’ll pass historic hotels, volleyball courts, and shuffleboard players. You’ll hit top speed going north for a full mile. The wind hits your hair as you cruise the intracoastal waterway going south. It’s truly the best way to fly across the boardwalk.
  • 136 North 4th Street
    Equally summery and sexy, 4th & Ocean has the clothes you want to wear for a Florida weekend...from bikinis, to backpacks, to sunnies. Stocked with brands like Roxy and Billabong as well as up-and-coming designers, this store will fulfill all of your surf-style needs.
  • Vilano Beach, FL 32084, USA
    North Florida’s beaches hardly get the attention of those farther south or on the Gulf of Mexico. But there’s a lot to love about this laid-back surf community just north of St. Augustine’s busy historic district. The beach’s steep drop-off makes little waves jack up nicely, so Vilano is a favorite with surfers—especially on the incoming tide, when the waves are best. And Porpoise Point, on the southern end of the beach, is a great place to cast a line into the surf and fish. Facilities at the beach include parking, showers, pavilions that can be rented for gatherings, and picnic areas.
  • Inside the city’s most innovative restaurants, maverick chefs are defining modern Czech cuisine.
  • 1 Wildlife Dr, Sanibel, FL 33957, USA
    Florida’s nature is alive and well at this wildlife refuge, located on the north side of Sanibel Island. Rich with mangroves and seagrass, the protected, subtropical habitat is home to more than 230 species of birds as well as alligators, manatees, and many land mammals. Head here from October through April to see most of the shorebirds, or during the summer months if you’re looking for manatees in and around Tarpon Bay. All year long, you can also spot alligators during four-mile wildlife drives. Back at the information center, be sure to check out the great displays, which are free to all visitors.
  • Tourism is down, prices are up, social services are disappearing, and the government is bankrupt. Which means it’s a good time to get to know Seychelles.
  • 50 SW 12th St, Miami, FL 33130, USA
    The Hoxton is one of Downtown Miami‘s newest hotspots. The bar and restaurant is located in Brickell, usually the home to steakhouses and pub, but the Hoxton is a breath of fresh air. The 2-story bar and restaurant is like a beach house in the middle of a totally urban environment. You don’t even feel like you are in downtown once you enter the outdoor patio. You’ll feel like you are in the Hamptons with a variety of plush couches, mood lighting and soft music. The menu includes several seafood favorites including mussels, oysters and chilled Florida shrimp. The cocktails include fresh fruits, juices and herbs, each filled with the exotic flavors of South Florida. Be sure to stop in for happy hour. There’s music and live entertainment nightly, transforming the restaurant into a hot spot for dancing and jamming.
  • 1913-J S Kihei Rd, Kihei, HI 96753, USA
    With its thatched roof, bamboo bar, and surfboard decor, this beloved watering hole—often voted Maui’s best bar by locals—checks all the tiki boxes. Head here for live music, lanai seating, and late-night dancing, plus fun and fruity rum cocktails like mai tais, zombies, daiquiris, and piña coladas. Beyond its drinks, South Shore Tiki Lounge was recognized by the state of Hawaii as an outstanding business for its regular fund-raising efforts, which benefit local organizations like the Keiki Cupboard, Hawaii Wildlife Fund, Maui Humane Society, and Hawaii Animal Rescue Foundation. All that to say, you can feel good coming here to wash down a massive chili-cheese hot dog with a lychee-watermelon martini.