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The King Cole Bar is about as legendary as any bar in New York. Located in the St. Regis Hotel at Fifth Avenue and 55th Street, it has been the place to go for a cocktail since it opened in 1932—Salvador Dalí, John Lennon, and Marilyn Monroe are just a few from a long list of famous names who have dropped in for a drink. The bar sits off the St. Regis New York’s lobby and is presided over by the famous King Cole mural painted by Maxfield Parrish, with John Jacob Astor IV playing the part of the king, jesters to each side of him. Today it is still the ultimate setting to start a celebratory evening, or end one with a nightcap; it cemented its place on most lists of New York’s top bars with an extensive renovation in 2013. While the bartenders can prepare anything you might be in the mood for, you may want to order a Bloody Mary. The King Cole Bar boasts that it was the first spot where the drink (then known as a Red Snapper) was served in the United States (a claim, it should be noted, that is disputed by some other bars).

Former British prime minister Harold Wilson, who loved the Isles of Scilly and visited every summer (his wife, Lady Wilson, now 100, still does), is buried at the pretty Old Town Church in its atmospheric graveyard. The grave is modest compared to the grander tombs belonging to distinguished Scilly families, but not nearly as modest as the Wilsons’ nearby summer house, which is inconceivably tiny for a residence of one of Britain’s most important 20th-century statesmen.

Manhattan is full of boutique and luxury hotels, but Kimpton hotels are known for bringing both experiences together. Ink48, a hotel in Hell’s Kitchen, is no exception. Set in a former printing house, the hotel is close to everything without being too close. It’s accessible by both bus and subway and within walking distance of area restaurants, Times Square and the Javits Convention Center. Rooms are sleek and modern with flat screen televisions, animal print bathrobes and, of course, windows with views of the city. The hotel offers WiFi for loyalty program members and rents out bicycles to guests. The in-house gym and spa also help to keep you fit during your stay. The lobby has tea and coffee in the morning, flavored water in the afternoon, and wine at night. Print. Restaurant and The Press Lounge are the hotel’s highly acclaimed restaurant and bar that are both worth your time.

There are plenty of fancy doughnut shops. You know the type, the ones that count bacon or basil in their ingredient list. But if you’re looking for an old-school bastion of fluorescent lights and pink boxes full of fried dough, this is the spot. A family-run joint that has supplied prework breakfast and postbar bingeing since the 1960s, Bob’s draws a crowd day and night for the fresh doughnuts made from scratch. Bob’s bakes all the nostalgic favorites: glazed, chocolate, sprinkles, sugar, and fresh apple fritters, and crumb-topped doughnuts. You might also notice a giant doughnut in the window. Like a dare, this doughy beast invites you to take Bob’s Big Donut Challenge. Finish the beast within three minutes, and you’ll get your money back plus a Bob’s Donuts T-shirt and bragging rights, not to mention an inevitable stomachache.

Suppose I told you there was a small, remarkably idyllic and fairly unpopulated island in the Caribbean just a short distance from the mainland United States, an island so immaculate, plans were in the works to make it a National Wildlife Refuge, an island with a beach rated one of the best beaches in the world, an island where you could basically do whatever you wanted along its iridescent shores with little chance of being interrupted by prying eyes.... What’s the first thing you’d do? Well, if you were the U.S. military back in 1901 and the destination in question was the island of Culebra, you’d blow it all to hell! For nearly 75 years, bombs pounded Flamenco Beach on Culebra, la “Última Virgen,” while the U.S. military used it for target practice. Protests drove the Navy away, but some relics remain on the once pristine sands as a reminder of how never to treat one of the best strips of beach in the world. During the weekends, Flamenco Beach can get fairly crowded with “mainland” Puerto Ricans taking the ferry over for a day in the sun, so I recommend you make time during the week for a more secluded experience. There are vendors nearby, but not too near, to make your stay a pleasant one with local cuisine and plenty of ice-cold beer.

Among the original guests to pop in at Dr. Thomas Bond’s 1769 Georgian home on South Second Street was none other than Benjamin Franklin. Together the duo chartered Pennsylvania Hospital, the first public hospital in America, and Bond was an influential figure in Philadelphia throughout the Revolutionary War into the first turbulent decades following the founding of the country. Today, the four-story red-brick home within Independence National Historical Park has been meticulously restored, offering history buffs a taste of Philadelphia at the dawn of America. Original architectural details restored to their full 18th-century splendor include the modillion cornice at the roofline, the parlor’s Rumford fireplace, and the grand staircase connecting the third and fourth floors that was subsequently copied in other prominent buildings around town, including the still-standing City Tavern.

Each guestroom has been furnished with Federalist-style reproductions, with a few antiques sprinkled around. Ten rooms offer queen beds, with the two original bedrooms nearest the first floor adding small sitting areas with working fireplaces.

When traveling to Miami, it’s important to get a taste of the Cuban culture that started this community decades ago. To immerse yourself in Latin music and Cuban tradition, head to Hoy Como Ayer, a high-end Cuban nightclub in Little Havana. The wood-paneled walls are adorned with portraits of music icons like Celia Cruz and Benny More, stained glass and picturesque old Cuban ads. On any given night you might see one of the best musicians and acts in the Latin Music scene. The most popular event Spam Allstars on Thursdays, where you’ll see the house band perform Latin-fusion music on a small stage at the front of the bar. You might even see a Latin celebrity or two hiding in the corners.

For a taste of the good life, head to South Beach, known for its Art Deco hotels lining Ocean Drive and Collins Avenue, glittering nightlife, and see-and-be-seen vibe. The long stretch of beach, starting with the pier at the top of historic Washington Avenue, is a great place to take in the Miami of postcards and enjoy the sunset over the cityscape. This is where you’ll find some of Miami’s best shopping, top-tier nightlife, and award-winning restaurants, not to mention great people-watching and luxury-car spotting.

At 4,235 acres, Mission Bay Park is the largest man-made aquatic park in the U.S. Here, water-sports enthusiasts can enjoy everything from kayaking, windsurfing, and wakeboarding to snorkeling, scuba diving, and fishing, while landlubbers can take advantage of several trails and grassy areas. For equipment rentals, head to the Mission Bay Aquatic Center, located right on the bay.

Ancient Hawaiians believed their souls would leap into the spirit world from this lava shoreline on the western tip of Oahu. These days, people jump off here in gliders instead, soaking up views of the Waiʻanae coast to the south, Mokuleʻia to the north—and the glorious, denim-blue Pacific stretching from here to eternity. Take a 5.4-mile round-trip hike and check out the albatross sanctuary on Kaʻena’s wild coastal acreage (free to visit). Keep an eye out for monk seals, one of the world’s most endangered species, found only in Hawaii. Watch for their silvery-gray sausage shapes as they lounge on the beach, but give them space. Always retreat if a seal awakes, vocalizes, shies away, or tries to shield a pup.

Key West doesn’t have many swimmable beaches, but this elegant 1920 oceanfront resort sits on the largest private one in town—an 1,100-square-foot strand punctuated with tall palms. While the shoreline itself is on a rocky shelf, a long dock extends out to the shallows for laps and snorkeling. Just off the beach, two large pools are set into green lawns and lush landscaping in front of the Spanish-style main building, which is on the National Register of Historic Places. The hotel’s wooden coffered ceilings, arched entryways, red-tile roofs, and other key architectural details recall the hotel’s glamorous heyday, while the clean, refreshed rooms are entirely modern, with sleek wood-framed beds, white linens and curtains, and ocean views. Children under 16 stay for free and babysitting is available for adults who want to take a break at the Spa al Mare, which has an open-air cabana right on the sand for al fresco massages and treatments.

Just 10 minutes from downtown Orlando, in village-like Winter Park, the Alfond Inn has a unique legacy: The boutique lodging was created to provide income for scholarship funds at neighboring Rollins College, one of Florida’s oldest liberal arts schools. If helping students isn’t reason enough to book a stay, the hotel offers lots more incentive. A skylit domed atrium in the Spanish colonial–inspired main building draws your eye to a rotating collection of artwork curated by Cornell Fine Arts Museum, and pet-friendly guest rooms are simple and cheerful. While the hotel is not a full-fledged resort, it offers guests plenty of opportunities to linger. Fire pits and rocking chairs are dotted around the property, and shaded areas for loungers enhance the rooftop pool’s already undeniable appeal. Hamilton’s Kitchen restaurant serves modern Southern cuisine paired with wines selected by an award-winning sommelier. And shops, wine bars, and independent boutiques like Rifle Paper Co. line the town’s Park Avenue, a few blocks away. You can also take a pontoon boat tour for views of many of the Mediterranean-style mansions along the waterfront. Perhaps best of all, Disney and Universal theme parks are only a half-hour drive away.

At the Hyatt Centric, luxury amenities meet front-door access to 7,300 acres of ski terrain, including the 314 trails, 40 chairlifts, and six natural half-pipes that make up the Park City Mountain area of Canyons Village. For even more adventure, the hotel’s in-house activities company, Wasatch Adventure Guide, can arrange for dogsledding, fly-fishing, heli-skiing, hot-air ballooning, and even ice-climbing excursions. If you’d rather soak up some culture, there’s complimentary seasonal transport to Park City’s charming Main Street and its dozens of galleries. After a long day of exploring, guests can unwind in the resort’s heated outdoor pool, or in front of their own stone fireplace. The 120 guest rooms and apartment-style residences offer a home-away-from-home feel, with even the standard rooms featuring a partial kitchen stocked with china for four. In case you don’t feel like entertaining, the on-site Escala Provisions Company Restaurant & Bar offers après-ski fare like classic fondue as well as a dinner menu with dishes like a grass-fed beef burger with tomato jam, pork belly, and pommes frites.

On a hilltop perch overlooking 8,000 acres of grounds designed by famed landscape architect Frederick Law Olmsted, the Inn on Biltmore Estate’s 210 rooms and suites evoke traditional 19th-century manor houses, with dark mahogany beds and desks, billowing window treatments, and comfortable overstuffed chairs; book a room with a balcony to breathe fresh mountain air while appreciating views of rolling hills—or simply take in the vista from the hotel’s veranda. The formal dining room showcases seasonal specialties using estate-raised cattle and lamb, vegetables from the on-site garden, and wine from the property’s own winery, where you can participate in a free tasting, then ride back in a complimentary shuttle. If you’re looking for something more casual, the lobby lounge and library bar offer salads and sandwiches—and no dress code. But the main attraction is the 250-room Biltmore château, the Gilded Age mansion George Vanderbilt built here in the late 1800s, and its 16th-century tapestries, Renoir and Sargent originals, and 65 fireplaces.

If there’s a hub of the hubbub in Kennebunkport, it’s Dock Square, a colorful jumble of onetime fishing shacks that now house galleries, stores, and restaurants. Prowl through the shops to find unusual clothing, distinctive souvenirs, fine art, crafts, taffy and fudge, pottery, canvas bags, specialty foods, presents for pets, and, of course, the usual trinkets and T-shirts. Most of these spots are built on wharves over the tidal Kennebunk River, and it’s worth climbing to second-floor ones, such as Good Earth, for the water—or mudflat—views. The bridge connecting Dock Square to Kennebunk’s Lower Village offers another good vantage point, and the Clam Shack is one of the area’s best places to indulge in fried clams or a lobster roll.