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A modest three-story building in the Ferreirasdorp area of Johannesburg, Chancellor House once contained the first black law firm in South Africa, opened by Nelson Mandela and Oliver Tambo at the height of apartheid. It was here that the two attorneys fought for those accused of crimes against the state—many of which they were also held accountable for later in life.

Left to languish for years, Chancellor House was restored to its former glory in 2010 and now features a freedom struggle museum on the ground floor. One particularly fascinating display includes a timeline with photographs and interesting events from Mandela’s life, including a picture of him sparring with Jerry Moloi on the rooftop of the South African Associated Newspapers Building. Many of the displays are also visible from the street so passersby can learn more about Mandela and Tambo while exploring the surrounding neighborhood.

Founded in what was previously an artists’ residence, Brody House fittingly takes its name from Hungarian author Sándor Bródy. Each of the 11 air-conditioned rooms features a bohemian mix of upcycled furniture—think sofas with frames crafted from old shipping pallets and accent walls made with old wooden doors—and some have claw-foot tubs. The hotel is part of a larger effort that includes condo-style accommodations (Brody Apartments), a grand suburban villa (Brody Villa), and an art gallery (The Art Yard). However, the group’s best-known property is Brody Studios, a private-members club for the local arts communities featuring bars, workshops, and even a recording studio. All guests staying at Brody sites get free access to the space and its regular calendar of dance parties and literature- and art-related events as well as the occasional English-language comedy show.

Occupying most of a 38-floor Times Square building, the Reverie Saigon initially made waves for its over-the-top flourishes: the house cars are a limited-edition Rolls-Royce Phantom Dragon and a Maybach, both parked out front; the lobby features a $500,000 jade-and-gold Baldi clock; and the property feels like it used all the marble and Murano glass in Italy. What’s surprising, then, is how well it all works—and how quickly you might feel at ease. A large part of that is thanks to the warm, attentive service (sniffle once, for example, and ginger tea will appear at your doorstep) and the 286 airy guest rooms themselves, which—though full of whimsical touches by international design houses like Visionnaire and Provasi—manage to call to mind serene sanctuaries floating high above the city bustle. The on-site dining options (including places for traditional Cantonese, fine-dining French, and modern Italian) draw local crowds, and the two-story spa features an ozone-infused outdoor pool equipped with underwater speakers—plus some of the best therapists in town.

When eating at the Sea House Restaurant, it’s hard to decide what is actually better: the view of Molokaʽi across the water, or the Molokaʽi sweet potatoes used in the frittata. Either way, both combine for a memorable breakfast on the island’s northwestern corner. Opened in 1963 when tourists were just discovering Maui, the Sea House restaurant celebrated its 50th anniversary in 2013—thereby making it one of the oldest restaurants in West Maui. Even with the history, fame, and ocean views, it’s one of the island’s most affordable restaurants. Most items on the breakfast menu will cost you $12 or less, and when you’re done with your meal, you can splash in the waters of protected Napili Bay. The Sea House sources many of their ingredients from local Hawaiian farmers (such as the Molokaʽi sweet potatoes), and they also follow traditional fishing calendars when choosing their fish for the menu. This is a great option for beginning the day on the island’s northwestern coastline and is a filling starting point for later adventures toward Honolua Bay and beyond. Or, just relax on the sands of Napili beneath the shade of a rustling palm. After all, there are only three hours between the end of breakfast and the start of the Sea House happy hour—an affordable menu that starts at 2 p.m. and has been voted one of the best on Maui.

Though it lacks a beach, this family-owned and professional diver–managed resort on the rocky coast just south of George Town has direct ladder access into the Caribbean. Grand Cayman’s two famous underwater sites, Eden’s Rock and Devil’s Grotto, are just a short swim away, and boat trips offer the option of two daily dives (including night dives). Images by some of the world’s most respected underwater photographers decorate many of the tiled and comfortable smoke-free rooms, some of which have kitchens and private balconies or terraces. The vibe is laid-back; post dive, guests sit by the pool or swap stories at the palapa bar, which has the island’s best sunset vista. Managers Anne Briggs and Lisa Evans, the granddaughters of Sunset House’s founders, make sure everything runs smoothly and ensure visitors explore the best of Grand Cayman both on shore and underwater.

An intimate gem whose only shortcoming (in some eyes) is that it does not sit on Pink Sands Beach, the Rock House Hotel & Restaurant was a labor of love for the late Wallace Tutt, an interior designer to the stars who was best known for designing Gianni Versace’s Miami mansion. Ten individually decorated rooms in the 1940s private home turned boutique hotel echo that property’s grandeur with king size beds and seaside motifs, as well as sumptuous linens and stone lion heads mounted on the walls in the restaurant. But the real story here is the service: There is always a picnic basket on-hand in every room, a library of games and books is available for perusal on rainy days, and the concierge is happy to arrange in-room pampering treatments if the walk to the neighboring spa feels like too much trouble.

Cherry Hill Historic House and Farm at 321 Park Avenue is a social center and a tourist draw. Built in 1845, it was once a thriving 73-acre farm owned by William A. Blaisdell and was occupied during the Civil War. Today, it is owned by the City of Falls Church and operates as a museum showcasing 18th and 19th-century furniture and tools, a buggy shed, a tackle barn, a corn crib, a well-house, and “necessary” (outdoor toilet). Guided tours are offered Monday-Thursday from 10 a.m. to 3 p.m. and Saturdays (April-October) from 10 a.m. to 1 p.m. In addition, events and public programs such as afternoon teas, concerts, children’s activities, workshops, weddings, and receptions occur year round.

San Francisco’s seven hills and extensive coastline offer plenty of impressive views; why not enjoy them with a delicious meal or bubbly drink? The Burger Bar on the top floor of Macy’s and the Rotunda at Neiman Marcus overlook Union Square. Bay-side eateries like Epic Roasthouse offer travelers water views, while the Cliff House (shown) and the Beach Chalet are right on top of Ocean Beach. To see the city glittering at night, visit the Top of the Mark bar at the Intercontinental Mark Hopkins Hotel or the Americano at the Hotel Vitale, in full view of the Bay Bridge’s Bay Lights.

Visitors seeking an immersive-history experience can get a chance to travel back in time and check out the homes, stories, and daily routines of early Philadelphians, from everyday citizens to the city’s better-known inhabitants from the past. Buildings along Elfreth’s Alley, the country’s oldest continually occupied residential street, reveal the lives of the city’s earliest residents. Most of the houses on the block are private homes, but houses numbered 124 and 126 have been preserved as a public museum. Guided tours begin in the Museum Shop (Number 124). Private tours of the Alley and Museum House are available all year round.

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.

OK, we didn’t exactly go far for dinner. We were staying in the Ace Hotel, just two doors down, but we were jet-lagged and hungry. We had seen many people hunched over enormous sandwiches through the window of this traditional-style deli at lunchtime, and we were surprised to see they were still open at 7:30pm. So we went in. We liked the simple, homely decor. We liked the smells emanating from the kitchen. We liked the fact that when we decided not to have sodas, the matronly server said, “Nah, you don’t need them honey, I’ll just keep the water coming.” We looked at the menu. We ordered two hot dogs, and a side order of pastrami fries. The waitress looked at our innocent little faces and told us we’d only need a half portion, as a whole portion of pastrami fries was “pretty big.” Our hot dogs arrived. They were delicious, and stacked with homemade relish. Our fries arrived. The “half portion” was so large we laughed out loud, then stuffed ourselves with the delicious cheese-pastrami-potato concoction until we should by rights have passed out. We got the check. It came to $14. We blessed Kenny & Zuke’s, and all who sail in her.

In some ways, the Cliff House Hotel is just a resting place for people looking to eat in its highly regarded Michelin-starred restaurant, but the hotel’s loft-style bedrooms are also among the most modern and stylish anywhere in this country. (Plus, each room has a terrace or veranda, and even the rain-forest showers have sea views.) The House Restaurant, though, is a highlight, and it’s unusual in Ireland because Dutch chef Martijn Kajuiter prepares food that is highly wrought, inventive, and beautifully plated—but also deliciously unpretentious. That sense of unfussiness might have something to do with the dining room itself, which is neither too stark nor too clubby, and edged by a glass wall overlooking the calm blue waters of the Celtic Sea. The hotel overlooks Ardmore Bay, 140 miles south of Dublin, and the spa’s impressive yoga program, indoor infinity pool, stone outdoor baths, and Jacuzzi can help guests counterbalance any evening’s indulgences.

My favorite part about living in Hawaii is the view from where I live. I am tremendously blessed to have the spectacular ‘perch’ that I do looking over Diamondhead, Waikiki, Honolulu, and past the airport to Ko’olina. If you are looking to see such a spectacular view of Southern Oahu, drive up Round Top Drive to Pu’u Ualaka’a State Park for sunset. You will find a large grassy area to share a picnic or lay back and watch the clouds roll by. Or you can stand up a bit higher at the lookout and identify all the places and roads you have been while in Honolulu. If hiking is more your style, there are plenty of trails up on this scenic route as well. Or, perhaps, you will just enjoy the curly queues and hairpins of the the Tantalus-Round Top Drive loop. No matter what you do, it is a refreshing reprieve from the busy scene in Waikiki!

John Rutledge was an active player in early American politics, signing the Constitution and serving as South Carolina’s first governor. But his townhouse on Broad Street, now the John Rutledge Inn, was built before he even attended his first Continental Congress. The house was embellished and expanded over the years, including the addition of elaborate lacelike ironwork that still stops passersby in their tracks. The inn comprises the main building and two carriage houses. In the 1980s, a major renovation prepared it for its new life as an inn, restoring the parquet floors, marble fireplaces, and crown molding to fully honor the property’s past.

Rooms in the main house evoke the property’s Colonial Era origins, with canopy beds and brass fireplace screens. All rooms have Tempur-Pedic mattresses, property-wide Wi-Fi, and flat-screen TVs help guests remember that they’re still in the 21st century. Around the property, visit the sumptuous ballroom for evening sherry, or stroll the lush, secluded courtyard.

Muntri Mews in Penang is my kind of hotel. Formerly an old mews house, its owners have fitted it out with clean, comfortable rooms that retain the charm of their days as stables (think romantic mosquito nets and wooden beam architectural details). The hotel is small and the service is personal and friendly. Breakfast on the hotel’s patio in the heart of historic Georgetown is the perfect way to start a day of meandering through the back streets of this historic, character-filled foodie heaven.