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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.

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.

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.

The Lake House at Ferry Point on Lake Winnisquam is in Sanbornton, New Hampshire. We were staying at this B&B for a couple of days as we explored the Lakes Region. The house is over 200 years old and has been lovingly restored to its former glory. It used to be the summer home of the Pillsbury family. It is the only lake front B&B in the region and is across the road from Lake Winnisquam. The view is one of quiet beauty..the house on a rise, the point across the road with its gazebo, dock, the little sandy beach, the hills and mountains in the distance. No detail has been overlooked by John and Cindy Becker, the innkeepers. As we walked into the welcoming foyer, we were met by John who showed us around the breakfast room, and living room with its bookcases and large hidden TV. The front porch has comfortable wicker furniture in which to relax and enjoy yourself. John took us up to our room. Each room is named after an area lake. There are 9 rooms. Our room had a huge four-poster bed with a sitting area. John showed us the “Welcome Basket” of goodies...razor, tooth paste, tooth brushes, maple popcorn, buffalo sticks, candy rocks, and bottles of water. The bathroom had fluffy white towels, a blow dryer, orange scented Tarocco shampoo, condition, and moisturizer. Breakfasts are created by John and are yummy. He also has cookies available all the time. You can tell that John, Cindy, and their children love this house and enjoy their guests.

Willemstad’s first colonial settlement started as a hub for Dutch slave traders. Now a World Heritage site, this modern city center has a distinct Euro-Caribbean atmosphere, its preserved colonial buildings housing fashion boutiques, art galleries, and sidewalk cafés. Wander down Punda’s narrow cobblestoned alleys, then snap a signature photo at the Queen Wilhelmina Park’s giant Curaçao and Dushi signs. The neighborhood gets extra lively during the free Punda Vibes event every Thursday from 6 p.m. to 10 p.m., featuring an outdoor market, live music, and local folkloric dancing.

Set within the 24-acre oasis of Montage Kapalua Bay, this pop-up bar and lounge pairs Veuve Clicquot Champagne with Maui’s world-class sunsets. Open Thursday through Sunday from 3:30 p.m. to 7 p.m., the Champagne Hale (pronounced HAH-leh, which is the Hawaiian word for house) serves a range of bubbly, from Veuve’s signature Yellow Label, Rosé, and La Grande Dame labels to special Rich and Rich Rosé offerings, available for the first time on the island. Pair your sips with light bites like Kualoa Ranch oysters, bigeye tuna tartare, and burrata toast with pickled strawberries and pistachio pesto, then take in the views as the sun goes down over the Pacific. From the bar’s clifftop perch above Namalu Bay, you’ll enjoy stunning vistas of the ocean as well as Molokai and Lanai islands in the distance.

For an exceptional look at one of Brussels’ finest Art Nouveau buildings, head to the Maison St. Cyr. This ornate, narrow house was designed by Belgian architect, Gustave Strauven, who worked for the father of Art Nouveau, Victor Horta, from the age of 18. The house was built between 1901-03 as the residence of Georges de Saint-Cyr. The building has been recently restored, however, as it is up for sale, it is not possible to visit inside. While in the neighbourhood, wander through the lovely Square Ambiorix, where you will find many other beautiful houses circling a vibrant city park.

Who is Sir Albert? This issue might perplex the uninitiated because the hotel and its staff insist that the mysterious aristocrat transformed his private mansion into a collection of sleek and fashionable pieds-à-terre for the international cognoscenti who come to Amsterdam. In reality, the 19th-century red-brick building was once a diamond factory, built to be so sturdy that the trams wouldn’t shake it, and, while that rich history is reflected in some of the angular and clean-lined decor, it’s more fun to imagine that a wealthy eccentric has designed the stylish and spacious rooms and left you in the hands of a staff used to realizing whims before they’re even imagined.

The rooms themselves are indulgent in a minimalist way, with dashes of both Japanese modernism and midcentury Scandinavian design in the black wooden floors, oversized white soaking tubs, and all the latest technology; clearly, Sir Albert is well traveled. He also must have a taste for authentic Japanese cuisine, considering the house restaurant is inspired by traditional Japanese pubs and attracts discerning foodies and hip young locals alike. He clearly travels in trendy circles, considering his house’s location in lively De Pijp; his appreciation for art, too, is evident in the proximity to the Museumplein.

When I first moved to the island, I joined a friend in the Old City for a tour and lesson on the history of Puerto Rico. When passing by this little section of town near Pigeon Park, my friend and native-turned-tour-guide said that this was the smallest house in Old San Juan. Wow, okay, so this little yellow portion is technically a house? I’ve visited this site several more times since then and have never actually seen anyone enter or leave this door. Whether it’s true or not, it makes for a cool story and great photo.

Located on the Samaná Peninsula, 300 feet above Playa Cosón and the Atlantic Ocean, this 18th-century, plantation-style home impresses with Victorian trim and wraparound terraces perfect for sipping cocktails in the shade. Inside, antiques from Asia, Europe, and Turkey; rugs from Istanbul; and details like Brazilian hardwood floors and French doors add further charm. The six guestrooms, all housed on the second floor, feature four-poster beds, mahogany soaking tubs, and private terraces—rooms 5 and 6 have the best ocean views.

Breakfast and dinner are served on vintage china in the main house, while lunch takes place a seven-minute shuttle ride away at the Beach Club. This is where you’ll also find the inn’s pristine beach, a nearly 90-foot stretch of sand that’s mostly empty, great for swimming, and considered one of the country’s best places for kiteboarding. When you’re not lounging here, visit the town of Las Terrenas (just 10 minutes away) or try to spot the humpback whales that migrate from as far off as Greenland and Iceland to mate and calve in the warm waters surrounding the Samaná Peninsula (every January through March).

Situated on Northeast Portland’s Alberta Street, smack in the middle of the Alberta Arts District, Caravan is an unique alternative to the same old hotels or vacation rentals. The hotel is comprised of six tiny, individually styled houses for rent, from the cabin-like Skyline (made mostly from upcycled material) to the Amazing Mysterium (a vaguely steampunk affair modeled after a vardo gypsy wagon, with lovely additions such as stained-glass windows and lots of built-in shelving). In true Portland style, the houses are clustered together in a “pod,” similar to how many of the city’s famous food carts are arranged. In lieu of a lobby, there’s a central outdoor common area with a fire pit (s’more-making is encouraged, and supplies are provided). Note that live bands perform for guests and a limited number of community members on Wednesday evenings during the summer months, and the whole area gets busy on the first Thursday of every month, when Alberta Street transforms into a pedestrian-only night market-cum-street party that lasts well into the evening.

Designed by Danish architect Jørn Utzon, the Sydney Opera House was inspired by its dramatic setting on Bennelong Point in Sydney Harbour, a location that’s long been sacred to the native Gadigal people. While construction took 16 years, including four years to figure out the spherical solution to the icon’s soaring sails, any controversies melted away when the masterpiece was completed in 1973. The same outside-the-box thinking that built the shell-shaped sculpture seeps through its walls today in the form of boundary-pushing opera, theater, and dance as well as contemporary music and mind-opening lectures. The landmark is also home to the beloved Opera Bar and Bennelong Restaurant upstairs, where diners can eat pavlova shaped like the landmark in which they sit.

A historic New York state resort, Mohonk Mountain House first opened in 1869 in the Hudson Valley, about 90 miles from New York City. This Victorian castle has welcomed five U.S. presidents (including Bill Clinton) in addition to countless artists, authors, and actors. Surrounded by thousands of acres of nature, the resort is perched on a cliff overlooking Mohonk Lake. Guests travel specifically for the dramatic, vibrant fall foliage and expertly manicured gardens. Rates are all-inclusive and comprehensive—all meals and activities are included for a single nightly rate. Yoga classes, boating, tennis, horseback riding, and rock climbing are all popular activities. During the winter, ice skating and cross-country skiing lure guests into the great outdoors. Rooms with wood-burning fireplaces and a huge spa with heated indoor and outdoor pool create a peaceful retreat.