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What must life have been like back in 1739. That was the year the foundation stones were laid for Fort James on the northern entrance to St. John’s Harbour. Upon completion of the fort, it became customary for every vessel passing to pay a fee of 18 shillings to the captain of the fort or risk a shot being fired across its bow! With 10 cannons capable of firing 24 lb balls for over a mile on the ramparts, as you can imagine, ships generally paid the fee. Today, Fort James still sports its signature cannons pointing menacingly out into the harbour. Most of the other structures within the fort though, have crumbled. In their place, at least on the north side of the fort, is a quaint restaurant: Russels. There you can cap off your trip back in time with “old-fashioned rum punches”, fresh fish, peas and rice, and other traditional fare... Something like they must have eaten back in 1739.

Quirky is the word for Castle Leslie Estate in Monaghan—near the border between Northern Ireland and the Republic of Ireland—where rooms are arranged at the end of higgledy-piggledy corridors and long flights of stairs. The winding layout and overstuffed armchairs in the lobby make the vine-swathed, 19th-century castle feel like a family residence—and it feels even more homey when you see the castle’s nonagenarian owner, Sir John Leslie, Fourth Baronet (or Sir Jack to guests), chatting with visitors in his pajamas around midday.

There are a thousand acres to explore, three lakes to row around, forests to get lost in, streams to follow, and horse trails to trot along (starting in the equestrian center and livery near the main house). So at the end of the day there’s nothing left to do but sit by the fire and engage Sir Jack in a long chat. Rooms are scattered throughout the estate: in the castle, of course, but also in the former hunting lodge, stable mews, and village cottages.

With its Spanish moss-draped oak trees and beautiful stucco buildings, the College of Charleston‘s campus is long on atmosphere and makes a great place for a stroll. Randolph Hall, a magnificent edifice built in 1828 and one of the six college buildings on the register of National Historic Landmarks, has appeared in movies from The Patriot to Dear John, and in the Civil War miniseries North and South. Also of note, the President’s House, once the parsonage of St. Philip’s Church, is the oldest building on campus.

The little town of Baie-St.-Paul has been a haven along the north shore of the St. Lawrence since the 1670’s, when the French began settling here. Today, just a couple of hours from Québec city by car, it’s an artist’s colony full of charming galleries and restaurants. I hadn’t been here in over a decade when I brought my wife here for her first visit. The dramatic Charlevoix region (the rolling landscape northeast of Québec city) was one of her favorite areas, and we spent an afternoon here, reveling in the cool green, soaking up the contrast from home in Arizona...

Architect Moshe Safdie’s Habitat 67 apartment complex was built for Expo 67, a key moment in Montreal‘s emergence as one of the world’s cultural capitals. While many buildings from the late 60s haven’t fared well with time, Habitat 67 still achieves Safdie’s goal: demonstrating that contemporary housing projects can be original and appealing works that create a sense of community among their residents. For a public who had come to associate housing projects with off-putting towers set in windswept plazas, Habitat 67 was a revelation with its 354 prefabricated concrete blocks stacked to construct 146 units. Apartments here continue to be coveted and command a premium price. Habitat 67 is a little out of the way from most of the other sites you’ll likely visit, on a peninsula facing Old Montreal. Take a cab to get there and note that the complex is private property—you’ll be turned away by security if you try to enter but you can admire this modernist vision from the street.

Located in the 160-year-old Leinster Hall, The Stack has to be seen to be believed. Its recently refurbished interiors are both outrageous and sublime, with emerald and sapphire walls, a leopard-print couch, and a rainbow of velvet chairs. There’s a beautiful garden out front, a brasserie and bar downstairs, and a private club on the top floor. Dining here feels like you’ve gained entry to a private, Old Cape Town world, but with a modern menu. Standout dishes include the duck rillette and the onion tart with king oyster, shiitake, and shimeji mushrooms.

A visit to John Watling’s Distillery offers both a tour of a historic estate in downtown Nassau and the opportunity to sample locally made John Watling’s rum. The distillery, the only locally owned one on the island, is housed in the Buena Vista Estate, which began construction in 1789. The estate grounds encompass tropical gardens and a 200-year-old water well. Visitors can also take a free tour of the museum and distillery, where you can see the aged white oak barrels filled with rum. Finish the tour with a cocktail from the on-site Red Turtle Tavern, or pick a bottle of John Watling’s rum from the store.

Salamander Resort & Spa has one of the best equestrian facilities in the U.S. Horse lovers can book a stay in one of the hotel’s 168 rooms, but the facilities are also open to the public. The 340-acre resort has a 22-stall stable and nine paddocks. Professional riders and former Olympic horsemen are amongst some of the instructors who give lessons and hold clinics. The hotel offers overnight boarding for guests who want to bring their own horses and the Salamander Spa even offers a Horse & Human treatment for horse and rider.

Telluride’s literary mecca, this beloved store is stacked with more than 10,000 books at any given time. The expertly curated regional books section is a fount of the Wild West’s writing prowess, with illustrative tomes on the town’s lurid backstory (you’ll want to peruse Tomboy Bride: A Woman’s Personal Account of Life in Mining Camps of the West). When your eyelids get heavy, head to the tiny coffee bar—squirreled away at the back of the shop—for a caffeine jolt to bolster an afternoon of reading.

For a New York experience that’s equally extravagant and convenient, visitors should consider a stay at this five-star hotel, located just blocks away from Midtown Manhattan sites like Central Park, the Museum of Modern Art, and Carnegie Hall. Built in 1904 by John Jacob Astor, the Beaux-Arts building houses 239 rooms across 20 floors, plus an incredibly prized means of accessing each one—an original brass-and-marble staircase runs from the lobby level to the 19th floor (a development that cost Astor $1 million of his $5.5 million investment in the hotel). Once guests do land in their rooms, it will be tough to leave thanks to the signature butler service, available 24/7 for any number of requests, from the everyday to the once-in-a-lifetime. One of your asks should most definitely be a reservation at the on-site King Cole Bar, where bartender Fernand Petiot allegedly invented the Bloody Mary in 1934.

In partnership with the Four Seasons Rancho Encantado, the new groundbreaking equestrian program EQUUS practices a decade-old field known as equine integrated learning. The theory is that, as our animal companions since ancient time, horses can teach us about us—participants spend quiet time moving among horses in a corral, interacting with them, and reacting to them, and, through this, learn about nonverbal communication and setting boundaries, thus gaining confidence, inspiration, and strength. At these stables in the foothills of the Sangre de Cristo Mountains, guests harness the power of the herd to gain (often very emotional) insights into themselves.

Speakeasies and secret bars are an ongoing trend in Australian cities, namely Melbourne and Sydney. Down an unassuming alley off Crown Street, behind an equally unassuming doorway, lies Shady Pines Saloon—if it weren’t for the alcohol license on the door and the bouncer outside, you would never know it was there. Inside, the décor is reminiscent of an old hunting lodge or saloon in the American West, with mounted animal heads, vintage beer trays, dim lighting, Johnny Cash on the stereo, and peanut shells coating the floor. Mustachioed bartenders mix craft cocktails and can advise you on their selection of bourbons and whiskeys. The fresh-pressed apple juice and whiskey is always tasty, while the mystery moonshine in the “leg bottle” makes for an adventurous choice.

At Salt Water Farm, students return to the land—and the sea—to learn forage, fillet, and feast.

Formerly Las Alcobas, a Luxury Collection Hotel, Napa Valley.

Located just a short walk from the downtown area of the charming small town of St. Helena, Alila Napa Valley blends old and new in totally indulgent ways. The center of the 64-room property is a Victorian-style mansion that dates back to 1905. The house has been renovated and is now home to Violetto, an intimate, fine dining restaurant led by award-winning Executive Chef Thomas Lents. The nightly tasting menu, inspired by Northern Italy and Southern France, highlights local ingredients from Napa with items like homemade pastas, fresh salads, and duck confit. Guests can also join for a la carte snacks in the lounge and bar or on the beautiful, wrap-around veranda (don’t miss the chickpea panisse).

Behind the old mansion is the spa, whose building was designed to replicate an old barn with clapboard walls and high ceilings. The vibe is distinctive yet without pretense. Angled around these buildings are stand-alone, three-story structures that house the majority of the guest rooms. Featuring a warm, minimalist aesthetic that highlights, rather than distracts from, the beautiful vineyards it overlooks, each of the spacious guest rooms are decked out in natural materials such as oak, jute, and Carrara marble. Rooms come with cozy bathrobes, well-stocked mini-bars, and inviting balconies with fire pits that will make you want to lounge and linger.

All of this is centered around a large, open-air bar, event reception area, and swimming pool. Though compact, the pool is nestled in an exquisite setting with vineyard views. If you can manage to peel yourself away from the hotel, the property also has bicycles that guests can use to get around town or pedal around the newly built Napa Vine Trail. Or, simply walk a few hundred feet to the winery next door, Beringer, for a sampling of their world-renowned wines. Whatever you choose to do—be it lounge with a glass of wine at the new poolside bar, or retreat for a massage in the on-site spa—you can’t go wrong at this beautiful Napa wine country resort.

Along with the beautiful scenery, parents will appreciate the many amenities that make Bermuda’s beaches the perfect place for beach bums of all ages. Lifeguards, gentle water, and nearby facilities are always a welcome sight for parents of small children. Clearwater Beach, on the eastern end of the island, has clear, shallow water and a 36-acre public park with restrooms and a playground. Picnic facilities, shade trees, and gentle water make Shelly Bay a good choice for the smallest of surfers, swimmers, and shell seekers. Horseshoe Bay Beach has lifeguards, showers, restrooms, and a nearby café. John Smith’s Bay, Elbow Beach, and Somerset Long Bay are more great beaches for families with kids.