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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.

The cultural heart of Wellington is right downtown on Cuba Street. Here art galleries rub shoulders with boutique cafes, and there’s more than an enough independent bookshops, thrift stores, and quirky bars to keep even the most alternative traveler sated. If you’re looking to mingle with locals and really get a feel for what makes Wellington special, look no further than Cuba Street. And if you have a hectic New Zealand itinerary, Cuba Street is a great spot to just relax and enjoy the capital.

On a recent inner city tour I attended with tour operator, Past Experiences, we went past some of the local stores, one of which was a Muti Store. Muti is the Southern African traditional medicine which is prepared by a Sangoma or traditional healer. The medicines range from plant materials to mineral compounds and even zoological specimens. This particular store carried all that and more (traditional dress, traditional weapons, etc), as store owners try to capitalise on the very diverse African market that filters past.

The gorgeous Cour Vendôme Center is all the way upmarket, and a fantastic place to window shop, or spend a few buckets on a saucy new swimsuit—maybe one size larger than usual, considering how delicious the French fare on St Barths is.

Dining in a beach chair—or at least a chair by the beach—is an essential part of the experience at Spice Mill Restaurant, which looks directly across the water to St. Kitts’ sister island of Nevis. The menu here journeys across the global culinary landscape, but the fish and produce are sourced as locally as possible—including from the restaurant’s own gardens. Expect fine dining with your toes in the sand.

Any hotel in San Francisco that has been operating for more than a century certainly has some stories to tell, and the Westin St. Francis is no exception. From socialites to celebrities to politicians, it seems every bold-faced name has slept (or attended late-night soirees) in its Bliss and Faville–designed towers. Today, guests to this distinctive 1,195-room property still enjoy top-notch service with some thoroughly modern touches: The 1904 landmark building recently underwent a $45 million renovation by Dallas-based interior design firm Forest Perkins, inspired by San Francisco’s moniker as “The Paris of the West.” Guest rooms are painted in Parisian blue, goldenrod yellow, and peony pink, and feature original crystal chandeliers. Downstairs, travelers can marvel at the lobby’s master clock—the first example in the western United States—and study a collection of photographs by Ansel Adams depicting the hotel’s long-lost Patent Leather Bar. Pro tip: Let the hotel’s resident historian bend your ear during a historical tour.

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.

In spite of a world where nowadays every street is full of huge chain stores, we can still find treasures like this tiny shop. In the romantic Largo do Carmo, this charming shop is decorated in ‘50s style with red velvet sofas and classical stacked boxes. It sells exclusive and unique handmade shoes. The great quality of shoes made in Portugal is well known abroad. (The singer Rihanna designs shoes that are manufactured in the north of the country; Shakira wears Portuguese shoes; and, if you are fond of royalty, did you know that Princess Kate wore Portuguese shoes at her wedding?) Women can find heeled shoes or Oxford shoes (also known as men’s shoes). Men can find timeless classics. Everything sold is unique, trendy, and bold. After belonging to the same family for three generations, in February 2012 the shop was sold. But luckily, it was sold to another family!

The wording is irresistible: “Get a taste of history.” On the grounds of one of the oldest Spanish missions (est. 1691) in Arizona, tortillas cooked over a mesquite fire, in the shade of mesquite trees, steps from an adobe church--this is Tumacácori. Drive about an hour south of Tucson. Just 20 miles from the Mexican border, this mission/Nat’l Historical Park was originally established by the Jesuits. The remaining structure (surprisingly intact) dates from the early 19th century, when Franciscans and the native Tohono O’odham stacked some ninety thousand adobe bricks together to build their church. Spaniards and Basques settled the Santa Cruz River valley, missionaries brought fruit trees and foreign religion...After the Colonial period, support from the government in Mexico dwindled, Apache attacks increased, and by the 1850’s, when the U.S. acquired this territory, the mission had been abandoned. Tortillas are made outdoors most weekends fall through spring; call ahead to confirm. (520-398-234) [pronunciation note--Tumacacácori: “too-mah-KAH-koh-ree”]

If your dream vacation involves the ultimate in luxury, the St. Regis should be at the top of your list. The 151 rooms feature hand-crafted chandeliers, original artwork, and macassar ebony furnishings, as well as Italian marble bathrooms that have soaking tubs and TVs hidden in the mirror. But the real draw is the service: All guests have access to the butler desk, which can fulfill requests both big and small, from unpacking your suitcase to delivering the morning newspaper, and designated pool chamberlains mist guests with Evian and deliver frozen-fruit skewers and coconut water at the 40,000-square-foot Pool Piazza, complete with red-striped chaises and waterside bar. While the promise of massages in the Remède Spa and afternoon tea in the English-style Astor Court make it hard to leave the resort-like premises, the hotel’s location a five-minute walk from the Buckhead shopping complex may sway you. And if you need help hauling your spoils to your room, remember there’s a butler waiting just around the corner.

The famous Hotel St-Barth Isle de France officially became a Cheval Blanc property in 2014, reopening as the Cheval Blanc St-Barth Isle de France. In 2018, after a renovation made necessary by Hurricane Irma, the property also debuted a design concept by architect Jacques Grange, complete with 19 new rooms, freshly landscaped gardens, and one-of-a-kind artwork by Jean-Michel Othoniel. In addition to two gourmet restaurants overlooking the ocean, the resort features the only Guerlain spa in the Caribbean, staffed by Cheval Blanc’s trademarked “alchemists”—employees whose sole purpose is to tailor-make memorable experiences for guests. While Cheval Blanc is always popular with couples, its clientele shifts depending on the time of year. Around the holidays and spring break, families come for offerings like the “Pour les Bébés” menu of homemade baby food. In the late spring and summer, honeymooners are drawn by poolside champagne tastings.

A laid-back beachy vibe with a compelling overlay of French style is the hotel’s hallmark. Comfy rattan furniture is offset by a palette of blues and light shades, and rooms are stocked with custom Leanor Greyl products to protect from salt and sun.

The Prague Castle complex, which sits on the top of the hill above the city, dominates the skyline, and houses multiple palaces, churches, halls, and museums. The crown jewel of the complex is St. Vitus Cathedral. Construction of this Gothic and neo-Gothic masterpiece began in 1344 and took nearly six centuries to complete. The largest and most important church in Prague, which is surrounded by smaller chapels, is also the spiritual heart of the city. Bohemian and Czech kings and queens have been coronated here and are also laid to rest here underneath the cathedral. The exterior with its heavy bronze doors and carved stone is massive and imposing, but once you enter, the soaring Gothic ceiling overwhelms you with a feeling of lightness. The interior is filled with golden sunlight and glowing colors from the stained glass windows, designed by prominent 20th-century Czech artists, including art nouveau master Alphonse Mucha.

I don’t use the word “best” lightly, but Salvaggio’s deserves it. For decades, they’ve been serving up the best classic sandwiches in Boulder at their three locations—a kiosk on Pearl St. in front of the courthouse, a shop at 26th and Pearl St. and one up on University Hill. They use all Boar’s Head meat, fresh baked bread, and wonderfully spicy chilis. In the morning, they do big sloppy egg sandwiches.

Opened in early 2018, Harbor Club is a modern resort housed on Rodney Bay Marina on St. Lucia’s northwest coast. The overall feel is crisp and aquatic, with the bright-white building resembling a cruise ship on the harbor. Given the hotel’s marina setting, there is no direct beach access, but there is a sparking complex of swimming pools with mountain and water views. The hotel also provides complimentary shuttle service via a fast boat to the beach on Pigeon Island Nature Preserve, as well as towels and chairs for a day on the sand. Guest rooms are like spacious ship cabins, decorated in cool shades of blue with views of the marina or mountains. Eight swim-up rooms on the ground floor even feature private patios directly over the swimming pool area. The hotel’s half-dozen restaurants include Caribbean-Asian fusion spot 14North on the top floor, a modern sushi bar, and farm-to-table eatery Julia’s, and more options are available a short walk from the property. A full-service spa and fitness center, nightly live entertainment, and sunset cruises round out the amenities.

It’s worth planning an entire trip around Vincy Mas, St. Vincent’s carnival celebration. The event begins in late June and lasts for 12 days, bringing with it costumes, parades, parties, food, competitions, the naming of a “calypso monarch” and “carnival king and queen,” and lots and lots of music, from steel pan to soca and calypso. The biggest parades—Monday morning’s J’Ouvert and Tuesday’s all-day Mardi Gras—take place on the last two days of the festival.