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Mandarin Oriental’s first Caribbean resort has all the amenities you’d expect from the luxury brand—with the price tag to match. Nestled within lush greenery overlooking the white sands of Godahl Beach, the 26 suites and villas, which sit on the grounds of a 1,200-acre estate on the island of Canouan, are elegantly appointed with modern furnishings, marble baths, and rosy accents befitting the hotel’s name. Here, though, it’s all about the public spaces, including a Jim Fazio–designed golf course overlooking sparkling blue waters, a hilltop spa specializing in island-themed treatments, and four elegant restaurants serving every kind of cuisine, from pan-Asian to Italian. At Turtles, a cocktail lounge straight out of the Hamptons, opt for the Pepper Bliss, made with rum, bell pepper syrup, and pineapple juice.

Picky eaters should make a beeline for eco-friendly Baked in Telluride, where menu offerings include gluten- and dairy-free cakes and cookies, plus traditional deli counter delights like Reubens bursting with enough pastrami to power you through an afternoon of black-diamond skiing. Don’t leave without trying the puff-pastry vegetarian burrito or a slice of the sourdough-crust pizza.

A two-minute ferry ride from St. Vincent’s Villa Beach brings you to Young Island—the first of the Grenadines. Here, the Young Island Resort welcomes guests and visitors alike to its beachside restaurant for casual breakfasts, local curry buffet lunches, prix-fixe dinners, and barbecue parties. Seated in an open-air hut surrounded by tropical flowers, you can dine on local specialties like freshly caught fish and lobster while enjoying the ocean breeze. Whatever you order, pair it with the restaurant’s signature bread, which comes in banana, coconut, cinnamon, white, wheat, and raisin varieties and gets sliced tableside right before your eyes. Just know that reservations are required to eat here, no matter the time of day.

If you’re hoping to see all of Laguna in a short amount of time, hop on the free trolley, which runs in five neighborhoods during the week and along the Coast Highway on weekends. Hours vary by day and season, but are long enough to make the trolley a fun, convenient way to get around town. For special occasions from September through mid-June, you can even charter a trolley for a tour or a memorable ride to your event.

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.

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.

Many rivers to cross, and beaches to check out, and swimming holes to test: Jamaica offers visitors a busy schedule of taking it easy. When the most difficult hike on your itinerary ends at a rain forest waterfall, you know you’ve come to the right island.

Any trip to Puerto Rico must include at least one perfect day in the old city of San Juan. The island overflows with a rich culture and history that you can first experience here in San Juan right after stepping off the plane. Spend a day roaming the old city, exploring cobblestone streets with hidden gems and restaurants, art galleries and shops. These are the must-see places to complete your perfect day in San Juan.

Just a five-minute boat ride from St. Vincent, Young Island is both a private resort and the first in the Grenadine islands chain. Here, you’ll find a small, white-sand beach facing the channel that separates the island from the mainland. It’s technically for hotel guests only, but go for lunch at the very good beachside restaurant and bring your bathing suit—the resort won’t mind if you take a quick dip after your meal.

Even though it’s just 200 yards off the coast of St. Vincent and accessible via a two-minute ferry ride, Young Island feels worlds away from the cares of mainland life. The resort’s 29 guest cottages, which are outfitted with tropical-chic wicker furnishings, stone walls, and louvered windows, provide a plush landing spot after days spent diving among sea turtles and sea horses, hiking neighboring trails to spot the ruins of Fort Duvernette, and swimming up to the Coconut Bar, located on a floating platform 30 feet offshore. Each week, the on-site restaurant serves up Caribbean barbecue favorites like pigeon-pea-and-pumpkin stew, corn fritters, and molasses-glazed wings, making for a delicious stay.

Locally hand-crafted braidings are something of a St Barths specialty item, and the perfect souvenir to pack into your bag. You’ll find them at shops and boutiques throughout the island, though Latanier’s are considered among the finest.

Playful shoe designer John Fluevog’s flagship store is right in Gastown on Water Street in a gorgeous two-storey glass-fronted building that houses the design team upstairs and you’ll find his eccentrically elegant designs on the ground floor. I love his designs, and there’s always a cute message on the soles so make sure you flip them over to look when you visit.

If you weren’t sure what you were looking for, you might miss Marco Stabile’s Ora d’Aria restaurant on Via dei Georgofili. The hint of a large birdcage peeking through a tall window in an expansive and otherwise-unadorned wall is all that alerts you to the presence of greatness. White Saarinen tulip chairs are the next thing you see once you’ve decided to explore past the birdcage, and while the dining rooms, both upstairs and down, are not elaborate, they are perfectly suited to let Chef Stabile’s food be the true showpiece. Though his cuisine is not traditionally Tuscan, and nor are all of his ingredients, Stabile’s culinary creations are a delight, finally winning over the hearts of food-savvy Florence residents and every visitor who learns that a meal at Ora d’Aria is a must when in the Tuscan capital. If you’re looking to save a little while still experiencing excellence, Ora d’Aria is also open for lunch.

Changuu Island, also known as Prison Island, is about a 30-minute boat ride from Stone Town. The water around the island is crystal-clear and cerulean blue, which makes snorkeling here hard to resist, but a visit also lets you gain an understanding of a grim period of Zanzibar history. In 1860, the small island was used as a prison for disobedient slaves. By 1893, construction of an actual prison complex was completed, but instead of housing prisoners, it was used to quarantine yellow fever cases. Nowadays, the island is home to some endangered Aldabra giant tortoises, given to the island in 1919 by the British governor of the Seychelles. Some of those original tortoises are supposedly still alive here to this day!

The trendy neighborhoods of Wicker Park and Bucktown have some of the best shopping. Retro lovers can find vinyl records, comic books, vintage dresses, used books and more. Art lovers should make time to drink some wine and support local artists during First Friday at the Flatiron Arts Project . All curious travelers shopping in Wicker Park and Bucktown will be rewarded with unique arts, vintage goods, and quirky finds.