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My first night at Galley Bay, I decided to take in their signature dining experience at Ismay’s. This is their top-of-the-line restaurant. Menu items include baked escalope of mahi mahi with olive and pine nut crust parsley; roasted cherry tomatoes, chilled caponata, sweet potato wafers, and balsamic reduction; and gratin of shrimp, crimson grapes, fresh dill, and champagne cream. Certainly impressive names, but perhaps the most impressive is the name of the restaurant itself. You see, when the then unnamed restaurant was being built in 2008, employees overwhelmingly suggested it should be named after one of their own: Ms. Ismay Mason. Ismay had been with Galley Bay for 45 years at that time during which she’d never called in sick and was a steadfast member of the team and community at large. Five years later, when Ismay finally retired, the tribute to her contribution toward the exceptional vibe of Galley Bay continued with the formation of The Ismay’s Foundation which provides for further career training and education within the community. Incidentally, I had the grilled beef mignon and sauté of shrimp, fondant potato, lemon, parsley and white wine emulsion.

Foodies (and those simply interested in local color and a good meal) should head to San Lorenzo and its covered Mercato Centrale. Florence’s main market for edibles is housed in a 19th-century glass-and-iron building. On the ground floor, delis, stands, and butcher counters sell a fantastic array of local fruit and vegetables, cheeses, dried porcini mushrooms, baked goods, balsamic vinegars, and olive oils plus fresh fish, poultry, and meat. Upstairs, a modern food hall has opened: Stalls sell prepared foods and meals for happy and immediate consumption at a central seating area.

Hidden Pond blends Maine cottage living with its own quirky, Instagram-worthy take on luxury. The enclave of 14 colorful one- and two-bedroom clapboard bungalows is spread over 60 acres of birch groves and balsam fir, just a 10-minute drive from downtown Kennebunkport. Each private house comes with a full kitchen that practically begs to be used, with first-rate cooking equipment and serving pieces and, for guests staying in the two-bedroom cottages, the option to send along a grocery list prior to arrival. However, dining at Hidden Pond’s farm-to-table Earth restaurant, with its awe-inspiring chandelier made from a preserved apple tree, shouldn’t be missed. For an even more memorable experience, guests can supper in one of two private garden sheds, which are outfitted with a sole table surrounded by hurricane lanterns, pitchforks, and potted plants, and situated steps from a chef’s garden that supplies ingredients for every meal. The Tree Spa is aptly named: Treatment rooms are nestled in the treetops eight feet above ground and are reached via wooden footbridges.

For nearly three centuries, workers serving the nobility at Castello Banfi in Tuscany lived in a small hamlet within the castle grounds. In 2007, however, the stone houses within their tiny village were completely renovated under the direction of Italian interior designer Federico Forquet, catapulting Castello Banfi into a new era of grandeur. Today, the property welcomes guests from November through March in two guest rooms and 12 suites, each with wood-beamed ceilings, countryside views, and bathrooms stocked with “vinotherapy” products made from the estate’s Sangiovese Brunello. A central garden with a pergola, a heated outdoor pool, secluded lounging spaces, and alfresco massage tents offer plenty of ways to take in the surrounding vineyards. If you’re feeling more active, take a cooking class with the chef (held a short drive away at the estate farmhouse), tour the Banfi winery, or venture out to nearby historic towns like Montalcino and Siena.

One part tourist trap, one part beloved café, Les Deux Magots is a legendary spot that everyone should visit at least once when in Paris. Most famous as the place where the likes of Simone de Beauvoir, Jean-Paul Sartre and Ernest Hemingway spent their days writing at its tables, the café serves decent coffee and hot chocolate—but skip the spendy menu unless you’re really hungry. The best seats are on the terrace, under that iconic green awning, where you can just sit back and people-watch on this busy corner of Saint-Germain-des-Prés.

The Art is a worthy base for those looking to explore the galleries of the Denver Art Museum, the Clyfford Still Museum, and the Kirkland Museum of Fine and Decorative Arts, which are all within a few minutes’ walking distance. In fact, the glass-walled property feels a bit like an exhibition space in its own right: Upon arrival, guests are greeted by Leo Villareal’s dazzling 22,000 LED–bulb installation above the entrance, while hundreds of other works by the likes of Frank Gehry appear throughout the public spaces—see them on a guided tour of the hotel’s art collection, offered on Saturdays. Minimal guest rooms have light wood furnishings, luxury linens, and neutral walls—the better to serve as a blank canvas for more original artwork—as well as windows overlooking the mountains or city lights. If you’ve worked up an appetite with all that cultural appreciation, order the signature burger with spicy mayo at FIRE restaurant, or sip a Matisse martini with Colorado-made vodka on the fire pit–warmed terrace.

Located in historic downtown Williams, Arizona, just outside of Grand Canyon National Park, Red Raven Restaurant is cozy and casual with a brick exterior painted fire-engine red. The kitchen is small but sends out gourmet comfort food to diners seated in its high-ceilinged dining room. They tuck into dishes such as portabella and zucchini fries with a balsamic reduction sauce, broiled pork medallions topped with cilantro pesto and tempura-style broccolini, and a lamb and vegetable stew made with Guinness. Seating at this husband-and-wife–owned establishment is limited, so definitely call ahead.

Given its prime La Jolla location—with a Pacific panorama to match—this stylish, modern bar could get away with serving almost anything. But lucky for spirits enthusiasts, George’s Level2 (one of three venues that make up George’s at the Cove) literally wrote the book on San Diego’s craft cocktail scene: Stephen Kurpinsky, head barman and director of spirits and beer, collaborated with his staff to produce Neighborhoods of San Diego, a beautifully bound compendium of drinks, each representative of—and photographed in—a distinct corner of the city. As you flip through the book, which doubles as the bar’s menu, you’ll get the local lowdown—learning, for example, that around 25,000 pedestrians enter the United States via the San Ysidro border crossing daily. But mostly, you’ll learn that choosing a drink here is nearly impossible. The most popular option is the La Jolla: tequila infused with mango, lime zest, and chili blended with fresh lime juice, agave syrup, and a saline-and-suspended-seaweed ice cube. If you’re looking for something with fizz, the Little Italy—with prosecco and balsamic strawberry shrub, among other treats—is the way to go.

Owners Bryan Lewis and Eric Gaspard recently opened the Twisted Cork Café, a wine-focused restaurant located in the historic Frenchtown district of Charlotte Amalie. The neighborhood, which is busy with cruise passengers during the day, slows down to a more mellow island speed in the evenings. Daily specials, which often feature just-caught fish and produce from an on-site garden, are recommended.

Chef Silver Iocovozzi, of James Beard Award-nominated Asheville restaurant Neng Jr.’s, recommends delights on and off the table during this 48-hour itinerary filled with the best of the city.