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Come for the history, stay for the chowder. Bostonians have been slurping down oysters at America’s oldest continuously operating restaurant since 1826, and while you won’t find Union Oyster House on any haute dining lists, it’s well worth a stop when you’re walking the Freedom Trail or exploring the area around Faneuil Hall. Sidle up to the semicircular oyster bar right inside the front door just like Daniel Webster once did, or feast on a classic New England shore dinner in the upstairs dining room, away from the crowds. There you’ll find a plaque marking the booth where JFK liked to scarf baked beans and clam chowder—one of the restaurant’s many reminders of its long history of catering to celebrities.

Get a bird’s-eye view of Laguna and its famous sunsets at the Rooftop Lounge, which sits atop La Casa del Camino hotel. Drinks here include a lengthy list of red, white, and sparkling wines as well as specialty cocktails like mojitos in strawberry, mango, and ginger flavors. To pair with your sips, there’s a range of small bites, from barbecue meatballs with blue cheese slaw to bacon-wrapped dates and coconut-breaded shrimp. Just be sure to come prepared with sunglasses and a hat, as shade is limited, and bring your four-legged friend—the bar is dog-friendly.

At the Wine Gallery, oenophiles and wine novices alike gather to sip old favorites or try new varietals. The team here crisscrossed the globe to curate an impressive menu of limited-edition wines, 25 of which are available by the glass. All are well-priced and accessible to even the most basic of tastes, but should you have trouble choosing, the friendly staff is available to make suggestions and help you discover new flavors and aromas with every sip. Once you’ve picked a wine, pair it with something from the food menu, which is built around the restaurant’s wood-fired oven. Options range from small plates like oven-roasted meatballs to charcuterie boards, crispy pizzas, and entrées like flatiron steak with hand-cut herbed frites. Swing by on a night when there’s live music, or make plans to attend one of the regular tastings to learn even more about the wines on offer.

At this rooftop bar on the South Coast Highway, guests can pair breathtaking ocean views with well-made cocktails and delicious bites. There’s also nightly live music and plenty of high-def TVs throughout the space, making this the perfect place to party the night away or simply catch a game. Drinks range from craft beers and 22 wines by the glass to specialty cocktails like cucumber-jalapeño margaritas, while the food leans Southern, with options like gumbo, butter brisket, and jambalaya. Check the website before you go to see who’s playing that night; it could be anyone from a local DJ to a ’90s rock cover band.

Generally speaking, shopping isn’t a big draw on St. Vincent, but if you’re searching for the perfect souvenir, you can’t do better than Nzimbu Browne’s famous banana art. Besides tourism, banana production is a driving force behind St. Vincent’s economy. By using the industry’s waste products—the banana leaves—Browne creates sustainable art with a strong sense of place. His works depict local scenes, brought to life with snippets of dried, multicolored leaves. If you’re not into art, he also makes goat-skin drums and tie-dye clothing. His studio is located on McKie’s Hill in Kingstown, but he often sets up shop in front of the Cobblestone Inn on Upper Bay Street.

The renowned Meadowood Resort mixes the grandeur of a chalet with the amenities of a five-star resort—located in a private canyon within minutes of downtown St. Helena. The shaded, secluded property revolves around 99 rooms, most of which have high and exposed ceilings, private patios or balconies, wainscoted walls, and beds so comfortable you may never want to get up. Other amenities make Meadowood distinctive, too: Many rooms have heated bathroom floors; some also have deep soaking tubs. Elsewhere on the 250-acre property, all guests have access to the on-site spa, which was renovated in 2017; an on-site fitness center; hiking trails; tennis courts; and a daily wine reception. There’s even a croquet lawn—feel free to grab a mallet and hit some balls or sign up to take lessons with the Napa Valley’s only croquet pro. Of course the on-site restaurant, The Restaurant at Meadowood, is another big draw. More casual meals can be ordered from The Grill. Guests are entitled to a complimentary house car for transport into St. Helena or Yountville.

Even with the summer crush on the French Riviera in full swing, there are quiet escapes to be found. In particular, I like to take walks along the Sentier du Littoral, the coastal footpath that stretches the length of the French Mediterranean coast. My favorite segment is in St. Tropez, where I head by boat from Ste. Maxime (the Bateaux Verts leave every 10 minutes). From the ferry landing, I start walking—through the narrow streets and old port, under the imposing citadel that has guarded residents since around 1600, past the cemetery, and onto a narrow path that ribbons around the St. Tropez Peninsula. The 7-mile route takes me by inlets of crystalline water, hidden villas whose residents I always wonder about, and past dozens of little beaches that are significantly more serene and less crowded than the frenzy of those found along Pampelonne Bay, where this piece of the trail ends. You can hoof the two miles back to the village, or take the bus.

Dinner at Le Toiny Restaurant is a full frontal assault on the senses; as if the spectacular ocean-side setting were not enough, the culinary witch doctors at Le Toiny, led by executive chef Jean-Christophe Gille, whip whimsical French classics into contemporary Caribbean masterpieces with just the right amount of gusto. Le Toiny is open daily for breakfast, lunch and dinner, and features the Tuesday Fish Market, and the Sunday “Brunch du Toiny.”

We were offered the chance to visit Pompeii or Herculaneum when we docked at Sorrento. People rave about Pompeii because it’s absolutely huge and gives you a great sense of just how sophisticated Roman civilisation was. Herculaneum, by contrast, was a Roman seaside town, a sort of holiday resort, and doesn’t offer the same kind of scale. Still. I remembered my Latin lessons, and how we’d learned that while Pompeii’s buildings were smashed and burned by the falling volcanic ash, Herculaneum was actually preserved in the thick mud that engulfed it. And it’s true: wandering around the archaeological remains of the town, you feel like you’re in a place that’s only recently been abandoned. The wine shop (above) still has its amphorae stacked to the side, the houses have beautifully preserved frescoes and mosaics. What it lacks in size it more than makes up for in detail.

The Place Bonaventure is widely recognized as one of the most important buildings constructed in Canada in the 1960s, though that’s not to say it’s universally loved. It’s a regular contender for the title of Montreal’s ugliest building. For the student of architecture, however, whether armchair or otherwise, it’s worth a visit to see an outstanding example of brutalist architecture. Architect Raymond Affleck’s vision was to turn the city inside-out in a building appropriate for its location in a cold climate. The Place Bonaventure was designed to include a conference center, hotel, and several floors of retail space, all along internal streets while the building presents a foreboding exterior of ribbed concrete (echoing the design of the seminal Architecture School at Yale University by Paul Rudolph) to the street. The entire complex included 3.1 million square feet of floor space, making it the largest building in the world when it was completed (in 1967). Much of the retail space was converted to offices in later renovations, though the conference center and the hotel (now the Hôtel Bonaventure Montréal) remain. The photo here was taken inside the hotel—a walk around their common spaces will give you a taste of Affleck’s vision for a new urban architecture.

Deep in the wilderness about an hour’s drive north of Kingstown, Dark View Falls cascade off a cliff and into a pair of natural pools, where everyone gathers to swim in the crisp, clear water. The hike to the falls takes only about 10 to 15 minutes, but involves crossing a jungle-style bamboo bridge across the Richmond River. After passing through a clearing in a picturesque bamboo grove, you’ll arrive at the first fall, where you’ll find a gazebo, changing room, picnic area, and viewing platform for enjoying the beautiful scenery. Another short, more difficult walk will take you up to the second fall, directly above the first.

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.

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.

Dasheene, the restaurant in the award-winning Ladera Resort, is a magical place unlike any other on the island. The open dining room, overlooking the sea, is so close to the Pitons that you feel as if you could reach out and touch the peaks. The menu, which focuses on ingredients sourced from local farms and plantations, puts a creative spin on classic St. Lucian cuisine, including plantain gratin with a coconut rum sauce, and roast conch. The restaurant is open for breakfast and lunch as well, but there’s no beating the romantic atmosphere and sunset views at dinner, which make a meal here well worth the high price.

Vesper Bar at The Cosmopolitan is our favorite spot for a serious Old Fashioned—or Elderfashioned, the house’s riff, which gets a dose of St. Germain.