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Near the Dominican Republic’s northwestern border with Haiti, the city of Montecristo, and El Morro National Park, this 12-room lodge makes a great base for exploring subtropical forestland and boating through mangroves. Warm woods, neutral tones, and black-and-white photos decorate the lovely understated guestrooms, while comfy loungers and lush greenery surround the bean-shaped pool. Spend your days bird-watching in the national park, deep-sea fishing, kayaking, or snorkeling off the cactus-covered Seven Brothers Island, then head back to the hotel for traditional Dominican dishes at El Morro, wood-fired pizzas at Restaurant Bubí, or drinks at the lobby bar.

“This family-run restaurant on the fishing island of Pellestrina is quite far out—probably 45 minutes by boat. But in the summer months, it’s a lovely ride, breezy and fresh. Once you’re at the restaurant, you sit on a pontoon and see nothing but the spread of la laguna and the occasional boat speeding past. They do wonderful fish here. It’s incredibly fresh and they’ll bring you an array of mixed antipasti to start. The oven-baked turbot on potatoes with baby artichokes and baby tomatoes is fantastic. So, so good.”

Read about more of McAlpine’s Venice favorites.

This famous Vashon Island creamery maintains a toehold on the mainland in the Chophouse Row Building on Capitol Hill. It sells cheese, including the gooey bloomy-rinded Dinah’s treasured by top Northwest chefs. But all products pale beside the simple richness of Kurtwood Farms ice cream. Churned on-site in Seattle, it’s made with Jersey cream and milk, organic cane sugar, and pastured eggs. Yes, you can order farm-fresh flavors, like bay laurel, lemon verbena, and even Sungold tomato jam. But connoisseurs prefer the real deal, straight up. “The taste is pure Puget Sound, it’s the grass the cows are eating,” notes the Emerald City’s columnist-in-chief Dan Savage.

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.

Take a riverboat up the Wailua—which translates as the “river of the great sacred spirit"—fed by the Mount Waialeale shield volcano, one of the wettest spots on the planet. Seven temples once stood along Hawaii’s longest and only navigable freshwater passage. Today, the remains of four are still visible, alongside petroglyphs and rocks where the island’s alii (royalty) would give birth. Stretch your legs at the stunning Fern Grotto: Verdant plants blanket the roof of the volcanic-rock cave there. Smith’s offers 80-minute tours there on open-air boats, which include the songs and stories of ancient Hawai’I, plus a bonus hula lesson (smithskauai.com).

A local institution, the Lobster Pot serves up its crustacean namesakes, among other Caribbean delicacies, on a vista-blessed seaside deck. If you can, arrive at sunset for the nightly tarpon feeding (much more engrossing in person than you’d imagine). And even if you don’t get there exactly at the appointed hour, you can still spot these giants as they continue to patrol the dramatically floodlit waters off the restaurant’s deck for leftovers. As you take in the view, you’ll be eating the likes of lobster-and-mango salad, lobster bisque, or lobster sautéed in a tomatoey, peppery blend and served with fried plantains, rice, and beans.

Maria e Susanna Sent has several shops where they sell their glass jewelry, the cutest one of them all just off the Ponte San Moisè in San Marco. This boutique is about as big as a broom closet, and that is certainly part of its charm. The real impact, though, comes from the jewelry this artistic duo started creating on the island of Murano back in 1993. Their line of mostly necklaces and bracelets is made in a unique process that creates murrine and filigree glass and plates in glass fusion. They also have shops in Murano and in Dorsoduro near the Peggy Guggenheim Museum.

While exploring Burano, break for a fabulous seafood lunch at Al Gato Nero. The “black cat” restaurant is the creation of Ruggero Bovo, who has been cooking up some of the tastiest fresh fish and seafood here since 1965. “I love the fish of the Venetian lagoon and the Adriatic Coast, the raw material which has fed my island for generations and which I still have the fortune of getting fresh every day,” Bovo says. Fish and seafood are the star attractions on both the appetizer and main menu selections, but there are also options for vegetarians and carnivores. The pasta here is homemade, as are the delicious desserts.

Cooked in an open pit over pimento wood, the jerk preparations here are all authentic and—according to most locals—the best on the island. Traditionally spiced chicken and pork, as well as a less fiery fish version, served in a tin container along with rice and peas and festival bread (akin to hush puppies). Getting your order to stay means eating while perched on wooden barrels, which certainly adds local flavor. While enjoying the delicious meal, you’ll get to observe the seemingly endless line of customers, and perhaps get a ringside view of a lively and noisy game of dominoes.

For those wanting an active adventure on the water, Captain Alan’s Boat Charters offers snorkeling as well as clothing-optional boat trips. Their Snorkel and Beach excursion allows you to experience four hours of snorkeling and swimming around St. Maarten, Pinel Island, and the uninhabited Tintamarren while riding in one of their 30- to 38-foot off-shore power boats. Enjoy a swim with tropical fish and sea turtles, and then head back onto the boat for snacks, an open bar, and music. Captain Alan’s Boat Charters also offers a 6-hour adventure, trips to nearby Anguilla and St. Barth’s, and a clothing-optional nude cruise.

When I first moved to the island, I joined a friend in the Old City for a tour and lesson on the history of Puerto Rico. When passing by this little section of town near Pigeon Park, my friend and native-turned-tour-guide said that this was the smallest house in Old San Juan. Wow, okay, so this little yellow portion is technically a house? I’ve visited this site several more times since then and have never actually seen anyone enter or leave this door. Whether it’s true or not, it makes for a cool story and great photo.

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.

For people who lament that they weren’t born into Downton Abbey–style gentility, Ballyfin, which opened in 2010 after nearly a decade-long restoration, is a fast track to 1820s-era refinement from the moment guests pull up to the front drive. A team of butlers and maids line up on the stone estate’s front steps to unload bags and whisk visitors into the lobby, and from there the Ballyfin experience is a dreamy blur: drinking tea out of antique china while wrapped in an Irish-wool blanket by the fire; being lulled to sleep during a massage in the basement spa; soaking in a clawfoot tub and surveying the meticulously sourced antiques in one of 15 rooms.

Guests are basically lords or ladies for a night or two at this neoclassical home an hour west of Dublin in the county of Laois (pronounced “Leash”). For those who bore of pure leisure, there’s a stone tower to climb, horses to ride, 600 acres to explore, and a lake to walk laps around or row through. The pricey room rates can (almost) be rationalized by the inclusive evening champagne receptions, fancy three-course dinners, snacks, picnic lunches, and Irish breakfasts.

Chiseled from a sandstone-and-brick wool factory on the site of Sydney’s first hospital, the Harbour Rocks Hotel is one of the most historic accommodations in the Rocks—and maybe the most haunted. Hotel staff say part of the building, named Scarlett’s Cottages after a well-known lady of the night, is watched over by Eric, a man who once lived here and who still searches for Scarlett in the labyrinthine corridors after she swore her love to him and then disappeared. Ghosts aside, the hotel’s 59 rooms are peaceful, with high ceilings, Georgian arched windows, brick walls painted dark gray, Old West–style textiles, and wool carpeting that recalls the building’s former life. The place is filled with fun artifacts, too, from the ancient luggage lift to old maps and letters framed on the walls. The early-20th-century history that pervades the building is also found in every direction outside its doors.

Housed in a 19th-century French hospital, the Covent Garden Hotel is the oldest and most historic of Tim and Kit Kemp’s celebrated Firmdale hotels portfolio. Opened in 1996 by the husband-and-wife team, it bears a staid style that reflects its early position in the cannon of hotels, which have since become far more exuberant and quirky. The hotel’s muted, pared-back look will undoubtedly appeal to those who crave discretion. It’s not unusual to spot venerable British actors tucked away in a corner, quietly conducting a meeting. This is, after all, the heart of Theatreland—or London’s West End—where a recognizable clientele comes with the territory. However, the Covent Garden Hotel is by no means the see-and-be-seen spot of its media-magnet sister properties, including Charlotte Street Hotel, The Soho Hotel, and Ham Yard. Instead, go here to sequester yourself with a book in the upstairs drawing room, which, with its crackling stone fireplace and wood-paneled walls, resembles the traditional lounge of an English country house.