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Surrounded by bold artwork inside and magnificent ocean views outside, guests are never quite sure where to direct their gaze when they arrive at Ellerman House. A stay here is a bit like visiting an elegant and attentive friend, starting with the complimentary airport pickup straight through all the thoughtful, personalized touches (guests might find a bottle of their favorite vodka already stocked in their room). The hotel owner is a well-known aficionado of South African art, and his private collection graces the walls of the guestrooms and public spaces. True art fans should be sure to visit the on-site gallery to view masterpieces by Louis Maqhubela, Wayne Barker, and Angus Taylor. If it’s not occupied, also sneak a peek at the breathtaking wine gallery, which features a wall made of soil from the Cape Winelands and a spiral-shaped wine rack modeled after a corkscrew.

Sitting on the edge of a cliff, this luxuriously appointed hotel makes for one of the best spots in Cape Town for a sundowner. Have a cocktail on the terrace while watching the fiery African sun meet the tumultuous Atlantic waves.

No hotel in Jamaica blends better with its surroundings than the aptly named Rockhouse, a string of villas clinging to the top of a sea cliff at the western tip of the island. Local stone, timber, and thatch are the building materials, and a harmony of design and setting is the result. The feel is rustic, but not rough (the showers might be outdoors, but the rooms are air-conditioned), and the feeling carries over to the pool, which sits on a rock platform halfway down the cliff face, from where sunbathers can don snorkel and mask and clamber down into a usually calm Caribbean. Even the restaurant hangs over the water, adding emphasis to the promise of dishes being fresh from the sea.

As does practically every hotel in Jamaica, Rockhouse has its celebrity stories, going back to the early ‘70s when Bob Marley, Bob Dylan, and the Rolling Stones added their names to the guest register. But it wasn’t until 1994, when a group of Australian owners took over, that Rockhouse began to evolve its reputation as one of the most Jamaican of Jamaican hotels. It happened in part because Rockhouse has none of the formality that some of the island’s best-known hotels, with their British colonial roots, still possess. And in part because of its active role in funding local education projects, it’s a valued, and popular, part of the community. That, and the restaurant’s homemade jerk sausage is legendary.

Conveniently located near the subway, museums, and upscale boutiques and galleries of Toronto’s swish Yorkville neighborhood, the Park Hyatt Toronto originally opened in 1929. Seventy years later, a south tower was added to the hotel, with the art deco–influenced lobby space linking the two. The spacious rooms have a soothing palette of pale peach, dusky pink, beige, and gold. The Annona restaurant has a similarly rich color scheme, boldly decked out in shades of plum and gold, with plush banquettes and floor-to-ceiling windows overlooking Yorkville. The 18th floor offers sweeping views over Queens Park and the CN Tower, but the main attraction may be the Roof Lounge’s bartender, Joe Gomes: He’s been shaking up cocktails here for the past 50 years, so guests can order a martini from a man who knows how to make them just right. A host of other extras, including complimentary town car service within a five-kilometer radius, free Wi-Fi, and even a kosher kitchen, add to the hotel’s charms.

St. Lucia’s iconic twin peaks—Gros Piton and Petit Piton—dominate the island’s scenery, soaring 2,500 feet from the sea on the island’s southwest Soufrière corner. Designated a World Heritage Site along with the surrounding Pitons Management Area, these volcanic spires take every first-time visitor’s breath away. There are various ways to experience the Pitons. The brave hike either peak—Petit Piton is more strenuous, and the trail isn’t marked; Gros Piton has marked trails and is a two- to three-hour hike from the village of Fond Gens Libre. Others opt to take it easy and sail past them on a catamaran cruise, or view them from land along the coast or from the terrace of La Haut’s restaurant. Sugar Beach, facing Gros Piton, offers a frontal view of the peaks as you swim.

Henry VIII has been an island favorite for 40 years. Not surprisingly, given its namesake, the restaurant serves some typical English dishes — bangers and mash, fish and chips — but the menu also includes some of the island’s best sushi. The food comes with ocean views that are especially spectacular at sunset. “This is my local place,” Mike says. “It’s just a two-minute drive from my house. They take good care of their guests. On Saturday nights, a DJ plays old-school music and every day there’s an awesome cross section of people here: locals, visitors, and expats. It’s a good place to dance the night away, and the sushi is off the hook.”

Located in the middle of New York harbor, less than half a mile from Manhattan (and even closer to Brooklyn), 172-acre Governors Island feels like a world unto itself, far from the bustling city. It has played a key role in the defense of New York at various points and two fortifications here, Fort Jay and Castle Williams, reflect that history. From 1966 to 1996, the island was a Coast Guard station; since it closed, the city, state, and federal governments have discussed various plans for the island’s development. In the meantime, it is open to the public for six months each year, from May 1 to October 31, when it is possible to wander among the Coast Guard barracks, visit the commander’s house, and bike around the mostly car-free island. Ferries depart from both Manhattan and Brooklyn starting at 10 a.m. and running until 6:15 p.m. on weekdays and 7 p.m. on Saturday and Sunday. During many weekends in the summer, art fairs, food festivals, and other events help draw visitors to the island, but even if you go on a day without anything special scheduled, a journey here provides a refreshingly different perspective on New York.

It is not quite accurate to say that this 13-room beachfront property on sparsely populated South Andros Island is off the beaten path. Sure, there are no roads to bring you here, and the only neighbors are the denizens of the 125-acre nature preserve that surrounds it, but a seaplane flight from Nassau will have you wading ashore in just 15 minutes. Once settled into their thatch-roofed private villas, guests gravitate toward the Great Room for fruity drinks, fresh-caught meals, and tall tales. While there is every kind of watery diversion, from bonefishing to scuba diving—and nature tours, too—it’s the kind of place where kicking your feet up is the most strenuous thing you’ll do all day, and where privacy is so valued that beach butlers won’t intrude unless, in one of the older nautical traditions, you raise a flag to indicate that you require food and drink.

There certainly are other ways to while away a summer day in Greater Portland, but you’d be hard-pressed to find a better experience than island-hopping aboard a Casco Bay Lines ferry. Sure, you can simply ride out to an island for a look-about and return, or enjoy a sunrise, sunset, or moonlight cruise. But for a real immersion, consider the Mailboat Run. You’ll be among islanders, visitors, pets, and freight to-ing and fro-ing between Little Diamond, Great Diamond, Long, Cliff, and Chebeague islands. The 2½-to-3½-hour working cruise is offered twice daily year-round; bring your own picnic lunch on the morning run or snacks for the afternoon one.

How do you make sense of diverse, dizzying São Paolo? Talk to the people who make the sushi, spray the graffiti, and build the giant watermelons.

The Bridges of Samaná, also called the “Bridges to Nowhere,” are a string of bridges connecting the small islands that stretch across the outside of Samaná harbor. They are remnants from a project in the 1960s and ’70s by President Joaquín Balaguer to build a restaurant on one of the islands, connected to the mainland by a pedestrian bridge. The restaurant never opened, but the bridges and the shell of the building remain as curious relics of recent history.

Head south of town to the tiny beach bar at Mata Rocks Resort. Squirrel’s Nest is a peaceful spot to enjoy a few cocktails while taking in views of Belize’s well-renowned Barrier Reef. For years, I called Mata Rocks my hotel of choice when I visited Belize as a tourist. I spent the bulk of my days lounging by the pool and chatting with the bartenders at Squirrel’s Nest. Longtime bartenders Sherilyn and Criselda are two of the nicest people on the island and serve up some pretty awesome drinks. Try Mata Rock’s specialties like the Mata Colada or Pink Squirrel. Open daily, closing hours vary but usually around 8-8:30pm.

A great find in Southern Maine, a beautiful five mile beach with spectacular views and long stretches of white sand. No place can compare to the beauty that this beach embraces that families have come to summer for many generations. A perfect day to relax, take advantage of the many water activities out in Goose Rocks Bay overlooking Timber Island. There’s something for everyone around every corner of Goose Rocks. Be sure to check it out while your in Southern Maine. Just bear in mind during the summer months you will need a parking sticker, which can be purchased directly from the Kennebunkport Police Department or Kennebunkport Town Hall.

Named for the wife of Governor Lachlan Macquarie, who presided over New South Wales in the early 1800s, this site provides one of the most spectacular views in town. Find the historic carved-rock ledge in the Royal Botanic Garden, east of the Opera House, where you’ll drink in a vista encompassing the Bridge, harbor and distant mountains, along with historic sites like Kirribilli House (the prime minister’s residence), the island of Fort Denison and the Navy Dockyards at Woolloomooloo.

Right in the center of town, Capri Tiberio Palace mixes la dolce vita glamour with a globe-trotting sensibility that’s equal parts quirky and elegant. Wanderlust-inducing knickknacks such as globes, vintage trunks, and an eclectic collection of art stud the public spaces, and bookshelves are stocked with coffee-table tomes from the publisher Taschen. A white baby grand provides the soundtrack for aperitivo hour at the Jacky Bar, where wicker poufs, striped blue-and-white banquettes, and Panama hats repurposed as wall decor signal vacation vibes; things are slightly more reserved at the terrace restaurant, a formal space whose brightly colored dishes (think seared scallops with almond sauce and beef tartare with chestnut cream as well as kosher fare) are rivaled only by the panoramic views of the island’s craggy peaks coast and azure sea. And the indoor-outdoor swimming pool, though small, is a savior in the summer heat.

The Maria Islands—Maria Major and Maria Minor—off the southeastern coast are among the region’s most pristine environments. You can visit the protected wildlife reserve via a 20-minute boat ride from Pointe Sable. On Maria Major, a verdant trail leads you past a variety of unusual tropical flora and fauna, most notably the habitats of six rare native reptile species. Look for St. Lucia’s whiptail lizard and the racer, a nonvenomous grass snake that might appear from a rock crevice. Snorkeling off the beach is part of the experience, too, as the island’s waters are rich with coral reefs. The reserve, a birder’s paradise most of the year, is closed to the public in the summertime to accommodate the nesting season of migratory birds that flock here from Africa.