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The Caves, just west of Negril, is aptly named. While the 12 cottages and one villa sit atop honeycombed cliffs, the Blackwell Rum Bar, a private dining venue, and the massage table of the hotel’s Aveda Concept Spa are actually in underground grottos open to the sea. The setup is very Treasure Island, and the flicker of candlelight and the echo of waves off cave walls make it uniquely romantic. Each of the thatch-roofed cottages is as colorful as a paint box, and each gives a sense of being alone at the end of the land. This is one of music mogul Chris Blackwell’s Island Outpost properties, so the vibe at the Jacuzzi, sauna, or salt-water swimming pool is hip but relaxed. Although famed Seven Mile Beach begins almost where the cliffs end, the hotel itself has no beach, which is why a tradition at the Caves is to begin the day by jumping from the cliffs into the usually calm Caribbean below—or at least thinking about it.

This restaurant is such an institution that it predates the city’s most iconic landmark—the Hollywood sign. In a way, Hollywood was born in Musso & Frank’s red booths, back when the famed boulevard was still a dirt road. The restaurant opened in 1919, and much of the menu remains from the first chef, Frenchman Jean La Rue, who used to specially prepare fettuccini alfredo for silent film stars Douglas Fairbanks and Mary Pickford. Only two executive chefs have held the job since. Dinner dishes such as lobster thermidor and grenadine of beef take you back half a century, while chicken pot pie (on Thursdays only) and steaks, cooked on L.A.’s oldest open-fire grill, taste comfortingly familiar. Don’t miss brunch, which features Greta Garbo’s favorite Flannel Cake, a cross between a pancake and crepe invented by chef La Rue in the 1920s. In keeping with the authentic vintage spirit, martinis are strictly stirred—never shaken—and served with a mini glass sidecar containing the rest of the drink in its own tiny ice bucket. Pro tip: Order the off-menu slow-roasted prime rib, finished on the mesquite grill and served rare.

Petra flourished more than 2,000 years ago, trading with Rome as an equal before being abandoned after a series of earthquakes in the 4th and 6th centuries C.E. It wasn’t until the 19th century, when European explorers “rediscovered” it, that the ancient city returned to the public consciousness. Now, visitors can walk down the narrow canyon of the siq to the city entrance—as dramatic an approach as any to a tourist attraction on the planet. The canyon opens up onto the carved facade of the Treasury, Petra’s most iconic site. From there, you can explore the cliffside tombs with their colorful bands of sandstone, the Street of Facades, and the amphitheater hewn from living rock. The ancient center lies some distance off, along with the splendid old Monastery, which sits at the top of a steep but rewarding climb. Consider buying a three-day ticket and visiting at different times of day to enjoy the changing light—early in the morning is best for the Treasury, while late afternoon is better for the Royal Tombs.

While many walked through the streets of the small town, I decided to head along the river and came across this beautiful view of Lake Brienz.

On the ultra-exclusive island of Mustique, Basil’s Bar is a stargazer’s paradise—and not just at night. It’s a favorite of celebrities, meaning you never know just who will be seated at the next table. A series of roofs cover the open-air deck to shade diners from the hot sun and occasional shower as they enjoy tropical cocktails and freshly grilled lobster. Come for the dance party on Wednesday, the happy hour on Thursday, or the sunset jazz every Sunday at 5:30 p.m. Basil’s also hosts the Mustique Blues Festival at the end of January, with live music each night for two straight weeks.

Hong Kong’s tram system dates back to 1904 and still plies some of the same routes, stopping on average every 820 feet. Locals affectionately call the trams Ding Ding because of the bells rung when the trams approach a stop. The main line runs across the whole northern edge of Hong Kong Island, along what was once the waterfront, between Kennedy Bay and Shau Kei Wan Road, passing through the Central Business District and bustling Causeway Bay area. The six routes cover 19 miles and more than 100 stops. Most cars are double-decker and were rebuilt in the 1980s or later, but No. 120 dates back to the 1950s and still sports seats made of rattan and teakwood.

Boasting some of the best views in Kauai, this dreamy eatery serves up spectacular sunsets alongside splurgeworthy lunches and dinners. Start with the signature Monkeypod Mai Tai: A potent blend of Old Lahaina rums and orange curaçao, graced by honey foam. Then try the Thai-inspired coconut crab cakes, followed by the oven-roasted Jidori chicken with goat-cheese polenta or the wasabi-crusted fish with passion-fruit beurre blanc. Vegetarians won’t go hungry either, thanks to dishes like coconut corn chowder sweetened with local lemongrass and slow-roasted beets with tomato-cilantro salad and tempura asparagus. Often voted the island’s top restaurant by Honolulu Magazine, Beach House has also won a steady streak of awards from Wine Spectator.

Set in a tropical garden in the suburb of Fannie Bay, this superb museum and gallery is the best place to learn all about the art, history and culture of the Top End (the nickname for this northernmost section of the Northern Territory). The excellent collection of indigenous art includes both traditional and contemporary works. One gallery is devoted to the tragic events of Cyclone Tracy, the natural disaster of 1974; another covers the boats of the Pacific Islands. The museum’s most popular exhibit may well be Sweetheart: the stuffed carcass of a five-meter (16-foot) male saltwater crocodile that once terrorized the billabongs (waterways) outside Darwin.

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.

Tucked in a condo complex just north of the bridge, Coco Loco’s is a cozy little pool and beach bar. On hot days, take advantage of the swim-up bar stools or hang out on the picnic tables closer to the beach. What Coco Loco’s lacks in size, it definitely makes up for in personality. Owners Sue and Steve have done a wonderful job with fostering a community spirit, especially with many of the expats on the island. Look for a number of weekly activities like trivia and cribbage that keep the bar hoppin’ pretty much every day. Open daily noon to 10 p.m.

Mylopotas beach is a stretch of sunny beach lined with bars, restaurants, hotels, and a youthful party scene. Depending on the day or time of day this stretch of beach could be quite and lazy in the sun or have music and people dancing on cars. Either way Karma beach bar is a chill open air bar with pillow seating on the raised floor and hammocks hanging everywhere. The pizza is delicious and perfect for a light beach snack on a sunny day. They have a great drink menu including island cocktails and prosecco fruit mixers. We lounged our first day away in the hammocks here sipping on cool drinks.

The Pacific Asia Museum’s collection includes art and artifacts from the Pacific Islands and Asia, and the museum offers free cell phone audio tours in multiple languages. The audio tour includes a curatorial tour, a family-friendly tour focusing on animals and legends that appeal to kids, and a poetry series featuring original music and poetry relevant to the collections. Even if you’re not a shopper, don’t miss the gift shop as you leave. One of the highlights of my visit was discovering the gift shop’s collection of old photographs (certified, authentic, and matted for sale)—most are originals taken in Asia during the 1800s and early 1900s.

The absolute best way to explore the rolling hills and secluded beaches of southern Guam is on two wheels. Start in Tamuning, where you’ll find affordable scooter rentals at Scooter World on Pale San Vitores Road. Take Marine Drive to the capital city of Hagatna, then turn on Highway 4 through the villages of Sinajana, Chalan Pago, Yona, Talofofo, Inarajan, and Merizo, finishing up at the southern tip of the island. Along the way, you’ll encounter verdant mountains, dramatic cliffs, and sparkling black sand beaches. If you get hungry, fill up on burgers at Jeff’s Pirates Cove and soft-serve ice cream at the Mobil gas station in Talofofo; both are local favorites.

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.

If you’re hungry for a deliciously carb-heavy Hawaiian plate lunch, why not go to Rainbow Drive-in and enjoy a meal fit for a president? It’s true: President Obama ate there as a kid and tries to make it back during his visits. Starting at 7 am, you can order up a big plate of mahi-mahi, eggs, and rice (or the omnipresent Spam). Lunch specials include loco moco, BBQ ahi, fried chicken, and chili dogs, with plenty of gravy poured over everything. Best of all, nothing on the menu is over $9, making this a rare bargain on a very expensive island. Stop at their shop next door for seasonings and souvenirs on your way out.