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There aren’t too many opportunities in the Caribbean to ride on horseback to a cave. In Los Haitises National Park, located three hours west of the resorts of Punta Cana, Fun Fun (pronounced “Foon Foon”) Cave is officially known as the largest cave in the Caribbean. Though the cave itself is in the National Park, access to the land goes across a private ranch and requires a guided tour. While the nearly three-hour drive from the resorts of Punta Cana is a lengthy, bumpy, journey into the interior, the scenes from the window provide an authentic glimpse into rural Dominican life. Sugar cane sways, schoolchildren wave, and mangoes drip from the trees. Upon reaching the ranch where you begin the tour you are shimmied into a jumpsuit and saddled onto your horse. A 45-minute ride through the shaded forest brings you to the edge of the National Park. From here it’s another 30 minute walk through sun-swallowing trees until you reach the entrance of Fun Fun Cave. Sliding into a harness and climbing gear, entering the cave requires a 50 ft. repel into a tiny hole which can barely fit your shoulders. Once at the bottom, it’s a one hour slog through the depths of the darkness before reaching the other exit. Inside the cave, stalactites and stalagmites pepper the areas which fall in the beam of your flashlight, and at some areas you are forced to swim through the soothing, subterranean waters. Here, a lone rope helps guide visitors through the hidden recesses of the cave.

Housed on a 1,100-foot stretch of beachfront, Grace Bay Club is as stylishly current as it was in 1993, when it became the first luxury hotel to open on the then nearly empty sands of Grace Bay. From its original 21 rooms, the upscale property has grown to 82 suites, each of which features ocean views, a private veranda or patio, and chic interiors by renowned designer Thom Felicia. Guests can also look forward to superior service, including a personal concierge available day or night via a provided cell phone.

When hunger strikes, there’s the oceanfront Infiniti Restaurant & Raw Bar, which boasts sea-to-table fare and the longest bar in the Caribbean, as well as several other family-friendly venues, including The Grill. If it’s pampering you seek, make time to visit the spacious Anani Spa, where you’ll find six treatment rooms, including one just for couples. A spa tent is also available for beachfront massages.

Offering something more immersive than classic resort dining, Banyan Tree Vabbinfaru has a four-course menu that can be served right on the beach. Watch a chef prepare your gourmet Maldivian lobster dinner right in front of you while you listen to the soothing sounds of waves lapping at the shoreline and enjoying the fresh sea air. Alternatively, choose the Sharkpoint option and tuck into sea scallops and lobster on a secluded stretch of sand. For a dose of culture, head to the open-air Naiboli Bar on a Friday night and take in a traditional bodu beru performance on the beach.

The family-owned Yandup Island Lodge is located on a private island across from the remote Playon Chico community on the Caribbean coastline of San Blas, Panama. The eco-lodge offers two tours a day: a visit to a beach on one of the archipelago’s deserted islands and a cultural tour that connects guests to the local Kuna Yala indian community.

Housed in the Mariners Hotel overlooking Villa Beach, The French Verandah Restaurant satisfies diners with delicious French cuisine, prepared with a Caribbean twist. Expect such unique dishes as lobster crêpes and fish in green pepper sauce, as well as more standard French fare like grilled beef tenderloin with Béarnaise. Views of boat “traffic” and Young Island set the stage for casual dining during the day, while candlelight and twinkling stars up the romance come evening.

Pier 1’s greatest appeal is its setting: The open-air restaurant and nightclub occupies a pier that extends out into the Caribbean in Montego Bay. By day and into the early evening, the restaurant draws visitors and locals interested in a good meal with a stellar water view. At night, regular parties start late and run into the wee hours of the morning. Skip the noisy chain restaurant-bars down the street and try something more Jamaican, instead.

Watching the sun set on Jamaica‘s west coast is a bona fide activity. The island’s red skies are a sight to behold. I have yet to experience a better Caribbean sunset than in Jamaica. From Montego Bay all the way to Negril--famous for having the best--to Whitehouse, get your camera and Red Stripe ready for the last hours of daylight. You won’t lack for choice of seafront bars or scenic spots--from the trendy Pier One in Montego Bay to the wooden shack watering holes along Negril’s West End cliffs. Wherever you end up, there’s a very good chance you’ll get hooked on this daily sunset viewing routine.

All of Mexico City‘s neighborhood markets are fun to browse, with their rows and rows of colorful stalls and equally colorful characters, and you can’t go wrong ducking into any one of these mercados as you come across them in your wanderings. Mercado Medellín is particularly favored among expats from other parts of Latin America, as it specializes in foodstuffs from Caribbean and Central and South American countries. This is also a superb market to visit if you’re hungry. Vendors sell everything from Colombian ajíaco to Cuban ice cream, so don’t hesitate to graze your way through the treats on offer.

Weaving its way along the river, and among the various parks of downtown Itasca, the Itasca Riverwalk is a great way to do some small town exploring. The paths link the Springbrook Nature Center, to the Caribbean Waterpark, to the Fitness Center and to many more wonderful park district sights. You can hoof it, bike it, and when it snows, some have even snowshoed it (just rent your kicks from Springbrook and you’re all set). Exploring the path with friends or family is a great way to take in the great outdoors, get a little exercise, and get to know Itasca.

This vibrant neighborhood is just north of Wynwood and the Miami Design District and is getting increasing attention from visitors for its independent galleries, street murals, hot restaurants, and cool bars. It’s also a great place to experience a strong Afro-Caribbean culture and tradition. On the third Friday of every month, the Little Haiti Cultural Complex puts on Big Night in Little Haiti, a concert series showcasing local bands, dance troupes, and some of the biggest names in Kreyol music. Although after-parties are held at neighboring establishments, things typically climax with a procession on nearby streets, picking up pedestrians as the night goes along.

Enjoy these stunning oceanview and beachside cabanas at The Westin Lagunamar Ocean Resort, a seaside resort in Cancun, Mexico. Enjoy the turquoise blue waters of the Caribbean, a sweet haven for the sun-seekers. A perfect place to soak under the sun, swim or people-watch. $400/night.

Work your way from Excelsior’s top floors (slinky Chloé dresses, Balmain leather jackets) to the main floor (watches, speakers, a sea of colorful iPad cases), then down to the subterranean floors for the impressive wine shop and restaurants.

You’ve made it to the splendid isolation of Ulleung-do island’s north shore...Now, where to sleep? “Chusan Ilga Pension” is one of the island’s best choices: above the waves, on a clifftop beneath a volcanic peak, with a granite Buddha overlooking the greenery to the west and a fishing village just down the steep road to the east... This is rustic comfort: the floors are heated in the traditional Korean manner, the timbers are exposed, but the double-paned windows can either shut out the roar of the sea or let in the salty breeze, as you wish. Downstairs is a restaurant that serves the local seafood and mountain vegetables. There are several buildings on this clifftop, but the one with the restaurant offers three rooms with balconies almost directly above the sea; ask for one of these. To get here: take the coastal road from the port where you disembark from the ferry. You can’t get lost--there’s only one coastal road. Go counterclockwise around the island. Once you reach the north side, look out for the Elephant Rock in the sea and Songotsan peak on your right. Soon you’ll see a sign for Seongbulsa Temple, pointing up an almost immpossibly steep road. Start climbing and after the first bend, Chusan Ilga will be on your right. (The website is in Korean only, but the central tourist office in Seoul can phone for you; you’ll have to wire money through a Korean bank to confirm your room.)

If you’re looking for a great snorkel experience accessible to Waikiki, I found Hanauma Bay a great spot. Turtles and fish galore.

The Dead Sea has deservedly become known as something of a spa destination, with visitors helping themselves to goopy masks of the local, mineral-rich mud for decades. For something slightly more luxurious, book an appointment at Zara Spa in the Mövenpick Resort. Done up in raw stone, elaborate tiles, and polished plaster, the five-star facility evokes the Jordanian desert combined with a Moroccan riad. It also boasts one of the widest range of treatments in the entire Middle East, plus expertly trained therapists to ease you into a truly relaxed state of mind. The traditional hammam is a particular delight, but be sure to also indulge in popular treatments like the black mud body wrap or the hot-and-cold-stone massage. When you book a service, you’ll also have access to the spa’s top-notch facilities, which include hydro, flotation, and infinity pools as well as a juice bar and state-of-the-art fitness center.