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If you’re staying on the east coast or close to Kingston, Wickie Wackie Live! is the place to be for some live reggae on the beach. For just a small entry fee, you’ll get to enjoy excellent local performances seaside—often held on Saturday evenings, 8 p.m. until midnight. There are onsite food and trinket vendors, as always, and the atmosphere is one fit for a wide audience, including families. Wickie Wackie is one of only a few live venues in Jamaica where up and coming artists get to show off their skills. Many made their debut here before rising to stardom.

A popular and new cultural attraction in Montego Bay, the Rastafari Indigenous Village offers a fun and insightful day of Rastafari history, music and food to anyone interested in immersing and learning about this unique group. The day begins with a hike to the village, reached by spelunking across a river, and a medicinal plant tour. It continues with various activities, including culinary demonstrations of Rasta “Ital” or organic, vegetarian dishes, drumming circles and stories on the evolution and struggles of Rastafari culture in Jamaica. It’s an easy reach—about 20 minutes from Montego Bay—and a good pick for those short on time.

One of my favorite spas in Jamaica is located at the well-known Jakes Resort, in Treasure Beach. Small, cozy and away from the big resort towns, it’s a wonderful place to unwind. Opt for a long full body massage in one of only four oceanfront treatment cabanas, with doors open on the sea ahead. The spa prides itself in using fresh ingredients from its on site gardens. When you’re done, walk over to Jack Sprat for a quick bite with a view and take a nap on the beach—not necessarily in that order.

This stunning white-sand stretch, just a five-minute drive east of Port Antonio, is the only beach in Jamaica with waves high enough to surf. Boston Bay is also one of the few remaining public strands on the island. It continues to attract more locals than tourists and as such is nearly vendor-free. You can watch kids splashing about on their boards, or you can rent your own for a Surfing 101 lesson. Be forewarned: As at many beaches, sometimes the waves are flat, but you can console yourself with a short stroll down the beach to the famous Boston Bay jerk chicken stands.

What began in 1854 as a high school—then grew into a college and, later, a law school—has served as one of San Antonio’s top hotels since 1968. Located near the River Walk, not far from the city’s historic district, the leafy former campus is centered around a seven-story, Spanish colonial-style main building with 338 guest rooms. Each one mixes original touches like wood-beamed ceilings, exposed brick walls, and French doors with modern amenities like HDTVs, marble baths, and Wi-Fi (complimentary for loyalty club members). Some even look out on the River Walk, while others offer views of a verdant garden. Healthy extras like in-room fitness kits, a 24-hour gym, and a year-round heated pool help offset the indulgences served at the on-site restaurants and bars, which include the fine-dining Las Canarias (don’t miss the popular Sunday brunch.) Younger guests can look forward to game-filled backpacks and scavenger hunts, while adults will enjoy the award-winning spa and restaurant at La Mansion’s sister property, Mokara, located across the river.

Have you ever had a drink while standing at the top of a 1,700-foot vertical drop, as the sun sets into the ocean? That’s what you get at Lovers’ Leap, less than a half-hour’s drive from Treasure Beach. Pay a small entrance fee and walk through the bar to reach the balcony with the jaw-dropping view. Of course, there’s a legend to go with the name of the cliff: Two enslaved lovers jumped together from this spot to their deaths to escape from their colonial master who wanted the girl for himself. A wood carving of the lovers stands just outside the entrance. The sunset panorama here is arguably the most stunning view in all of Jamaica.

Bourbon Beach, a popular beachfront music venue on Negril’s Seven Mile Beach, hosts local bands, reggae artists, or themed parties on an almost-nightly basis, to the delight of tourists and locals. People-watching at Bourbon Beach is great, the drinks stiff, and you get to dance in the sand to live reggae in Jamaica. The music starts up around 10 p.m. and continues until 2 a.m. Upstairs, a wide-open deck is open for stargazing or getting away from the crowd. Cover charges are only collected on nights when a recording artist performs. Alfred’s, nearby, is another longstanding option, offering live local acts three times a week for a US$5 cover.

Located across the way from Half Moon Resort, Sugar Mill Restaurant is set on the grounds of an old plantation. Couples and small groups dine at candlelit tables either on a covered terrace or out on the lawn, and the splashing of the mill’s waterwheel and the chirping of crickets are an accompanying sound track to the top-notch service and Caribbean fusion menu. Order a bottle from the well-stocked wine cellar, visible as you enter the restaurant. For special occasions, a private table beside the waterwheel can be reserved. (In the mood for a lighter, slightly more casual meal? A tapas menu is available in the restaurant lounge.)

The laid-back restaurant Carbon Caribbean Cuisine takes you on a culinary journey around the Caribbean. You can order typical dishes from Cuba, Jamaica, Puerto Rico, and, of course, the Dominican Republic. Popular with locals, Carbon offers a glimpse of island life beyond the beaches and resorts.

Reach Falls is an off-the-beaten-path delight. Located up in the John Crow Mountains on Jamaica’s east coast, this 30-foot jade-colored cascade tumbles into several pools in the surrounding rain forest. You’ll need a bathing suit and a waterproof camera to capture the natural splendor. Local guides are available to help you make your way across the swimming holes and levels, and show you the best spots. Or you can explore it solo. Because of its distance from tourism spots, there are no crowds, no harassment, just an entrance fee to your very own Garden of Eden. On-site changing rooms are available as you exit by the parking lot. Small fun fact: The falls play a minor role in the 1988 Tom Cruise movie Cocktail.

Perched on a hill between the busy Zona Sul and hip Santa Teresa neighborhoods, Casa Marques is an all-suites boutique hotel with unparalleled views of Rio. The French-Brazilian couple behind the property blended minimalist modern design with contemporary Brazilian art, creating a space that’s as sleek and subtle as a gallery. Stark white, rooms are decorated with unique local art and artisan-made rugs. Standard suites feature pingo de riga (floor-to-ceiling), wood-framed windows, while master suites include a balcony and expanded bathroom with soaking tub. On the roof of the colonial mansion, there’s an infinity pool and bar overlooking Guanabara Bay, Sugarloaf Mountain, and Christ the Redeemer. Rates include breakfast on the terrace or in the warm, stylish kitchen lounge, complete with traditional tapioca and Brazilian iced tea. Note that Casa Marques’ stellar scenery means it’s challenging to access—plan on taking taxis whenever you can tear yourself away from the hotel vistas.

Get a handmade leather wallet, purse, or passport holder—without breaking the bank. Since 1949, local secret Armando Rioda (hidden on the 2nd floor of a building near the Spanish Steps) has been turning out top-notch, handcrafted leather goods. Sketch out your design with one of the shop’s master craftsman, pick your own leather, even get it monogrammed. Small wallets start at about 50 euros and purses at 100 euros, so for a unique, bespoke leather item, the prices couldn’t be more fair.

The newly opened Parque Fluvial Renato Poblete was once a garbage dump and squatters’ before the nearly 50 acres were taken by the government and transformed into this handsome park. Dividid into two areas, “El Cauce” (The Channel) is 17-acre flood plain with three water mirrors. The second, known as “Brazo del río” (River’s Arm), covers 32 acres and boasts a lagoon formed by the Río Mapocho, now a place for water sports. Like in most Chilean parks there are soccer fields and a cycling path that belongs to part of a circuit covering over 20-miles and multiple neighborhoods. On the weekends, Santiago families congregate here under the sun for a pinic. Tuesday to Sunday, 9:00 a.m. to 9:00 p.m. Avenida Presidente Balmaceda 2800, near Costanera Sur, Quinta Normal

During the harvest season, navel oranges are sorted by machine based on their size. The smallest ones fall into boxes early on the conveyer while the largest ones make it all the way to the end. Orange Patch has some of the best fresh-squeezed orange juice I’ve ever had! Definitely worth a pit stop to pick up some fresh citrus fruits. I love the tangelos, kinnow mandarins and rio red grapefruit best!

The roots of this Mediterranean Revival-style boutique hotel go back to 1914, when a local grocer created the tropically inspired property to house his visiting vendors. Nearly a century later in 2010, hotelier and style guru Liz Lambert added the place to her mini-empire, reviving the grounds that still feature magnolia, palm, and cypress trees planted by the original owner. Set on a quiet section of the River Walk near the museum corridor, the restored building (which is on the National Register of Historic Places) houses 27 guest rooms decorated in a designer-meets-flea market aesthetic, with bright pops of color and plenty of personality. All are pet-friendly, and feature stocked SMEG fridges, Red Flower bath amenities, custom serape bathrobes, and complimentary coffee and Wi-Fi; suites have sitting areas, terraces, or other perks. Room service comes from the in-house Ocho restaurant, but it’s better to head down and eat there in person to take in the cheery setting, river views, pan-Latin menus, and cocktails that highlight rum (as a nod to Havana) and tequila (an homage to San Antonio’s Mexican roots). A regular calendar of happy hours, musical performances, and cultural events round out life at this vibrant hotel.