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No matter your passion, Portland has you covered. The tax-free shopping wonderland is loaded with stores to tickle the fancy of shoppers both casual and obsessed. From Powell’s City of Books—easily one of the best bookstores in the United States—to Wildfang, where the coolest patriarchy smashers hang, and, yes, all the chain stores, Portland’s got the goods. Some of the city’s shopping hubs include downtown Portland, Pioneer Place, 23rd Avenue, and the Pearl District. Fuel up with some java at the coffee shop of your choice because there is serious shopping to be done.

Montego Bay and the west coast of Jamaica attract first-timers to the island, and it’s easy to see why: white-sand beaches, the most glorious sunsets in Jamaica, plush resorts, a wide variety of restaurants, and a lively music scene. But there’s also plenty to see and do in the west coast interior away from Montego Bay: rivers, cenotes, and waterfalls such as the stunning Mayfield Falls.

Whether you’re searching for a caffeine boost to kick off a day in Portland or you’re on the hunt for a perfect place to perch for some people watching, the city’s cafe scene offers plenty of options. From drip coffee to espresso drinks at third wave coffee roasters to donut spots and bakeries that also serve up good java, your time in Portland is about to get turbocharged. Don’t forget to pick up some to-go beans from local coffee roasters. You’ll want to brew up some of Portland’s coffee scene long after your visit.

Once a fishing village, Negril—Jamaica’s favorite laid-back beach town—is at once a party scene and a romantic escape. Go bar-hopping or beachcombing on Seven Mile Beach (also known as Negril Beach), dine seaside atop dramatic cliffs in the West End of town, swim in nearby waterfalls, explore the vibrant markets, or jam barefoot to live reggae. There’s no place in Jamaica quite like Negril.

Portland has long been one of America’s culinary “it” cities and that won’t change anytime soon. The city’s cooks do so many things so very well: from doughnuts to dishes that focus on seasonal and locally-sourced ingredients. Eat around the world without leaving the city limits with visits to the legendary food cart scene as well as top spots like Ava Gene’s, Kachka, and Hat Yai (their Thai fried chicken will make you want to move to Portland). Pull up to one of these restaurant tables and you’ll find yourself challenged and delighted and definitely eager for more.

You can take your rented bike and pedal down to a waiting Zipcar and get out of town. From the mountains to the coast—and everything in between—you’ll enjoy an easy break from the urban outlook, usually with an hour of driving, or less.

Jamaica Jazz and Blues, held just outside Montego Bay, is one of the Caribbean’s most well-known festivals. It hosts some of Reggae’s top stars alongside a host of well known American artists--past performers include the likes of Gladys Knight, Celine Dion and Maroon 5. The three-night concert is not a strictly jazz affair, but it’s a great time and one of the most fabulous international events in Jamaica. The large stadium accommodates several VIP tents for those who pay to receive all-star treatment, hopping from one all-inclusive food and drink tent to another, sampling local dishes from top chefs during or after performances. Part of the festival also includes a shopping village, showcasing some of the best art and other handmade Jamaican crafts. The large space and manicured lawn makes it ideal for strolls while the music plays on.

On the Caribbean island of Tobago, you’ll find sand, surf—and the fastest goats on the planet. Now if they’d just run in a straight line….

A journey through one of the world’s last, best travel secrets.

Who’s got the best view up in the Blue Mountains? It’s not Strawberry Hill, it’s the Jamaica Defense Force! The view from the military barracks and training ground—a short drive up from Mount Edge Guest House—is stunning, with the peaks and the coastline stretching ahead. Too bad you can’t stay here. But you can certainly get a ride up and quickly take in the scenery and a snapshot. If you’re lucky, you’ll spot the troops during a drill.

With settlement dating back to 1699, the “Little City” is named for The Falls Church, an 18th-century Anglican parish (for whom President George Washington was a vestryman). At only 2.2 square miles, this historic suburb of Washington, D.C. is known for its urban village community, nationally ranked school system, restaurants, and a thriving Hispanic and Vietnamese community.

Aqua Nature Park, a well-maintained and verdant retreat 40 miles east of Negril, offers visitors a chance to take a dip and cool off in the Venture River. The river, which flows through a swimming hole on the property, has small, colorful fish and a cascade. Owner Steven delights in conducting walking tours of his family’s property, and can teach you quite a bit about the Jamaican plants and fruits he grows. (Don’t miss seeing the enormous cotton tree.) A casual restaurant and bar, with some reggae playing in the background, rounds this experience out into a lovely, low-key afternoon escape for couples, families, or anyone looking for a taste of real Jamaica.

The west coast of Jamaica doesn’t sleep. If it isn’t some daytime live tunes on the beach, or a street party in the wee hours, it’s the evening live Reggae available in multiple seafront venues. At night, the island takes on a different energy and everyone comes out to enjoy the fresh air and the tunes. Almost every other Jamaican seems to have a natural talent for music. It’s no wonder, then, that there are plenty of local acts to go around, often performing covers of Bob Marley, from MoBay to Negril. Recording artists also show up regularly--from Beenie Man to Beres Hammond. Along the highways and neighborhoods streets are the latest posters, flyers or billboards announcing upcoming live Reggae shows. When in doubt, head to Pier One in Montego Bay, or Alfred’s, Bourbon Beach and Jungle Nightclub in Negril. Better yet, ask the locals, who love their music. The sound of Reggae is never too far off.

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.

You’ll more than likely gasp when you first glimpse this 180-foot-deep, jade- and sapphire-colored body of water surrounded by verdant rain forest. Though you can spot it from the road as you drive along Port Antonio’s east coast, the Blue Lagoon is best appreciated while gliding across it on a bamboo raft. The entire scene looks straight out of the movies, which is why locals would probably tell you that it was a location for the eponymous 1980 movie starring Brooke Shields (which, in fact, was filmed in Fiji). Even if you don’t hop on a raft for a float, at least get out of the car to take in the stunning view. (An on-site restaurant and deck were closed for renovation some years back and still haven’t reopened.)