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Portland isn’t exactly the kind of city that’s known for being “fancy,” which was why it was so bold for the Starwood Luxury Collection to add a sleek 15th floor to the top of the iconic Meier & Frank department store building downtown—and turn the top nine floors into the swankiest hotel in town. Who would’ve thought that Louis XVI chairs, tufted white leather and teal velvet, crystal chandeliers, and ornate wallpaper would work so well in the city of plaid, beards, and twee bird patterns? In true Field of Dreams fashion, Starwood built it and the travelers came out of the woodwork, hungry for a luxury hotel that embodies the Rose City with everything from environmentally conscious practices and farm-to-table restaurants to an extensive art collection and rooftop honey bee colony. All that’s to say nothing of the private club-like Library, a collaboration with Portland icon Powell’s Books (the world’s largest bookstore) that allows hotel guests to borrow from a curated collection of 3,000 books during their stay. As it turns out, it’s not all that hard to dress Portland to the nines.

Named after a famous escaped slave, this steep staircase carves into a high plateau. On your way up, stop at the farmhouse and donate $5 per person to the local family that maintains the vertiginous track, or hire a guide to enrich your experience. At the bottom, you can cool off in a tributary, then walk along the Layou River. Once you reach the Bells Schoolhouse, head left to the road where the hike began.

This is where everyone stops to smell the roses in the Rose City. Celebrating its centennial in 2017, the International Rose Test Garden is the nation’s oldest continually operating rose test garden (where varieties are evaluated for characteristics such as disease resistance, bloom size, and fragrance). Originally conceived as a way to preserve different varieties of European roses from the destruction of World War I, the garden today contains 10,000 plants across 4.5 acres in Washington Park. Best of all, it’s completely free, whether you want to compare green thumbs with professionals or take in the views of Mount Hood while breathing in the perfumed air.

Situated in the historic West End—what some consider to be Portland’s prettiest area—this red-brick, Federal-style mansion has housed a Prohibition-era hideout, a boarding school and, for the past two decades, the intimate Danforth Inn. Today, its nine rooms are uniquely furnished with a mix of contemporary European pieces and Asian influences, as well as nearly a million dollars’ worth of modern art.


A small garden blooms with lilacs, fragrant herbs, and edible flowers in the spring and summer, while 13 working fireplaces—there’s one in each room and two in the West End Suite—make for cozy evenings come fall and winter. After a renovation completed in 2015, Tempo Dulu, a 36-seat Southeast Asian restaurant, opened with dishes like grilled lobster with spring onion cake, and dramatic design details such as a live-moss chandelier.


In 2017, the inn expanded on the Asian theme with its Opium bar; decor is meant to evoke a 1920s Shanghai speakeasy, and cocktails include the Danforth Swizzle, a rum-based drink accented with Chinese five spice–infused bitters.

If you’re looking for a break from the beach and the noise, head to Konoko Falls Park (formerly known as Coyaba River Garden) for a quiet picnic, swim, and nature walk through beautifully manicured gardens. The Mahoe tiered waterfalls—a smaller, just-as-picturesque version of Dunn’s River Falls but rarely crowded—cascade through the park, and an on-site museum showcases the history of Jamaica’s first inhabitants, the Taino. The park offers gorgeous views of Ocho Rios’s bay below. Climbing and swimming in the falls, at your own pace, is great fun.

Right around the corner from Powell’s Bookstore and Sizzle Pie, the vibe here is fantastic. The walls are kind of spartan, there’s a record player in the corner, and you can roam on free Internet to your heart’s content. These guys definitely know the food scene here and have great tips. My iced chai latte? Served in a mason jar. Yum and Yum. And those caneles, pictured? They were featured in Portland Monthly. I believe Courier is following the ice cube trend with one big block of ice in either a square or rectangle. I also love the everyday musings on their blog.

Situated on Northeast Portland’s Alberta Street, smack in the middle of the Alberta Arts District, Caravan is an unique alternative to the same old hotels or vacation rentals. The hotel is comprised of six tiny, individually styled houses for rent, from the cabin-like Skyline (made mostly from upcycled material) to the Amazing Mysterium (a vaguely steampunk affair modeled after a vardo gypsy wagon, with lovely additions such as stained-glass windows and lots of built-in shelving). In true Portland style, the houses are clustered together in a “pod,” similar to how many of the city’s famous food carts are arranged. In lieu of a lobby, there’s a central outdoor common area with a fire pit (s’more-making is encouraged, and supplies are provided). Note that live bands perform for guests and a limited number of community members on Wednesday evenings during the summer months, and the whole area gets busy on the first Thursday of every month, when Alberta Street transforms into a pedestrian-only night market-cum-street party that lasts well into the evening.

Rising from the ashes of the 60’s Red Lion Hotel is the east side’s latest entry into Portland’s hip hotel scene—the Eastlund. Cut from the same pedigree as the downtown Modera Hotel, the Eastlund is a welcome upgrade in the evolving convention center area. The fun starts in the bright, expansive lobby, where eye-catching art welcomes visitors. The staff is tuned to deliver exceptional customer service, and the vibe is genuine and unpretentious. Amenities include great food, local spirits, tech-savvy rooms, and super-fast Wi-Fi throughout the property.

The rooms and public spaces put art front and center, while the meeting areas are wired for productivity. Business and leisure travelers also benefit from attention to detail and a staff committed to getting it if it’s not already available. The efficient, comfort-forward rooms boast big flat-screens and colorful décor, and the river and city views from the upper levels are spectacular day and night. An easy MAX ride from the airport, The Eastlund is also delightfully located within walking distance of a variety of transportation, entertainment, meeting, and dining opportunities. With so many on-site amenities, however, you might just find yourself pleasantly planted during your Portland stay.

This is one of the new hot bars, just a few blocks down from the Jupiter Hotel on SE Grand and Morrision. Checkpoints: skinny hot bartenders in wifebeaters who shake up some inventive cocktails, a DJ, a 110-year old piano, a horseshoe bar and an impressive late night menu (cuban sandwiches, anyone?). I had the Sam Issacs which was mentioned in Portland Monthly as the drink to have but not even on their menu. It has bourbon, mint, blackberries and lime. It’s DELICIOUS. Portland seems to have a thing for libations with ginger beer and I’m loving it. I followed up with 96 Tears, a combination of vodka, lime, ginger and ginger beer. This was light but boozy. The perfect way to start a night or in this case, I’d end it here if you want to dance.

Anyone taking diligent notes on Portland decor is sure to notice similarities in design from location to location beyond a love for taxidermy. Much of that Rose City decorating style emanates from Schoolhouse Electric. Located in a 115-year-old redbrick warehouse and factory building in an industrial part of the city’s West Side, Schoolhouse Electric sells everything from perfect reproductions of 1960s-era IBM clocks to more vintage sconces and analogue clocks than you can shake a stick at. The store’s Ristretto Roasters coffee bar provides a caffeine boost when your energy for curated doorknobs reaches its limit.

Stroll 15 minutes through a lush rainforest to this gorgeous 40-foot waterfall grotto, located deep within the World Heritage site of Morne Trois Pitons National Park. Railings and a broad, well-maintained trail make the trip accessible even to non-hikers, though the tree-fringed pool—which is open to swimmers—gets unpleasantly packed when cruise ships pull into port. Serious photographers should haul along tripods and cable or remote shutter releases to capture the low-light, but oh-so-lovely scenery, which has become one of Dominica’s top attractions.

Stroll inside the Errol Flynn Marina, located right in Port Antonio town, for a waterfront respite along manicured lawns and sailboats. Enjoy an afternoon “I-Scream” cone from the on-site Devon House, a household name in Jamaica. There are public benches by the water, as well as bars and restaurants. If you can, stay long enough to enjoy the sunset.

Though few tourists venture to Kingston, the capital and hub on the eastern coast of Jamaica, music fans should make the day trip to visit Bob Marley’s former home, now a museum dedicated to Marley’s life and impact on the world. A guided tour of this museum takes about an hour and a half and includes a 20-minute video presentation. Even devoted reggae fans will likely learn more about Bob than they ever knew. Exhibits include multiple awards, guitars, and his bed with an engraved headboard depicting a lion.

Following a powerful earthquake in February 2011, the Christchurch Cathedral was severely damaged, and while there is an ongoing ideological and economic debate over whether or not the Gothic-style church can, or should be, repaired, the Anglican parishioners of New Zealand‘s second-largest city can now worship in this fascinating edifice made of, among other things, 96 giant cardboard tubes. Designed by Shigeru Ban, a Japanese architect who specializes in building temporary structures following natural disasters, the Cardboard Cathedral (formerly called Christchurch’s Transitional Cathedral), was erected in less than a year. Its excellent acoustics are also regularly utilized for concerts and events.

Few venture this far east in Jamaica, but those who do will find one of the most authentic sides of the island, and the most secluded of getaways. A charming fishing village about thirty minutes past Port Antonio, Long Bay is as peaceful and scenic as it gets, with just a handful of affordable, casual guesthouses perched atop dramatic cliffs and overlooking a long stretch of deserted beach. No frills here, just nature and culture. The fresh ocean air, the roadside fresh seafood shacks and friendly locals will have you staying longer than you planned. Be sure to drive along the coastal highway and head as far as Manchioneal, another stunning fishing village that feels thousands of miles away from the touristy side of Jamaica.