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Housed in a converted elementary school dating back to 1915, this sprawling hotel complex has long drawn out-of-towners and local Portlanders alike with its bars, restaurants, miniature movie theater, and even a heated soaking pool that’s open to the public for a small fee. While these amenities—along with the hotel’s sprawling school grounds and proximity to the popular Alberta Arts District—are enough to make it one of the most attractive spots to stay in town, its real cred shines through in the 57 guest rooms, many of which are actually converted classrooms (and still have some of the original scholastic features, such as chalkboards, integrated into the room design). Don’t leave without sampling some of the McMenamins signature brews in the Boiler Room Bar, housed in what was once the school’s boiler room.

When it comes to pub crawling in Portland, Deschutes Brewing is a classy stop to regroup and recharge in the Pearl. With more than a dozen taps pouring the usual suspects along with a collection of seasonal and experimental brews made specifically for Northwest tastes, the bar has something for every beer lover. The kitchen serves fresh, sustainable fare, including vegetarian and gluten-friendly options. Try the beer-battered halibut or the smoked brisket. The steamed clams with a side of sweet potato fries will also keep you going until your next destination.

Local is the operative word in the Portland, Maine food scene. Ask a waiter what Atlantic Day-Boat halibut is exactly, and he’ll spin a story about the local captain who pulls in with the day’s catch. At the height of summer, it seems that every ingredient is caught, raised, foraged, or grown in the vicinity. So it’s no surprise that Maine oysters take pride of place at Eventide Oyster Co. Sure, there are some bivalves from New York and the West Coast, but my advice is to quiz the waitress about the ones from West Bath, Casco Bay, and the Damariscotta River. A hit of frozen Tabasco came on the house, but these plump beauties are best with just a squeeze of lemon.

There certainly are other ways to while away a summer day in Greater Portland, but you’d be hard-pressed to find a better experience than island-hopping aboard a Casco Bay Lines ferry. Sure, you can simply ride out to an island for a look-about and return, or enjoy a sunrise, sunset, or moonlight cruise. But for a real immersion, consider the Mailboat Run. You’ll be among islanders, visitors, pets, and freight to-ing and fro-ing between Little Diamond, Great Diamond, Long, Cliff, and Chebeague islands. The 2½-to-3½-hour working cruise is offered twice daily year-round; bring your own picnic lunch on the morning run or snacks for the afternoon one.

Doughnuts are to Portland what coffee is to David Lynch, both essential fuel and calling card. While there are many pretenders to the title of the city’s best doughnuts—Voodoo Doughnuts certainly sells the most Instagrammable food products—Blue Star, from ubiquitous local restaurateur Micah Camden, is the most consistent. Flavors range from powdered sugar to maple bacon to passion fruit cocoa nibs, sold fresh daily until no more remain. The downtown location gets crowded early on weekends, so plan ahead. In a pinch, grab them at Blue Star’s airport location—which makes asking a friend to pick you up at the airport a sweet request indeed.

With more than 400 shipwrecks and its fair share of coral reefs, St. Kitts is a favorite of the scuba set. To try your hand at the hobby, consider staying at Bird Rock Beach Hotel, which houses one of the island’s most popular dive operators. Here, guests can charter a boat to nearby Devil’s Cave and swim among barracuda, lobsters, and nurse sharks, then retire to one of 46 tropical-hued rooms overlooking the sea. Less adventurous travelers can visit the on-site dolphin park, sunbathe on the private beach, or simply sip rum punches from the pool’s swim-up bar. Hotel staff is also happy to arrange off-site activities like catamaran cruises, rainforest treks, and volcano crater tours.

Tastee and Juicy may be the two most popular brands of Jamaican patties, but one definitely should not miss out on the super premium patties on offer at Devon House Bakery. Set on the grounds of the historic Kingston mansion, just a few minutes from such notable area hotels as the Courtleigh, Jamaica Pegasus, and the Knutsford Court, Devon House Bakery espouses some serious Old World cafe charm. A fine selection of sinful sweets – brownies, butter cookies, cakes, muffins – awaits inside. So too does one of the most amazing Jamaican patties I’ve ever tried. Options go well beyond the usual beef with fish, pork, shrimp, and lobster elevating the typical Jamaican patty to new heights. The best choice, though, is the curry goat. Spicy and succulent, the Devon House goat patty melts in your mouth while warming your soul. Pure, delicious niceness and most certainly the very best Jamaican patty I’ve ever had. Don’t miss it!

I was on a cruise in Italy when I heard about this place. I’d mentioned that I was heading to Portland, and a fellow cruiser, a native of the town, had told me that if they had one recommendation it would be the ice cream at Salt and Straw.

What she didn’t tell me was that the flavors are not your usual vanilla, chocolate, and raspberry ripple. In fact, the first thing I tasted at Salt and Straw was their new “Bollywood” recipe, which included carrot custard and cardamom, which sounds almost sensible when you considered that some of their most popular flavors include prosciutto and goat cheese.

There was a huge line, even on a Friday mid-afternoon, but it was worth it for the almond brittle with salted ganache, not to mention the apple pie with real chunks of cheddar cheese. They’re doing their best to “Keep Portland Weird” here...and it tastes good.

The Tin Shed is probably nowhere near wherever you might be in Portland but that matters not. Get a cab and go over there because the biscuits are so good they’ll make you wanna slap yo mama! You serve yourself coffee while you wait under the covered patio seating, they welcome dogs and their bloody mary is spectacular. This place rocks. Go check it out.

Located along a stretch of coastline that’s sometimes called the birthplace of jerk cuisine, the Boston Bay Jerk Center is hard to miss. Various meats are cook on open pits using a technique that may explain why jerk never tastes so good at home: Uncured pimento logs are placed over a bed of hot coals, and the meat is laid directly on the green logs. The whole operation is then covered up by a sheet of corrugated zinc and cooked until it’s black on the outside and tender underneath. You can place your order by the quarter, half, or full pound. Don’t forget to add jerk sauce, which you can also buy by the bottle as a souvenir.

When the Last Bookstore debuted in 2005, the name was meant to be ironic. Now, in a world of Kindles and iPads, digital books (or at least digital bookstores) are the norm, and brick-and-mortar establishments such as the Last Bookstore are a dying breed. That hasn’t stopped this Downtown L.A. icon from growing. The shop still buys, sells, and trades new and used books and vinyl records just as it did when its doors first opened over a decade ago, and it shows no signs of stopping anytime soon. Come in to browse the store’s impressive collection, to hang out for an afternoon, or to catch author talks and more. The Last Bookstore puts on some killer events, and past speakers have included the cast of Portlandia, How to Kill a City author Peter Moskowitz, and Holocaust survivors. Oh, and they occasionally give away free concert tickets on their Instagram account, so it’s worth a follow even if you’re not a die-hard bookworm.

Graceful palms and lush gardens greet guests at Grotto Bay Beach Resort. Situated on 21 acres, this peaceful colony of cottage-style rooms overlooks the beautiful blue water of Bailey’s Bay in the Parish of Hamilton. Tangerine salt body scrubs, sweet milk and lavender facials, and hot stone massage will melt away all of the exertion of snorkeling excursions, golfing, exploring the resort’s on-site cave, or bicycling around the island. On the other hand, why not take it easy and lounge by the pool, which features a swim-up bar, or on one of the resorts private beaches. Dine among the island ambience of palms, rattan furnishings, and ceiling fans in the Hibiscus Room or Palm Court Dining Room. Afterwards, you can enjoy drinks and tropical breezes on the terrace before retreating to guest rooms outfitted in bright prints and tropical tones.

I wouldn’t normally visit a hotel restaurant just for the purpose of having a sandwich. But this is the second restaurant by Vitaly Paley, one of Portland‘s most beloved chefs, and I’d been told it was a good place for lunch. I hadn’t guessed that most of the menu would be sandwiches, and I have to admit to feeling a little disappointment when I saw it. I shouldn’t have. The dungeness crab reuben was a flaky fish marvel, while the heirloom tomato salad I had with it was a perfectly pert accompaniment. The homemade cream soda, meanwhile, was as sweet and delicious as anything in an Enid Blyton novel, and it had me suppressing the urge to exclaim “How jolly!” Anyway. That’s just me. If you like a sandwich, I think you’ll probably like these.

A novel way to combine great food with a classic city tour, the double-decker Crystal Bus provides delicious sightseeing. Nibble Chinese dim sum prepared by the restaurant One Dim Sum (which was awarded a Michelin star in 2012), while driving past more than 20 of Hong Kong’s most famous sites (and stopping at one for photos), from the Hong Kong clock tower to the 1881 Heritage Building, a 197-foot-high Ferris wheel, and Portland Street, the city’s famous red-light district, known for its neon. Each tour—one at lunch goes from Kowloon to Hong Kong Island and another at teatime from Kowloon to New Territories—lasts about 2.5 hours. Both start at No. 7 Hankow Road, Tsim Sha Tsui, in Kowloon.

As a child, William Butler Yeats spent his summer holidays in County Sligo, and the lakes and hills inspired many of his most famous poems, such as The Lake Isle of Innisfree. Take a leisurely day and follow the Yeats Trail around the locations in the area that he loved, taking in Glencar Lough, the Isle of Innisfree, Rosses Point, Benbulben, Lissadell House, and finally the churchyard at Drumcliffe Parish Church, where Yeats is buried.