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On a quiet residential street one block from the popular vintage shops, bars, and restaurants of Milwaukee Avenue, the Wicker Park Inn is one of the best values in Chicago, attracting an eclectic clientele of older couples, families who book the whole place for weddings and other special occasions, and young travelers eager to live like a local amid the vibrant culture of the Wicker Park and Bucktown neighborhoods.

Prior to being rechristened as Independence Hall, this building was used and known as the Pennsylvania State House. The founding fathers of the United States met here in the Assembly Room to debate and adopt both the Declaration of Independence and the United States Constitution. For a time the building fell into disrepair, but an 1824 visit from the Marquis de Lafayette (who had served as a soldier under George Washington) compelled the city to rescue and preserve this historic site. Entrance to Independence Hall is by guided tour only; tickets are required from March through December, but no tickets are needed in January or February. Fun fact: For a short time, the basement served as the city’s dog pound!

A multipurpose contemporary art center that opened in November 2011 in the Ottoman Bank building, Salt has a library with thousands of shelves of art publications—the most important, impressive collection in the city.—Sylvia Kouvali

If you travel out to the end of Line 9, you’ll find yourself back in England. No kidding. Opened in 2006, this satellite city is part of the government’s “One City, Nine Towns” initiative. While they intended to house up to 10,000 residents here and filled the village with apartments, shops and restaurants, the concept flopped and it feels more like a TV set than a cultural hamlet. Nonetheless, it’s a fascinating place to take a stroll and stop for a spot of earl grey. How to get there: jump on line 9 and take it to Songjiang New Town station. From there, you’ll need to grab a taxi (<15RMB) to taiwushi xiaozhen).

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.

Opened in 1880 as Canada‘s first natural history museum, the Redpath Museum has a charmingly old-school Victorian quality to it. The collection of artifacts assembled by intrepid explorers ranges from taxidermy and Egyptian mummies to geological samples and—one of its most prized possessions—a handwritten letter from Charles Darwin. The museum is located at the heart of McGill University, long one of Canada‘s most important institutions of higher learning. Most of the buildings on campus, all in a handsome gray stone on a lovely bit of green in downtown Montréal at the base of Mount Royal, date from the 19th and early 20th centuries.

Winter snow can frost the tallest peak in Hawaii, technically measuring 13,800 feet. In fact, Mauna Kea holds the world record at 33,500 feet tall when measured from its submerged base to its summit (compared with Everest’s 29,000 feet)! The dormant volcano is home to the native gods and ideal for stargazing, either with the naked eye or the summit’s Subaru Telescope (book ahead). Go earlier and you’ll get an orange blaze—and maybe an elusive green flash—during sunset, too. Note that the high altitude poses serious health risks: Stop for a half hour at the visitor center to acclimate. Plan for steep, winding roads passable only via 4WD. Do not visit the mountaintop within 24 hours of scuba diving.

Nothing defines Boston quite as much as the town’s devotion to sports (10 championships since the turn of the century doesn’t hurt), and with all due respect to the five-time-Super-Bowl-champion Patriots, it’s Fenway Park, not Gillette Stadium, that’s the temple of sports fandom. Opened in 1912, the quirky green bandbox between Lansdowne Street and Yawkey Way is almost as famous for its obstructed-view seats as it is for its fabled Green Monster wall in left field, but that’s a price Sox fans gladly pay in exchange for maintaining Fenway’s historic layout. It’s both intimate and loud on game day even in years when the Sox aren’t contenders (tickets are often hard to come by, so plan ahead); the old ballpark also is open for one-hour, behind-the-scenes tours that take you inside and atop the Green Monster. You’ll be able to stroll around the field (the warning track, not the grass), and visit the press box, the Pesky Pole, and (on days with no games) the dugouts and bull pens.

Qibao, in Chinese, means ‘seven treasures’. And a treasure it is. The closest water town to Shanghai, it holds both the charm of an ancient, canal-traversed village as well as one of the most famous food streets in Shanghai. Head to Qibao Old Street for a culinary tour de force. And while you shouldn’t leave without sampling the Hai Tang Gao (rice cakes with a red bean filling) or--if your nose can handle it--the stinky tofu, there’s more to this little water town than the snacks. Round out your cultural venture with a shadow play show, a trip to the Qibao Temple or even a cricket fight. How to get here: Jump on Line 9 to Qibao Station and take exit 2 to reach the old town.

Adventurous souls should plan on a moonlit dip in the bioluminescent Glistening Waters, also known as Luminous Lagoon. Boats leave from a marina, located an hour north of Montego Bay, on scheduled night tours. As your tour boat speeds out into the dark of night, you’ll spot fluorescent blue streaks in its wake—bioluminescence that’s created when living microorganisms (in this case, dinoflagellates) are disturbed. You can jump in for a swim, too, and glow in the dark as you splash about. It’s an amazing phenomenon to witness, and it’s said to exist in only five lagoons or bays in the world. Back at the marina, the Glistening Waters restaurant offers beautiful views, as well as pre-cruise drinks and food.

Chill out from the sun at the Blue Hole Mineral Spring, a 50-foot deep turquoise natural pool sitting 20 feet below a cave opening. Jump off the cliff edge like the Jamaican divers on site, if you’re feeling brave. Otherwise, head down slowly on the ladder and let go from a closer distance (like I did). There’s a small entrance fee to this park--located about a half-hour drive south of Negril in the town of Brighton--which includes access to an on site bar and restaurant, as well as an outdoor traditional swimming pool. But my guess is you’ll be too tempted by the underground shimmering and therapeutic fresh water.

Perhaps due in large part to the city’s notoriously harsh, never-ending winters, Montrealers have a profound appreciation of their green spaces, always jumping at the chance of spending a couple of hours outdoors, basking in the sun. The Mont-Royal Mountain is the most popular, however, simply by its size (529 acres!), its fabulous views over the city and its architect — Frederick Law Olmsted. Parc Lafontaine and Parc Sir Wilfrid Laurier are also local favorites, where sunbathers, young families, BBQ-ers and joggers mingle happily, enjoying every minute of the all too short summer months. The two parks are located near delicious take-out counters (Ma poule mouillée and Lapin pressé, respectively) making it a perfect pique-nique opportunity.

The Ottoman Bank Museum is in the basement of SALT Galata, an arts center located in the former Ottoman Bank. It’s a destination that will appeal mostly to those interested in the history of the Ottoman Empire in its decline at the end of the 19th century. But doesn’t everyone find the late Ottoman period fascinating? The struggles that characterized the era, with a country torn between its Ottoman past and a desire to both modernize and Westernize, played out at the bank. The institution that would become the state bank of the Ottoman Empire was founded in 1856 as a joint venture of British and French banks and the Ottoman government and was managed by a committee of British and French financiers until it was effectively dissolved during World War I. The museum includes many surprisingly engaging displays and documents tracing the bank’s history—its commercial ventures, demographic information on investors and employees, charts detailing the economic turmoil of the period. Architectural plans of the headquarters illustrate its unusual design that featured a neo-classical entrance facing the European quarter and an Ottoman-inspired rear elevation, facing Istanbul’s Old City across the Golden Horn. Deposit slips, photos of employees, and old bank notes in the original vault are on display in almost exhausting, encyclopedic comprehensiveness. If your interest wanes, you don’t need to feel any pressure to linger—entrance is free.

If you are looking for a fun, buzzing eating scene in the Wall Street area, this is it. Stone Street is a narrow, cobblestone street lined with restaurants and bars and filled with outdoor, communal tables. During lunch on nice days, an energetic crowd of casual business types from the Wall Street area fill the alley with loud laughter and clinking glasses. And after work—especially on Wednesday and Thursday nights—it’s a busy social scene. Stone Street was the first paved street in NYC. It starts at Hanover Square (off William Street 2 blocks south of Wall Street). Look for the imposing brownstone India House with the famous Harry’s Bar in the basement and walk around the building. Directions may sound complicated, but once you get in the area, follow the buzz of the crowd or ask one of the locals. About ten years ago, this historic corridor had a $2 million restoration of its cobblestone streets and vintage lamp posts, which helped usher in the new restaurants and the young crowds. Popular eateries include Adrienne’s Pizza Bar, Vintry Wine & Whisky and Ulysses Pub. Also on this street is Harry’s; opened in 2006, it is a new generation offshoot of the historic Harry’s at Hanover, a high-profile eatery in the financial district from 1972 to 2003. Food festivals also attract a hungry crowd. Look for Stone Street Fest in May and the Oyster Festival in September.

La Isla de Guilligan (Gilligan’s Island, though not the one from the television show) is a popular hangout for Puerto Rican locals. I myself am only home for several weeks a year and I still go once or twice every year. The island is sometimes isolated and sometimes crowded. It boasts snorkeling (I’ve spotted many anemones, fish, crabs, starfish, and barracudas), calm water perfect for floating and swimming, and several trees from which you can jump into the water. It’s off the coast of Guanica, and there are two ways to get there. Either take a ferry (call 787-821-5706 for more information) or rent a kayak from Mary Lee’s by the Sea. If you choose to do the latter, you might want to take your kayak to Isla Ballena (see my highlight “Kayaking and Snorkeling and Hoping for Whales”). This tends to be a day trip, so I suggest you have some food. You can either pack up your own or, if you take the ferry, place an order before embarking and tell them when you’d like to have it delivered. There are picnic pavilions that you can claim if it’s a calm day or you get there early.