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Chances are that when you return home after your trip to Key West, someone will ask you if you went to the Green Parrot. It’s that kind of iconic bar, the kind your parents’ friends ended up at over spring break in college long ago. The bar started as a local grocery store about a hundred years ago; the building became the Brown Derby, a bar that was popular first with the submarine sailors from the naval base down the street.


When the naval base closed in the ‘70s, the bar transitioned into a hangout for fishermen and local sailors and the hippies that began to drift into town. The Green Parrot still has the air of a honky-tonk, lit exclusively by spotlight and neon, with a roster of almost-nightly live music, mostly of the bluesy, rollicking sort.

True to its name, this is an old bar, with Victorian-style décor, stained glass, art nouveau lamps, and red velvet sofas. You can find a long list of cocktails, as the manager has history in the Miami cruise ship industry. From the food menu, try the Old Vic steak—or some toast or a sandwich, if you want something lighter. There is a button to call the waiter and another one to regulate the light intensity.

On the banks of the Macal River, at the edge of downtown San Ignacio, you’ll find a sprawling Saturday market where everything from shoes and clothing to housewares and fresh produce is for sale. Local people shop for supplies and gather to catch up on gossip at the food stalls. The market is somewhat divided between produce sellers and souvenir vendors, but as the market has grown, the separation seems to have floundered a bit. Leave enough time to wander every aisle and stall to ensure no gem is left undiscovered. Locals recommend the tacos and pupusas as the best choices for lunch, and the snow cones topped with evaporated milk for a snack. Buses also park just next to the market in a dirt lot, so transportation is not difficult if you’re coming from outside of town.

Dating to 1521, the Cathedral of San Juan Bautista isn’t just one of the oldest buildings in San Juan—it’s the second-oldest cathedral in all of the Americas. Go inside to see the tomb of Spanish explorer Ponce de León, who founded the first settlement on Puerto Rico and in 1509 was named the island’s first governor. The remains of St. Pio, a Roman martyr, can also be seen in the cathedral—the saint’s mummy has been displayed here in a glass box since 1862.

Set down a small alley just a few meters from Piazza San Lorenzo, the art gallery Il Vicolo is a lovely spot to browse, and purchase, contemporary art in the ancient city. One of the oldest galleries in town, Il Vicolo routinely changes their artistic focus - thus one can come back often for pieces and exhibits from new, well-followed, and even young emerging artists.

Whether you sit on the benches out front and people watch or stroll along Main Road and window shop, exploring the village of Kalk Bay on a summer’s day is so much better with a cone in hand.The Ice Cafe is one of the oldest ice cream parlors in Cape Town. The flavors are robust and all natural, the texture is perfectly creamy (like gelato). Cones are not overpriced like some other newer options in town.

Like to have a meal with historic spirits? Visit the oldest tavern in MA. and one of the most historic watering holes in America. First erected in 1780 in Charlestown, George Washington dropped in for refreshments and Paul Revere counted it among his favorites. Featuring traditional tavern fare for lunch and dinner, it’s a great pit stop after burning up calories climbing the Bunker Hill Monument just up the street.

Serene. That’s how I would describe the pool at the Lone Pine Hotel in Penang, Malaysia. This lovely boutique hotel is one of the oldest hotels in Penang, established in 1948. Recent renovations have made it into a charming ‘modern classic’ beach getaway. It’s under the management of the exclusive E and O Hotel. So you can expect beautiful rooms and good service, but at a more affordable price.

On the non-descript, busy corner of Bucareli and Morelos streets in Mexico City is a café with a famous history: Fidel Castro and Che Guevarra met here at Café La Habana several times, chain smoking and drinking strong coffee, to plan the Cuban Revolution. Nowadays, you can still get excellent coffee—and pretty good food—while you plan something a little less dramatic (but more enjoyable), like your vacation itinerary. Old journalists and businessmen congregate here for hours on end while salt-of-the-earth, slightly surly waitresses take your order and bring you your food and drink. Come for breakfast and order their chilaquiles, motuleños, or molletes, and wash it down with an espresso or café americano.

Fearing a British takeover of its ill-gotten trading post, the Dutch East India Company built this star-shaped castle (known as Kasteel de Goede Hoop) between 1666 and 1679 to defend its territory. Now the oldest building in South Africa, the castle served as the center of Cape Town‘s civilian, political, and military life. The austere facade opens up to a striking central lawn and commanding buildings that, in their restored form, represent Dutch, English, and French architectural styles. History buffs will go nuts here: Check out the William Fehr Collection, the African pottery exhibit, and the Castle Military Museum.

On this rainy afternoon that I visited, Kitchener’s had the DJ on the decks mixing up a storm inside the venue, with patrons being able to browse the goods with their drinks in hand all the while being able to do a little boogie! Whether it’s on the weekend or during the week, Kitchener’s does get very full, but is always good fun! On the weekend’s the bar transforms into a bustling, bar/market with jewellery, vintage books, clothes and more on sale. A cool fact about Kitchener’s: It has the honour of being the second oldest bar in Johannesburg. Check out their full list of events on their Facebook page

This beautiful square is one the city’s oldest; set in Le Marais, it’s surrounded by grand houses and an arched walkway lined with galleries and quaint cafés. At Number 6, you’ll find the former home of Victor Hugo, author of “The Hunchback of Notre-Dame.” The park at its center is a popular place to gather al fresco in the warm weather.

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.

In the blink-and-you’ll-miss-it village of Volcano, on the slopes of Mauna Loa and just outside of Hawai’i Volcanoes National Park, are a handful of B&Bs and cottage rentals (see also Volcano Rainforest Retreat). Among the oldest—but no less charming for its 25 years—is Volcano Village Estate (previously known as Hale Ohia).


It’s a small cottage colony, with guest quarters scattered around a two-acre estate thickly carpeted in emerald-green moss and shaded by stands of soaring sugi (Japanese cedar) trees. The main house, a quirky Queen Anne style Victorian with a miniature turret and stone chimney that make it look like it was lifted right out of a children’s storybook, dates back to the 1930s when the manager of a sugar plantation built it as a summer holiday home. The gardens were planted by the same master landscape architects responsible for the Liliʻuokalani Gardens in Hilo (at one time the largest Edo style garden outside of Japan).


All guest quarters are sweetly decorated, in a largely Craftsman style with ceramic tiles and soft woods; some have pretty, stained-glass windows. But on a chilly Volcano night—and most of them are since the town sits at 4,000 feet—nothing is quite as romantic as curling up by the fireplace in one of the three stand-alone cottages, unless, of course, it’s sitting in the garden and watching the dazzling night sky, which is reason enough to stay on this side of the island.

The Leopard at des Artistes is more than a restaurant. It’s an Upper West Side landmark, a Manhattan treasure and genuine New York classic. It was once Cafe des Artistes, a restaurant where luminaries from the worlds of art, politics and publishing dined in secluded elegance, surrounded by naked nymphs - each one painted in 1937 by Howard Chandler Christy in the glowing murals that line the dining room to this day. A lot has changed in 97 years behind the doorway at One West 67th Street that now welcomes you into The Leopard. In 1917 the restaurant catered exclusively to artists who lived in the building above - Norman Rockwell, Rudolf Valentino and Isadora Ducan were among its original clientele. But after a renovation in 1975, Cafe des Artistes became a dining destination for the Who’s Who of media - Barbara Walters, Diane Sawyer, Peter Jennings and more dined in the soft-lit, intimate restaurant on a regular basis. With the arrival in 2011 of new owners, Gianfranco and Paula Bolla-Sorrentino and Chef Vito Gnazzo, a new dining experience was introduced to One West 67th Street. Celebrity is no longer a must for a table in this illustrious space (although you will see many here). What you discover on the other side of a door framed by velvet drapes is a classic, elegant setting where the center of attention is you and Southern Italian cuisine prepared with joy and genius. Bossa Nova and jazz set the mood. This is a restaurant that whispers, “Welcome to the real New York.”