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The Thoroughbred Club is in the lobby of Charleston Place hotel, right in the middle of downtown Charleston. They serve up classic cocktails (try their gussied-up negroni) and also have a great tea service, with live music every afternoon and evening.

The classic cocktail list at The Rarebit is hard to beat: Moscow mules served in gorgeous copper mugs, Manhattans with a touch of Benedictine. The food menu is composed of similarly solid throwbacks: a pork chop with mac and cheese and green beans, a perfect chicken club sandwich.

Cypress Point Park offers a relaxing nature escape in the city. Plentiful amenities include a children’s playground, a disc golf park, covered pavilions, and jogging trails.

For a reasonably priced Island eatery, Kona Canoe Club has pupus (appetizers), salads, sandwiches, burgers, fish & chips, and several local entrees. The location is phenomenal for sunset and every dish is served with aloha!

You can find all sorts of shipyard treasures at Nautical Antiques in Galveston. They have ship lanterns, wheels, flags, glass floats, and figureheads—plenty to choose from for a cool souvenir to represent your time on the Texas coast. Photo via Nautical Antiques Facebook page

Never has a yummy treat been mired in such controversy as the Whoopie Pie. First, how did this burger-shaped cake with the sugary cream filling get its name? Does the name come from the exclamation that schoolchildren shouted upon opening their lunch bags to discover these delights? Or does it come from the Amish farmers, who were rewarded with these portable “pies” in their lunch boxes? My vote (and Pennsylvania Dutch lore) favors the school kids. But wait—there’s more controversy! While I am one hundred percent certain that these little cakes called pies originated in my lovely state of Pennsylvania, it seems that the state of Maine has also laid claim to their origin, even going so far as to name the Whoopie Pie as its “official state treat.” Other research points to somewhere in New York state as their birthplace. We may never know… There was a time not long ago when Whoopie Pies felt much like a prized local secret because no one outside of Pennsylvania had ever heard of them (excepting, I guess, some of those Mainers). These days, though, you can even find Whoopie Pies in the bakery sections at Trader Joe’s and Whole Foods. But the most authentic and delicious version can only be found at the Amish bakery Beiler’s in the Reading Terminal Market. My personal favorite is the pumpkin flavor, but the chocolate is also delicious. Or maybe try the oatmeal, or the red velvet. Better yet, try one of each—they’re portable!

Shop for an authentic souvenir in Everything but Match, a store inspired by a T-shirt line designed by the owners’ 6-year-old daughter. In this shop in Old San Juan, you’ll find original art, accessories, and children’s clothing made by local artists and artisans. From unique jewelry to brightly colored throw pillows, you’re sure to fall in love with something unique to bring home in your suitcase.

Perched high above the Bay of Positano, Il San Pietro is the epitome of Italian seaside glamour—the hotel has attracted a coterie of international VIPs since its opening in 1970, including Gregory Peck, George Clooney, and Julia Roberts—but retains the charm of a family-run inn. Michelin-starred Zass restaurant culls ingredients from the property’s organic gardens, which spill down to the sea across 10 terraces teeming with local produce, and rooms feature custom ceramic tiles made in local factories using traditional techniques. If the 400 steps down to Positano’s only private beach sound daunting, an elevator cuts through the rock to water level, where tangerine loungers on the stone sundeck give way to a cove with sandy shores. Here, breezy Carlino restaurant serves up lemon spaghetti beneath a cheerful thatched roof. Prefer more active endeavors? Hugging the cliff face above, seaside tennis courts serve up sets with a dazzling view.

The Palatine Hill was home to an early Roman settlement and had major significance for the city’s history. Legend states that Romulus founded Rome on that hill in 753 B.C.E., and Romans even maintained a cult site sacred to the founding father for about 1,000 years. When the emperors rose to power, they chose the Palatine as the location for their sprawling villas and built enormous marble-clad structures to showcase their wealth and power. Today, the ruins of their majestic estates rise above the Forum and Circus Maximus, reminders of the grand imperial past. A visit is included in the price of a ticket to the Forum or Colosseum.

Renowned Costa Rican architect Ronald Zürcher looked to his country’s colonial past when designing this hacienda-style property—witness its central courtyard, arched doorways, and terra-cotta roofs. Set amid a 30-acre coffee plantation just outside the capital city of San Jose, the hotel’s 308 traditional accommodations follow suit with dark wood furnishings, but a modern aesthetic pervades renovated guest rooms with streamlined furniture, intricately patterned bathroom tiles, and expansive views that extend from green lawns to forested mountains and urban skyline; some include small balconies that overlook the hotel’s two pools. On-site dining options include gourmet takes on Costa Rican fare at Hacienda Kitchen, Peruvian specialties at La Isabela, and fresh-made sushi at La Castilla, as well as a sports bar and café. The open-air great room invites reading and quiet conversations, but if you’re up for something a little more energetic, there are tennis courts, a driving range, a fitness center, and invigorating coffee scrubs at the spa.

In the heart of El Viejo San Juan, the Plaza Colón (Columbus Plaza) is so much more than a place honoring an important piece of San Juan’s history. Sure, snapping an Instagram photo in front of the bronze statue of Christopher Columbus, credited for the first discovery of the island, is definitely a “must-do.” Find a local and in your best Spanish accent say “Perdón, podría tomar una foto por favor?” Or play it safe and ask another tourist in English (they’re not hard to find!). Either way, stay and hang out. Explore the local artists’ tents (like this one, with rings and bracelets made from brightly colored ceramic beads and recycled aluminum, customized to fit). Pick out unique, inexpensive gifts for loved ones and, of course, something to remember the trip! And don’t ignore the ringing bell of the sorbet vendors selling “coco frio” for $1. Try a scoop of papaya y piña to help cool off in the heat of the Puerto Rican sun.

Once a separate municipality, San Ángel—in the city’s south, nestled into its western foothills—is a leafy, genteel enclave whose relative isolation adds a soigné feel (for better or worse) you won’t find in neighboring Coyoacán. Ground zero for promenading is quaint Plaza San Jacinto, whose cute parish church (and beautiful cloister garden) is a sort of spiritual last stand amid the surrounding area’s high-toned consumerism. That said, the plaza’s true spirit comes alive Saturdays, at the so-called Bazar Sábado, an artisanal market that fills the area with stall after stall of handmade jewelry, textiles, crafts, and accessories, plus a great deal of art—some finer, some less so—in styles that go from hippie to haute. Strolling musicians and performers add to the carnival atmosphere.

With its thatched roof, bamboo bar, and surfboard decor, this beloved watering hole—often voted Maui’s best bar by locals—checks all the tiki boxes. Head here for live music, lanai seating, and late-night dancing, plus fun and fruity rum cocktails like mai tais, zombies, daiquiris, and piña coladas. Beyond its drinks, South Shore Tiki Lounge was recognized by the state of Hawaii as an outstanding business for its regular fund-raising efforts, which benefit local organizations like the Keiki Cupboard, Hawaii Wildlife Fund, Maui Humane Society, and Hawaii Animal Rescue Foundation. All that to say, you can feel good coming here to wash down a massive chili-cheese hot dog with a lychee-watermelon martini.

Hawaiians once lived in harmony with the land: farming, fishing, and harvesting fruit. Today, the state imports 80 to 90 percent of its food. Visit Kaloko-Honokōhau to catch a glimpse of the Big Island’s ancient agricultural traditions, which residents are working hard to revitalize. The park’s landscape of rugged rock contains more than 200 archaeological sites, ranging from fishponds and elevated planters to petroglyphs, lava-tube shelters, and hōlua (toboggan-like slides). Watch for native species like the fragrant pua pilo flower and the endangered Hawaiian stilt, a subspecies of the black-necked stilt. A sugar-white beach stretches north from Honokōhau’s boat harbor and often attracts sea turtles.

The state-of-the-art, 36,700-seat Marlins Park in the heart of Downtown is the home of the Miami Marlins baseball team. It has a retractable roof that takes just 13 minutes to go from fully closed to fully open, and there’s a floor-to-ceiling glass-walled concourse that overlooks glittery downtown Miami. The venue also houses a nightclub and several bars and restaurants—even one with a swimming pool. Take a group tour to see one of the country’s most high-tech baseball fields up close, including the field, the clubhouse, the batting cage area, the home run sculpture, the bobblehead museum—and the aquarium at home plate.