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Find great St. Lucian soul food right in the heart of Gros Islet at a traditional pastel-colored house turned restaurant. Generous meals—pork chops, fresh fish, lamb chops, curried goat, corn, rice and peas—are cooked and grilled outdoors and served up at picnic tables in front or on a side garden terrace. The food is plated as artfully as in more upscale establishments. Don’t skip the rum cocktails or the homemade dessert of the day. The place gets busy quickly, so arrive early for both lunch and dinner service—particularly on Friday nights when Gros Islet fills up for its weekly fish fry.

Donosti Librería is the bookstore that movies are made of. In the family for 40 years, the shop’s beautiful art nouveau façade hides a calming interior. Walls are stacked with books, handpicked by the owners, and the overall atmosphere is the perfect blend of peaceful and provocative.

Casas del Bosque is an award-winning boutique winery just outside Casablanca where, besides tasting the vintages, you can also learn how to prune grapevines or even the basics of wine-making in one-day workshops. You can also tour the estate on bicycle, along with a picnic lunch. If you just want to walk through the vines, you’ll find everything at its prettiest in December and January. Tanino, the Casas del Bosque’s excellent restaurant, has a menu designed to showcase the wine.

If mountain biking sounds a bit too extreme take to the trails on a monster scooter. The scooter version of a Big Wheels, it has extra large tires that provides stability but still allows you to pick up speed and brake like a mountain bike. From Saas-Grund, we took the gondola up to Hahsaas mountain station, which overlooks the Saas Valley. A nearly four-mile trail leads back down to the village (In the winter you can rent rodels, or sleds, and sleigh down). The views can be very distracting but we had to keep our eyes on the trail so we didn’t collide with any mountain goats.

What do Al Capone and Bruce Willis have in common? They both did time here at Eastern State Penitentiary. (OK, Willis wasn’t an inmate, but he did shoot the film 12 Monkeys here.) The facility’s first inmate was brought through these doors in 1829, and the prison was in use until 1971. After closing, it became a target for vandals and housed a sizable colony of stray cats. Real estate developers proposed repurposing it as condominiums (high-security, of course), but preservationists won out. They raised funds to stabilize the crumbling interior and remove trees that were growing inside some cells. Wander through its stark interior and learn about the fascinating history of this unique site and its previous tenants, including Capone. Don’t miss the special art installations that are on display here all year round.

Around for over 10 years, this small “ital” (vegetarian) and vegan spot dishes out flavorful, affordable, and creative lunches in the one-table interior of a green house in Soufrière’s downtown. Favorites include the house pizza, a pie with whole-wheat crust topped with lentils, cabbage, pumpkin, and cheese. Other options include salads, veggie burgers, empanadas, smoothies, fresh juices, and a special cocoa tea. The atmosphere is about as casual as it gets, with a TV loudly blasting as locals stop by for a bite and to hang out.

Bar Hidalgo 56 is probably one of my top three pintxo bars in the entire city. With a bar stacked full of equally delicious pintxos, a menu of hot pintxos that is incredibly varied and delicious, and an attention to product that you simply don’t find in other bars, Hidalgo 56 is worth a visit. Try the volcano of morcilla.

I dare you to visit Planet Modular and not leave with a stack of new notebooks, Japanese masking tape, or sparkly envelopes. It’s unequivocally a supplies haven for artists and crafty DIYers, and while I don’t fall into either of those categories, I’m a sucker for colored gel pens and stationery. One loop around this shop, and you’ll understand why Berlin ranks high in creative design.

Wandering around Rabat, trying to get to the waterfront, we stumbled upon this cemetery which turned out to be enormous and mysterious, with tombstones literally stacked upon one another and tumbling all the way down to the sea. Tens of thousands of beautifully engraved tombstones. I’d never seen anything like it before.

If you’re hoping to see all of Laguna in a short amount of time, hop on the free trolley, which runs in five neighborhoods during the week and along the Coast Highway on weekends. Hours vary by day and season, but are long enough to make the trolley a fun, convenient way to get around town. For special occasions from September through mid-June, you can even charter a trolley for a tour or a memorable ride to your event.

The popular Gros Islet Fish Fry, also known as the Jump Up, is one big neighborhood party. The narrow streets of Gros Islet fill up with locals and tourists by 7 p.m., and by then the food shacks are busy: Hungry patrons shout out their orders and wait impatiently as the seafood steams and fries. While you wait for your food, grab a seat at a picnic table and throw back some Piton beers. Dance it all off after dinner as DJs blast soca, reggae, and international music. Whether you’re a dancer or not, stop here for your Friday dinner and some Saint Lucian vibes.

Tucked away on the second floor of a courtyard building in the residential Recoleta neighborhood, the shoe store Comme Il Faut is a magnet for tango dancers. Customers provide their shoe sizes to cheerful saleswomen, and stacks of shoeboxes—in every color and heel height—emerge from the back.

If you’re staying in the Soufrière area, head north to nearby Anse la Raye, a fishing village that hosts a fun Friday night fish fry. It’s not as crowded or boisterous as Gros Islet’s weekly jump-up, but it’s lively enough to give a taste of island “liming,” or hanging out with friends at the end of the workweek. Order your fish of choice, throw back some cold beers, and glimpse a slice of laid-back fishing-village life.

Hundreds of years ago, at the height of Florence’s Renaissance heyday, visitors to this cultural capital wouldn’t have stayed in the kinds of luxury hotels that now line its picturesque streets. Rather, the well-heeled would have come at the behest of friends, lodging in private homes whose unassuming facades in the best neighborhoods belied their sumptuous interiors and private gardens, outfitted with art and artifacts collected from around the world.

A guesthouse to its core, Casa Howard continues this Florentine tradition; there is neither lobby nor restaurant, and the owner Massimiliano Leonardi di Casalino lives in his own apartment here while in town (note, it can be rented when he’s away). Jennifer Howard Forneris, one of the design-conscious proprietors who has since passed away, was the daughter of renowned textile designer Luciano Forneris. She gave each room its own look, with finds from her and Leonardi di Casalino’s world travels. A media room is the sole common area, and a hammam steam room and an on-site concierge service are the only nods toward traditional hotel services. Insider recommendations are personalized according to guests’ preferences, and the honor bar feels more like a friend’s (well-stocked) fridge.

There isn’t much to do in Laborie, but the colorful spot on the southwestern coast offers visitors the experience of an authentic St. Lucian fishing village. The point is to slow down to local speed. Enjoy the views of the white-sand shore lined with pirogues, the traditional fishing canoes. Walk around the village, where plywood homes and ancient churches exist alongside newer structures. Whet your appetite with a trip to the open-air market, where you’ll spot green figs (bananas) and cassava bread for sale. Settle in for a grilled lobster lunch with a side of breadfruit at Mama Tilly’s. Then walk north along the water to Rudy John Beach Park, a shaded stretch of sand ideal for an afternoon nap and sunset.