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The Shockoe Slip in Richmond, Virginia has many quaint shops, good restaurants, and several upscale hotels. One of those hotels is the Berkeley Hotel. This boutique hotel is beautifully furnished. The rooms and bathrooms are richly decorated. Breakfast, lunch, and dinner are offered in the hotel restaurant. Access to the Jamestown Center fitness club is included for guests. The attentive staff will be happy to assist you in any way they can. Nearby you will find the Richmond City Hall, the Virginia State Capital, the James River, and many other historic sites. A stroll down Cary Street is fun whether you are going to a restaurant or shopping or sightseeing. I have stayed at the Berkeley several times and have never been anything but pleased with the service and the hotel.

What began in 1854 as a high school—then grew into a college and, later, a law school—has served as one of San Antonio’s top hotels since 1968. Located near the River Walk, not far from the city’s historic district, the leafy former campus is centered around a seven-story, Spanish colonial-style main building with 338 guest rooms. Each one mixes original touches like wood-beamed ceilings, exposed brick walls, and French doors with modern amenities like HDTVs, marble baths, and Wi-Fi (complimentary for loyalty club members). Some even look out on the River Walk, while others offer views of a verdant garden. Healthy extras like in-room fitness kits, a 24-hour gym, and a year-round heated pool help offset the indulgences served at the on-site restaurants and bars, which include the fine-dining Las Canarias (don’t miss the popular Sunday brunch.) Younger guests can look forward to game-filled backpacks and scavenger hunts, while adults will enjoy the award-winning spa and restaurant at La Mansion’s sister property, Mokara, located across the river.

While many cities have rivers, few take advantage of their waterways quite like San Antonio does. One of the city’s most popular tourist attractions, the River Walk runs along the San Antonio River and features both quiet stretches for jogging and livelier areas lined with colorful bars, restaurants, and shops. For an immersive experience, take a boat tour and learn more about San Antonio’s history and architecture.

In Miami’s trendy Mary Brickell Village, Perricone’s Marketplace & Cafe is the kind of place you can just relax in. The indoor/outdoor patio keeps you out of the blazing Florida sun but still provides a romantic ambience. To start, tear into baked Brie cheese wrapped in puff pastry dough brushed with drawn butter and powdered brown sugar. The top is then sprinkled with shaved almonds and sticky apricot jam. The melty cheese combined with the sweet sugar and jam is a perfect introduction to an unforgettable meal. Continue to the bruschetta bread basket, the lobster ravioli in a pink vodka sauce, and the lamb chops seasoned with rosemary and served perfectly pink atop a bed of couscous and steamed asparagus. Other highlights include the salmon in a lemon-butter sauce. For dessert, sample the house cake, a combination of chocolate and hazelnuts. As rich as a brownie, it’s the kind of dessert that you want to savor and pairs nicely with vanilla bean gelato. There’s an awesome Italian market in the lobby to stock up on pesto, seafood dip, and plenty of to-go truffles. Be sure to try the peanut butter teardrop.

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.

From a members-only beach club in the 1960s, The Dunmore has evolved into a 16-room boutique stay whose spirit and decor evoke that era. Local interior designer Amanda Lindroth oversaw a major renovation when the hotel’s current owners bought the property in 2010. Wicker and rattan furniture, patterned prints, and spaces that are as much outdoors as indoors create a look that is somewhere between late British colonial and timeless Bahamian. Although the landmark sits on Harbour Island’s Pink Sands Beach, a pool with an airy pavilion adds to The Dunmore’s reputation as a place of amiable gathering. After a day of sunfilled fun, head to the on-site restaurant, where chef Cindy Hutson, one of the region’s rising culinary stars, prepares modern twists on island delicacies—think grouper curry with lychee and grilled pineapple and banana fritters with rum caramel.

The recently renovated and reopened Philadelphia History Museum showcases an impressive collection of art, objects, and artifacts spanning 330 years of the city’s history. Dating back to 1826, the building itself plays into the journey through the past. The biggest draw for me, however, is the rotating Made in Philadelphia exhibit which looks at the city’s contributions in craftsmanship and manufacturing throughout history (particular nod to the ‘Craft Brewing’ feature which focuses on brewing from the days of William Pen right up through the revival of microbreweries in the 20th century). And if you’re keen on vintage Philly, I highly recommend the much-lauded Facebook page Old Images of Philadelphia. It isn’t associated with the museum but offers a heartwarming virtual walk through the city’s storied past.

Visitors to Philadelphia should not miss out on an iconic local treat—the soft pretzel. Sure, you can find them pretty much everywhere in Philly, but the real deal is baked fresh daily. At the Reading Terminal Market, go to the place where they’ll roll and twist the dough right in front of you—Miller’s Twist—where the soft pretzels are fresh, hot, and buttery (and beyond delicious). Locals line up here daily for fresh soft pretzels and pretzel dogs (hot dogs rolled inside a pretzel bun). There are only fresh pretzels here, still warm from the oven, baked to golden perfection, and brushed with melted butter. The aroma is intoxicating. You’ll want more than one! Save room for a milkshake made with fresh local ice cream.

The newly refurbished Sheraton Kona Keauhou Bay Resort is stylish, with a large pool and water slide. But it was the history and the view from the hotel (located off the famous Ali’i Drive) that won me over. The hotel gives you an excellent vantage point to the bay around which King Kamehameha III was born (stillborn, as legend has it). He grew up to become Hawai’i’s powerful and benevolent ruler, and sought to unite the people. He called The Big Island his home and is beloved by many. The hotel offers several notable cultural markers, including two heiau (Hawaiian temple) replicas.

Located in Leslieville in the East End, Swirl is in a small, converted apartment above a dog store in Leslieville. I love the decor here, from the tables made from doors or antique sewing machine bases to the artwork by local artists FAME. It’s a tiny place but it packs a punch. There’s no kitchen, so they have these amazing appetizers and desserts preserved in small Mason jars. Wine prices are affordable (and they have about three beers available now). On top of all of that, they host theme nights. For instance, you can watch Mad Men whilst sampling accurate cocktails from the era; board game nights; bubbly nights; and cinema Sundays. Suffice it to say, it’s one of my favorites. Warning: it’s tiny in here. Not meant for a big group, but perfect for a date.

Blue Heaven is a favorite in Key West—Jimmy Buffett even mentioned it in one of his famous beach tunes. The whimsical courtyard is filled with brightly colored tables and chairs, twinkly lights, foliage, and stray animals. The bar and restaurant is owned and operated by a husband and wife whose creative backgrounds in art and literature inspired the space. There’s a mini art gallery, a sandwich shop, and roaming roosters on the grounds. Once a boxing ring (with Ernest Hemingway as referee), the spot now pays tribute to the Caribbean, with bright accents and Cajun seasonings on the menu. Menu highlights include the scallops, which are locally celebrated, served with white wine and lemon butter with tomatoes, onions, mushrooms, and lots of garlic. Locals say the Key lime pie is one of the best in town.

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.

The friendly vibe at Delly Deck makes island eatery an ideal spot for celebrating special occasions or just grabbing breakfast or lunch with friends and family. Considered by locals to be a landmark (it’s been around for 40 years!), Delly Deck has a solid breakfast menu, with a range of omelet choices and standard but tasty lunch selections such as sandwiches, wraps, salads, and burgers. Cocktails—frozen and not—as well as beer and wine are on offer, though you probably can’t get into too much trouble before the 4 p.m. closing time.

Petra flourished more than 2,000 years ago, trading with Rome as an equal before being abandoned after a series of earthquakes in the 4th and 6th centuries C.E. It wasn’t until the 19th century, when European explorers “rediscovered” it, that the ancient city returned to the public consciousness. Now, visitors can walk down the narrow canyon of the siq to the city entrance—as dramatic an approach as any to a tourist attraction on the planet. The canyon opens up onto the carved facade of the Treasury, Petra’s most iconic site. From there, you can explore the cliffside tombs with their colorful bands of sandstone, the Street of Facades, and the amphitheater hewn from living rock. The ancient center lies some distance off, along with the splendid old Monastery, which sits at the top of a steep but rewarding climb. Consider buying a three-day ticket and visiting at different times of day to enjoy the changing light—early in the morning is best for the Treasury, while late afternoon is better for the Royal Tombs.

No hotel in Jamaica blends better with its surroundings than the aptly named Rockhouse, a string of villas clinging to the top of a sea cliff at the western tip of the island. Local stone, timber, and thatch are the building materials, and a harmony of design and setting is the result. The feel is rustic, but not rough (the showers might be outdoors, but the rooms are air-conditioned), and the feeling carries over to the pool, which sits on a rock platform halfway down the cliff face, from where sunbathers can don snorkel and mask and clamber down into a usually calm Caribbean. Even the restaurant hangs over the water, adding emphasis to the promise of dishes being fresh from the sea.

As does practically every hotel in Jamaica, Rockhouse has its celebrity stories, going back to the early ‘70s when Bob Marley, Bob Dylan, and the Rolling Stones added their names to the guest register. But it wasn’t until 1994, when a group of Australian owners took over, that Rockhouse began to evolve its reputation as one of the most Jamaican of Jamaican hotels. It happened in part because Rockhouse has none of the formality that some of the island’s best-known hotels, with their British colonial roots, still possess. And in part because of its active role in funding local education projects, it’s a valued, and popular, part of the community. That, and the restaurant’s homemade jerk sausage is legendary.