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Situated off the eastern shore of Long Island, The Chequit is old school in an elegant way. The hotel occupies a big white building, surrounded by grassy lawns, impeccably maintained hedgerows, and towering deciduous trees, and features bright, homey rooms, complete with large windows that let in plenty of natural light. While all the rooms have been refurbished, those in the main house retain much of their original architecture, lending them a certain vintage charm. The Chequit operates on a bed-and-breakfast model, and guests can either take their morning meal in the lobby or opt to have a lighter option sent straight to their room. While the target audience here is weekenders seeking an escape from New York City, the hotel is also a popular spot for weddings and retreats, with two meeting rooms and full catering services available from on-site Red Maple Restaurant.

Charleston is a relatively small city to sport a food court, and Workshop’s out-of-the-way location on the Peninsula’s Neck underscores that. Situated in a Silicon Valley-esque complex of start-up office spaces, you’ll need to drive to get there, and once at the modern, industrial food hall, you’ll be faced with some tough decisions. The rotating vendors have included Juan Luis, a Tex-Mex spin from BBQ master John Lewis, and seasonal booths where the city’s up-and-coming chefs test out their latest concepts, from Japanese sliders to shareable Indian small plates. Although the vendors change regularly, there’s always a coffee shop, a craft pizza or burger stand, and a variety of ethnic options, making Workshop a must on any dining tour of Charleston’s latest and greatest. It’s also directly adjacent to Edmund’s Oast Brewing Co., a popular hangout and generally regarded among the city’s best breweries.

Hotel Zelos brims with understated luxury. Rooms are kitted out with on-demand movies and music, in-room spa services upon request, and a complimentary honor bar stocked with organic treats. The hotel’s 4th and Market Street location puts it within walking distance of Union Square, AT&T Park and the Moscone Center. For further distances, guests can borrow free bikes. The hotel’s crowning jewel, though, is Dirty Habit, it’s rooftop restaurant and bar. A favorite among locals as well as tourists, Dirty Habit’s film-noir-inspired dining room offers guests a chance to play the part of old Hollywood glamour while nibbling on seasonally inspired dishes like seared king salmon and sipping inventive craft cocktails (try the Bonzai, a mix of whiskey, orgeat, grapefruit, lemon, and matcha green tea).

Often described as the Grand Canyon of the Pacific, this 10-mile-long Kauai valley is a kaleidoscopic array of scarlet earth, verdant valleys, and raw volcanic crags. Bands of color streak the corrugated landscape, each representing a different eruption and layer of lava. Waimea Canyon Drive has a series of lookouts; among the most popular is Waimea Canyon (past the Mile 10 marker on Highway 550), where a number of rivers once cascaded down the gently sloping shield volcano. When part of its flank collapsed, the rivers combined with dramatic results. Continue into the mountains to explore Koke’e State Park beyond. Its small, free museum contains a 3-D map, which sheds light on the canyon’s wild beauty, while the gift shop specializes in local art, crafts, and Niihau shell jewelry.

There certainly are other ways to while away a summer day in Greater Portland, but you’d be hard-pressed to find a better experience than island-hopping aboard a Casco Bay Lines ferry. Sure, you can simply ride out to an island for a look-about and return, or enjoy a sunrise, sunset, or moonlight cruise. But for a real immersion, consider the Mailboat Run. You’ll be among islanders, visitors, pets, and freight to-ing and fro-ing between Little Diamond, Great Diamond, Long, Cliff, and Chebeague islands. The 2½-to-3½-hour working cruise is offered twice daily year-round; bring your own picnic lunch on the morning run or snacks for the afternoon one.

Maria e Susanna Sent has several shops where they sell their glass jewelry, the cutest one of them all just off the Ponte San Moisè in San Marco. This boutique is about as big as a broom closet, and that is certainly part of its charm. The real impact, though, comes from the jewelry this artistic duo started creating on the island of Murano back in 1993. Their line of mostly necklaces and bracelets is made in a unique process that creates murrine and filigree glass and plates in glass fusion. They also have shops in Murano and in Dorsoduro near the Peggy Guggenheim Museum.

In D.C.’s Georgetown neighborhood, Cady’s Alley is a cluster of shops and design firms specializing in high-end home furnishings, kitchens, and baths. If you’re a jewelry lover, head to JewelersWerk—they offer one-of-a-kind, contemporary design pieces. The pedestrian-only alley part of Cady’s Alley is reminiscent of a European shopping street. If you want to escape from the hustle and bustle of the main shopping area of Georgetown, come here. Do a bit of window shopping and then take a break at Kafe Leopold Konditorei, a nice Austrian eatery located in the center of the alley. You really can’t go wrong with a well-brewed cup of coffee and a pastry.

Tucked off the casino floor, the Bellagio Gallery of Fine Art holds its own when it comes to well-established works of art. The gallery is small compared to the massive museums found in the likes of Paris and Washington, DC, but it is more than adequate for its intentions. In the city, few places are as quiet and thoughtful as the BGFA. Partnering with fine art institutes from around the world, the BGFA features a couple rotating exhibits each year. Past exhibits have featured work by Andy Warhol and Monet as well as Fabergé pieces.

The Bean Counter is a locally owned café in the heart of Georgetown. This small, cozy eatery with chartreuse walls is a neighborhood favorite. Stop by for a quick breakfast or come for lunch, when you’ll find a nice selection of soups, salads, and made-to-order sandwiches and wraps. If you want to do like the locals, try the laudable Cuban sandwich. In the afternoon, the Bean Counter is the perfect place for a cup of freshly brewed organic, fair-trade coffee and a homemade cookie. Order at the counter and then slip out through the narrow side alley to enjoy the secret garden in the back.

If one is going to throw around the word “iconic,” let’s make sure it’s used appropriately. As with Zuni. The awkwardly shaped restaurant—it’s in a narrow storefront with wider spaces on the mezzanine—was opened in 1979 by Billy West. West’s best move was hiring chef Judy Rodgers in 1987. She put in a brick oven—and thus the Zuni roast chicken was born. This dish, more than any other (except perhaps the Caesar salad), defines Zuni. The chicken is roasted in the brick oven and served over a bread salad: greens with chewy bread croutons. Simple, perfectly cooked, and seasonal. Rodgers died in 2013, but the restaurant soldiers on without her. The menu changes with the season and with what the local farms are growing, and will doubtless explain the provenance of your meat. Rodgers, along with her peer across the bay, Alice Waters, pioneered California cooking, and the cooks who have passed through here have gone on to define today’s vibrant restaurant scene.

When you think of a chocolate factory, a hip and airy space in the heart of one of the city’s hottest neighborhoods may not spring to mind. But therein lies the surprise that is Dandelion Chocolate: part factory, part café, part boutique, and located in the heart of the Mission. Like beans for coffee and grapes for wine, Dandelion brings the idea of single-origin sourcing to each bar it creates. Rather than add strange ingredients to alter the flavor of the chocolate, Dandelion uses just two ingredients—cocoa beans and sugar—which allows each bean’s unique flavor and terroir to shine. Drop in for hot chocolate (with handmade marshmallows) or a chocolate dessert created by Dandelion’s pastry chef, shop for gifts, and take a twirl through the factory, where beans are roasted, cracked, sorted, winnowed, ground, and tempered before being molded. Each bar is wrapped by hand in gorgeous paper and ribbon and affixed with a label that tells a story about the cocoa bean’s origin. For a deeper dive into chocolate, Dandelion has a schedule of classes for adults and kids, and even leads trips to cocoa farms.

D.C.'s most recognized landmark—and the world’s tallest freemasonry structure—transports visitors on a 70-second-long elevator ascent to its 500-foot observation deck. A National Park Service Ranger accompanies you and shares the history of this obelisk dedicated to the President and General who was regarded as “First in war, first in peace, and first in the hearts of his countrymen.” Consider that at completion in 1884, only men were allowed to use the then-steam powered elevator because it was deemed to dangerous for women whose only option was to climb 897 steps to get to the top. Timed tickets are now required to enter and are available on a first come, first serve basis at the monument lodge located along 15th Street NW. Tip: although the ticket window opens at 8:30am, it’s best to line up 1-2 hours early as tickets are usually gone by late morning.

Note: The monument is closed for renovations until early 2019.

Local shops and the Big Island go hand in hand. Kona is home to plenty of homegrown shops, but if you are just looking for that great piece of literature to read on the beach, Kona Stories is a fantastic little book shop worth browsing around. Beach goers and holiday makers should be able to find something to pass the time or entertain them while they stay in Hawai‘I.

One of the island’s best lookouts, Drake’s Seat offers a panoramic view of Magens Bay and the U.S. and British Virgin Islands to the east. The site is named for Sir Francis Drake, who is said to have kept watch over the harbor from this vantage point. (Was Drake benevolently watching over his own fleet or looking for ships to plunder? The answer will depend on whether you subscribe to the British’s regard of him as a celebrated explorer or to others’ belief that he was a brutal privateer.)

You’ll go for the fresh fish--namely salmon, black cod, and halibut. But you’ll want to stay forever thanks to the increasingly-excellent restaurant scene. Yes, Alaska is finally on the map when it comes to destination dining. Enjoy one of the state’s top dining spots right outside Denali National Park, stellar wine lists all around Anchorage, and plenty of smoked salmon all down the Kenai Peninsula. Pro tip: Head to the top floor of the Captain Cook Hotel on clear nights for apps and cocktails and a view of Cook Inlet that you’ll never forget.