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The hippest kid on the block has risen from the most unlikely of origins: the Fenway Motor Hotel, a run-down mid-century relic that once housed all manner of misbehaving musicians. Today the hotel feels more like an of-the-moment Los Angeles enclave, with mid-century furnishings, floor-to-ceiling Mondrian stained-glass windows, and upscale bathrooms. Local music and pop-culture memorabilia decorate the rooms and foyers, from framed Boston Phoenix covers (the city’s now-defunct alt-weekly) to vintage speakers and ‘70s-era phones.

In keeping with the rock-and-roll theme, both the lobby and the outdoor pool area regularly host live music. Lansdowne Street, home to legendary clubs like House of Blues, is just steps away, and of course no visit to Boston is complete without a stop at next-door Fenway Park (tours of the ballpark are available daily and year-round).

The largest luxury hotel in the city, the Charleston Place takes up a full city block with entrances on King and Meeting streets; the latter leads to the grand lobby, with its imperial open-arm staircase, 12-foot crystal chandelier, and Italian marble floors. Its 433 large guest rooms have old-fashioned Southern details like mahogany and damask furnishings. The hotel’s lower level houses fine-dining restaurant Charleston Grill, an attractive hotel bar, a large indoor saltwater pool with a retractable glass roof, and a shopping arcade with designer stores. The hotel recently began a $150 million renovation but will remain open as the property is upgraded from stem to stern.

Set in the Catskills, the Graham & Co is a boutique hotel that has reimagined the classic weekend mountain getaway. Located about two-and-a-half hours from New York City, this retreat offers spacious minimalist rooms, some with kitchenettes. Details include Mexican blankets, Tivoli radios, and custom bath amenities that are available for purchase at the front desk. The Graham & Co is designed as a place to sit back and read while putting your feet up next to the fire pit. Plenty of outdoor activities (fishing, hiking, skiing) are nearby, but many guests settle into the property and its Adirondack chairs, hammocks, and picnic area for a welcome escape from the bustle of city life. Explore the town of Phoenicia on a complimentary bike or simply stay put at this unpretentious mountain property.

Situated on 10 acres in the heart of downtown, this 24-story hotel lives up to its name with 775 elegant guest rooms, appointed with handcrafted cherrywood Richelieu furnishings, floor-to-ceiling windows, Italian marble bathrooms, and spacious balconies. Public outdoor spaces include an immaculately manicured courtyard garden with a central fountain, a pretty-as-can-be terrace café serving house-made breads, and an outsize pool lined with loungers, all against a backdrop of classic white granite. To top it off, the hotel also features a colorful toy store with costumes galore, a jewel box of a sweets shop with macarons and other divine confections, and a men’s haberdashery. The lobby lounge hosts a live jazz band on weekend nights, and the staff tends to a crackling open fire during cool weather.

Among the original guests to pop in at Dr. Thomas Bond’s 1769 Georgian home on South Second Street was none other than Benjamin Franklin. Together the duo chartered Pennsylvania Hospital, the first public hospital in America, and Bond was an influential figure in Philadelphia throughout the Revolutionary War into the first turbulent decades following the founding of the country. Today, the four-story red-brick home within Independence National Historical Park has been meticulously restored, offering history buffs a taste of Philadelphia at the dawn of America. Original architectural details restored to their full 18th-century splendor include the modillion cornice at the roofline, the parlor’s Rumford fireplace, and the grand staircase connecting the third and fourth floors that was subsequently copied in other prominent buildings around town, including the still-standing City Tavern.

Each guestroom has been furnished with Federalist-style reproductions, with a few antiques sprinkled around. Ten rooms offer queen beds, with the two original bedrooms nearest the first floor adding small sitting areas with working fireplaces.

The Huffington Post named the Hilo Farmers Market the best in the United States. For fresh local flavors, the market is open every day except Sunday. The big market days are on Wednesdays and Saturdays where more than 200 vendors including farmers and crafts people gather to sell their goods. If you’re looking for local souvenirs to take home or just a place to grab a quick fresh and tasty lunch, the Hilo Farmers Market will provide a beautiful morning or afternoon of shopping and eating.

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.

Lake Mary is as bike-friendly as a city can be. Throughout the day—especially on the weekends—locals and bikers from neighboring cities can be found out and about getting exercise or enjoying a leisurely and scenic ride. Alongside the bikers on the path are rollerbladers and walkers. The Lake Mary stretch of the Cross Seminole Trail is about four miles, and runs parallel to the residential Rinehart Road. Tip: A good place to park your bike and take a break is behind Panera or Peach Valley Cafe on International Parkway and Lake Mary Boulevard. This is also the prettiest portion of the trail, with pastoral scenery away from traffic.

San Antonio’s west side is one of the city’s cultural hubs. Latin and Mexican-American influences are vibrantly displayed through public art and murals. The area around Guadalupe Street is an especially rich place to explore. You’ll find art around every corner, cultural centers, theaters, coffee shops, and bakeries. One of the best resources I came across was the San Antonio Neighborhood Tours sponsored by the City of San Antonio Office of Cultural Affairs. You can download free PDFs of the guides here: http://www.saculturaltours.com/. We did the West Side Murals Y Mas Tour. It was an awesome experience that included more than 50 unique sites.

New Mexico has the reputation for 364 days of sunshine every year. But occasionally it snows a lot, blanketing and softening the rocky scenery New Mexico is so famous for. Ghost Ranch is a conference center about 50 miles northwest of Santa Fe, made famous by Georgia O’Keeffe, who lived in Abiquiu for many years and painted almost every formation with her unique style. You can stay at Ghost Ranch or nearby Abiquiu in one of several B&Bs. For more information, consult the Ghost Ranch website.

Semana Santa (Holy Week) in Oaxaca is generally made up of rather somber events. In contrast with other holidays, this is the most serious, much more so than Day of the Dead, which is often celebrated in a lighthearted way. The gravity of the events being commemorated are reflected in the observances that take place during this week. The Friday before Easter, which is the day that commemorates Jesus’ crucifixion, is marked by a silent procession along the main pedestrian street in Oaxaca, Calle Macedonio Alcalá. The procession takes place in the late afternoon, and winds its way through the city streets. Observers are asked to remain silent in order to maintain the solemnity of the event. You will notice that some of the participants in this procession wear the pointed hoods which in the United States are strongly associated with the Ku Klux Klan and seen as a racist symbol. In Mexico, as in Spain where these hoods originated (long before the existence of the Klan), they are seen as a symbol of penitence; they are meant to hide the identity of the wearer so that their participation in the procession is not done for show, but as a personal expression of repentance.

Down a side street not far from MoTown Museum and the Wayne State University’s main campus is one of the city’s hidden art gems. Lincoln Street Art Park is an evolving community collaboration between local artists, the Michigan Council for Arts and Cultural Affairs, the Detroit Recreation department, and the adjacent recycling center. Visiting the outdoor site, particularly on a sunny day, is akin to walking into the rugged studio of an artist, complete with seating area, mini library, and house pet. In this case, a giant dinosaur twice the size of an average loft’s ceiling, but reminiscent of a pet nonetheless. I explored the park alone, but I think it would be a wonderful place to visit for a couple on a date and a really good option for kids to roam and explore at leisure. The outdoor exhibit is open rain or shine, 24 hours a day, seven days a week, 365 days a year and is free to the general public. The park is located at 5926 Lincoln Street, Detroit, Michigan 48208.

After strolling Storm King Art Center or DIA Beacon, Tarry Lodge is the perfect stop on your way back to New York City. Mario Batali opened it up as a neighborhood restaurant for the Port Chester crowd and a go-to for out-of-town Manhattanites who love his Italian comfort food. Don’t miss the clam, chili, and oregano or pistachio and goat cheese pizzas. Waits can be long so if you’re trying to beat traffic just get take out from their curbside service.

This brand-new hotel next to the massive, newly opened Music City Center convention space is one of Nashville’s hottest places to stay. Opened in fall of 2013, it’s also in the heart of the action and within easy walking distance of Schermerhorn Symphony Center, the honky-tonks of Lower Broadway, and the Country Music Hall of Fame and Museum. But even if you never left the building, you’d find 800 rooms, five restaurants and live music spaces, a spa and rooftop pool deck.

The Madinat Jumeirah hotel’s Pierchic restaurant sits at the end of a private pier, facing the famous sail-shaped Burj Al Arab hotel. Redesigned in 2014 with a stunning Swarovski-crystal chandelier over the bar, Pierchic is one of the city’s most romantic dining rooms. For intimate drinks, get a table in the separate bar “pod” over the water. The menu focuses on seafood and manages to be elegant without being fussy. The setting alone makes it worth the trip (and the price) If you want to have dinner, make sure to book well in advance..