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From the first “woof” of welcome from the resident Canine Ambassador, guests feel a part of this storied hotel’s century-plus history. Located in the Back Bay, not far from Beacon Hill, Newberry Street, and the Freedom Trail, the landmarked Fairmont Copley Plaza houses 383 comfortable guest rooms, each featuring modern-elegant decor as well as signature pillow top mattresses, 46-inch TVs, and coffee makers. Snag a room on the Fairmont Gold concierge floor for extras like private check-in, complimentary Wi-Fi, and use of a snack-stocked lounge.

Sweeping views of the city can be enjoyed from the 3,000-square-foot rooftop gym (which is lined with floor-to-ceiling windows) and the sophisticated event spaces (which, decorated with chandeliers and ornate furnishings, are a top pick of Boston brides). The hotel’s convenient location makes it easy to sample the city’s great eats, but you’ll do well if you stay in, too, thanks to the handcrafted cocktails and farm-to-table dishes served at the on-site OAK Long Bar + Kitchen.

La Casa de La Abuela is a Oaxaca mainstay, on the corner between the Zocalo and the Alameda, Oaxaca’s two central squares. Find the entrance on Hidalgo street, and climb the steps up to the second floor. As soon as you enter you’ll see a big clay comal and a woman making fresh tortillas, the sign that this is the real deal: authentic Oaxacan food. They serve local specialties including four kinds of mole (almendrado, coloradito, amarillo and mole negro). Choose a spot by the window to enjoy your meal while you watch the action in the square below.

Rather than diving right into the hard stuff, sip one of the 35 craft beers on tap at the new SLS hotel’s Umami Burger beer garden. Pair it with an Umami pork belly sausage, served only at these bar stools.

Vendors first set up shop at the Italian Market in the mid-to-late 1880s, and today, the spread of stalls, stores, and eateries runs all along South 9th Street in Philadelphia’s residential Bella Vista neighborhood. A trip here involves all the senses: sights, sounds, vibrant colors, and, most intoxicating of all, the combined aromas of spices, coffee, and just-baked bread. Along this stretch, shoppers can find fresh fruits and vegetables, eggs, fish, seafood, meats, cheeses, pastries, homemade pasta, ice cream, chocolates, and tea. The 10-block market area also includes a great variety of restaurants. Overwhelmed by the choices? Stop at the Visitor Center for suggestions. The market operates all year round, and in all types of weather.

In 1862, the Panaderia La Patria (The Homeland Bakery) was established in the mountain town of Morovis. One of the oldest bakeries in the island, La Patria offers a variety of traditional Puerto Rican sweets like flan and quesitos (a pastry filled with cheese whipped with vanilla, eggs, and sugar). But we all know the bakery best for its “pan de la patita echa.” (“Echar la pata” is slang and can have various meanings, one of which is to start or throw yourself into something.) This is a kind of lard bread made only in Puerto Rico that looks like it has its legs crossed. Ask them to show your the century-old red oven in which they make their different breads and pastries.

Quinta de La Rosa was built in an unusual location, on a hill with steep stairs that connect the different levels besides the Douro River. The Bergqvist family has been making Port wine since 1815. The Quinta de La Rosa estate was offered as baptism gift to Claire Feuheerd, Sophia’s grandmother, in 1906. Guests can stay in traditional family House or in the new and more modern building.

In the historic Candelaria district, the 42-room Hotel de la Ópera occupies two colonial townhouses and parts of a 1940s art deco mansion. Head up to the rooftop restaurant, El Mirador, to enjoy ajiaco (potato soup with corn, chicken, and aji chili) along with views of the city’s main cathedral. From $162. 57/(0) 1-336-2066. This appeared in the August/September 2013 issue. Image courtesy of Hotel de la Ópera

The tony suburb of Houghton, whose best-known resident was Nelson Mandela, is home to leafy lanes lined with stately estates. Not too far from the Mandela family manse is the Residence, a stylish boutique property that lives up to its name, evoking a private lair of a chic distant relative that guests are fortunate enough to visit for a spell.

The rooms are plush, with velvet headboards, sumptuous rugs, and glittering chandeliers, but the bathrooms are a sight to behold: the gleaming marble tiles and outdoor showers and tubs merit a special mention. Nods to the nautical can be found in the Boat Lounge, where mini sailboats and life preservers inspire the decor. There’s often a pianist tickling the ivories in the Piano Lounge, where guests can retire with a post-prandial cocktail.

While San Francisco and L.A. often steal the limelight from Sacramento, I often remind myself that Sacramento has long been the center of much of California’s history. The Leland Stanford Mansion is one place where that history is reflected. The mansion, located in Downtown Sacramento just blocks from the Capitol, is worth visiting not only because of its historical value but also for its beautifully restored interior and exterior. The mansion was built in the Renaissance Revival style soon after Sacramento was founded in the mid-1800s. Seeing the architectural details up close is impressive. In 1861, it was bought by Leland Stanford, Governor of California, a U.S. senator, and founder of Stanford University. One interesting fact is that after Stanford’s death, his wife donated the mansion to be used for the children of California, and in 1900, it became an orphanage. After a $20-million renovation, the mansion opened for tours in 2005. It has also been designated a National Historic Landmark. Tours are offered here Wednesday through Sunday every hour beginning at 10:00 a.m. (the last tour begins at 4:00 p.m.). The tour allows visitors to see what such a residence would have looked like in the 1860s and 1870s. You can also walk through the Victorian gardens. The tour can accommodate groups, but groups of more than 10 must make reservations two weeks in advance.

Formerly the residence of the Maharajah of Jaipur, and now one of Jaipur’s most elegant luxury hotels, the 19th-century Rambagh Palace has had a front-row seat to history—and has hosted a long list of royals, dignitaries, and celebrities along the way. As an homage to those regal roots, the hotel’s fine-dining restaurant spotlights the cuisine of four of India’s former princely states: Rajasthan, Awadh, Punjab, and Hyderabad. In what used to be the palace’s banquet hall—still dripping with gilded mirrors and Italian frescos—enjoy dishes like laal maas (a Rajasthani spicy lamb curry), chicken cooked with raw mango and saffron, skillet-grilled lobster, and apricot-stuffed cheese dumplings simmered in tomato gravy. Cap off the night with a drink in the nearby Polo Bar, which serves fine spirits and cocktails inspired by the royal equestrian sport.

While the Cycladic island of Serifos has stayed blissfully under the radar for most tourists, savvy Athenians have been quietly snapping up property while preserving its dusty charms. COCO-MAT Eco Residences, opened by the eponymously named Greek sleep-product company, is emblematic of this mindset: Its 13 rooms were reclaimed from stone miners’ houses built in 1910 at the foot of a hillside, just steps from the sand and calm waters of Vagia Bay. The one- or two-bedroom units feature bedrooms on the (cooler) bottom floor and living spaces and kitchenettes above (they’ll do the grocery shopping); you choose your mattress preference from the brand’s sustainably made line. Carved into the cliff face, the Lounge Bar serves buffet breakfast in the morning, lunch and light snacks during the day, and dinner in the evening—including right on the shore (for an additional charge). The hotel also supplies car or motorcycle rentals should you want to explore the island, and also will arrange diving trips and excursions to different beaches.

This natural soup-n-burger joint lies far from the tourist hordes, on a quiet residential street in the San Frediano neighbourhood. The kitchen and takeaway operation (open lunch and dinner) stands on one side of the road while opposite there is a pared-down modern restaurant (open for dinner only) with a tiny courtyard. Organic vegetables and herbs and locally produced beef go into tasty, seasonal soups (creamy cauliflower with truffle or earthy lentil and kale) and juicy burgers and there are gluten-free, vegetarian and vegan options too. Don’t miss the delicious desserts such as the rich flourless chocolate cake. The drinks list features excellent organic wines from the owner’s estate, craft beers and organic fizzy drinks.

In a country with so many castles, Schloss Greinburg doesn’t rank as one of the most awe-inspiring. It is, however, particularly notable for two things. Greinburg is considered Austria’s oldest residential castle (origins dating back to 1488) and it has been owned by the House of Sachsen-Coburg & Gotha, arguably the most influential European royal family, since 1823. The castle was even briefly owned by Queen Victoria of England. Highlights of a guided tour include the rich stucco ceiling, grand chandeliers and ruby red walls of the Dining Room, and splendid courtyard, and numerous portraits showcasing their royal connections throughout the castle. Views from the castle overlook the small town of Grein and the Danube.

Parque Forestal is Santiago’s lung and central park. Created for the first centennial celebration in 1910, the park has become an iconic area of the city with elegant residential apartment buildings along the perimeter. One of the most enjoyable ways to spend an afternoon is walking under the century-old trees and then strolling the cobblestoned streets of the adjoining Lastarria area. Parisian-style facades, cafés full of intellectual life, boutiques, museums like Bellas Artes (a copy of the Petit Palais in Paris), restaurants, and bars all bring this neighborhood to life.

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.