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White Elephant has been a Nantucket landmark for nearly a century, with more rooms than a typical inn but without sacrificing the intimacy and personal service of a small property. Located on the waterfront a short walk from Brant Point Light, the inn has a sprawling lawn with chaises for relaxing, as well as shuttle service to the area’s beaches. Accommodations range from king-bedded guest rooms (each with a private balcony or patio) in the main inn building to spacious garden cottages (some with kitchens and fireplaces) and penthouse-like lofts in downtown Nantucket. A small spa offers therapeutic massages, facials, and body treatments. A luxury resort that is truly family-friendly, kids and babies can get fully kitted out for bath time, mealtime, or beach time with a wealth of amenities and toys. The Brant Point Grill is a local favorite for an al fresco lunch, lobster dinner, or Sunday brunch (complete with Bloody Mary bar). The White Elephant also provides regular transfers on the 21-passenger boat, Lady Wauwinet, to the Wauwinet Inn’s restaurant TOPPER’S, which cultivates its own oysters.

The Wauwinet makes the most of its coastal setting between the Atlantic Ocean and Nantucket Bay. Next to the Coskata-Coatue Wildlife Refuge, the resort has 32 rooms, plus four cottages with separate living rooms and the three-bedroom Anchorage House across from the main inn. In addition to private beach access and bikes to explore the island, guests can take out a kayak, play a game of tennis, or watch a movie in their room with hot buttered popcorn. A spa offers sea-inspired facials, massages, and body treatments. TOPPER’S restaurant is known for its Retsyo oysters, harvested only 300 yards from the restaurant, and offers transfers to and from White Elephant Hotel’s Brant Point Grill on its 21-passenger boat, Lady Wauwinet. The inn also provides regular shuttle services to the ferry and Nantucket town (about 10 miles away), and outside of peak summer season will drive guests to the village of ‘Sconset in its 1947 Woody station wagon.

A classic New England bed and breakfast with a boutique hotel vibe, the Union Street Inn is housed in an impeccably maintained 1770 whaling captain’s home just off Main Street in downtown Nantucket. A short walk from the Hy-Line ferry and harbor, the inn has a convenient location in town (including parking, a huge perk on the island) and can also outfit guests with beach gear for a day on the sand. A quintessential gray-shingled exterior contrasts with the bright blue chinoiserie patterns and crisp white Frette and Matouk linens in the inn’s 12 immaculate rooms. Union Street’s cherry on top is the made-to-order gourmet breakfast, which might feature fresh peach cinnamon rolls or homemade carrot cake, depending on the season.

The water is usually calm and a bit warmer on the Nantucket Sound side of the island. Steps Beach is off Cliff Road about four miles from town, sandwiched between Dionis and Jetties, and is not on most people’s radar. Before you take on the massive set of stairs leading down, enjoy the view of Great Point Light off to the right. Steps Beach offers protected shores with gentle waves washing onto the sandy beach, and gray-shingled mansions dotting the surrounding sand dunes. Come prepared, as there are no lifeguards or facilities, and make sure to save some energy to make the climb back up the steps.

The Common becomes extraordinary on winter evenings when the Christmas tree is up and soft lights seem to hold back the twilight chill, but the truth is there’s no bad time to visit the nation’s oldest public park. The former cow pasture has been a focal point for Boston’s history and culture since its inception in 1636—a site for riots and rallies from the Revolutionary War to the Vietnam War era as well as weddings, hangings, and burials. Summer splashing and winter skating at the Frog Pond are local traditions, and you can spend hours wandering from landmark to landmark (like Augustus Saint-Gaudens’s famous bas-relief Memorial to Robert Gould Shaw and the Massachusetts Fifty-Fourth Regiment, or the Soldiers and Sailors monument atop Flag Staff Hill). Or you can just laze in the sun on the park’s west-side lawn.

Nothing defines Boston quite as much as the town’s devotion to sports (10 championships since the turn of the century doesn’t hurt), and with all due respect to the five-time-Super-Bowl-champion Patriots, it’s Fenway Park, not Gillette Stadium, that’s the temple of sports fandom. Opened in 1912, the quirky green bandbox between Lansdowne Street and Yawkey Way is almost as famous for its obstructed-view seats as it is for its fabled Green Monster wall in left field, but that’s a price Sox fans gladly pay in exchange for maintaining Fenway’s historic layout. It’s both intimate and loud on game day even in years when the Sox aren’t contenders (tickets are often hard to come by, so plan ahead); the old ballpark also is open for one-hour, behind-the-scenes tours that take you inside and atop the Green Monster. You’ll be able to stroll around the field (the warning track, not the grass), and visit the press box, the Pesky Pole, and (on days with no games) the dugouts and bull pens.

At the beginning of the 20th century, a physics professor in Massachusetts inherited a ton of money. He promptly headed for the South Pacific, settling there and founding what’s now the Harrison Smith Botanical Garden. Maybe Smith had a slight Noah complex: He brought in plants from around the world, which means an African flower might sit next to a South American fern. The problem is that he inadvertently killed off the native plants with his imports. Still, the garden is a lovely spot to wander around, a sampler box of world botany.

One of the most popular spots on the island, Cisco Brewers began as a winery 25 years ago and has now grown into a destination that showcases offerings from the Nantucket Vineyard, Triple Eight Vodka, and the Cisco Brewers beer label. Summer weekends there is a lively crowd listening to music and taking advantage of the food carts and raw bar. For a tour and a more intimate view of the production, visit during the week. There is a seasonal shuttle available and the new bike path makes Cisco all the more accessible.

Galley Beach has one of the best locations on Nantucket. With views out over the ocean from the dining room and tables spilling onto the beach, there’s not a bad seat in the house. It’s a popular spot with a stylish crowd, and the martinis flow freely. Come early to snag a seat for sunset, one of the best shows in town, and as the evening gets underway enjoy the breeze on your face and scrunching your toes in the sand while tiki torches light up the night.

It’s easy to stay health-focused, even on vacation, if you stop by the Lemon Press. This adorable space in the middle of town has fresh cold-pressed juices and super smoothies. Liquid Sunshine is a winning combination of mango, peach, and organic apple juice. And if you are looking for damage control from the previous evening, try the Scenic Root or Georgia Green. Both will help you get back on track. Also on the menu are delicious sandwiches and photo-worthy toasts.

For an especially scenic drink, try the umbrella-shaded Beachside Bistro at the Summer House. Down a flight of stairs into the gentle dunes, you can’t get much further east unless you want to go swimming. A full bar is available and you can snack on the likes of lobster salad or crab cake. Come at sunset, and even though you won’t see the sun itself, the entire sky glows pink and dreamy as the waves roll in.

Cru is a spectacular location for a drink, with the harbor and Billionaires Row as its backdrop. The outdoor patio is great for people-watching, as is the silky-smooth stone-topped bar. The tart and refreshing Crucomber is the signature cocktail: a mix of bison grass vodka, lemon, cucumber, and toasted sesame. If you want to snack, the cocktail pairs well with any of the delightfully fresh crudos and oysters on the menu. After a few, take a walk along the pier and fantasize about life aboard a luxury yacht.

Award-winning Nautilus offers seasonal cocktails, over 20 wines sold by the glass, and an extensive list of mezcal, beer, and sake. Warm and friendly, this is the kind of place where you’ll no doubt meet the folks sitting next to you at the bar. Owned by a threesome who know their way around the industry, the lively, hip scene almost feels like you’re at a cool friend’s cocktail party.

Mile-long Newbury Street, lined with handsome 19th-century brownstone homes, is synonymous with shopping in Boston; it’s also the place to go to get your hair done up nice. Between Arlington Street and Massachusetts Avenue you’ll find an eclectic mix of boutique and designer shops, hair salons, art galleries, and restaurants that generally skews upscale (Tiffany’s, Chanel, Dolce & Gabbana) but also includes the original location of the Newbury Comics record store and a T.J. Maxx. Eminently strollable and dotted with sidewalk cafés, Newbury Street is the hip heart of the Back Bay neighborhood, perfectly distilled at eye-candy drinks-and-dining hot spots like Sonsie and Stephanie’s on Newbury.

“What better way to understand yoga than to travel to its birthplace?” says Katie Christ. Two years ago, the food stylist put her life in San Francisco on hold to spend two months studying at the Ramamani Iyengar Memorial Yoga Institute (RIMYI) in Pune, India. “It was the biggest luxury I have ever allowed myself.” Katie had been practicing Iyengar yoga, a style of hatha yoga that focuses on alignment and uses props like blocks and belts, for more than 10 years when she decided she wanted to study in India.

She applied to RIMYI, where the venerable B.K.S. Iyengar (above), the founder of Iyengar yoga, occasionally teaches with his son and daughter. “It’s not for the faint of heart,” says Katie. “There’s no music. No incense.” RIMYI requires each applicant to have eight years of Iyengar experience plus a letter of recommendation from his or her yoga teacher. Acceptance can take up to two years. The year before she attended, Katie traveled to Pune for two weeks to experience life in the city.

That first visit happened to coincide with B.K.S. Iyengar’s 90th birthday. “I had no Indian garb appropriate for the festivities, so I went shopping, and in one afternoon I saw so much. A woman making a rangoli, a traditional folk art design, let me try to draw one with colored powder on the street. At the market I saw a man whose sole job was to peel garlic bulbs. I tasted the most amazing chai, made by a chai wallah who used pliers to crush fresh ginger into a pot of milk with tea leaves and ground spices. I knew I wanted to stay. [On my second trip] these experiences would become part of my everyday routine.”

The institute doesn’t provide housing, so Katie used her first visit to find a flat to rent for her two-month stay. “I had the perfect commute: a 10-minute walk through a public garden where I would watch teens flirting on benches and women in saris and sneakers taking their morning power walks.” Classes were held six days a week: two-hour sessions led by a member of the Iyengar family and three hours of open practice each day, and an hour of pranayama (controlled breathing) once a week. “In open practice, I experienced incredible generosity from students who were advanced teachers,” says Katie. “If someone recognized that I was struggling, they would come over to help me achieve better alignment. Several times Geeta Iyengar [the daughter of B.K.S. Iyengar] called out to give me specific instruction.

I felt incredibly fortunate, considering there were up to 120 students in a class.” When she wasn’t in class, Katie and her Australian neighbors, all senior Iyengar teachers attending the institute, would hit the markets and seek out the best chai, Indian sweets, and chappals (sandals). On Sundays they took trips to sights like the ancient sculptures and paintings in the Ellora and Ajanta caves. Katie felt her body becoming stronger and her head becoming clearer with each passing day. “The goal of yoga is to calm the chatter of the mind. When I arrived I had tons of chatter,” she says. “After practicing so intensely every day for two months, the chatter became a murmur.”

From $450 for a one-month program, not including meals and accommodations. 91/(0) 20-2565-6134, bksiyengar.com. This story appeared in the January/February 2012 issue.