Where the Heart Is

On a sunny Tuesday afternoon in August, summer vacationers swarm Martha’s Vineyard, and The Richard, a hotel in Edgartown, is booked solid. So are its four nearby sister hotels, as they have been for much of the season. 

It’s easy to see why. In The Richard’s flower-filled garden, a fashionable visitor curls up among the cushions of a massive white wicker throne. At The Christopher, four blocks away, freshly baked chocolate chip cookies welcome guests to an elegantly eclectic midcentury sitting room.  

Down the street at The Sydney, Anne Tamer Hajjar ’90, G’95, the proprietor of all this hospitality, presides over a cathedral-ceilinged common room, chatting cheerfully with a curious school-age patron. 

As director of hotels for Hajjar Management, the Milton, Mass.–based property management and development company, Hajjar manages a growing portfolio of boutique lodgings, featuring high-end service and jewel-box-like rooms. Like her hotels, Hajjar is accommodating and chic with a playful streak—and like most of them, she came to this business as a second act. 

Hajjar grew up in a modest two-family West Roxbury home with her parents and two older sisters. Her childhood was “wonderful,” she said, but shadowed by fears for her pharmacist father, who had a heart attack when she was a kindergartner and remained sick, at times unable to work, throughout her school years. As a senior at Boston Latin School, Hajjar was thrilled to be accepted at Northeastern, her father’s alma mater, but pivoted to UMass Boston when her father’s failing health rendered her family unable to help her pay for college. He died when she was a freshman, and her oldest sister succumbed to cancer the following year. 

“It was just a horrible time period for me,” said Hajjar, who paid her tuition bills through long hours selling designer clothing at Filene’s. “It wasn’t fun, it was work. But you either take the option you’re given, or you curl up and die, and I certainly wasn’t going to do that. I wanted a college education, and I wasn’t going to blow it.” 

Hajjar fell in love with two things during her time at UMass Boston: her husband, Chuck, whom she met at a church dance, and her psychology classes. “I was very idealistic and wanted to save the world and empower women,” she said, “and psychology was so interesting to me.” After she and Chuck were married, she returned to UMass Boston to get her master’s degree in mental health counseling, first taking an internship at a shelter for victims of domestic abuse in Quincy, then a job as a counselor at a shelter in Cambridge. She staffed the crisis hotline and helped women and children make and carry out plans to escape their abusers and start new lives. 

“I really dove into that,” she said. “I’d come home at seven o’clock at night and go to bed so I could get up for work the next day. I had a great life with a great guy, and I thought ‘Everybody should have this great life.’” But the all-consuming work took a toll on them both—“you get these calls that just go right through you”—and with Chuck’s business growing, she left counseling to begin her own family. 

The seeds for Hajjar’s career as a hotelier were planted years later, when the family built a house on Martha’s Vineyard. 

“I kind of fell into it,” she said. She recalled joking to Chuck that the only way they’d be able to find parking in Edgartown would be to buy their friend’s eight-room hotel. “We both laughed about it, but a couple months later, we found out the friend wanted to sell it. And I said”—this time with conviction—“‘We need to buy that hotel.’” 

Chuck pointed out that she had no direct experience running hotels. But his company, Hajjar Management, was by then a partner in two hotels in Boston: the Charlesmark Hotel and the Harborside Inn. So he agreed to take the plunge. 

“That first year, he set a goal, and I beat his numbers. He was flabbergasted,” Hajjar said. “He said, ‘You need to find another place now!’ So little boutique hotels became my babies.” Since then, Hajjar has launched nine hotels: five in Edgartown, three in Newport, Rhode Island, and one in Salem, Mass. 

Though her careers are very different, Hajjar sees a throughline. “When I map it out, it’s about trying to elevate people and their energy and their power. With counseling, I wanted to help women see a better life for themselves. And hospitality is about making people happy and making them feel welcome and warm. I want people to feel at home. But better. A better version of home.” 

The winning hotel-ements 

What makes a hotel “boutique”? Boutique hotels are loosely defined as “stylish” and small—under 100 rooms, and often a fraction of that. But different sources offer differing criteria for these trending lodgings—from urban locales and luxury services to imbuements of “personality” and “je ne sais quoi.” Anne Hajjar told Beacons her recipe for a successful boutique abode. 

// LOCATION 

“Number one is obviously the location and the building. I love these historic buildings!” said Hajjar. For her, the sweet spot is a storied home in a picturesque coastal destination city. Her first hotel, The Sydney, occupies a 19th-century house that was built by record-setting whaling captain Charles Fisher. Her newest, The Merchant, in Salem, Mass., a mansion once visited by George Washington, is built over the home of a witch-trial executioner whose victims allegedly still visit. And her favorite? “It’s like kids, you shouldn’t pick a favorite,” said Hajjar, laughing. “But The Cliffside [Inn, in the Newport summer home of painter Beatrice Turner] is such a gorgeous building.” 

// DÉCOR 

“The décor: really welcoming,” said Hajjar, who is adamant about the power of collaborating with a great interior designer. “We go in and make them—I wouldn’t say modern, but updated, with bright colors.” Each of her hotels has its own design inspiration. With her Edgartown properties, it’s the personalities of their namesakes: her children. (Her eldest son gets his nod in the name of the Charlesmark Hotel.) “Just like my kids are all different, the hotels are all different. Similar amenities, but different styles.” 

// ATTENTION TO DETAIL 

Hajjar’s interiors are full of eye-delighting details, from quirky wallpaper to decorative flourishes—like The Sydney’s barnacle-shaped mirrors—that deepen their sense of place. She’s also careful to keep original elements that give the buildings their character. “I keep staircases, I try to keep woodwork,” said Hajjar. And never to be forgotten: “Cleanliness! You open up a drawer, and I don’t want to see sand in it. We are very vigilant.” 

// PERSONNEL 

Hajjar is quick to praise the team members at her hotels, who include local professionals, international students, and Vineyard teens, many of whom return season after season. “I have the best staff,” said Hajjar. “My managers and staff go out of their way. People so appreciate hospitality and kindness and a smile.”