Facing dwindling budgets and ever-rising attendee expectations, incentive travel planners often must think creatively to execute memorable programs for VIPs and top performers. For example, when it’s too complicated or too expensive to fly large groups to far-flung destinations, hosting regional incentive events might just be the perfect solution.
The Northeast region contains many luxury locales to choose from. One successful program that leveraged the benefits of its location took place on Massachusetts’ island haven Martha’s Vineyard. When a New York City-based client in the banking industry approached KG Events & Design, based in Edgartown on the island, to help plan their company’s 2024 summer incentive program for 55 delegates, they were interested in staying local.
“They chose Martha’s Vineyard because of the remoteness and beauty the island offers while still remaining relatively close to New York City,” says KG Events & Design founder and Creative Director Kristen Gosselin. “With previous incentive trips, they would lose an entire day to travel, which was counterproductive to their busy schedules; having attendees fly in directly from New York City and the Tri-State Area meant they arrived in approximately 30 minutes.”
The group’s home base was the Harbor View Hotel near historic downtown Edgartown, which was the perfect fit for their needs. “It’s set back from town with stunning views of the harbor and [Edgartown Lighthouse], while also remaining walkable to town,” says Gosselin. “The hotel offers a very luxurious atmosphere with incredible hospitality.”
The group enjoyed a different dining experience each night of the trip, making their way around the island sampling cuisine that ranged from thoughtfully curated traditional American fare to meals that highlighted fresh, locally caught seafood. “Food was a very big part of the conversation from the beginning of planning this trip with our client; they wanted to prioritize healthy meals for their attendees,” explains Gosselin, who teamed up with a wellness partner, Ali Krupnik from MyWellCo, based in Beverly Hills, California, to serve as a liaison between the client’s needs and the entire food experience.
While the company held daily meetings, attendees also had ample free time to take scenic bike rides through Edgartown, cast lines with locally based fishing charter Boylermaker Charters, and kick back and relax on sunset sails through Vineyard Sound on Mad Max, a 50-foot catamaran. “Martha’s Vineyard is like an adult playground that offers a lot of versatility in activities and in the landscape,” says Gosselin. “The client loved that attendee activities were thoughtfully planned and aligned well with Martha’s Vineyard’s luxurious, laid-back atmosphere.”
Relaxing Retreat
Debra Tassone, director of sales for Discover Long Island, encourages planners to book incentive trips on New York’s Long Island because attendees don’t have to travel far to get an elevated experience across several regions. “Just minutes from New York City, it’s easily accessible via three airports, the Long Island Rail Road, and two ferry systems,” says Tassone. “Guests often feel they’re visiting a [far-off] destination they can’t quite identify—Italy, the countryside, a coastal village—yet they’re just a short distance from home.”
On Long Island, groups can explore the Gold Coast area’s historic mansions, gardens, and arboretums, or travel east to the North Fork, home of 60-plus vineyards, lavender fields, rolling farmland, and scenic country roads. For an upscale vibe, The Hamptons feature luxury lodging and stunning South Fork beaches. “While visiting Montauk, at the tip of our island, groups can go whale or dolphin watching, indulge in our spas, and receive the royal treatment at our beachfront properties,” says Tassone.
Paula Reynolds, owner of Paula’s Concierge Tours in Sparta, New Jersey, hosted a group of 40 retail employees from Australia last September who were seeking water-based adventures. During one portion of the trip, Reynolds whisked attendees by seaplane from New York City to Sag Harbor, a historic village on the east end of Long Island.
“We gave people free time to walk down Main Street and shop, then we chartered a sailboat and went out onto Gardiners Bay for a relaxing day full of music and laughter,” says Reynolds. On the party bus back to the city, attendees enjoyed wine, beer, and snacks. “There was lots of laughter and fun,” she adds. “That’s how you measure [the success of] what you do, by the volume of [the collective] laughter.”
Reynolds also has organized incentive programs at Wölffer Estate Vineyard in Sagaponack, New York, in the heart of The Hamptons. “I think the vineyards are overlooked on Long Island,” she says. “You can’t experience this in New York City.” She notes Wölffer Estate offers a notable lunch program during which attendees can tour the vineyard then visit the tasting room.
“In my prep, I find out what people are interested in and then I fill in my venues,” says Reynolds. “That’s how you become successful.”
Big-City Experience
“Boston is perfect for incentives because you can get from the airport to downtown with minimal traffic in less than 30 minutes,” says Kimberly McCarthy, general manager of Portfire Events, an event-planning company based in York, Maine, that services all of New England. “The biggest draw is that Boston has something for everyone: There’s a lot of history for people who are interested in getting immersed in the destination, and we bring people over to Harvard University and the Cambridge area as well. We do walking tours and get people on the water doing schooner excursions, talking about lobstering and oysters.”
Last August, McCarthy brought 400 attendees who worked for an insurance company and came from across the U.S. to Boston. Home base for the three-day program was The Westin Copley Place, Boston, where the welcome reception featured themed decor and food throughout the ballrooms that represented the city’s many diverse neighborhoods.
“That first night, [attendees] really got immersed in the Boston experience,” says McCarthy. The reception featured areas decorated as the Boston waterfront, the Cheers Boston bar in Beacon Hill, Fenway Park, the North End, and more. The North End setup included a live cannoli-filling experience for dessert.
The next day offered a chance for people to explore on their own or choose from eight activities, including bowling, a history tour of The Freedom Trail, walking food tour, and more. “We had rides on the Adirondack II and Adirondack III [schooners], [toured] a movie trail to see all the famous locations where Boston-set movies have been filmed, and did ‘Behind the Base,’ an exclusive experience at Fenway Park where attendees get to go behind the ‘Green Monster’ [left-field wall],” says McCarthy. The group’s off-site dinner took place at the Museum of Fine Arts Boston. “They closed down the museum and held an exclusive experience for [the attendees] that included seeing the ‘Van Gogh: The Roulin Family Portraits’ exhibit,” she says.
Hidden Gem
“When people think of Maine, they think of the wilderness, the woods, and the moose,” says McCarthy. “Most don’t know about southern Maine, so they’re missing out on the coastline, the beautiful hallmark setting we have here, and the small towns.” McCarthy brought 146 delegates from across the U.S. who work at an Iowa-based insurance firm to southern Maine last June. McCarthy says this client typically rotates their incentive destinations between the East and West coasts, and selected Maine this time for a fresh, distinctive East Coast experience.
“Maine offers a unique blend of seaside charm, authenticity, and understated luxury,” McCarthy says. “Its quaint, seaside towns; scenic landscapes; and relaxed pace create an ideal setting for high-performing attendees seeking a destination that feels both rewarding and genuinely memorable.”
McCarthy’s team immersed attendees in the locale with a surprise and delight at each stop. One highlight of the program was the tented clambake held at The Viewpoint Hotel in York overlooking the cliffs, with stunning views of the photogenic Nubble Lighthouse.
“Attendees were welcomed with wine and locally made craft beer, complemented by interactive and regionally inspired elements, including an oyster-shucking station, lobsterman demonstration, and a live painter capturing the experience,” says McCarthy. “We highlighted the rugged coastline of Maine in our tablescape with area rocks, florals, and grasses.”
The upscale host property, Cliff House Maine in Cape Neddick, offered dramatic oceanfront views, while dine-around venues The Front Porch Piano Bar & Restaurant and M.C. Perkins Cove in Ogunquit, and The York River Landing and Nick’s Steakhouse in York, provided a range of tasting experiences that showcased the region’s culinary diversity. A mix of leisure and experiential activities included golf, whale watching, sailing excursions, lobster-boat cruises during which attendees got to pull up a trap and touch a live lobster, and shopping trips via trolley to nearby coastal towns. Client feedback was overwhelmingly positive, reports McCarthy.
One universal key to hosting a successful incentive program? Giving your attendees time to enjoy all the host location has to offer at their own pace. McCarthy notes, “Maine’s coastal towns offer a storybook-like atmosphere, and building free time into the schedule for exploration enhances the overall experience and leaves a lasting impression.”
