Why settle for one paradise when you could live in two? That’s the theory that sends so many Sarasota snowbirds off on their annual summer migration. After all, we can’t have enough life in our all-too-brief span here, so alternating between two different but equally idyllic settings is a brilliant way to expand and enrich our time on earth. We asked some local snowbirds what drew them to their summer retreats—and what the rest of us should do and see there, should we venture into their neighborhood on our summer travels.

Recapturing the mystique of seaside childhood summers. Since childhood, Phil Kaltenbacher has summered on Martha’s Vineyard, that picturesque island of farms and fishing villages just off the coast of Massachusetts, and when he introduced it to his Norwegian bride, Unni, 31 years ago, she instantly fell in love with it, too. Although in recent years, “Hollywood has moved in,” the island still retains its beauty and tranquility, Unni says.

Every May, Unni and Phil leave Sarasota for a secluded Cape Cod-style home that overlooks Vineyard Sound, a lake, and a garden “that blooms with every flower you can imagine,” she says. Unni loves walking their dogs through the woods, playing golf, or showing the island to the many friends who stay in their guest house. And just as when he was a teenager, Phil spends his days boating and fishing—including gathering clams right outside their door for New England lobster dinners with clam chowder.

Among the highlights on Unni’s tours: the historic fishing village of Menemsha, including a stop at the take-out window of Larsen’s Seafood for just-caught lobster and clams to eat on the dock. Visitors also thrill to the colorful clay cliffs and sweeping sea views from Gay Head, and love Carly Simon’s eclectic little Midnight Farm shop in Vineyard Haven. And they always stop by Mad Martha’s for “the best ice cream in the world.”

Chilling out while watching the grass grow. While Sarasota swelters in the 90s, Neil and Sharon Moody are sitting on the spacious terrace of their lodge in Evergreen, Colo., listening to the rushing roar of the crystal-clear creek and watching elk wander by. Much like Sarasota, says Sharon, Evergreen attracts artists—including some of the former owners of their 1940-era mountain lodge. But unlike in Sarasota, where their days are packed with meetings, tennis and other commitments, the Moodys slow down and unwind in Evergreen. Neil feeds the trout in his pond, and Sharon reads stacks of books and cooks—that fresh mountain air inspires wonderful homemade soups and stews, she says. And though Denver is just 45 minutes away, “I don’t like to leave Evergreen,” she confesses—partly because their daughter and three grandsons live there.

Summer visitors can count on cool, dry mornings and afternoons in the 70s, beautiful blue skies and gorgeous flowers, says Sharon. In addition to hiking, mountain biking and seeing the sensational rock formations in Evergreen’s state park, she recommends enjoying a pitcher of beer and sandwiches on nutty, whole-grain bread at the nearby Bucksnort. “It’s like going back into another era,” she says, as you drive past little cabins overlooking a creek to arrive at the rustic restaurant.

Enjoying art and natural beauty. Elenor and John Maxheim actually have three homes—a winter residence in Sarasota, a summer home in Charlotte, N.C., and, two hours away, a three-bedroom retreat with a big stone fireplace and a wraparound porch on three wooded acres overlooking Grandfather Mountain in North Carolina. They built the mountain house, which is in Linville, almost three years ago, Elenor says, and they’re now spending about five months a year there. Their golf course is “the highest in the world,” says Elenor, “with views so spectacular you can hardly play golf.” The Maxheims, who are collectors, also appreciate that the well-known Penland art school nearby attracts a wide variety of artists.

Elenor recommends staying at Linville’s Esceola Lodge, a rustic but elegant inn complete with babbling brook, and sampling the casual Cajun fare at the nearby Louisiana Purchase. And if you love art, pick up a map for a self-guided studio tour. In just one day, you can see a “phenomenal” range of art, pottery and crafts as you watch artists at work right in their homes.

Savoring old-world sophistication. Before Gil Waters met Austrian-born Elisabeth, he’d been to Vienna and thought it was “as nice as any city in Europe,” in part because of the innovative planning that’s created pedestrian-only streets during the daytime in the city’s bustling historical center. After they married, Elisabeth, whose grown children live in Vienna, convinced him they needed a pied-à-terre there. Their apartment is small but within a short stroll of outdoor cafés, pastry shops, boutiques, castles and bustling street life—complete with Mozart-playing musicians. 

During the summers, they take in concerts and the opera, do lots of walking and enjoy such local fare as wiener schnitzel, red sauerkraut, and of course, those famous Viennese pastries. And because the city is so centrally located, Gil says visitors can use it as a jumping-off point to visit Prague, Budapest and other European cities. A good place to stay: the Hotel Europa, not fancy but respectable, and half the price of more famous hotels downtown.

Relaxing on one of America’s most golden ponds. The ultra-fashionable Hamptons may be where New York socialites create buzz in the gossip columns, but for former New Yorkers Howard and Carol Phillips, it’s a place to unwind from the frenetic pace of their Sarasota social life. From May to September, they live in East Hampton, considered one of the most beautiful villages in America, in a 5,000-square-foot, one-story house nestled into six acres overlooking famous Georgica Pond. Though they are surrounded by homes (including those of some of America’s most prominent people), from their living room they see only acres of water and green lawns and the tops of a few structures. During the week, they live quietly, golfing, playing tennis and barbecuing; on the weekends, the Hamptons come alive, but though they attend a few parties, it’s nothing like “the social life we’re involved with in Sarasota,” Howard says.

The main thing for visitors, Howard says, “is to figure out who you can stay with,” since East Hampton is a residential rather than tourist community. But he does recommend the Maidstone Arms, a lovely small inn with cottages out back, and says the village offers wonderful restaurants, from the famous Palm Restaurant to trendy little spots like Rick & Tony’s. His best tip for summer visitors? Schedule your trip against the crowds, spending your weekend in Manhattan, when everybody is out of the city, and the weekdays in East Hampton, when things are quiet.