Marc Telio, Entrée Canada, Vancouver
A native Montrealer, Telio is well versed in the gamut of Canadian destinations, whether it's the pristine beaches of British Columbia's Clayoquot Sound, the charming villages between Montreal and Mont Tremblant, or the ice wineries of Ontario's Niagara Wine Peninsula. His connections can have you snowboarding with an Olympic gold medalist or taking a private cooking class with an Iron Chef (604-408-1099; marc@entreedestinations.com).

Caribbean
Terry McCabe, Altour, Paramus, New Jersey
Recommended Generalist
McCabe's tight relationships with luxury hoteliers—particularly with Four Seasons, Preferred Hotels, Rosewood, and Starwood's Luxury Collection, since she sits on those companies' travel agent advisory boards—translate into preferred treatment for her clients at many of the Caribbean's big-name properties. She favors islands where the Old Caribbean can still be found (e.g., the Grenadines) and long stretches of undeveloped beach with small hotels that won't break the bank (e.g., the Bahamas' Out Islands). Choose her if you want to visit multiple islands in one trip—she's a whiz with airline logistics (201-477-7000; terry.mccabe@altour.com).

Becky Veith, Becky Veith Travel, Erie, Pennsylvania
Veith's frequent trips to the Caribbean have left her with encyclopedic knowledge of the all-inclusives and the ability to match you to the right beach getaway at the right price. Choose her if you're taking the kids (814-866-5721; becky@travelxperts.com; beckyveithtravel.com).

Costa Rica
Leigh Ann Cloutier, Rico Tours, Austin, Texas
Cloutier spends about six weeks a year in Costa Rica and is familiar with all the country's landscapes, from its lush cloud forests to its rocky volcanoes. Though she particularly enjoys directing her clients to up-and-coming destinations such as Canto Ballena—a whale-birthing area Cloutier calls "the next great beach location"—she gets equal pleasure from scouting the best hotels, always in a variety of price ranges (512-303-0001; lac@ricotours.com).

Richard Edwards, Green Spot, Billings, Montana
Edwards spent 12 of the past 20 years living in Costa Rica and now returns annually for at least 2 months. Passionate about responsible and sustainable travel, he guides clients to properties that combine the best creature comforts with a dedication to reducing their environmental footprint (877-891-3539; richard@greenspottravel.org; greenspot.travel).

Ecuador and Peru
Clark Kotula, Geographic Expeditions, San Francisco
A former Cusco-based guide who lived in Peru for eight years, speaks both Spanish and Quechua (the native language), and still has a ton of friends there—whom you may well meet in the course of your travels, as they own the restaurants and manage the inns—Kotula arranges everything from hard-core treks to villa vacations. His network of handpicked guides and drivers can take you beyond Machu Picchu to treasures such as the Huacachina Oasis—the largest sand dunes outside the Sahara. Kotula brings similar expertise and connections to bear on the places he often explored when he lived in South America: Ecuador, the Galápagos Islands, and Colombia, which Geographic Expeditions is adding as a destination in 2009 (800-777-8183; clark@geoex.com).