Walt Disney World®

For many families, a trip to Disney World is a time-honored rite of passage. The iconic theme park offers a chance to indulge in childhood fantasies of magic and adventure—all in one centralized location. Tammy Sofonia, an American Express Travel Specialist, has been there 72 times, and each time she falls in love a little bit more. “There are 25 hotels to choose from down there,” she says. “Between the resorts and the theme parks and Hollywood Studios and all the special events, it really is a different experience each time.” Sofonia encourages her clients to stay for at least four days on each visit, since there are four theme parks to hit up: “A misconception is that there is nothing to do at Epcot Center, but actually two of the top rides are there: Nemo and the Test Track.” The best bet for seeing all four parks in one trip is to stay at a hotel on the monorail; the extra price is likely worth the convenience. Plus, many of the rooms can sleep up to five people, so larger families don’t need two rooms. “Grand Floridian, Contemporary and Polynesian are the high-end resorts, but they save you so much time,” Sofonia says. Looking to keep the cost down? Consider going in the summer, when specials include 30 percent off rooms, or fall, when kids eat for free.

Turks & Caicos

Beautiful beaches. Freshly caught fish. Kid-focused resorts. The Turks & Caicos has become one of the Caribbean’s most popular destinations because it has invested heavily in protecting and developing its own natural resources. Direct flights arrive from as far west as Dallas, allowing families to frolic in the turquoise sea before lunch. Luxury hotels along Grace Bay have thoughtful amenities: Grace Bay Club separates families from singles within its resort, and has opened a luxury all-inclusive, Verandah, right next door. Then there’s Beaches—the classic family all-inclusive resort—which has partnered with Sesame Street, Xbox and Crayola to provide quality entertainment for all ages. “Grace Bay Beach allows guests to walk up to the watersports desk and grab a snorkel and mask, then walk down the beach to some of the best snorkeling anywhere,” says Kelley Murray, a Vermont-based American Express Travel Insider. “Last time I was there we saw stingrays, sea turtles, all kinds of colorful fish, eels, even one lobster.” She’s been to every Caribbean island in her 30 years as a travel agent, but keeps going back (and sending clients back) to Turks. “It’s the sort of place where the kids are never bored. And when the kids are happy, the parents are happy,” she says.

Greek Isles

Dewayne Gill, an American Express Travel Insider, has been to Greece four times recently, and he’s ready to go back. He considers it a truly singular family destination. “Number one, it’s educational—there is so much history,” he marvels. He likes to spend just a day in Athens to visit the Acropolis and the Museum of the Acropolis, and then move on to Plaka, the oldest part of this ancient city. Then he boards a ship. “Instead of flying from island to island, a cruise,” he says, "brings the island up close." Gill waxes poetic when he thinks about the moment his most recent cruise ship pulled into Santorini, which looked like a snow-topped mountain from a distance. “I like to take the donkeys round and round to the top of the island, where every house is painted white with blue roofs; it’s just magical,” he says. His other favorite family spot is equally as inspiring: Mykonos, striped with windmills and narrow roads, evokes a simpler way of life, a place where kids can personally witness how the Greeks really live today.

London, England

London has often been one of the first—if not easiest—destinations for families traveling abroad. There is little language barrier, direct flights from most U.S. cities, and an extensive public transportation system: the city offers an ease of travel unlike by any other European city. Now the city offers so much more. The West End has brought successful runs such as Matilda and Les Miserables to stateside theater districts. The London Eye has given new meaning to what a Ferris wheel can be. Los Angeles–based Brendan Vacations specializes in trips to Britain, and begins nearly every holiday further afield with a jaunt through London. Some of the best-known sites—Big Ben, Westminster Abbey, the Victoria & Albert Museum of Childhood, the Tower of London and Parliament—are always on the itinerary, but during downtime, travel professionals like Daniel Guerrero, director of marketing for Brendan Vacations, encourage guests to dive deep into whatever interests them. And there is no obscure hobbyist that won’t find their fill in London. Like Sherlock Holmes? He’s got a museum. Like gore? Try the Dungeon. Into food? Head to Borough Market and chat up the butchers. There’s even The Golden Hinde, Sir Francis Drake’s galleon, moored in Pickfords Wharf, which offers a look into historic pirate lore.

Mexico

Unlike so many other beach retreats, the country of Mexico meets many of the requirements of a successful family beach vacation. There is culture, food, quality service, a wide range of beaches and direct flights from across the U.S. “Resort destinations in Mexico can make sense for families who like a little variety, not just a beautiful beach,” says Angela Armutcu, an American Express Travel Insider. She sends her clients to the ancient Mayan ruins along the Caribbean, to the unspoiled colonial towns in the Yucatan, and to the rugged landscapes of Cabo San Lucas, where artists still live in communities much as they did decades ago. Armutcu admits to having to do a little extra prepwork for some clients—the country is vast, and most resort towns are far from the headline-making border cities—but once she gets them down there, Armutcu finds her clients energized by the choices offered in Mexico. More often than not, they come back yearning to return to somewhere else within Mexico’s borders. “There are at least 100 properties on that Caribbean side of Mexico alone,” Armutcu says. Many, she continues, are priced below their Caribbean counterparts, yet offer equal levels of service and accommodation. “And the Caribbean doesn’t have the rich history that Mexico does.” Recently, Armutcu spent time in Punta Mita and Puerto Morales, and was impressed by their family offerings. “I always say: I went last year, and the year before, and I’m going again.” The best part about going back? “There are always beautiful new places to discover.”

Cruise to Alaska

Much has changed on the Inside Passage of Alaska. “A few years ago, it was not a kid-friendly destination,” says Judy Martinez, an American Express Travel Insider. “Grandma and grandpa liked to go there, but it was very unattractive to young people.” No infrastructure meant passengers were stuck on a ship that offered little in the way of diversions. Recently, Martinez says, “The destination realized...that most families don’t only want sun and fun—and Alaska really is the final frontier in the U.S.” While families and older couples still come out for the awe-inspiring feeling of being up close and personal with the glaciers and fishing villages, the cruise lines themselves are altering the perception of the place. Regent Seven Seas Cruises, for one, has an explorer program in which kids learn about the effects of global warming on the glaciers and how that can impact life in Los Angeles or Miami. Bigger companies like Princess Cruises have added outdoor movie theaters and activity programs for young people. As a result, “the average age of a cruiser there has come down 15 years,” Martinez says. “And you should see the look on the faces of those kids when a naturalist pulls up a piece of crystal clear glacial ice. That image is exactly what grandma and grandpa want in their photo album.”

Kenya

An African safari is considered by many to be a trip of a lifetime. In Kenya’s Masaai Mara, however, the safari experience truly comes to life. This is where the annual Great Migration takes place, where up to four million wildebeest traverse the savannah in search of water and food. Every zoo you’ve visited pales in comparison to seeing this incredible struggle for survival before your very eyes. “Going on safari as a family is something you’ll treasure forever,” says Pieter Boerma, of Wilmington, Delaware-based Kensington Tours. “Staying in our tented camp in Kensington Mara West, you can hear the animals at night and get to visit the local tribes in the day.” On a typical itinerary, Boerma advises clients to spend a day or two acclimating in Nairobi; then he sends them to Naivasha, “an area known for its rhino and flamingos.” By boat, families get to view the animals from the water, then walk along Lake Crescent Islands to glimpse the herbivores. Next stop before heading deep into the bush: an elephant orphanage, where families can bathe and even sponsor a baby. For every family, Boerma recommends a few solid days in the Mara, mixing up safari drives and daily village visits to keep kids engaged—even though there is a strong chance to see the Big Five on every game drive. Quite frequently, he hears from parents that the highlight of the trip wasn’t spotting the pride of lions, it was making bows and arrows with Masaai warriors. This is the kind of trip, Boerma adds, that your kids will want to share with their own children one day.