Behind every travel-obsessed family, there is usually one travel-obsessed planner. That’s the person who does the research, cashes in frequent-flier miles, haggles for hotel upgrades, uncovers the best ice cream shops, and generally provides the momentum for the entire trip. Meet five travel masterminds (and it’s not always the mom or dad) who guide their families all over the globe. How do they do it?Read their tips—then follow in their footsteps!
Livia Corona Secrets of a Successsful Travel Planner
| Credit: Livia Corona

The planner James Chung, president of Reach Advisors, a marketing firm. He and his wife, Christine, a law-school professor, have two children: Connor, 6, and Caitlin, 4. Home base Slingerlands, New York

James used to work 70-hour weeks, so he rarely saw Connor awake for the first nine months of his life. Then he launched his own business, devising a four-day-a-week schedule that allows time for family—and travel, his passion. For now, the Chungs focus on U.S. destinations such as Cape Cod, New York City, and ski resorts in Colorado and Vermont. But James has plans for ancestral journeys to Korea and Ireland around the bend.

Before any big trip

I find children’s books and DVD’s relevant to the destination—when we went to Vail, I packed The Snowy Day. For a trip to Crested Butte, I printed out the trail map for Connor. This gets the kids excited about where we’re going.

Always with us

A digital camera. Once we’re home, we organize our photos with Google’s Picasa—it’s free, and so easy to use it practically does the job for you.

Key car accessory

We have a Thule Mountaineer car-top ski box, which we often use to stow luggage. It provides leeway when we’re packing; plus it enables me to see out the back and gives us a little elbow room.

Best time to go

Before Connor started school, we always traveled in the off-season. We’d avoid the tourist crush and get great deals. Every year we rent a house in Wellfleet that we found in the classified section of Harvard’s alumni magazine. We used to get the place for the whole month of September for what it costs to rent for a week in July or August.

Road rules

Now that we have to travel with the pack, I dip into frequent-flier miles for upgrades—it’s great to get off the plane first. On the road, we look for suite hotels so we don’t all have to sleep in the same room—otherwise we might kill each other!

The planner Alex Pommer, 16, high school junior. His parents, Danuta and David, own a dental lab. Home Base Warren, New Jersey

Not only does Alex actually like to travel with his parents, he plots out all the Pommers’ trips—one of many Internet-savvy teens who are calling the shots when it comes to family vacations. An honor roll student and member of a roller-hockey team, Alex has parlayed his planning know-how into a part-time job at a cruise travel agency. He can recite the names of all the hotels he’s stayed in, and loves ferreting out deals. Want a great place to stay in Helsinki?Ask Alex.

The research stage

First my parents and I decide where we want to go, then I start searching online for good buys. For a major trip, I’ll go to eight or nine big sites like Travelocity, Priceline, and, but you can often find deals in unexpected places. I was looking for a cruise two summers ago and stumbled across a great package on Continental’s site (we all have frequent-flier accounts with them). The rate was comparable to others I’d seen, but they were offering a room upgrade (a bigger balcony on a higher deck), plus miles for booking on their site. My dad was happy about that.

Orlando our way

We’ve been to Orlando 10 times and usually stay at the Hilton. It’s a four-star hotel right on park property, offering the same privileges that Disney-owned resorts do—but it’s cheaper. I got to bring a friend on one of our trips; he paid his airfare and my parents covered our room. It was great to have someone to go on the rides with—we couldn’t get enough of Test Track at Epcot.

Favorite hotels

We like the Starwood chain, which includes Westin and Sheraton. The Hotel Danieli in Venice, which is just a bridge away from St. Mark’s Square, is part of their luxury collection—I spent a night there on a trip through Europe I took with Weissman Teen Tours this past summer. The Hotel Kämp, in Helsinki, where my parents and I stayed in an enormous room with a marble bath a couple of years ago, is also part of the group. It’s my No. 1 hotel in the whole world.

Giving the local fare a try

In Estonia, we tasted bear (really salty); in Helsinki, reindeer in chocolate sauce (delicious).

Wish we were still there

Our trip on Grandeur of the Seas, one of Royal Caribbean’s smaller boats, was one of our best. We got to see the Bahamas, Cozumel, and Key West, and didn’t have to pack and unpack. The excursions were a little pricey, but worth it—we saw Tulum and the Mayan ruins, and my father and I tried snorkeling. On the days we were at sea, I went to the Teen Club and got to know some great kids. We still talk online.

Where we’re heading next

I’ve been obsessed with New Zealand ever since I did a school project where I created a 14-day bike tour through the southern part of the country. I researched hotels, activities, and logistics—and got an A+. Now I really want to go!

The planner Gail Gross, M.D. She and her husband, Georges Sulmers, a recently retired pilot for United, have six children between them: DeeDee, 17; twins Teri and Toni, 22; Claire, 26; André, 30; and Georges, 40. Home base Atlanta, Georgia

Gail, a busy ob-gyn, was the widowed mother of year-old twins when she married Georges, a pilot with three teens of his own. The couple then had DeeDee, but this Brady Bunch has never been housebound. Georges’ airline discounts meant Gail could take the three youngest on monthly outings to the Caribbean. Every winter the clan hit the slopes in Steamboat Springs or Vail, and they also took off on one or two big trips a year (Costa Rica, Rome, South Africa). Now, with almost all of the children grown, they still love to travel as a pack.

My never-fail planning method

For our trip to Egypt in 2004, I came up with a strategy that I now use whenever we’re going someplace exotic. I first go to a high-end tour operator’s site to see how they structure their excursions; I take that itinerary as a starting point, then find someone locally to do it cheaper. For Egypt, I e-mailed 20 travel agents—I found them on Google, and just cut-and-pasted the same query letter over and over. Once I got their responses, I rejected the highest and lowest bids, figuring they were unrealistic, then asked for references from the others. Some agents put in bids as high as $3,000 per person for an eight-day tour that included a Nile cruise and four nights in Cairo, but a company called KET Travel ( did it all for just $450 per person. And it was so terrific, we added extra days.

Unforgettable vacation

Georges thought I was crazy years ago when I told him I was bringing the children (the twins were 8, and DeeDee was 3) dogsledding in Ely, Minnesota. Now he says it was our best family trip, partly because of our amazing guide, Paul Schurke from Wintergreen Dogsled Lodge ( We stayed at three different lodges and went from place to place by sled. The kids helped harness the dogs in the morning and mush them during the rides. It was yap, yap, yap all day, and so much fun.

The planner Diane Danielson, CEO of the Downtown Women’s Club, a Boston-based networking group, and mother of Andrew, 7. Home base Cohasset, Massachusetts

Diane grew up traveling—her parents would even take her out of school for trips to Europe—and she doesn’t let being a single mom stop her from hitting the road with her own son. She brought Andrew to the south of France when he was just 17 months old, and continues to go there with him every summer for two to three weeks (her parents own a second home in Ste. Maxime). The pair goes to the beach each summer, skiing in the winter, and somewhere else fun in between. The upshot: Andrew is a seasoned traveler who automatically removes his shoes at airport security and never, ever kicks the seat in front of him.

Single-mom strategies

We usually head places where I have a support system. We went to New York City one spring break because we could stay in the apartment of a friend who has kids. In Vail, we visited a family with three teenage daughters who were happy to babysit. No matter where we travel, I try to have some time alone. When Andrew is in ski or snowboard school, I head to the spa. And in France, my parents and son know that every day I go jogging and swimming—it’s part of the routine. But I do give Andrew a say in our plans. In France, we visit castles because he likes knights and dragons, and I suffer through Aqualand, a waterpark, at least once each trip.

On-the-go M.O.

When Andrew was a toddler, I had a stroller that converted into a car seat, TriplePlay’s Sit’n’Stroll, which was great for the plane and meant fewer luggage hassles. Now that he’s older, he hops on my rolling suitcase—belly-down, with both hands on the handle—and I can make it through a crowded airport always knowing where he is. If we’re traveling overseas, I book the latest flights possible so he’s tired when we board. On the plane, he changes into pj’s and sleeps.

Not strictly business

When I was asked to speak at Colby College, Andrew and I snuck in a weekend in Maine. The highlight was a place called Strawberry Hill Farms (, where we watched maple syrup being made, searched for beaver dams, and learned to spot deer poop.

Our trip wish list

We want to get to San Diego for the zoo, Legoland, and the Birch Aquarium. Looking ahead, I’ve asked Andrew to keep a log of places around the world he wants to visit someday. So far the list is movie-driven—Madagascar (because of the film, of course), Egypt (he was fascinated by the pyramids in The Prince of Egypt), and the White Cliffs of Dover (they’re in Chitty Chitty Bang Bang). Now I have to find a kids’ movie that takes place in Paris!

The planner Andrea Swenson, stay-at-home mom and school volunteer. Her husband, Paul, is a health-care executive. They have two kids: Lucy, 16, and Sam, 14. Home base Piedmont, California

Andrea has been toting her children to far-flung places since they were born. She took Lucy to the Cotswolds and Puerto Vallarta before her first birthday, and rented a villa outside Florence when Sam was just one (though, she admits, the 20-hour journey practically did her in). As a foursome, the Swensons have been everywhere from Botswana to Angkor Wat. There’s almost no place this gung-ho family won’t go.

Nobody does it better

We rarely use a travel agent—no one else is as obsessive as I am. Instead, I spend a ridiculous amount of time online rooting around for deals. I use Orbitz to research flights, then book directly with the airline—usually United (I’m a Premier Executive member, so I get double miles). For hotel rooms, I start on Orbitz, then go to the hotel’s Web site to make reservations—they often have deals that include breakfast or a free night’s stay. I follow up directly with the hotel for specifics, like bed sizes. We often stay on the club floor. You pay more, but you get the food and drinks they put out during cocktail hour; on occasion, after a long day of sightseeing, that’s supper.

Keeping the troops entertained

For car trips, audiobooks are terrific; we listened to most of the Harry Potter series that way. Now that our kids are older, they bring their iPods and portable speakers and we take turns sampling each other’s music. We always have a deck of cards on hand. We started with Uno, but these days we alternate between Hearts and Oh Heck! If it’s rainy, we get into these massively long games in our hotel room.

We’ll never forget…

Going to Beijing over Thanksgiving vacation. We had the Great Wall almost to ourselves. In Japan we visited Hakone, an hour west of Tokyo, and stayed in a ryokan, or traditional inn (, that overlooks Mount Fuji. We had a 16-course meal and slept on tatami mats.

Look what we brought back!

Last February, we hit Barcelona, Seville, and Madrid in a week. Lucy and I couldn’t believe the espadrilles only cost four euros. We each came home with seven pairs!