What sort of traveler uses The WOW List?  You might assume it’s travelers who can’t plan their own trips, but you’d be wrong. It’s people who have planned so many trips so well that they have an exhaustive grasp of just how much you miss out on when you don’t utilize the best local expertise and connections—and a deep appreciation of just how much time and effort such meticulous planning takes.

Jeff Bernfield, for instance. He’s a physician from the Chicago area who has used Wendy’s recommended Trusted Travel Experts (TTEs) more than anyone else—a whopping 15 times. With his wife, and sometimes with the rest of his family, he’s been all over the globe on trips arranged by these destination specialists, including Italy, Africa, England, Japan, Costa Rica, the Galapagos Islands, Norway, even Disney World. As you’d expect, he’s got a lot of tips to share when it comes to collaborating with travel specialists. So, in a phone call after a trip to Florence, Italy (where Wendy surprised him with a WOW Moment loyalty reward), we asked Dr. Bernfield to share his advice for how to get the best trip possible.

You’re more than capable of arranging your own travel. Why do you use The WOW List?

I could plan each trip myself—I’m a voracious researcher—but it’s so much easier to let one of these experts plan the whole thing for you and not worry about what could go wrong and what you’d do if something went wrong. I never ever have to worry because, even if something might go wrong, they fix it. They always fix it. It doesn’t happen very often, but it’s like having an insurance policy.

How do you choose which travel specialist to use for each trip?

What I usually do, I email Wendy. Wendy knows me by now, so I tell her where we’re going, and she’ll recommend the right one for me.

Do you read the reviews posted about each travel specialist on WendyPerrin.com?

I read all of the TTE’s reviews on Wendy’s site before contacting that TTE. I want to find out what that travel expert has planned and whether they’ve done something special—like, say, getting a traveler into Downton Abbey. I’ve never been able to get that; my wife is an obsessed Downtown Abbey fan but I couldn’t pull it off. My point is: If I read something in a review, that might tip my hand.

What’s most important to you in a travel planner?

I’m pretty big on communication and being accessible. Some Trusted Travel Experts are just incredible and if you shoot them an email, you get a response in ten minutes.

Do you prefer email or phone?

I definitely like the phone call. I always like to talk to somebody and know who I’m dealing with before I do business with them. And I like to have a back-and-forth discussion. I’m not the kind of person who says give me an itinerary for Southeast Asia and then I just do that itinerary. That’s not my nature. I like to pick people’s brains. I ask them: Why are you recommending this over this? I do a lot of reading, so maybe I’m on somebody’s dartboard somewhere [Laughs], but I like to have discussions about the itinerary.

In that first phone call, what should a traveler tell the Trusted Travel Expert?

I’ll tell them from the start what I’m looking for, and I’ll ask what are some of the things you offer, and then I’ll listen. I also ask about private experiences, since we like to dig into the culture and history. I always tell the TTEs: Let’s do something different, something that other people won’t do, don’t know to do. When we planned our trip to Japan, the Trusted Travel Expert sent us a list of 20 private experiences and told me to pick from them. I picked them all. I’m not saying everyone can or should do that, but I think if you like doing things different, that’s one of the advantages of having these experts plan your itinerary. So you’re not just going to the Louvre, not just doing the things any travelers can do; you’re going to someone’s home, taking a cooking lesson, taking a samurai sword lesson, meeting a priest at a high temple. In Italy we got to go to a dairy farm and see how they make Parmigiano-Reggiano cheese. If you like doing different cultural experiences, there are a lot of assets that people on Wendy’s list have that I would try to find out about.

What are some of the questions travelers should ask?

I start with: What do you offer that’s different from the average tourist things? What cultural experiences can you access? Example: My wife is a picky eater. It so happens that she loves pizza, but in northern Italy pizza is not as common as in southern Italy. I told our Italy travel specialist, Maria, that my wife loves pizza, and would it be possible to take a pizza-making lesson?  At first she said, “Huh, I don’t know, pizza’s not that popular in northern Italy.” But she called me back a couple hours later and she said, “I got it!” She had arranged for us to meet a chef who would give us a pizza lesson. I asked the question, I didn’t know what kind of answer I would get, but if you have something specific in mind, ask for it—because even if they don’t normally do it, unless you ask for something impossible, they’re going to try really hard to accommodate your request. That’s important.

What else is important to communicate to your Trusted Travel Expert?

You have to know what you are and what you want. We don’t like beaches. We don’t like to sit around and do nothing. Some travel specialists will schedule you starting at 11am, but we get up at 7am. So you need to know what you want and ask the questions. Then we can figure out if they can handle my needs. It’s like anything else: You talk to somebody. Some are easier to talk to, more communicative, have an easy-going personality—but you figure that out quickly. That’s why a phone call is so important.

Thinking about reaching out to a WOW List travel specialist? Wendy’s got key advice for you too: How To Get The Best Possible Trip.