Make Your Next Trip Extraordinary

How to Get an Extraordinary Trip That’s a Great Value: FAQs

by Wendy Perrin | June 14, 2022

Wendy answers your Frequently Asked Questions about how to collaborate with a Trusted Travel Expert to get the best possible trip.

1. The Trusted Travel Expert wants to schedule a phone/Zoom appointment to discuss my trip. Is that necessary?

Yes. The Trusted Travel Expert (TTE)’s job is to design a trip tailored to your needs and interests, which means you need to be specific, thorough, and honest about what those needs and interests are. The TTE has a lot of important questions to ask and will glean much more telling answers in a live conversation than via email. The design of your trip is a collaboration, and what you get out of that collaboration is directly related to what you put into it and the care you take in articulating your trip goals and answering the TTE’s questions thoroughly.

2. Can I delegate that conversation to someone else—like my assistant?

No. That would be like sending your friend to be fitted for your custom-tailored suit. The live conversation allows you to hammer out your trip preferences, dislikes, and goals in depth. After the phone call, if you think the TTE does not “get” you, call it quits. If there isn’t a good rapport, that’s a signal that you need to ask me to connect you with a different TTE. (Email me at

3. Does it cost more to use a Trusted Travel Expert than if I book the trip on my own?

It depends on the destination and type of trip. TTEs can save you money via reduced rates that they negotiate with hotels and other travel suppliers at their destinations. They negotiate special benefits and amenities too (e.g., early check-in, upgrades, complimentary meals). At the same time, their arrangements can cost more because they employ the best local private guides whom they have personally vetted, they use the newest cars and safest drivers who know all the shortcuts, they pay to eliminate time-consuming hassles such as lines and crowds, etc. Their trips include special touches and perks that you would not be able to procure on your own—and most of these special touches you won’t know about, or appreciate the value of, until you’re actually taking the trip. Their prices also include the local infrastructure to be able to come to the rescue in an emergency. So, typically, you’ll pay more than if you booked on your own, but you’ll end up with a more rewarding trip in the end. If a TTE doesn’t convince you that the value they will add to your particular trip will be worth the higher cost, don’t book through that TTE. Feel free to reach out to me at Ask Wendy, and I can try to suggest someone else.

4. Do Trusted Travel Experts charge trip-planning fees?

It depends on the type of trip, the destination, and how much work and time are required. If the trip is a cruise or a five-star resort stay with no customized components, usually the travel supplier pays a large enough commission, and not much work is required on the TTE’s part, so there is no fee. If the trip is a custom-tailored itinerary, often there is a fee. Ask the TTE to explain what their fee is and everything you get for that fee.

5. Is the fee a deposit toward the cost of the trip, or is it an additional charge?

Sometimes it’s a deposit—this protects the Trusted Travel Expert in case they do a ton of work on your behalf and then you cancel—and sometimes it’s an additional charge. Often the fee takes the form of a mark-up that’s incorporated into the total trip price you’re quoted. In such cases, you may be quoted a lump-sum price for your itinerary, with no breakdown of the prices for its different components. This lack of transparency, which is standard practice in the luxury travel-planning world, can be frustrating for prospective travelers. But the fact is that the local hotels and other businesses that provide the Trusted Travel Experts with exclusive reduced rates do so on the condition that the TTEs not reveal those rates. Sometimes a planner is able to provide a partial breakdown, either by day or by type of expense (e.g., accommodations, private guides, transportation). If you’re presented with a lump-sum price and need to cut costs, explain that you’d feel more comfortable investing X thousand dollars in this trip, and ask the planner how they would suggest that you reach that figure.

6. What’s in the price that the Trusted Travel Expert will quote me?

The TTE’s price almost always includes more than just accommodations. (It’s easy to book hotels on your own, after all—although, unless you’re using an expensive credit card with serious hotel benefits, you won’t get the same preferred treatment.)  The price quoted by the TTE will likely include private and exclusive travel experiences and transportation that may cost more than generic sightseeing tours.  So, when coming up with your estimated daily budget for a trip, don’t factor in only the price of accommodations.

7. If I find a lower price on the Internet than the price a Trusted Travel Expert has quoted me, what should I do?

You should let the TTE know this and request an explanation as to why their price is higher. Often, if it’s a hotel, the TTE’s price will include extras (e.g., taxes, service fees, daily breakfast, early check-in, an upgrade) that are not included in the price you see on the Internet. If it’s an activity or excursion, the experience that the TTE is recommending is probably not the same experience that you’re finding on the Internet. And remember that Internet rates often come with surprise charges. So be sure you’re comparing apples with apples.

8. If I have already booked most of my trip, should I contact a Trusted Travel Expert for just a few small components?

No.  If you’ve already booked all your hotels, for example, and all you need is a guide for two days, it will not make financial sense for you to use a Trusted Travel Expert. Every excellent travel specialist’s business model is based on complete trips, typically of five days or longer, embellished with all the special touches and insider experiences (based on superlative on-the-ground connections) that sophisticated travelers appreciate. The fewer and smaller the trip components you ask for (e.g., a tour guide or private car for a day), the more the TTE will need to charge for each component, and the less value for money you will receive overall.  By contrast, the more of your trip a TTE designs and books, the more they can save you wasted time, money, and pitfalls at your destination, get you special treatment, and be your advocate in case of unforeseen circumstances.

9. Is there a benefit to me to connect with the Trusted Travel Expert via

Yes. First, the Trusted Travel Expert will mark you as a V.I.P. traveler, which means that, when and where possible, you’ll get special benefits and priority treatment. Second, your trip gets entered into the trip-support service. Additional benefits are explained here: How To Get The Best Trip Possible.

10. What’s the trip-support service?

I’ll automatically watch over the planning of your trip; my team and I will keep tabs on your experience to make sure that the TTE lives up to their pledge and upholds the values that got them onto The WOW List in the first place. I will send you advice (via email) during your trip-planning process; when you return, I’ll invite you to post a review of your experience. The goal is to make sure you’re getting everything you need from the Trusted Travel Expert; I want to ensure they’re living up to my standards. Your email address will not be used for any other purpose.

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    I always enjoyed reading your column in Conde Nast and always felt confident in the information you shared. I’m so glad I can use your expertise on future travel.

  2. Connie Streitz

    So excited to find your site. Followed your articles, suggestions of tour guides etc. from Conde Nast Traveler

  3. Doug Havely

    We have utilized Earl Starkey for a trip to Turkey, Donna Thomas for a trip to New Zealand and Wanda Radetti for aCroatia/Slovenia trip. All of them did an outstanding job planning extraordinary trips. They were easy to work with and absolutely brought a lot of value. Earl even stopped by a hotel we were staying at in Bodrum to say hello as he was on a business trip. This was totally unexpected but was a nice touch.

  4. Janet Sacks

    Thanks so much for all this information. My sister and husband have booked trips through you and IC Bellagio 4 times now.

  5. Armando D. Guerra

    Thank you! I appreciate the FAQ’s. Being that it’s my wife’s 50th birthday and we have some “picky” travelers. I want her trip to be “perfect”.

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