How Can You Plan Me A Trip To A Place You Haven't Been?

Photo courtesy of @caitlinsoutherlevine and @fromthesaltmine, two honeymooners I sent on a kickass trip to New Zealand, A PLACE I HAVE NOT BEEN.

Photo courtesy of @caitlinsoutherlevine and @fromthesaltmine, two honeymooners I sent on a kickass trip to New Zealand, A PLACE I HAVE NOT BEEN.

A question I get asked frequently is:

“How can you plan me a trip to a place you haven’t been?”

A fair question, and probably one I would have been asking prior to joining the travel industry.

I have two answers:

  • My job isn’t to be an expert in a particular destination; it’s to be an expert in you.

  • Planning a trip when it’s your profession isn’t like planning a vacation for yourself.

This is gonna be a long one, so settle in, kittens.

Becoming an expert in you

My job, principally, is to discern what it is that you really want and need from your travel experience. For some clients, this is really easy to articulate. For others, they need a lot of nudging to give me the details I need to prepare really exceptional experience.

I have an intake form that has a wide variety of questions on it. The reason I ask things like “what’s a restaurant you’d go to on a special occasion?” or “when you picture yourself on this trip, what are you doing?” is I’m trying to get as much information as possible. The best clients are ones that come out right away with the more personal things, like “I’m afraid to fly” or (my personal favorite) “we can all ride horses but none of us can ride a bicycle.” Cool…that helps me and my destination partners come closer to a bullseye with our first efforts which, in turn, makes you feel valued and respected. And don’t we all want to feel that way?

The more I know about you, the more of an expert in You I become, the more targeted my initial proposals are…you can get on with the delicious anticipation of a well-planned trip without any of the headaches of actually planning.

When I would plan my own vacations, prior to starting Anthology Travel, my process looked something like this:

  • Decide where to go.

  • Check google flights to see what the options look like; book cheapest flight possible that doesn’t have multiple layovers.

  • Go to TripAdvisor and check the hotel rankings; find hotel in mid-range price point and either head to Expedia to book or check out apartments at VRBO.

  • Obsessively research where to go shopping in said destination.

  • End up having mediocre food experiences, spend a lot of time wandering around the city, and not really interact with anyone there. If we booked an apartment, inevitably there would be some sort of issue with the credit card machine, or the key, or the person not showing up on time, or, on one particularly memorable trip to Paris in January, not having working heat.

Now that I do this professionally, things are…different. For my own trips, and for my clients. I’ll use my most recent trip to Portugal as an example and then explain how I diverge from that when dealing with most client trips.

For my most recent Portugal trip, the process looked like this:

  • Decide when to go.

  • Research flight options on Google Flights, then head over an air consolidator’s website to see if they have a better price than does (I’m an AA loyalist).

    • What’s an air consolidator? They’re companies that buy airline tickets in bulk and act as a wholesaler. Because they’re buying seats in bulk under complex contracts, they’re able to offer fares that are lower than the published rates. The best rates I’ve seen are for international business and first class, although they occasionally come in better than the public fares for international economy or domestic first and business class.

    • In order to purchase air from a consolidator, you have to contact one directly or go through a travel agent. There’s generally a service fee charged by the consolidator and/or the travel agent. (Note: I don’t charge a service fee for handling air for my clients; I consider it part of the total package.)

  • Once I’ve got my flight, I move on to some rather intensive hotel research. For Portugal, we knew we’d be flying in and out of Lisbon, but didn’t have an itinerary in mind. Since I’m very hotel-focused, I wanted to make sure we were staying at properties I really wanted to experience.

    • I used the following travel agent-only resources to start my research: Travel42, which is an industry insider website that provides an honest overview of a large number of properties;, which provides me a little more information on the agent side than the consumer-facing site shows; and private Facebook forums with recommendations and reports by other travel advisors that I trust.

    • I used the following consumer-facing resources to supplement: The Telegraph’s travel section,, and Mr. & Mrs. Smith.

    • By the time I was done with those, I had a list of about 40 hotels. I plotted them on a google map of Portugal to see if there were any potential itineraries that leapt out at me.

    • There were two properties I knew I wanted to experience, Sao Lourenco do Barrocal and Six Senses Douro Valley. I knew we’d be in Lisbon for at least a few days and Porto for a night or two.

    • Once I’d decided on my selections, I either booked directly with the property (to establish a relationship) or through a wholesaler (to leverage their relationship).

  • Once flights, hotels, and rental car were squared away, I started thinking about what we’d do while there. For sure, I wanted a certain amount of wandering-around time, but I also wanted to set up a couple of low-key tours to interact with some locals and see a different side of the areas than I might be able to discover on my own.

    • For Sao Lourenco do Barrocal, that was easy - they list a ton of activities on their website and facilitated spa appointments, a trail ride, and an afternoon with an eminent local archaeologist.

    • For Lisbon, I set up a photo tour by searching Instagram for #lisbonphototour. We toured the Alfama district and it was a terrific experience; the guide/instructor was amazing and took us through spots he felt were especially good for composition or overviews of the city.

    • For the Douro Valley, we set up a wine tour using Domitur, a Portuguese destination management company (DMC). I’ll discuss DMCs a little bit more later.

  • I did some deep research on food (message boards on,, and food blogs are my main sources) and created a google map with the final contenders pinned to it. I also made a few restaurant reservations (this is more crucial in some destinations than others).

  • I created an itinerary for us in Travefy, with all the details (it updates flight changes automatically) and documentation.

  • Other things I do differently than I used to:

    • I buy travel insurance. Every trip, every time. I have an annual policy that covers me for little things like 4-day trips to Charlotte for a conference, but the coverage isn’t high enough for most of our international trips, so I buy a separate policy every time. I’m walking the walk, y’all. It’s SO important. Like all insurance, it just seems like an added cost until you need it, and then you’re so glad you have it.

    • I have Priority Pass so we have access to more lounges. I also have an airline-branded credit card, so I earn miles more quickly, which this year got me to Sapphire status with the oneworld alliance, so I can access certain lounges from their partner airlines when traveling. Being able to take a shower after an overnight flight is a blessing.

One thing I didn’t talk about above? PRICE. I knew approximately the budget we wanted to stick with and made decisions within that range. But I wasn’t booking the cheapest flight possible, nor the cheapest car, nor the lowest possible rate for the hotel. I was looking at the overall experience, which is what I do for my clients.

There are trade-offs when your main consideration is price - the terms and conditions are usually much more restrictive, and your experience will literally not be as good. It just won’t. When you book your hotel room through an OTA like Expedia, you’re at the bottom of the totem pole when rooms are assigned. Noisy, small, terrible views - those are the risks you take by going for the lowest price. If the hotel oversells their inventory, guests who booked through discount wholesalers or OTAs are the first ones ‘walked’ - sent to a different hotel. The last guests walked? Those who booked through reputable wholesaler, directly with the property, or, best of all, through a travel agent who has a relationship with the hotel.

So, what’s the difference when I’m planning a trip for you, and it’s a destination I haven’t been to?

The research portion is similar but, while I’m undergoing that research, I’m also talking to at least one, generally two, DMCs to get their take on the destination, what’s popular, what are the cool things we’re not going to be able to find via google.

DMCs are worth their weight in gold because they have on-the-ground connections, they’re able to help solve problems in real time (while I want to know if you have any issues, I’m likely not going to be in the same time zone as you), and generally have excellent negotiated contract rates with amazing hotels.

The general process with a DMC is:

  • You fill out my intake form.

  • We have a consultation call to clarify what you’re looking for; various administrative things ensue if we mutually decide to move forward.

  • I contact the DMC for a proposal for you while simultaneously starting my own research into flights and activities.

  • The DMC returns the proposal; I check it over for anything I don’t think is right for you, or that seems missing, then pass it along to you.

  • You provide feedback and the DMC and I refine until it’s perfect.

  • Once perfection is achieved, you pay a deposit and can start anticipating with joy your upcoming trip. Meanwhile, I continue researching restaurants, shops, off-beat things to see & do, etc.

  • We book your flights and talk about travel insurance.

  • Your final payment becomes due.

  • You pack, head out on the travel experience of a lifetime, and come home raving to all your friends about how amazing your trip was :)

So there you have it: why planning travel as your job isn’t the same as planning your own vacation…questions? Feel free to reach out to me.

Kathleen Sullivan