Tips for Getting Expert Help When Planning Your Next Trip

Jun 17, 2019

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The Points & Miles Backpacker is a weekly column appearing every Monday. TPG Contributor Brian Biros, who has backpacked the globe for the past 15 years, discusses how to fund this adventurous, budgeted and increasingly popular form of travel with points and miles. He’ll also explore all things backpacking-related. Read his story here and his high-level approach here.

Sure, you can always crack open a guidebook or load up your favorite travel website. But sometimes, what you really need is customized travel advice tailored to your specific trip and personal needs.

And knowing who (and how) to ask can greatly increase your odds of getting a helpful response — or any response at all.

Of course, you’re asking for someone else’s time when soliciting tips and advice, so you should make the effort to find answers on your own first. But if you get stuck, follow these guidelines to get the advice you need.

Research First

Many travel questions have already been answered (and you can probably find the information you need somewhere on The Points Guy).

Even as a TPG writer, for example, I still learn plenty from our existing content. So if I’d like to find the best way to book Emirates first class with points, I search with the key words from my question: “How to book Emirates first class with points.” You can even begin your search with “site:” to tell Google to only search your favorite source for trip planning and travel inspiration, of course.

If it’s not important enough for you to spend your own time researching, you probably shouldn’t ask for someone else’s help. Make sure it’s a serious inquiry before you enlist an expert.

Ask the Right Person

You probably already know who you consider to be a travel authority, whether it’s a host of a travel podcast or a high school friend with a great Instagram account.

Generally speaking, though, you’re more likely to get a response from someone you know personally. This is in no way a universal rule. Some travel personalities do a great job of engaging their audience (The Points Guy himself, Brian Kelly, even launched a hotline to help answer reader questions).

But if you send a request that goes unanswered, try to consider how many questions that person probably receives.

So if you’re planning a trip to Barcelona, you may have more success asking a family friend who studied abroad there. In-person conversations can work better than messages, too. Not only can you ask specific questions about your trip, but a person who knows you will have a better idea of what type of experiences to recommend.

If you want expert advice for visiting Barcelona, buy a guidebook. But for custom advice, ask friends. (Photo by Brian Biros / TPG)
If you want expert advice for visiting Barcelona, get a guidebook. But for custom advice, ask friends. Both, however, will likely recommend the Gaudi House Museum. (Photo by Brian Biros / The Points Guy)

Crowdsource for Answers

Asking questions in public message boards or on social media works very well because other travelers can see what has already been recommended, comment on other recommendations and maybe even learn something themselves.

The TPG Lounge on Facebook, for example, has 63,000 fellow points enthusiasts ready with advice. You can also search within the group first for your answer.

You can also reach out to several individuals, but don’t spam every traveler you know or follow. If someone is an authority on a destination or subject, ask him or her. I could tell you where to find the best caipirinha in Rio De Janeiro (it’s Caipirinha de Barril by Coelho in Lapa and Santa Teresa, for the record), but I can’t speak authoritatively on which Champagne you should order in Singapore Suites.

Enjoying a glass of Champagne in my A380 Residence.
Dom Perignon or Krug? This would be the Brian to ask. (Photo courtesy of Brian Kelly / The Points Guy)

Introduce Yourself

If you’re reaching out to someone you don’t know, start out with a brief introduction. There is a reason you picked this person for advice. Love his or her website, blog, column, Instagram? Let them know. Don’t write a novel: just a quick intro explaining who you are and why you came to them. Everyone likes to hear when their work resonates. Also, describe the steps you’ve already taken to try to find the answer so they know you’re serious.

Be Specific

“I want to go on a trip. Where should I go?”

It’s straight to the archive folder with an email like that. In order to solicit serious (and helpful) travel advice, you should be able to describe at least a few key parameters, such as the destination, your budget, your favorite activities and the type of trip you’re planning.

If I respond to that message recommending a backpacking route through the Balkans, and I hear this person was really hoping for a quick weekend beach getaway, I’ve wasted my time.

I do, however, still recommend backpacking through the Balkans. (Photo by Brian Biros / TPG)
I do, however, still recommend backpacking through the Balkans, including Gjirokastra, Albania. (Photo by Brian Biros / The Points Guy)

But Not Too Specific

“I have 252,000 Amex points, and I want to fly business class from Los Angeles to London for a wedding in July. Can you help me out?”

This isn’t asking for travel advice. This is asking for a travel agent. There are paid services that will help you book award travel, but asking someone to research a specific travel itinerary requires a huge time commitment (and, often, financial compensation).

It may not be too much to ask from a points-savvy friend, or anyone you’d feel comfortable asking for a favor. But if you wouldn’t ask this person to help you move into your new apartment, you probably shouldn’t expect them to book your family’s points trip to Europe.

Instead, you want your question to explain the criteria of the trip and makes a specific, reasonable ask. For example:

“I want to go to an island with a good, cheap backpacker vibe that’s no more than a few hours from the US. Bonus points for diving spots. Any places I should look into?”

In just a few minutes, I can point them in the direction of a few spots that will fit the bill.

Bocas del Toro, Panama has the perfect combo of a bustling backpacker scene and peaceful paradise. (Photo by Brian Biros / TPG)
Bocas del Toro, Panama has the perfect combination of a bustling backpacker scene and peaceful paradise. (Photo by Brian Biros / TPG)

Ask Again Politely

If you don’t get a response, understand that the person you’ve reached out to probably gets lots of requests.

Long before I wrote for TPG, I was the resident travel adviser for my family members, friends and neighbors. Adding in the additional requests I now get from readers and followers, I can’t get to them all. Also, I like to travel. So if you send me an email while I’m off the grid for a week at an ecolodge in the Solomon Islands, there’s a good possibility I’ll miss it. But if you try again a month later, I may be connected and able to respond.

I tell people I may not get to every email or question, but if you ask me twice, I will respond. I’d like to get to them all the first time, but if you care enough to ask again, I know it’s not a fleeting question.

Report Back After

Often I have message exchanges with someone preparing a trip only to never hear from that person again. Inspiring travel gets me excited — I want to know how everything went! If I need to update my recommendations, that is helpful, too. Did my favorite dive bar turn into an upscale sushi restaurant? That’s something I should know before my next visit. And if you have some favorites you found, pass those along.

filler filler
The Sunday night samba parties at Casa Rosa, a former brothel turned night club, were one of my favorite recommendations for Rio De Janeiro, until I learned on my last visit that the club had closed. (Photo by Brian Biros / TPG)

If you’re looking to back that pack up and get some guidance, send your questions to!

Feature photo by Paula May on Unsplash

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