Travel Guide Anxiety: When Your Friends Let You Plan Their Trip

Friends getting lost while planning a tripI travel alone most of the time because if I waited to travel with my friends, I would never go anywhere. I can’t count how many aborted travel plans I’ve made with my friends. From city meetups, to two-week holidays, to backpacking adventures across Europe, something always seems to “come up.” When it comes down to the wire, my friends rarely come through. Once in a blue moon, they make it. My friend Joe joined me in Belize, Kristin came to Amsterdam, Mike and Dustin came to Chicago, and Danielle backpacked Costa Rica with me.

I really enjoy traveling with my friends because it’s my chance to share my love of travel with them. I especially love when they visit one of my favorite destinations in the world. I feel like I’m showing them a special part of my life that not everyone gets to see. I’ll show them my favorite eateries, have them try amazing food, frequent my local hangouts, and hopefully make them fall in love with the destination as much as I have.

Today, three friends of mine arrive in Thailand for the holidays. I met Jesse and Joel in 2009 during La Tomatina, and we’ve remained close friends ever since. (I spent Thanksgiving with them last year.) Jesse’s girlfriend, Michelle, will also be joining us. It will be their first time in Asia. It will also be Michelle’s first time out of America. Amazing, huh? I imagine this will be quite an experience for all of them, especially Michelle. The chaotic streets of Bangkok are nothing like Portland, Oregon.

As excited as I am for their visit, I’m extremely nervous.

They’ve left the whole trip to me. Every detail of every day. While I’m excited (you know how much I love Thailand), I’m also worried. What if I screw up? Their experience depends entirely on my ability to plan and organize a great trip. I’m responsible for their happiness.

I know Thailand. I’ve lived here, explored most of the country, and come here every year. I know what they need to see and do, but what if it’s not perfect? Sure, we’ve discussed the trip and what they want, but there’s still this burden on my shoulders.

While I’ve planned city outings and such for friends, I’ve never been in charge of an entire visit before. No one has ever tossed me the keys and said, “You drive the whole way.”

At times, I’ve dreamt of being a tour guide. It must be so much fun, I think to myself. To share your passion with someone else in hopes of getting them as excited and hooked on it as you are. I have visions of leading excited groups of people through historic cities in Europe, explaining the history, and introducing them to great food. I’d be lying if I said it wasn’t an overly romantic image.

Now, I’m about to lead a 25-day private tour. I have to organize the logistics, take care of the accommodation, arrange hotels, and plan the itinerary. It’s nerve-racking, but I’m dealing with the anxiety by being thorough, booking everything in advance, and calming my nerves with a few beers.

If it goes well, then maybe playing tour guide is something I’ll do again in the future.

If not, I think I’ll just stick to giving budget advice, drinking beer, and letting my friends plan their own trips in the future.

  1. woohoo! I can feel your excitement plus nervousness from this writing, Matt!
    somehow I’m sure you’ll make a great tour for your friends.
    I hope your dream of becoming a tour guide & planner will come true!

  2. i’m sure you can do it!

    i’m always the one who plan the itinerary whenever i travel with my friends. well, all i ask for is to follow my plans, and dont put the blame on me should things go wrong. hah!

  3. You’ve got a passion for Thailand, so I’m sure you’ll do a fine job.

    I wound up in a “tour guide” role when I visited Laos. My friends biked the whole way, while I took buses. Since I would arrive in a town ahead of them, it became my responsibility to scout around for good guesthouses and handle logistics. Got stressful sometimes, but I wouldn’t trade the memories for anything.

    A country you love + friends you enjoy being with = unforgettable trip.

  4. I used to be the one to do most of the planning for trips with friends too. It is a bit stressful, but I have to admit I liked having the control :-)

    Don’t know if I could do it now after 13 months with little planning and being on my own.

  5. That would suck because ultimately you will be looked upon as an “expert” so if you screw it up then they may be gutted. But it sounds as if they have travelled before and if they are mates of yours then they will definitely enjoy any of the low-lights as well as rave about the highlights. Just enjoy the Singha’s!

  6. The longest tour I’ve ever conducted was 8 days and even that took multiple rounds of research, checking, and double-checing to make sure I was providing the most authentic, varied, and not too scheduled experience in Chile. Since it went well though, I’d be open to doing it again.

    Enjoy having your friends in Thailand with you! We had a blast in Costa Rica/Panama experience but I think this will be so much special being that you’re so familiar with this country. You’ll be fine :) have fun.

  7. That is a lot of pressure especially planning a trip for someone’s first time out of the US! It has got to help that it’s a country you know well and love though. Good luck and have fun.

  8. Jan

    I get that all the time when friends come to see me in Bangkok. I enjoy it most of the time and to be honest i enjoy showing off a bit with places i know that are special.
    However there is always the times i dislike and that is when guests fall back into the package tour mindset where they can’t even be bothered to think WHAT to do. I can take care about the WHERE, as long as i don’t have to constantly think of the WHAT. Thats just lazy and giving away any responsibility of having a good trip. Then it is a lot of stress for the “tour guide”.

  9. Don’t sweat it, dude.

    The best advice I can offer is: plan everything out, but keep it totally flexible. If they wanna lie around on the beach all day… do it! Wanna get crazy? Do it!

    I find every time a friend visits and we attempt a “rigid” schedule, it just causes more hassle than anything.

    Like Bruce Lee put it “Be water.”

  10. I have volunteered myself numerous times to be a tour guide to out-of-towners in my city and so far everyone has liked it. The thing is, they are most likely going to like it since they know nothing about Thailand, everything will just be new and fresh to them, Be a tour guide to someone who’s been to Thailand numerous times, then you’d have a competition, at least with your friends its their first time – everything is unexpected whether something goes wrong or not it’d just be an adventure. Remember the first time you travelled by yourself? Pretty much the same thing but with a compass. I’m sure they’d like what you have in store for them

  11. Ahhh I love love love having people out to visit me on the road. So many times on my travels I think “Oh so and so would love this,” or “I wish I could take her there!” But most of the time my friends pull out as well, so I’ve kind of stopped getting my hopes up. However, one person who always makes it out to visit me, wherever I am, is my dad. I look so forward to showing him off and showing him around some of my favorite places in the world. Enjoy your travels with your friends.

    • NomadicMatt

      My parents finally said they might actually come to Thailand. That would be pretty exciting, though I think they would complain about the craziness a lot. And I’m pretty sure they would not eat the street food.

  12. I like to just go with the flow and not plan too much. Usually when my buddies and I head off on a road trip we plan maybe a sporting event or a few things we certainly want to see, but past that we just let the wind take us. You will be amazed as the things you might experience if you don’t plan too much.

  13. Jake Aufderheide

    Well this would certainly be a weight for me, considering I don’t even plan my OWN itinerary, I just sorta take things as they come. I reckon it’s one of those things that comes with practice. I agree with what Adam said, don’t worry too much about sticking to the schedule. That’s when things get stressful!

  14. I can definitely related to the post. I recently had an experience of organizing a trip around Ontario, Canada for some friends coming over; it was very exciting and very thrilling at the same time to plan it.

  15. Good luck! I love playing tour guide and creating itineraries for friends and family, but it definitely makes me a bit nervous because of course if they hate it, it’s all your fault. I’m sure they won’t hate it though and that everything will go well. Enjoy!

  16. Every great adventure has its ups and downs, and hurdles. As long as you are with friends who are patient and understanding of those moments of travel. I went on a trip with some close friends and thankfully in my moments of stress and blunders they laughed and made light of the situations. Amazing people make for amazing adventures. When in good company it cant go wrong!

  17. You are right, Matt. I can’t tell you how difficult it is to find people to travel with. They always have some excuse (no money, no one to watch the cat, have to work, girlfriend/wife won’t let me go, etc.) to not make a trip.

    I guess they are going to wait until they are 90 years old or so to start traveling.

  18. Li

    Hi Matt! I feel your pain! I am currently planning a 22 day European vacation for my friends. I am so stressed! I hope things go smoothly for you! Any tips? P.S. Enjoy your trip!

  19. I totally understand your anxiety! Last month I planned a whole trip to Italy with my Dad and sister. I was a little nervous how my dad (who only travels first class business style) and my sister (who is not super adventurous) would react to the backpacking, hostel staying, adventure I planned out.

    Turns out they loved it! My best advice is tell them what to expect upfront, explain why traveling to a new place or in a different way is so awesome, and keep them 30% in their comfort zone.

    Good luck!!

  20. Cosmos

    I also find it stressful when trying to plan a trip with friends. They say they like to “see what happens” and don’t want to over plan but I find that you don’t end up doing anything if you are like that. I went to Nepal with a friend and my main reason was to go on a particular white water rafting trip. Lucky I stuck to my guns and organised it the minute we got there because it turned out to be the last trip of the season and we just got in! Actually was trying to get her to commit before we left Australia but she wouldn’t cos she doesn’t like feeling locked in to anything!
    So I find it a fine line to walk between over planning and being free to be spontaneous.

  21. I seriously understand this post. My friends left me in charge of planning our trip to Dominican Republic. Stressed me out for 3 months but it went flawlessly.

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